Oxalic Acid _ C2H2O4 - PubChem

61
11/5/2015 oxalic acid | C2H2O4 PubChem http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties 1/61 NIH U.S. National Library of Medicine National Center for Biotechnology Information OPEN CHEMISTRY DATABASE Search Compounds PUBCHEM COMPOUND OXALIC ACID Oxalic Acid Cite this Record Vendors Drug Information Pharmacology Literature Patents Bioactivities PubChem CID: 971 Chemical Names: Oxalic acid; Ethanedioic acid; 144627; Aktisal; Aquisal; Oxiric acid; More... Molecular Formula: CHO Molecular Weight: 90.03488 g/mol InChI Key: MUBZPKHOEPUJKRUHFFFAOYSAN UNII: 9E7R5L6H31 Safety Summary: Laboratory Chemical Safety Summary (LCSS) Modify Date: 20151031 Create Date: 20040916 Oxalic acid is a strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent. from MeSH Oxalic acid is an odorless white solid. Sinks and mixes with water. (USCG, 1999) Physical Description from CAMEO Chemicals 2 2 4

description

asam oksalat

Transcript of Oxalic Acid _ C2H2O4 - PubChem

Page 1: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

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NIH US National Library of Medicine National Center for Biotechnology Information

O P E NCHEMISTRYD A T A B A S E

Search Compounds

PUBCHEM COMPOUND OXALIC ACID

Oxalic Acid Cite this Record

Vendors

Drug Information

Pharmacology

Literature

Patents

Bioactivities

PubChem CID 971

Chemical NamesOxalic acid Ethanedioic acid 144shy62shy7 Aktisal Aquisal Oxiric

acid More

Molecular Formula C H O

Molecular Weight 9003488 gmol

InChI Key MUBZPKHOEPUJKRshyUHFFFAOYSAshyN

UNII 9E7R5L6H31

Safety Summary Laboratory Chemical Safety Summary (LCSS)

Modify Date 2015shy10shy31

Create Date 2004shy09shy16

Oxalic acid is a strong dicarboxylic acid occurring in many plants and vegetables It is produced in the body bymetabolism of glyoxylic acid or ascorbic acid It is not metabolized but excreted in the urine It is used as ananalytical reagent and general reducing agent

from MeSH

Oxalic acid is an odorless white solid Sinks and mixes with water (USCG 1999) Physical Description from CAMEO Chemicals

2 2 4

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Contents1 2D Structure

2 3D Conformer

3 Names and Identifiers

4 Chemical and Physical Properties

5 Related Records

6 Chemical Vendors

7 Drug and Medication Information

8 Pharmacology and Biochemistry

9 Use and Manufacturing

10 Identification

11 Safety and Hazards

12 Toxicity

13 Literature

14 Patents

15 Biomolecular Interactions and Pathways

16 Biological Test Results

17 Classification

18 Information Sources

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from PubChem

1 2D Structure

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from PubChem

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3 Names and Identifiers

31 Computed Descriptors

oxalic acid

from PubChem

311 IUPAC Name

InChI=1SC2H2O4c3shy1(4)2(5)6h(H34)(H56)

from PubChem

312 InChI

MUBZPKHOEPUJKRshyUHFFFAOYSAshyN

from PubChem

313 InChI Key

C(=O)(C(=O)O)O

from PubChem

314 Canonical SMILES

32 Other Identifiers

144shy62shy7

from DrugBank EPA Chemical Data Report ILOshyICSC NIOSHshyPocketGuide OSHA Occupational Chemhellip

321 CAS

205shy634shy3

from ILOshyICSC

205shy634shy3

from ECHA

208shy932shy1

from ECHA

322 EC Number

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213shy950shy8

from ECHA

0529

from ILOshyICSC

323 ICSC Number

RO2450000

from ILOshyICSC

RO2450000

from NIOSHshyPocketGuide

324 RTECS Number

3261

from ILOshyICSC CAMEO Chemicals

1759

from NJDOH RTK Hazardous Substance List

325 UN Number

9E7R5L6H31

from FDASPL Indexing data

326 UNII

Oxalic acid

from Wiki

327 Wikipedia

33 Synonyms

1 Acid Oxalic2 Aluminum Oxalate3 Ammonium Oxalate4 Chromium (2+) Oxalate

11 Ferric Oxalate12 Iron (2+) Oxalate (11)13 Iron (3+) Oxalate14 Iron Oxalate

21 Monosodium Oxalate22 Oxalate Aluminum23 Oxalate Chromium24 Oxalate Diammonium

31 Oxalate Monoammonium32 Oxalate Monohydrogen Monopotassium33 Oxalate Monopotassium34 Oxalate Monosodium

331 MeSH Synonyms

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5 Chromium (3+) Oxalate (32)6 Chromium Oxalate7 Diammonium Oxalate8 Dilithium Oxalate9 Dipotassium Oxalate10 Disodium Oxalate

15 Magnesium Oxalate16 Magnesium Oxalate (11)17 Manganese (2+) Oxalate (11)18 Monoammonium Oxalate19 Monohydrogen Monopotassium Oxalate20 Monopotassium Oxalate

25 Oxalate Dilithium26 Oxalate Dipotassium27 Oxalate Disodium28 Oxalate Ferric29 Oxalate Iron30 Oxalate Magnesium

35 Oxalate Potassium36 Oxalate Potassium Chromium37 Oxalate Sodium38 Oxalic Acid39 Potassium Chromium Oxalate40 Potassium Oxalate

from MeSH

1 oxalic acid2 ethanedioic acid3 144shy62shy74 Aktisal5 Aquisal6 Oxiric acid7 oxalate8 Oxaalzuur9 Oxalsaeure10 Kyselina stavelova

11 Acidum oxalicum12 Acide oxalique13 Acido ossalico14 Caswell No 62515 Ethanedionic acid16 Oxaalzuur [Dutch]17 NCIshyC5520918 Oxalsaeure [German]19 Acide oxalique [French]20 Ethaneshy12shydioic acid

21 Acido ossalico [Italian]22 Kyselina stavelova [Czech]23 EPA Pesticide Chemical Code 00960124 HOOCCOOH25 CCRIS 145426 AI3shy2646327 HSDB 110028 NSC 6277429 BRN 038568630 UNIIshy9E7R5L6H31

31 CHEBI1699532 MUBZPKHOEPUJKRshyUHFFFAOYSAshyN33 EINECS 205shy634shy334 STK37955035 Oxalicacid36 DSSTox_CID_581637 C0020938 DSSTox_RID_7793539 DSSTox_GSID_2581640 Oxalic acid standard solution

from PubChem

332 DepositorshySupplied Synonyms

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4 Chemical and Physical Properties

Molecular Weight 9003488 gmol

Molecular Formula C H O

XLogP3 shy03

Hydrogen Bond Donor Count 2

Hydrogen Bond Acceptor Count 4

Rotatable Bond Count 1

Exact Mass 89995309 gmol

Monoisotopic Mass 89995309 gmol

Topological Polar Surface Area 746 A^2

Heavy Atom Count 6

Formal Charge 0

Complexity 715

Isotope Atom Count 0

Defined Atom Stereocenter Count 0

Undefined Atom Stereocenter Count 0

Defined Bond Stereocenter Count 0

Undefined Bond Stereocenter Count 0

CovalentlyshyBonded Unit Count 1

from PubChem

41 Computed Properties

2 2 4

42 Experimental Properties

1 DryPowder2 OtherSolid3 PelletsLargeCrystals

from EPA Chemical Data Report

HYGROSCOPIC COLOURLESS CRYSTALS OR WHITE POWDER

from ILOshyICSC

Colorless odorless powder or granular solid

421 Physical Description

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

Oxalic acid is an odorless white solid Sinks and mixes with water (USCG 1999)

from CAMEO Chemicals

ANHYDROUS OXALIC ACID CRYSTALLIZED FROM GLACIAL ACETIC ACID IS ORTHORHOMBICCRYSTALS BEING PYRAMIDAL OR ELONGATED OCTAHEDRA

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

Colorless powder or granular solid [Note The anhydrous form (COOH)2 is a white powder]NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

422 Color

OdorlessNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

423 Odor

Sublimes

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

424 Boiling Point

1895 DEG C (DECOMPOSES)Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

1895 dec degCPhysProp

from DrugBank

1895degC

from ILOshyICSC

215 degF

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

425 Melting Point

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372 degF (Decomposes)(NTP 1992)

from CAMEO Chemicals

100 G AQ SOLN SATURATED 15 DEG C CONTAINS 671 G 100 G AQ SOLN SATURATED 20 DEG CCONTAINS 834 G 100 G AQ SOLN SATURATED 25 DEG C CONTAINS 981 G

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

VERY SOL IN ETHANOL SLIGHTLY SOL IN ETHER INSOL IN BENZENE CHLOROFORM PETROLEUMETHER

Weast RC (ed) Handbook of Chemistry and Physics 60th ed Boca Raton Florida CRC Press Inc 1979 p Cshy409

from HSDB

Water solubility of 220000 mgl at 25 deg CYalkowsky SH et al Arizona Data Base of Water Solubility (1989)

from HSDB

Water Solubility220000 mgL (at 25 degC)

YALKOWSKYSH amp DANNENFELSERRM (1992)

from DrugBank

Solubility in water g100ml at 20degC 9shy10 (moderate)

from ILOshyICSC

14 [g100mL]

from NIOSHshyPocketGuide

50 to 100 mgmL at 75 deg F(NTP 1992)

from CAMEO Chemicals

426 Solubility

190 17 DEG4 DEG C ALPHABudavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 693

from HSDB

Density (at degC) 19 gcmsup3

from ILOshyICSC

19

427 Density

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

19 at 59 degF(USCG 1999)

from CAMEO Chemicals

43(NTP 1992)

from CAMEO Chemicals

428 Vapor Density

054 mm 105 deg CClayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

lt0001 mmHg

from NIOSHshyPocketGuide

lt0001

from OSHA Occupational Chemical DB

0001 mmHg at 68 degF(NTP 1992)

from CAMEO Chemicals

429 Vapor Pressure

shy081

from ILOshyICSC

4210 LogP

038ADME Research USCD

from DrugBank

4211 LogS

OXALIC ACID CAN BE DEHYDRATED BY CAREFUL DRYING 100 DEG C BUT LOSSES OCCURTHROUGH SUBLIMATION OXALIC ACID DIHYDRATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc

4212 Stability

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1989 p 897

from HSDB

DECOMP PRODUCTS INCL CARBON MONOXIDE amp FORMIC ACIDNational Fire Protection Association Fire Protection Guide on Hazardous Materials 7th ed Boston Mass National FireProtection Association 1978 p 49shy224

from HSDB

see Notes

from ILOshyICSC

4213 Decomposition

shy24561 KJmolKirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 619 (1981)

from HSDB

4214 Heat of Combustion

pKa 1 146 pKa 2 440Clayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

4215 Dissociation Constants

Semishystandard nonshypolar 748

from NIST

4216 Kovats Retention Index

Crystal Structures 1 of 5

CCDC Number 929767

Crystal Structure Data DOI105517cc106hh6

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 2 of 5

43 Crystal Structures

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

CLICK TO LOAD

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

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from PubChem

6 Chemical Vendors

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7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4461

contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4561

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 2: Oxalic Acid _ C2H2O4 - PubChem

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Contents1 2D Structure

2 3D Conformer

3 Names and Identifiers

4 Chemical and Physical Properties

5 Related Records

6 Chemical Vendors

7 Drug and Medication Information

8 Pharmacology and Biochemistry

9 Use and Manufacturing

10 Identification

11 Safety and Hazards

12 Toxicity

13 Literature

14 Patents

15 Biomolecular Interactions and Pathways

16 Biological Test Results

17 Classification

18 Information Sources

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from PubChem

1 2D Structure

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from PubChem

2 3D Conformer

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3 Names and Identifiers

31 Computed Descriptors

oxalic acid

from PubChem

311 IUPAC Name

InChI=1SC2H2O4c3shy1(4)2(5)6h(H34)(H56)

from PubChem

312 InChI

MUBZPKHOEPUJKRshyUHFFFAOYSAshyN

from PubChem

313 InChI Key

C(=O)(C(=O)O)O

from PubChem

314 Canonical SMILES

32 Other Identifiers

144shy62shy7

from DrugBank EPA Chemical Data Report ILOshyICSC NIOSHshyPocketGuide OSHA Occupational Chemhellip

321 CAS

205shy634shy3

from ILOshyICSC

205shy634shy3

from ECHA

208shy932shy1

from ECHA

322 EC Number

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213shy950shy8

from ECHA

0529

from ILOshyICSC

323 ICSC Number

RO2450000

from ILOshyICSC

RO2450000

from NIOSHshyPocketGuide

324 RTECS Number

3261

from ILOshyICSC CAMEO Chemicals

1759

from NJDOH RTK Hazardous Substance List

325 UN Number

9E7R5L6H31

from FDASPL Indexing data

326 UNII

Oxalic acid

from Wiki

327 Wikipedia

33 Synonyms

1 Acid Oxalic2 Aluminum Oxalate3 Ammonium Oxalate4 Chromium (2+) Oxalate

11 Ferric Oxalate12 Iron (2+) Oxalate (11)13 Iron (3+) Oxalate14 Iron Oxalate

21 Monosodium Oxalate22 Oxalate Aluminum23 Oxalate Chromium24 Oxalate Diammonium

31 Oxalate Monoammonium32 Oxalate Monohydrogen Monopotassium33 Oxalate Monopotassium34 Oxalate Monosodium

331 MeSH Synonyms

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5 Chromium (3+) Oxalate (32)6 Chromium Oxalate7 Diammonium Oxalate8 Dilithium Oxalate9 Dipotassium Oxalate10 Disodium Oxalate

15 Magnesium Oxalate16 Magnesium Oxalate (11)17 Manganese (2+) Oxalate (11)18 Monoammonium Oxalate19 Monohydrogen Monopotassium Oxalate20 Monopotassium Oxalate

25 Oxalate Dilithium26 Oxalate Dipotassium27 Oxalate Disodium28 Oxalate Ferric29 Oxalate Iron30 Oxalate Magnesium

35 Oxalate Potassium36 Oxalate Potassium Chromium37 Oxalate Sodium38 Oxalic Acid39 Potassium Chromium Oxalate40 Potassium Oxalate

from MeSH

1 oxalic acid2 ethanedioic acid3 144shy62shy74 Aktisal5 Aquisal6 Oxiric acid7 oxalate8 Oxaalzuur9 Oxalsaeure10 Kyselina stavelova

11 Acidum oxalicum12 Acide oxalique13 Acido ossalico14 Caswell No 62515 Ethanedionic acid16 Oxaalzuur [Dutch]17 NCIshyC5520918 Oxalsaeure [German]19 Acide oxalique [French]20 Ethaneshy12shydioic acid

21 Acido ossalico [Italian]22 Kyselina stavelova [Czech]23 EPA Pesticide Chemical Code 00960124 HOOCCOOH25 CCRIS 145426 AI3shy2646327 HSDB 110028 NSC 6277429 BRN 038568630 UNIIshy9E7R5L6H31

31 CHEBI1699532 MUBZPKHOEPUJKRshyUHFFFAOYSAshyN33 EINECS 205shy634shy334 STK37955035 Oxalicacid36 DSSTox_CID_581637 C0020938 DSSTox_RID_7793539 DSSTox_GSID_2581640 Oxalic acid standard solution

from PubChem

332 DepositorshySupplied Synonyms

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4 Chemical and Physical Properties

Molecular Weight 9003488 gmol

Molecular Formula C H O

XLogP3 shy03

Hydrogen Bond Donor Count 2

Hydrogen Bond Acceptor Count 4

Rotatable Bond Count 1

Exact Mass 89995309 gmol

Monoisotopic Mass 89995309 gmol

Topological Polar Surface Area 746 A^2

Heavy Atom Count 6

Formal Charge 0

Complexity 715

Isotope Atom Count 0

Defined Atom Stereocenter Count 0

Undefined Atom Stereocenter Count 0

Defined Bond Stereocenter Count 0

Undefined Bond Stereocenter Count 0

CovalentlyshyBonded Unit Count 1

from PubChem

41 Computed Properties

2 2 4

42 Experimental Properties

1 DryPowder2 OtherSolid3 PelletsLargeCrystals

from EPA Chemical Data Report

HYGROSCOPIC COLOURLESS CRYSTALS OR WHITE POWDER

from ILOshyICSC

Colorless odorless powder or granular solid

421 Physical Description

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

Oxalic acid is an odorless white solid Sinks and mixes with water (USCG 1999)

from CAMEO Chemicals

ANHYDROUS OXALIC ACID CRYSTALLIZED FROM GLACIAL ACETIC ACID IS ORTHORHOMBICCRYSTALS BEING PYRAMIDAL OR ELONGATED OCTAHEDRA

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

Colorless powder or granular solid [Note The anhydrous form (COOH)2 is a white powder]NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

422 Color

OdorlessNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

423 Odor

Sublimes

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

424 Boiling Point

1895 DEG C (DECOMPOSES)Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

1895 dec degCPhysProp

from DrugBank

1895degC

from ILOshyICSC

215 degF

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

425 Melting Point

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372 degF (Decomposes)(NTP 1992)

from CAMEO Chemicals

100 G AQ SOLN SATURATED 15 DEG C CONTAINS 671 G 100 G AQ SOLN SATURATED 20 DEG CCONTAINS 834 G 100 G AQ SOLN SATURATED 25 DEG C CONTAINS 981 G

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

VERY SOL IN ETHANOL SLIGHTLY SOL IN ETHER INSOL IN BENZENE CHLOROFORM PETROLEUMETHER

Weast RC (ed) Handbook of Chemistry and Physics 60th ed Boca Raton Florida CRC Press Inc 1979 p Cshy409

from HSDB

Water solubility of 220000 mgl at 25 deg CYalkowsky SH et al Arizona Data Base of Water Solubility (1989)

from HSDB

Water Solubility220000 mgL (at 25 degC)

YALKOWSKYSH amp DANNENFELSERRM (1992)

from DrugBank

Solubility in water g100ml at 20degC 9shy10 (moderate)

from ILOshyICSC

14 [g100mL]

from NIOSHshyPocketGuide

50 to 100 mgmL at 75 deg F(NTP 1992)

from CAMEO Chemicals

426 Solubility

190 17 DEG4 DEG C ALPHABudavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 693

from HSDB

Density (at degC) 19 gcmsup3

from ILOshyICSC

19

427 Density

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

19 at 59 degF(USCG 1999)

from CAMEO Chemicals

43(NTP 1992)

from CAMEO Chemicals

428 Vapor Density

054 mm 105 deg CClayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

lt0001 mmHg

from NIOSHshyPocketGuide

lt0001

from OSHA Occupational Chemical DB

0001 mmHg at 68 degF(NTP 1992)

from CAMEO Chemicals

429 Vapor Pressure

shy081

from ILOshyICSC

4210 LogP

038ADME Research USCD

from DrugBank

4211 LogS

OXALIC ACID CAN BE DEHYDRATED BY CAREFUL DRYING 100 DEG C BUT LOSSES OCCURTHROUGH SUBLIMATION OXALIC ACID DIHYDRATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc

4212 Stability

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1989 p 897

from HSDB

DECOMP PRODUCTS INCL CARBON MONOXIDE amp FORMIC ACIDNational Fire Protection Association Fire Protection Guide on Hazardous Materials 7th ed Boston Mass National FireProtection Association 1978 p 49shy224

from HSDB

see Notes

from ILOshyICSC

4213 Decomposition

shy24561 KJmolKirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 619 (1981)

from HSDB

4214 Heat of Combustion

pKa 1 146 pKa 2 440Clayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

4215 Dissociation Constants

Semishystandard nonshypolar 748

from NIST

4216 Kovats Retention Index

Crystal Structures 1 of 5

CCDC Number 929767

Crystal Structure Data DOI105517cc106hh6

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 2 of 5

43 Crystal Structures

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

CLICK TO LOAD

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

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from PubChem

6 Chemical Vendors

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7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

1152015 oxalic acid | C2H2O4 shy PubChem

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

1152015 oxalic acid | C2H2O4 shy PubChem

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3461

NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4261

from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4461

contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4661

third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4961

may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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from PubChem

1 2D Structure

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3 Names and Identifiers

31 Computed Descriptors

oxalic acid

from PubChem

311 IUPAC Name

InChI=1SC2H2O4c3shy1(4)2(5)6h(H34)(H56)

from PubChem

312 InChI

MUBZPKHOEPUJKRshyUHFFFAOYSAshyN

from PubChem

313 InChI Key

C(=O)(C(=O)O)O

from PubChem

314 Canonical SMILES

32 Other Identifiers

144shy62shy7

from DrugBank EPA Chemical Data Report ILOshyICSC NIOSHshyPocketGuide OSHA Occupational Chemhellip

321 CAS

205shy634shy3

from ILOshyICSC

205shy634shy3

from ECHA

208shy932shy1

from ECHA

322 EC Number

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213shy950shy8

from ECHA

0529

from ILOshyICSC

323 ICSC Number

RO2450000

from ILOshyICSC

RO2450000

from NIOSHshyPocketGuide

324 RTECS Number

3261

from ILOshyICSC CAMEO Chemicals

1759

from NJDOH RTK Hazardous Substance List

325 UN Number

9E7R5L6H31

from FDASPL Indexing data

326 UNII

Oxalic acid

from Wiki

327 Wikipedia

33 Synonyms

1 Acid Oxalic2 Aluminum Oxalate3 Ammonium Oxalate4 Chromium (2+) Oxalate

11 Ferric Oxalate12 Iron (2+) Oxalate (11)13 Iron (3+) Oxalate14 Iron Oxalate

21 Monosodium Oxalate22 Oxalate Aluminum23 Oxalate Chromium24 Oxalate Diammonium

31 Oxalate Monoammonium32 Oxalate Monohydrogen Monopotassium33 Oxalate Monopotassium34 Oxalate Monosodium

331 MeSH Synonyms

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5 Chromium (3+) Oxalate (32)6 Chromium Oxalate7 Diammonium Oxalate8 Dilithium Oxalate9 Dipotassium Oxalate10 Disodium Oxalate

15 Magnesium Oxalate16 Magnesium Oxalate (11)17 Manganese (2+) Oxalate (11)18 Monoammonium Oxalate19 Monohydrogen Monopotassium Oxalate20 Monopotassium Oxalate

25 Oxalate Dilithium26 Oxalate Dipotassium27 Oxalate Disodium28 Oxalate Ferric29 Oxalate Iron30 Oxalate Magnesium

35 Oxalate Potassium36 Oxalate Potassium Chromium37 Oxalate Sodium38 Oxalic Acid39 Potassium Chromium Oxalate40 Potassium Oxalate

from MeSH

1 oxalic acid2 ethanedioic acid3 144shy62shy74 Aktisal5 Aquisal6 Oxiric acid7 oxalate8 Oxaalzuur9 Oxalsaeure10 Kyselina stavelova

11 Acidum oxalicum12 Acide oxalique13 Acido ossalico14 Caswell No 62515 Ethanedionic acid16 Oxaalzuur [Dutch]17 NCIshyC5520918 Oxalsaeure [German]19 Acide oxalique [French]20 Ethaneshy12shydioic acid

21 Acido ossalico [Italian]22 Kyselina stavelova [Czech]23 EPA Pesticide Chemical Code 00960124 HOOCCOOH25 CCRIS 145426 AI3shy2646327 HSDB 110028 NSC 6277429 BRN 038568630 UNIIshy9E7R5L6H31

31 CHEBI1699532 MUBZPKHOEPUJKRshyUHFFFAOYSAshyN33 EINECS 205shy634shy334 STK37955035 Oxalicacid36 DSSTox_CID_581637 C0020938 DSSTox_RID_7793539 DSSTox_GSID_2581640 Oxalic acid standard solution

from PubChem

332 DepositorshySupplied Synonyms

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 861

4 Chemical and Physical Properties

Molecular Weight 9003488 gmol

Molecular Formula C H O

XLogP3 shy03

Hydrogen Bond Donor Count 2

Hydrogen Bond Acceptor Count 4

Rotatable Bond Count 1

Exact Mass 89995309 gmol

Monoisotopic Mass 89995309 gmol

Topological Polar Surface Area 746 A^2

Heavy Atom Count 6

Formal Charge 0

Complexity 715

Isotope Atom Count 0

Defined Atom Stereocenter Count 0

Undefined Atom Stereocenter Count 0

Defined Bond Stereocenter Count 0

Undefined Bond Stereocenter Count 0

CovalentlyshyBonded Unit Count 1

from PubChem

41 Computed Properties

2 2 4

42 Experimental Properties

1 DryPowder2 OtherSolid3 PelletsLargeCrystals

from EPA Chemical Data Report

HYGROSCOPIC COLOURLESS CRYSTALS OR WHITE POWDER

from ILOshyICSC

Colorless odorless powder or granular solid

421 Physical Description

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 961

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

Oxalic acid is an odorless white solid Sinks and mixes with water (USCG 1999)

from CAMEO Chemicals

ANHYDROUS OXALIC ACID CRYSTALLIZED FROM GLACIAL ACETIC ACID IS ORTHORHOMBICCRYSTALS BEING PYRAMIDAL OR ELONGATED OCTAHEDRA

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

Colorless powder or granular solid [Note The anhydrous form (COOH)2 is a white powder]NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

422 Color

OdorlessNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

423 Odor

Sublimes

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

424 Boiling Point

1895 DEG C (DECOMPOSES)Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

1895 dec degCPhysProp

from DrugBank

1895degC

from ILOshyICSC

215 degF

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

425 Melting Point

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372 degF (Decomposes)(NTP 1992)

from CAMEO Chemicals

100 G AQ SOLN SATURATED 15 DEG C CONTAINS 671 G 100 G AQ SOLN SATURATED 20 DEG CCONTAINS 834 G 100 G AQ SOLN SATURATED 25 DEG C CONTAINS 981 G

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

VERY SOL IN ETHANOL SLIGHTLY SOL IN ETHER INSOL IN BENZENE CHLOROFORM PETROLEUMETHER

Weast RC (ed) Handbook of Chemistry and Physics 60th ed Boca Raton Florida CRC Press Inc 1979 p Cshy409

from HSDB

Water solubility of 220000 mgl at 25 deg CYalkowsky SH et al Arizona Data Base of Water Solubility (1989)

from HSDB

Water Solubility220000 mgL (at 25 degC)

YALKOWSKYSH amp DANNENFELSERRM (1992)

from DrugBank

Solubility in water g100ml at 20degC 9shy10 (moderate)

from ILOshyICSC

14 [g100mL]

from NIOSHshyPocketGuide

50 to 100 mgmL at 75 deg F(NTP 1992)

from CAMEO Chemicals

426 Solubility

190 17 DEG4 DEG C ALPHABudavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 693

from HSDB

Density (at degC) 19 gcmsup3

from ILOshyICSC

19

427 Density

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

19 at 59 degF(USCG 1999)

from CAMEO Chemicals

43(NTP 1992)

from CAMEO Chemicals

428 Vapor Density

054 mm 105 deg CClayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

lt0001 mmHg

from NIOSHshyPocketGuide

lt0001

from OSHA Occupational Chemical DB

0001 mmHg at 68 degF(NTP 1992)

from CAMEO Chemicals

429 Vapor Pressure

shy081

from ILOshyICSC

4210 LogP

038ADME Research USCD

from DrugBank

4211 LogS

OXALIC ACID CAN BE DEHYDRATED BY CAREFUL DRYING 100 DEG C BUT LOSSES OCCURTHROUGH SUBLIMATION OXALIC ACID DIHYDRATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc

4212 Stability

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1261

1989 p 897

from HSDB

DECOMP PRODUCTS INCL CARBON MONOXIDE amp FORMIC ACIDNational Fire Protection Association Fire Protection Guide on Hazardous Materials 7th ed Boston Mass National FireProtection Association 1978 p 49shy224

from HSDB

see Notes

from ILOshyICSC

4213 Decomposition

shy24561 KJmolKirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 619 (1981)

from HSDB

4214 Heat of Combustion

pKa 1 146 pKa 2 440Clayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

4215 Dissociation Constants

Semishystandard nonshypolar 748

from NIST

4216 Kovats Retention Index

Crystal Structures 1 of 5

CCDC Number 929767

Crystal Structure Data DOI105517cc106hh6

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 2 of 5

43 Crystal Structures

1152015 oxalic acid | C2H2O4 shy PubChem

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

1152015 oxalic acid | C2H2O4 shy PubChem

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

CLICK TO LOAD

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

CLICK TO LOAD

CLICK TO LOAD

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

CLICK TO LOAD

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from PubChem

6 Chemical Vendors

CLICK TO LOAD

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1861

7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3061

USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3161

from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3261

Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3361

TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3461

NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3561

Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3661

Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3761

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3961

12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5061

hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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from PubChem

2 3D Conformer

Magnify

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3 Names and Identifiers

31 Computed Descriptors

oxalic acid

from PubChem

311 IUPAC Name

InChI=1SC2H2O4c3shy1(4)2(5)6h(H34)(H56)

from PubChem

312 InChI

MUBZPKHOEPUJKRshyUHFFFAOYSAshyN

from PubChem

313 InChI Key

C(=O)(C(=O)O)O

from PubChem

314 Canonical SMILES

32 Other Identifiers

144shy62shy7

from DrugBank EPA Chemical Data Report ILOshyICSC NIOSHshyPocketGuide OSHA Occupational Chemhellip

321 CAS

205shy634shy3

from ILOshyICSC

205shy634shy3

from ECHA

208shy932shy1

from ECHA

322 EC Number

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213shy950shy8

from ECHA

0529

from ILOshyICSC

323 ICSC Number

RO2450000

from ILOshyICSC

RO2450000

from NIOSHshyPocketGuide

324 RTECS Number

3261

from ILOshyICSC CAMEO Chemicals

1759

from NJDOH RTK Hazardous Substance List

325 UN Number

9E7R5L6H31

from FDASPL Indexing data

326 UNII

Oxalic acid

from Wiki

327 Wikipedia

33 Synonyms

1 Acid Oxalic2 Aluminum Oxalate3 Ammonium Oxalate4 Chromium (2+) Oxalate

11 Ferric Oxalate12 Iron (2+) Oxalate (11)13 Iron (3+) Oxalate14 Iron Oxalate

21 Monosodium Oxalate22 Oxalate Aluminum23 Oxalate Chromium24 Oxalate Diammonium

31 Oxalate Monoammonium32 Oxalate Monohydrogen Monopotassium33 Oxalate Monopotassium34 Oxalate Monosodium

331 MeSH Synonyms

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5 Chromium (3+) Oxalate (32)6 Chromium Oxalate7 Diammonium Oxalate8 Dilithium Oxalate9 Dipotassium Oxalate10 Disodium Oxalate

15 Magnesium Oxalate16 Magnesium Oxalate (11)17 Manganese (2+) Oxalate (11)18 Monoammonium Oxalate19 Monohydrogen Monopotassium Oxalate20 Monopotassium Oxalate

25 Oxalate Dilithium26 Oxalate Dipotassium27 Oxalate Disodium28 Oxalate Ferric29 Oxalate Iron30 Oxalate Magnesium

35 Oxalate Potassium36 Oxalate Potassium Chromium37 Oxalate Sodium38 Oxalic Acid39 Potassium Chromium Oxalate40 Potassium Oxalate

from MeSH

1 oxalic acid2 ethanedioic acid3 144shy62shy74 Aktisal5 Aquisal6 Oxiric acid7 oxalate8 Oxaalzuur9 Oxalsaeure10 Kyselina stavelova

11 Acidum oxalicum12 Acide oxalique13 Acido ossalico14 Caswell No 62515 Ethanedionic acid16 Oxaalzuur [Dutch]17 NCIshyC5520918 Oxalsaeure [German]19 Acide oxalique [French]20 Ethaneshy12shydioic acid

21 Acido ossalico [Italian]22 Kyselina stavelova [Czech]23 EPA Pesticide Chemical Code 00960124 HOOCCOOH25 CCRIS 145426 AI3shy2646327 HSDB 110028 NSC 6277429 BRN 038568630 UNIIshy9E7R5L6H31

31 CHEBI1699532 MUBZPKHOEPUJKRshyUHFFFAOYSAshyN33 EINECS 205shy634shy334 STK37955035 Oxalicacid36 DSSTox_CID_581637 C0020938 DSSTox_RID_7793539 DSSTox_GSID_2581640 Oxalic acid standard solution

from PubChem

332 DepositorshySupplied Synonyms

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4 Chemical and Physical Properties

Molecular Weight 9003488 gmol

Molecular Formula C H O

XLogP3 shy03

Hydrogen Bond Donor Count 2

Hydrogen Bond Acceptor Count 4

Rotatable Bond Count 1

Exact Mass 89995309 gmol

Monoisotopic Mass 89995309 gmol

Topological Polar Surface Area 746 A^2

Heavy Atom Count 6

Formal Charge 0

Complexity 715

Isotope Atom Count 0

Defined Atom Stereocenter Count 0

Undefined Atom Stereocenter Count 0

Defined Bond Stereocenter Count 0

Undefined Bond Stereocenter Count 0

CovalentlyshyBonded Unit Count 1

from PubChem

41 Computed Properties

2 2 4

42 Experimental Properties

1 DryPowder2 OtherSolid3 PelletsLargeCrystals

from EPA Chemical Data Report

HYGROSCOPIC COLOURLESS CRYSTALS OR WHITE POWDER

from ILOshyICSC

Colorless odorless powder or granular solid

421 Physical Description

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

Oxalic acid is an odorless white solid Sinks and mixes with water (USCG 1999)

from CAMEO Chemicals

ANHYDROUS OXALIC ACID CRYSTALLIZED FROM GLACIAL ACETIC ACID IS ORTHORHOMBICCRYSTALS BEING PYRAMIDAL OR ELONGATED OCTAHEDRA

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

Colorless powder or granular solid [Note The anhydrous form (COOH)2 is a white powder]NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

422 Color

OdorlessNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

423 Odor

Sublimes

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

424 Boiling Point

1895 DEG C (DECOMPOSES)Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

1895 dec degCPhysProp

from DrugBank

1895degC

from ILOshyICSC

215 degF

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

425 Melting Point

1152015 oxalic acid | C2H2O4 shy PubChem

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372 degF (Decomposes)(NTP 1992)

from CAMEO Chemicals

100 G AQ SOLN SATURATED 15 DEG C CONTAINS 671 G 100 G AQ SOLN SATURATED 20 DEG CCONTAINS 834 G 100 G AQ SOLN SATURATED 25 DEG C CONTAINS 981 G

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

VERY SOL IN ETHANOL SLIGHTLY SOL IN ETHER INSOL IN BENZENE CHLOROFORM PETROLEUMETHER

Weast RC (ed) Handbook of Chemistry and Physics 60th ed Boca Raton Florida CRC Press Inc 1979 p Cshy409

from HSDB

Water solubility of 220000 mgl at 25 deg CYalkowsky SH et al Arizona Data Base of Water Solubility (1989)

from HSDB

Water Solubility220000 mgL (at 25 degC)

YALKOWSKYSH amp DANNENFELSERRM (1992)

from DrugBank

Solubility in water g100ml at 20degC 9shy10 (moderate)

from ILOshyICSC

14 [g100mL]

from NIOSHshyPocketGuide

50 to 100 mgmL at 75 deg F(NTP 1992)

from CAMEO Chemicals

426 Solubility

190 17 DEG4 DEG C ALPHABudavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 693

from HSDB

Density (at degC) 19 gcmsup3

from ILOshyICSC

19

427 Density

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1161

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

19 at 59 degF(USCG 1999)

from CAMEO Chemicals

43(NTP 1992)

from CAMEO Chemicals

428 Vapor Density

054 mm 105 deg CClayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

lt0001 mmHg

from NIOSHshyPocketGuide

lt0001

from OSHA Occupational Chemical DB

0001 mmHg at 68 degF(NTP 1992)

from CAMEO Chemicals

429 Vapor Pressure

shy081

from ILOshyICSC

4210 LogP

038ADME Research USCD

from DrugBank

4211 LogS

OXALIC ACID CAN BE DEHYDRATED BY CAREFUL DRYING 100 DEG C BUT LOSSES OCCURTHROUGH SUBLIMATION OXALIC ACID DIHYDRATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc

4212 Stability

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1261

1989 p 897

from HSDB

DECOMP PRODUCTS INCL CARBON MONOXIDE amp FORMIC ACIDNational Fire Protection Association Fire Protection Guide on Hazardous Materials 7th ed Boston Mass National FireProtection Association 1978 p 49shy224

from HSDB

see Notes

from ILOshyICSC

4213 Decomposition

shy24561 KJmolKirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 619 (1981)

from HSDB

4214 Heat of Combustion

pKa 1 146 pKa 2 440Clayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

4215 Dissociation Constants

Semishystandard nonshypolar 748

from NIST

4216 Kovats Retention Index

Crystal Structures 1 of 5

CCDC Number 929767

Crystal Structure Data DOI105517cc106hh6

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 2 of 5

43 Crystal Structures

1152015 oxalic acid | C2H2O4 shy PubChem

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

1152015 oxalic acid | C2H2O4 shy PubChem

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

CLICK TO LOAD

CLICK TO LOAD

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

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from PubChem

6 Chemical Vendors

CLICK TO LOAD

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1861

7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

1152015 oxalic acid | C2H2O4 shy PubChem

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3661

Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3761

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5161

from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5261

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 5: Oxalic Acid _ C2H2O4 - PubChem

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3 Names and Identifiers

31 Computed Descriptors

oxalic acid

from PubChem

311 IUPAC Name

InChI=1SC2H2O4c3shy1(4)2(5)6h(H34)(H56)

from PubChem

312 InChI

MUBZPKHOEPUJKRshyUHFFFAOYSAshyN

from PubChem

313 InChI Key

C(=O)(C(=O)O)O

from PubChem

314 Canonical SMILES

32 Other Identifiers

144shy62shy7

from DrugBank EPA Chemical Data Report ILOshyICSC NIOSHshyPocketGuide OSHA Occupational Chemhellip

321 CAS

205shy634shy3

from ILOshyICSC

205shy634shy3

from ECHA

208shy932shy1

from ECHA

322 EC Number

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213shy950shy8

from ECHA

0529

from ILOshyICSC

323 ICSC Number

RO2450000

from ILOshyICSC

RO2450000

from NIOSHshyPocketGuide

324 RTECS Number

3261

from ILOshyICSC CAMEO Chemicals

1759

from NJDOH RTK Hazardous Substance List

325 UN Number

9E7R5L6H31

from FDASPL Indexing data

326 UNII

Oxalic acid

from Wiki

327 Wikipedia

33 Synonyms

1 Acid Oxalic2 Aluminum Oxalate3 Ammonium Oxalate4 Chromium (2+) Oxalate

11 Ferric Oxalate12 Iron (2+) Oxalate (11)13 Iron (3+) Oxalate14 Iron Oxalate

21 Monosodium Oxalate22 Oxalate Aluminum23 Oxalate Chromium24 Oxalate Diammonium

31 Oxalate Monoammonium32 Oxalate Monohydrogen Monopotassium33 Oxalate Monopotassium34 Oxalate Monosodium

331 MeSH Synonyms

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5 Chromium (3+) Oxalate (32)6 Chromium Oxalate7 Diammonium Oxalate8 Dilithium Oxalate9 Dipotassium Oxalate10 Disodium Oxalate

15 Magnesium Oxalate16 Magnesium Oxalate (11)17 Manganese (2+) Oxalate (11)18 Monoammonium Oxalate19 Monohydrogen Monopotassium Oxalate20 Monopotassium Oxalate

25 Oxalate Dilithium26 Oxalate Dipotassium27 Oxalate Disodium28 Oxalate Ferric29 Oxalate Iron30 Oxalate Magnesium

35 Oxalate Potassium36 Oxalate Potassium Chromium37 Oxalate Sodium38 Oxalic Acid39 Potassium Chromium Oxalate40 Potassium Oxalate

from MeSH

1 oxalic acid2 ethanedioic acid3 144shy62shy74 Aktisal5 Aquisal6 Oxiric acid7 oxalate8 Oxaalzuur9 Oxalsaeure10 Kyselina stavelova

11 Acidum oxalicum12 Acide oxalique13 Acido ossalico14 Caswell No 62515 Ethanedionic acid16 Oxaalzuur [Dutch]17 NCIshyC5520918 Oxalsaeure [German]19 Acide oxalique [French]20 Ethaneshy12shydioic acid

21 Acido ossalico [Italian]22 Kyselina stavelova [Czech]23 EPA Pesticide Chemical Code 00960124 HOOCCOOH25 CCRIS 145426 AI3shy2646327 HSDB 110028 NSC 6277429 BRN 038568630 UNIIshy9E7R5L6H31

31 CHEBI1699532 MUBZPKHOEPUJKRshyUHFFFAOYSAshyN33 EINECS 205shy634shy334 STK37955035 Oxalicacid36 DSSTox_CID_581637 C0020938 DSSTox_RID_7793539 DSSTox_GSID_2581640 Oxalic acid standard solution

from PubChem

332 DepositorshySupplied Synonyms

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4 Chemical and Physical Properties

Molecular Weight 9003488 gmol

Molecular Formula C H O

XLogP3 shy03

Hydrogen Bond Donor Count 2

Hydrogen Bond Acceptor Count 4

Rotatable Bond Count 1

Exact Mass 89995309 gmol

Monoisotopic Mass 89995309 gmol

Topological Polar Surface Area 746 A^2

Heavy Atom Count 6

Formal Charge 0

Complexity 715

Isotope Atom Count 0

Defined Atom Stereocenter Count 0

Undefined Atom Stereocenter Count 0

Defined Bond Stereocenter Count 0

Undefined Bond Stereocenter Count 0

CovalentlyshyBonded Unit Count 1

from PubChem

41 Computed Properties

2 2 4

42 Experimental Properties

1 DryPowder2 OtherSolid3 PelletsLargeCrystals

from EPA Chemical Data Report

HYGROSCOPIC COLOURLESS CRYSTALS OR WHITE POWDER

from ILOshyICSC

Colorless odorless powder or granular solid

421 Physical Description

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

Oxalic acid is an odorless white solid Sinks and mixes with water (USCG 1999)

from CAMEO Chemicals

ANHYDROUS OXALIC ACID CRYSTALLIZED FROM GLACIAL ACETIC ACID IS ORTHORHOMBICCRYSTALS BEING PYRAMIDAL OR ELONGATED OCTAHEDRA

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

Colorless powder or granular solid [Note The anhydrous form (COOH)2 is a white powder]NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

422 Color

OdorlessNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

423 Odor

Sublimes

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

424 Boiling Point

1895 DEG C (DECOMPOSES)Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

1895 dec degCPhysProp

from DrugBank

1895degC

from ILOshyICSC

215 degF

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

425 Melting Point

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372 degF (Decomposes)(NTP 1992)

from CAMEO Chemicals

100 G AQ SOLN SATURATED 15 DEG C CONTAINS 671 G 100 G AQ SOLN SATURATED 20 DEG CCONTAINS 834 G 100 G AQ SOLN SATURATED 25 DEG C CONTAINS 981 G

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

VERY SOL IN ETHANOL SLIGHTLY SOL IN ETHER INSOL IN BENZENE CHLOROFORM PETROLEUMETHER

Weast RC (ed) Handbook of Chemistry and Physics 60th ed Boca Raton Florida CRC Press Inc 1979 p Cshy409

from HSDB

Water solubility of 220000 mgl at 25 deg CYalkowsky SH et al Arizona Data Base of Water Solubility (1989)

from HSDB

Water Solubility220000 mgL (at 25 degC)

YALKOWSKYSH amp DANNENFELSERRM (1992)

from DrugBank

Solubility in water g100ml at 20degC 9shy10 (moderate)

from ILOshyICSC

14 [g100mL]

from NIOSHshyPocketGuide

50 to 100 mgmL at 75 deg F(NTP 1992)

from CAMEO Chemicals

426 Solubility

190 17 DEG4 DEG C ALPHABudavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 693

from HSDB

Density (at degC) 19 gcmsup3

from ILOshyICSC

19

427 Density

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

19 at 59 degF(USCG 1999)

from CAMEO Chemicals

43(NTP 1992)

from CAMEO Chemicals

428 Vapor Density

054 mm 105 deg CClayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

lt0001 mmHg

from NIOSHshyPocketGuide

lt0001

from OSHA Occupational Chemical DB

0001 mmHg at 68 degF(NTP 1992)

from CAMEO Chemicals

429 Vapor Pressure

shy081

from ILOshyICSC

4210 LogP

038ADME Research USCD

from DrugBank

4211 LogS

OXALIC ACID CAN BE DEHYDRATED BY CAREFUL DRYING 100 DEG C BUT LOSSES OCCURTHROUGH SUBLIMATION OXALIC ACID DIHYDRATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc

4212 Stability

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1989 p 897

from HSDB

DECOMP PRODUCTS INCL CARBON MONOXIDE amp FORMIC ACIDNational Fire Protection Association Fire Protection Guide on Hazardous Materials 7th ed Boston Mass National FireProtection Association 1978 p 49shy224

from HSDB

see Notes

from ILOshyICSC

4213 Decomposition

shy24561 KJmolKirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 619 (1981)

from HSDB

4214 Heat of Combustion

pKa 1 146 pKa 2 440Clayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

4215 Dissociation Constants

Semishystandard nonshypolar 748

from NIST

4216 Kovats Retention Index

Crystal Structures 1 of 5

CCDC Number 929767

Crystal Structure Data DOI105517cc106hh6

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 2 of 5

43 Crystal Structures

1152015 oxalic acid | C2H2O4 shy PubChem

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

1152015 oxalic acid | C2H2O4 shy PubChem

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

CLICK TO LOAD

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

CLICK TO LOAD

CLICK TO LOAD

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

CLICK TO LOAD

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from PubChem

6 Chemical Vendors

CLICK TO LOAD

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1861

7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

1152015 oxalic acid | C2H2O4 shy PubChem

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3761

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3961

12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4061

Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5261

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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213shy950shy8

from ECHA

0529

from ILOshyICSC

323 ICSC Number

RO2450000

from ILOshyICSC

RO2450000

from NIOSHshyPocketGuide

324 RTECS Number

3261

from ILOshyICSC CAMEO Chemicals

1759

from NJDOH RTK Hazardous Substance List

325 UN Number

9E7R5L6H31

from FDASPL Indexing data

326 UNII

Oxalic acid

from Wiki

327 Wikipedia

33 Synonyms

1 Acid Oxalic2 Aluminum Oxalate3 Ammonium Oxalate4 Chromium (2+) Oxalate

11 Ferric Oxalate12 Iron (2+) Oxalate (11)13 Iron (3+) Oxalate14 Iron Oxalate

21 Monosodium Oxalate22 Oxalate Aluminum23 Oxalate Chromium24 Oxalate Diammonium

31 Oxalate Monoammonium32 Oxalate Monohydrogen Monopotassium33 Oxalate Monopotassium34 Oxalate Monosodium

331 MeSH Synonyms

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5 Chromium (3+) Oxalate (32)6 Chromium Oxalate7 Diammonium Oxalate8 Dilithium Oxalate9 Dipotassium Oxalate10 Disodium Oxalate

15 Magnesium Oxalate16 Magnesium Oxalate (11)17 Manganese (2+) Oxalate (11)18 Monoammonium Oxalate19 Monohydrogen Monopotassium Oxalate20 Monopotassium Oxalate

25 Oxalate Dilithium26 Oxalate Dipotassium27 Oxalate Disodium28 Oxalate Ferric29 Oxalate Iron30 Oxalate Magnesium

35 Oxalate Potassium36 Oxalate Potassium Chromium37 Oxalate Sodium38 Oxalic Acid39 Potassium Chromium Oxalate40 Potassium Oxalate

from MeSH

1 oxalic acid2 ethanedioic acid3 144shy62shy74 Aktisal5 Aquisal6 Oxiric acid7 oxalate8 Oxaalzuur9 Oxalsaeure10 Kyselina stavelova

11 Acidum oxalicum12 Acide oxalique13 Acido ossalico14 Caswell No 62515 Ethanedionic acid16 Oxaalzuur [Dutch]17 NCIshyC5520918 Oxalsaeure [German]19 Acide oxalique [French]20 Ethaneshy12shydioic acid

21 Acido ossalico [Italian]22 Kyselina stavelova [Czech]23 EPA Pesticide Chemical Code 00960124 HOOCCOOH25 CCRIS 145426 AI3shy2646327 HSDB 110028 NSC 6277429 BRN 038568630 UNIIshy9E7R5L6H31

31 CHEBI1699532 MUBZPKHOEPUJKRshyUHFFFAOYSAshyN33 EINECS 205shy634shy334 STK37955035 Oxalicacid36 DSSTox_CID_581637 C0020938 DSSTox_RID_7793539 DSSTox_GSID_2581640 Oxalic acid standard solution

from PubChem

332 DepositorshySupplied Synonyms

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4 Chemical and Physical Properties

Molecular Weight 9003488 gmol

Molecular Formula C H O

XLogP3 shy03

Hydrogen Bond Donor Count 2

Hydrogen Bond Acceptor Count 4

Rotatable Bond Count 1

Exact Mass 89995309 gmol

Monoisotopic Mass 89995309 gmol

Topological Polar Surface Area 746 A^2

Heavy Atom Count 6

Formal Charge 0

Complexity 715

Isotope Atom Count 0

Defined Atom Stereocenter Count 0

Undefined Atom Stereocenter Count 0

Defined Bond Stereocenter Count 0

Undefined Bond Stereocenter Count 0

CovalentlyshyBonded Unit Count 1

from PubChem

41 Computed Properties

2 2 4

42 Experimental Properties

1 DryPowder2 OtherSolid3 PelletsLargeCrystals

from EPA Chemical Data Report

HYGROSCOPIC COLOURLESS CRYSTALS OR WHITE POWDER

from ILOshyICSC

Colorless odorless powder or granular solid

421 Physical Description

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

Oxalic acid is an odorless white solid Sinks and mixes with water (USCG 1999)

from CAMEO Chemicals

ANHYDROUS OXALIC ACID CRYSTALLIZED FROM GLACIAL ACETIC ACID IS ORTHORHOMBICCRYSTALS BEING PYRAMIDAL OR ELONGATED OCTAHEDRA

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

Colorless powder or granular solid [Note The anhydrous form (COOH)2 is a white powder]NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

422 Color

OdorlessNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

423 Odor

Sublimes

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

424 Boiling Point

1895 DEG C (DECOMPOSES)Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

1895 dec degCPhysProp

from DrugBank

1895degC

from ILOshyICSC

215 degF

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

425 Melting Point

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372 degF (Decomposes)(NTP 1992)

from CAMEO Chemicals

100 G AQ SOLN SATURATED 15 DEG C CONTAINS 671 G 100 G AQ SOLN SATURATED 20 DEG CCONTAINS 834 G 100 G AQ SOLN SATURATED 25 DEG C CONTAINS 981 G

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

VERY SOL IN ETHANOL SLIGHTLY SOL IN ETHER INSOL IN BENZENE CHLOROFORM PETROLEUMETHER

Weast RC (ed) Handbook of Chemistry and Physics 60th ed Boca Raton Florida CRC Press Inc 1979 p Cshy409

from HSDB

Water solubility of 220000 mgl at 25 deg CYalkowsky SH et al Arizona Data Base of Water Solubility (1989)

from HSDB

Water Solubility220000 mgL (at 25 degC)

YALKOWSKYSH amp DANNENFELSERRM (1992)

from DrugBank

Solubility in water g100ml at 20degC 9shy10 (moderate)

from ILOshyICSC

14 [g100mL]

from NIOSHshyPocketGuide

50 to 100 mgmL at 75 deg F(NTP 1992)

from CAMEO Chemicals

426 Solubility

190 17 DEG4 DEG C ALPHABudavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 693

from HSDB

Density (at degC) 19 gcmsup3

from ILOshyICSC

19

427 Density

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

19 at 59 degF(USCG 1999)

from CAMEO Chemicals

43(NTP 1992)

from CAMEO Chemicals

428 Vapor Density

054 mm 105 deg CClayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

lt0001 mmHg

from NIOSHshyPocketGuide

lt0001

from OSHA Occupational Chemical DB

0001 mmHg at 68 degF(NTP 1992)

from CAMEO Chemicals

429 Vapor Pressure

shy081

from ILOshyICSC

4210 LogP

038ADME Research USCD

from DrugBank

4211 LogS

OXALIC ACID CAN BE DEHYDRATED BY CAREFUL DRYING 100 DEG C BUT LOSSES OCCURTHROUGH SUBLIMATION OXALIC ACID DIHYDRATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc

4212 Stability

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1989 p 897

from HSDB

DECOMP PRODUCTS INCL CARBON MONOXIDE amp FORMIC ACIDNational Fire Protection Association Fire Protection Guide on Hazardous Materials 7th ed Boston Mass National FireProtection Association 1978 p 49shy224

from HSDB

see Notes

from ILOshyICSC

4213 Decomposition

shy24561 KJmolKirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 619 (1981)

from HSDB

4214 Heat of Combustion

pKa 1 146 pKa 2 440Clayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

4215 Dissociation Constants

Semishystandard nonshypolar 748

from NIST

4216 Kovats Retention Index

Crystal Structures 1 of 5

CCDC Number 929767

Crystal Structure Data DOI105517cc106hh6

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 2 of 5

43 Crystal Structures

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

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from PubChem

6 Chemical Vendors

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7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

1152015 oxalic acid | C2H2O4 shy PubChem

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

1152015 oxalic acid | C2H2O4 shy PubChem

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

1152015 oxalic acid | C2H2O4 shy PubChem

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 7: Oxalic Acid _ C2H2O4 - PubChem

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 761

5 Chromium (3+) Oxalate (32)6 Chromium Oxalate7 Diammonium Oxalate8 Dilithium Oxalate9 Dipotassium Oxalate10 Disodium Oxalate

15 Magnesium Oxalate16 Magnesium Oxalate (11)17 Manganese (2+) Oxalate (11)18 Monoammonium Oxalate19 Monohydrogen Monopotassium Oxalate20 Monopotassium Oxalate

25 Oxalate Dilithium26 Oxalate Dipotassium27 Oxalate Disodium28 Oxalate Ferric29 Oxalate Iron30 Oxalate Magnesium

35 Oxalate Potassium36 Oxalate Potassium Chromium37 Oxalate Sodium38 Oxalic Acid39 Potassium Chromium Oxalate40 Potassium Oxalate

from MeSH

1 oxalic acid2 ethanedioic acid3 144shy62shy74 Aktisal5 Aquisal6 Oxiric acid7 oxalate8 Oxaalzuur9 Oxalsaeure10 Kyselina stavelova

11 Acidum oxalicum12 Acide oxalique13 Acido ossalico14 Caswell No 62515 Ethanedionic acid16 Oxaalzuur [Dutch]17 NCIshyC5520918 Oxalsaeure [German]19 Acide oxalique [French]20 Ethaneshy12shydioic acid

21 Acido ossalico [Italian]22 Kyselina stavelova [Czech]23 EPA Pesticide Chemical Code 00960124 HOOCCOOH25 CCRIS 145426 AI3shy2646327 HSDB 110028 NSC 6277429 BRN 038568630 UNIIshy9E7R5L6H31

31 CHEBI1699532 MUBZPKHOEPUJKRshyUHFFFAOYSAshyN33 EINECS 205shy634shy334 STK37955035 Oxalicacid36 DSSTox_CID_581637 C0020938 DSSTox_RID_7793539 DSSTox_GSID_2581640 Oxalic acid standard solution

from PubChem

332 DepositorshySupplied Synonyms

1152015 oxalic acid | C2H2O4 shy PubChem

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4 Chemical and Physical Properties

Molecular Weight 9003488 gmol

Molecular Formula C H O

XLogP3 shy03

Hydrogen Bond Donor Count 2

Hydrogen Bond Acceptor Count 4

Rotatable Bond Count 1

Exact Mass 89995309 gmol

Monoisotopic Mass 89995309 gmol

Topological Polar Surface Area 746 A^2

Heavy Atom Count 6

Formal Charge 0

Complexity 715

Isotope Atom Count 0

Defined Atom Stereocenter Count 0

Undefined Atom Stereocenter Count 0

Defined Bond Stereocenter Count 0

Undefined Bond Stereocenter Count 0

CovalentlyshyBonded Unit Count 1

from PubChem

41 Computed Properties

2 2 4

42 Experimental Properties

1 DryPowder2 OtherSolid3 PelletsLargeCrystals

from EPA Chemical Data Report

HYGROSCOPIC COLOURLESS CRYSTALS OR WHITE POWDER

from ILOshyICSC

Colorless odorless powder or granular solid

421 Physical Description

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

Oxalic acid is an odorless white solid Sinks and mixes with water (USCG 1999)

from CAMEO Chemicals

ANHYDROUS OXALIC ACID CRYSTALLIZED FROM GLACIAL ACETIC ACID IS ORTHORHOMBICCRYSTALS BEING PYRAMIDAL OR ELONGATED OCTAHEDRA

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

Colorless powder or granular solid [Note The anhydrous form (COOH)2 is a white powder]NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

422 Color

OdorlessNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

423 Odor

Sublimes

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

424 Boiling Point

1895 DEG C (DECOMPOSES)Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

1895 dec degCPhysProp

from DrugBank

1895degC

from ILOshyICSC

215 degF

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

425 Melting Point

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372 degF (Decomposes)(NTP 1992)

from CAMEO Chemicals

100 G AQ SOLN SATURATED 15 DEG C CONTAINS 671 G 100 G AQ SOLN SATURATED 20 DEG CCONTAINS 834 G 100 G AQ SOLN SATURATED 25 DEG C CONTAINS 981 G

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

VERY SOL IN ETHANOL SLIGHTLY SOL IN ETHER INSOL IN BENZENE CHLOROFORM PETROLEUMETHER

Weast RC (ed) Handbook of Chemistry and Physics 60th ed Boca Raton Florida CRC Press Inc 1979 p Cshy409

from HSDB

Water solubility of 220000 mgl at 25 deg CYalkowsky SH et al Arizona Data Base of Water Solubility (1989)

from HSDB

Water Solubility220000 mgL (at 25 degC)

YALKOWSKYSH amp DANNENFELSERRM (1992)

from DrugBank

Solubility in water g100ml at 20degC 9shy10 (moderate)

from ILOshyICSC

14 [g100mL]

from NIOSHshyPocketGuide

50 to 100 mgmL at 75 deg F(NTP 1992)

from CAMEO Chemicals

426 Solubility

190 17 DEG4 DEG C ALPHABudavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 693

from HSDB

Density (at degC) 19 gcmsup3

from ILOshyICSC

19

427 Density

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

19 at 59 degF(USCG 1999)

from CAMEO Chemicals

43(NTP 1992)

from CAMEO Chemicals

428 Vapor Density

054 mm 105 deg CClayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

lt0001 mmHg

from NIOSHshyPocketGuide

lt0001

from OSHA Occupational Chemical DB

0001 mmHg at 68 degF(NTP 1992)

from CAMEO Chemicals

429 Vapor Pressure

shy081

from ILOshyICSC

4210 LogP

038ADME Research USCD

from DrugBank

4211 LogS

OXALIC ACID CAN BE DEHYDRATED BY CAREFUL DRYING 100 DEG C BUT LOSSES OCCURTHROUGH SUBLIMATION OXALIC ACID DIHYDRATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc

4212 Stability

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1989 p 897

from HSDB

DECOMP PRODUCTS INCL CARBON MONOXIDE amp FORMIC ACIDNational Fire Protection Association Fire Protection Guide on Hazardous Materials 7th ed Boston Mass National FireProtection Association 1978 p 49shy224

from HSDB

see Notes

from ILOshyICSC

4213 Decomposition

shy24561 KJmolKirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 619 (1981)

from HSDB

4214 Heat of Combustion

pKa 1 146 pKa 2 440Clayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

4215 Dissociation Constants

Semishystandard nonshypolar 748

from NIST

4216 Kovats Retention Index

Crystal Structures 1 of 5

CCDC Number 929767

Crystal Structure Data DOI105517cc106hh6

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 2 of 5

43 Crystal Structures

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

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from PubChem

6 Chemical Vendors

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7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

1152015 oxalic acid | C2H2O4 shy PubChem

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

1152015 oxalic acid | C2H2O4 shy PubChem

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3061

USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

1152015 oxalic acid | C2H2O4 shy PubChem

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

1152015 oxalic acid | C2H2O4 shy PubChem

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 8: Oxalic Acid _ C2H2O4 - PubChem

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 861

4 Chemical and Physical Properties

Molecular Weight 9003488 gmol

Molecular Formula C H O

XLogP3 shy03

Hydrogen Bond Donor Count 2

Hydrogen Bond Acceptor Count 4

Rotatable Bond Count 1

Exact Mass 89995309 gmol

Monoisotopic Mass 89995309 gmol

Topological Polar Surface Area 746 A^2

Heavy Atom Count 6

Formal Charge 0

Complexity 715

Isotope Atom Count 0

Defined Atom Stereocenter Count 0

Undefined Atom Stereocenter Count 0

Defined Bond Stereocenter Count 0

Undefined Bond Stereocenter Count 0

CovalentlyshyBonded Unit Count 1

from PubChem

41 Computed Properties

2 2 4

42 Experimental Properties

1 DryPowder2 OtherSolid3 PelletsLargeCrystals

from EPA Chemical Data Report

HYGROSCOPIC COLOURLESS CRYSTALS OR WHITE POWDER

from ILOshyICSC

Colorless odorless powder or granular solid

421 Physical Description

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 961

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

Oxalic acid is an odorless white solid Sinks and mixes with water (USCG 1999)

from CAMEO Chemicals

ANHYDROUS OXALIC ACID CRYSTALLIZED FROM GLACIAL ACETIC ACID IS ORTHORHOMBICCRYSTALS BEING PYRAMIDAL OR ELONGATED OCTAHEDRA

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

Colorless powder or granular solid [Note The anhydrous form (COOH)2 is a white powder]NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

422 Color

OdorlessNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

423 Odor

Sublimes

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

424 Boiling Point

1895 DEG C (DECOMPOSES)Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

1895 dec degCPhysProp

from DrugBank

1895degC

from ILOshyICSC

215 degF

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

425 Melting Point

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372 degF (Decomposes)(NTP 1992)

from CAMEO Chemicals

100 G AQ SOLN SATURATED 15 DEG C CONTAINS 671 G 100 G AQ SOLN SATURATED 20 DEG CCONTAINS 834 G 100 G AQ SOLN SATURATED 25 DEG C CONTAINS 981 G

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

VERY SOL IN ETHANOL SLIGHTLY SOL IN ETHER INSOL IN BENZENE CHLOROFORM PETROLEUMETHER

Weast RC (ed) Handbook of Chemistry and Physics 60th ed Boca Raton Florida CRC Press Inc 1979 p Cshy409

from HSDB

Water solubility of 220000 mgl at 25 deg CYalkowsky SH et al Arizona Data Base of Water Solubility (1989)

from HSDB

Water Solubility220000 mgL (at 25 degC)

YALKOWSKYSH amp DANNENFELSERRM (1992)

from DrugBank

Solubility in water g100ml at 20degC 9shy10 (moderate)

from ILOshyICSC

14 [g100mL]

from NIOSHshyPocketGuide

50 to 100 mgmL at 75 deg F(NTP 1992)

from CAMEO Chemicals

426 Solubility

190 17 DEG4 DEG C ALPHABudavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 693

from HSDB

Density (at degC) 19 gcmsup3

from ILOshyICSC

19

427 Density

1152015 oxalic acid | C2H2O4 shy PubChem

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

19 at 59 degF(USCG 1999)

from CAMEO Chemicals

43(NTP 1992)

from CAMEO Chemicals

428 Vapor Density

054 mm 105 deg CClayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

lt0001 mmHg

from NIOSHshyPocketGuide

lt0001

from OSHA Occupational Chemical DB

0001 mmHg at 68 degF(NTP 1992)

from CAMEO Chemicals

429 Vapor Pressure

shy081

from ILOshyICSC

4210 LogP

038ADME Research USCD

from DrugBank

4211 LogS

OXALIC ACID CAN BE DEHYDRATED BY CAREFUL DRYING 100 DEG C BUT LOSSES OCCURTHROUGH SUBLIMATION OXALIC ACID DIHYDRATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc

4212 Stability

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1261

1989 p 897

from HSDB

DECOMP PRODUCTS INCL CARBON MONOXIDE amp FORMIC ACIDNational Fire Protection Association Fire Protection Guide on Hazardous Materials 7th ed Boston Mass National FireProtection Association 1978 p 49shy224

from HSDB

see Notes

from ILOshyICSC

4213 Decomposition

shy24561 KJmolKirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 619 (1981)

from HSDB

4214 Heat of Combustion

pKa 1 146 pKa 2 440Clayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

4215 Dissociation Constants

Semishystandard nonshypolar 748

from NIST

4216 Kovats Retention Index

Crystal Structures 1 of 5

CCDC Number 929767

Crystal Structure Data DOI105517cc106hh6

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 2 of 5

43 Crystal Structures

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

CLICK TO LOAD

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

CLICK TO LOAD

CLICK TO LOAD

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

CLICK TO LOAD

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from PubChem

6 Chemical Vendors

CLICK TO LOAD

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1861

7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 2061

from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 2261

1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4961

may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5061

hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5261

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 9: Oxalic Acid _ C2H2O4 - PubChem

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

Oxalic acid is an odorless white solid Sinks and mixes with water (USCG 1999)

from CAMEO Chemicals

ANHYDROUS OXALIC ACID CRYSTALLIZED FROM GLACIAL ACETIC ACID IS ORTHORHOMBICCRYSTALS BEING PYRAMIDAL OR ELONGATED OCTAHEDRA

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

Colorless powder or granular solid [Note The anhydrous form (COOH)2 is a white powder]NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

422 Color

OdorlessNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 94shy116 Washington DC USGovernment Printing Office June 1994 p 238

from HSDB

423 Odor

Sublimes

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

424 Boiling Point

1895 DEG C (DECOMPOSES)Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

1895 dec degCPhysProp

from DrugBank

1895degC

from ILOshyICSC

215 degF

from NIOSHshyPocketGuide OSHA Occupational Chemical DB

425 Melting Point

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372 degF (Decomposes)(NTP 1992)

from CAMEO Chemicals

100 G AQ SOLN SATURATED 15 DEG C CONTAINS 671 G 100 G AQ SOLN SATURATED 20 DEG CCONTAINS 834 G 100 G AQ SOLN SATURATED 25 DEG C CONTAINS 981 G

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

VERY SOL IN ETHANOL SLIGHTLY SOL IN ETHER INSOL IN BENZENE CHLOROFORM PETROLEUMETHER

Weast RC (ed) Handbook of Chemistry and Physics 60th ed Boca Raton Florida CRC Press Inc 1979 p Cshy409

from HSDB

Water solubility of 220000 mgl at 25 deg CYalkowsky SH et al Arizona Data Base of Water Solubility (1989)

from HSDB

Water Solubility220000 mgL (at 25 degC)

YALKOWSKYSH amp DANNENFELSERRM (1992)

from DrugBank

Solubility in water g100ml at 20degC 9shy10 (moderate)

from ILOshyICSC

14 [g100mL]

from NIOSHshyPocketGuide

50 to 100 mgmL at 75 deg F(NTP 1992)

from CAMEO Chemicals

426 Solubility

190 17 DEG4 DEG C ALPHABudavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 693

from HSDB

Density (at degC) 19 gcmsup3

from ILOshyICSC

19

427 Density

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

19 at 59 degF(USCG 1999)

from CAMEO Chemicals

43(NTP 1992)

from CAMEO Chemicals

428 Vapor Density

054 mm 105 deg CClayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

lt0001 mmHg

from NIOSHshyPocketGuide

lt0001

from OSHA Occupational Chemical DB

0001 mmHg at 68 degF(NTP 1992)

from CAMEO Chemicals

429 Vapor Pressure

shy081

from ILOshyICSC

4210 LogP

038ADME Research USCD

from DrugBank

4211 LogS

OXALIC ACID CAN BE DEHYDRATED BY CAREFUL DRYING 100 DEG C BUT LOSSES OCCURTHROUGH SUBLIMATION OXALIC ACID DIHYDRATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc

4212 Stability

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1989 p 897

from HSDB

DECOMP PRODUCTS INCL CARBON MONOXIDE amp FORMIC ACIDNational Fire Protection Association Fire Protection Guide on Hazardous Materials 7th ed Boston Mass National FireProtection Association 1978 p 49shy224

from HSDB

see Notes

from ILOshyICSC

4213 Decomposition

shy24561 KJmolKirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 619 (1981)

from HSDB

4214 Heat of Combustion

pKa 1 146 pKa 2 440Clayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

4215 Dissociation Constants

Semishystandard nonshypolar 748

from NIST

4216 Kovats Retention Index

Crystal Structures 1 of 5

CCDC Number 929767

Crystal Structure Data DOI105517cc106hh6

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 2 of 5

43 Crystal Structures

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

1152015 oxalic acid | C2H2O4 shy PubChem

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

CLICK TO LOAD

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

CLICK TO LOAD

CLICK TO LOAD

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

CLICK TO LOAD

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from PubChem

6 Chemical Vendors

CLICK TO LOAD

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1861

7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

1152015 oxalic acid | C2H2O4 shy PubChem

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3761

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3961

12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4061

Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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372 degF (Decomposes)(NTP 1992)

from CAMEO Chemicals

100 G AQ SOLN SATURATED 15 DEG C CONTAINS 671 G 100 G AQ SOLN SATURATED 20 DEG CCONTAINS 834 G 100 G AQ SOLN SATURATED 25 DEG C CONTAINS 981 G

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

VERY SOL IN ETHANOL SLIGHTLY SOL IN ETHER INSOL IN BENZENE CHLOROFORM PETROLEUMETHER

Weast RC (ed) Handbook of Chemistry and Physics 60th ed Boca Raton Florida CRC Press Inc 1979 p Cshy409

from HSDB

Water solubility of 220000 mgl at 25 deg CYalkowsky SH et al Arizona Data Base of Water Solubility (1989)

from HSDB

Water Solubility220000 mgL (at 25 degC)

YALKOWSKYSH amp DANNENFELSERRM (1992)

from DrugBank

Solubility in water g100ml at 20degC 9shy10 (moderate)

from ILOshyICSC

14 [g100mL]

from NIOSHshyPocketGuide

50 to 100 mgmL at 75 deg F(NTP 1992)

from CAMEO Chemicals

426 Solubility

190 17 DEG4 DEG C ALPHABudavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 693

from HSDB

Density (at degC) 19 gcmsup3

from ILOshyICSC

19

427 Density

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

19 at 59 degF(USCG 1999)

from CAMEO Chemicals

43(NTP 1992)

from CAMEO Chemicals

428 Vapor Density

054 mm 105 deg CClayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

lt0001 mmHg

from NIOSHshyPocketGuide

lt0001

from OSHA Occupational Chemical DB

0001 mmHg at 68 degF(NTP 1992)

from CAMEO Chemicals

429 Vapor Pressure

shy081

from ILOshyICSC

4210 LogP

038ADME Research USCD

from DrugBank

4211 LogS

OXALIC ACID CAN BE DEHYDRATED BY CAREFUL DRYING 100 DEG C BUT LOSSES OCCURTHROUGH SUBLIMATION OXALIC ACID DIHYDRATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc

4212 Stability

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1989 p 897

from HSDB

DECOMP PRODUCTS INCL CARBON MONOXIDE amp FORMIC ACIDNational Fire Protection Association Fire Protection Guide on Hazardous Materials 7th ed Boston Mass National FireProtection Association 1978 p 49shy224

from HSDB

see Notes

from ILOshyICSC

4213 Decomposition

shy24561 KJmolKirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 619 (1981)

from HSDB

4214 Heat of Combustion

pKa 1 146 pKa 2 440Clayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

4215 Dissociation Constants

Semishystandard nonshypolar 748

from NIST

4216 Kovats Retention Index

Crystal Structures 1 of 5

CCDC Number 929767

Crystal Structure Data DOI105517cc106hh6

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 2 of 5

43 Crystal Structures

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

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from PubChem

6 Chemical Vendors

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7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

1152015 oxalic acid | C2H2O4 shy PubChem

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

1152015 oxalic acid | C2H2O4 shy PubChem

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

1152015 oxalic acid | C2H2O4 shy PubChem

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 11: Oxalic Acid _ C2H2O4 - PubChem

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from NIOSHshyPocketGuide OSHA Occupational Chemical DB

19 at 59 degF(USCG 1999)

from CAMEO Chemicals

43(NTP 1992)

from CAMEO Chemicals

428 Vapor Density

054 mm 105 deg CClayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

lt0001 mmHg

from NIOSHshyPocketGuide

lt0001

from OSHA Occupational Chemical DB

0001 mmHg at 68 degF(NTP 1992)

from CAMEO Chemicals

429 Vapor Pressure

shy081

from ILOshyICSC

4210 LogP

038ADME Research USCD

from DrugBank

4211 LogS

OXALIC ACID CAN BE DEHYDRATED BY CAREFUL DRYING 100 DEG C BUT LOSSES OCCURTHROUGH SUBLIMATION OXALIC ACID DIHYDRATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc

4212 Stability

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1261

1989 p 897

from HSDB

DECOMP PRODUCTS INCL CARBON MONOXIDE amp FORMIC ACIDNational Fire Protection Association Fire Protection Guide on Hazardous Materials 7th ed Boston Mass National FireProtection Association 1978 p 49shy224

from HSDB

see Notes

from ILOshyICSC

4213 Decomposition

shy24561 KJmolKirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 619 (1981)

from HSDB

4214 Heat of Combustion

pKa 1 146 pKa 2 440Clayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

4215 Dissociation Constants

Semishystandard nonshypolar 748

from NIST

4216 Kovats Retention Index

Crystal Structures 1 of 5

CCDC Number 929767

Crystal Structure Data DOI105517cc106hh6

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 2 of 5

43 Crystal Structures

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

CLICK TO LOAD

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

CLICK TO LOAD

CLICK TO LOAD

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

CLICK TO LOAD

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from PubChem

6 Chemical Vendors

CLICK TO LOAD

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1861

7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

1152015 oxalic acid | C2H2O4 shy PubChem

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3661

Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3761

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3961

12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4461

contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4561

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5161

from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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1989 p 897

from HSDB

DECOMP PRODUCTS INCL CARBON MONOXIDE amp FORMIC ACIDNational Fire Protection Association Fire Protection Guide on Hazardous Materials 7th ed Boston Mass National FireProtection Association 1978 p 49shy224

from HSDB

see Notes

from ILOshyICSC

4213 Decomposition

shy24561 KJmolKirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 619 (1981)

from HSDB

4214 Heat of Combustion

pKa 1 146 pKa 2 440Clayton G D and F E Clayton (eds) Pattys Industrial Hygiene and Toxicology Volume 2A 2B 2C Toxicology 3rd ed NewYork John Wiley Sons 1981shy1982 p 4936

from HSDB

4215 Dissociation Constants

Semishystandard nonshypolar 748

from NIST

4216 Kovats Retention Index

Crystal Structures 1 of 5

CCDC Number 929767

Crystal Structure Data DOI105517cc106hh6

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 2 of 5

43 Crystal Structures

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

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from PubChem

6 Chemical Vendors

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7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 13: Oxalic Acid _ C2H2O4 - PubChem

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CCDC Number 929768

Crystal Structure Data DOI105517cc106hj7

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 3 of 5

CCDC Number 929769

Crystal Structure Data DOI105517cc106hk8

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 4 of 5

CCDC Number 929770

Crystal Structure Data DOI105517cc106hl9

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

Crystal Structures 5 of 5

CCDC Number 929771

Crystal Structure Data DOI105517cc106hmb

Associated Article DOI101021cg400668w

from The Cambridge Structural Database

IR 8279 (Sadtler Research Laboratories IR Grating Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

NMR 17060 (Sadtler Research Laboratories Spectral Collection)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

MASS 52 (National Bureau of Standards EPAshyNIH Mass Spectra Data Base NSRDSshyNBSshy63)Weast RC and MJ Astle CRC Handbook of Data on Organic Compounds Volumes I and II Boca Raton FL CRC Press Inc1985 p V1 946

from HSDB

44 Spectral Properties

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

CLICK TO LOAD

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

CLICK TO LOAD

CLICK TO LOAD

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

CLICK TO LOAD

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from PubChem

6 Chemical Vendors

CLICK TO LOAD

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1861

7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3561

Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3661

Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3761

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3961

12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

1152015 oxalic acid | C2H2O4 shy PubChem

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4561

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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1 of 3

NIST Number 229396

Library Main library

Total Peaks 20

mz Top Peak 45

mz 2nd Highest 46

mz 3rd Highest 29

Thumbnail

from NIST

441 GCshyMS

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

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from PubChem

6 Chemical Vendors

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7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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from NCBI

5 Related Records

from PubChem

51 Related Compounds with Annotation

Same Connectivity 7 records

Same Parent Connectivity 930 records

Same Parent Exact 920 records

Mixtures Components andNeutralized Forms 37111 records

Similar Compounds 279 records

Similar Conformers 396 records

from PubChem

52 Related Compounds

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

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from PubChem

6 Chemical Vendors

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1861

7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3661

Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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53 Substances

All 139987 records

Same 391 records

Mixture 139596 records

from PubChem

531 Related Substances

from PubChem

532 Substances by Category

PubMed 3531 records

Protein Structures 77 records

Taxonomy 2 records

Gene 11 records

from PubChem

54 Entrez Crosslinks

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from PubChem

6 Chemical Vendors

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7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3061

USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

1152015 oxalic acid | C2H2O4 shy PubChem

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3461

NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3561

Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3661

Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

1152015 oxalic acid | C2H2O4 shy PubChem

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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from PubChem

6 Chemical Vendors

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7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

1152015 oxalic acid | C2H2O4 shy PubChem

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 18: Oxalic Acid _ C2H2O4 - PubChem

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7 Drug and Medication Information

Ascorbic acid ingestion in high doses is associated with oxalate deposition in tissue in dialysis patients OxalatesHaddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

71 Drug Warning

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 1961

8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3761

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3961

12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4061

Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 19: Oxalic Acid _ C2H2O4 - PubChem

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8 Pharmacology and Biochemistry

Reducing AgentsMaterials that add an electron to an element or compound that is decrease the positiveness of its valence (FromMcGrawshyHill Dictionary of Scientific and Technical Terms 5th ed) See a list of PubChem compounds matchingthis category

from MeSH

81 MeSH Pharmacological Classification

TARTARIC amp OXALIC ACIDS ARE EXCRETED IN URINE UNCHANGEDParke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 141

from HSDB

The absorption of (14)Cshylabelled oxalic acid was studied in Wistar rats CDshy1 mice and NMRI mice Oxalic acid insolution was given to the animals by gavage either with water alone or with 0625 gkg body wt of xylitol Bothxylitol adapted animals and animals not previously exposed to xylitol were used Adaptation to xylitol dietsenhanced the absorption and urinary excretion of the label (oxalic acid) in both strains of mice but not in ratsEarlier studies have indicated a high incidence of bladder calculi in mice but not in rats fed high amounts of xylitolThe results of the present study offer one likely explanation for the increased formation of bladder calculi as a resultof over saturation of urine with oxalate Abstract PubMed

Salminen S et al Toxicol Lett 44 (1shy2) 113shy20 (1988)

from HSDB

82 Absorption Distribution and Excretion

IN RABBIT MAJOR ENDshyPRODUCT OF METAB OF (14)CshyETHYLENE GLYCOL IS RESP CARBON DIOXIDE(60 OF DOSE IN 3 DAYS) amp METABOLITES EXCRETED IN URINE ARE UNCHANGED ETHYLENEGLYCOL (10) amp OXALIC ACID (01) GLYCOLALDEHYDE GLYCOLLIC ACID amp GLYOXYLIC ACID AREINTERMEDIATES IN CONVERSION TO CARBON DIOXIDE

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 214

from HSDB

IN OXIDATIVE METAB OF ETHYLENE GLYCOL IN MAMMALS SPECIES VARIATIONS OCCUR WHICHEXPLAIN DIFFERENCES IN TOXICITY GLYCOL IS OXIDIZED BY MAJOR PATHWAY INTO CARBONDIOXIDE amp BY MINOR PATHWAY TO OXALIC ACID EXTENT OF FORMATION OF OXALIC ACID ISDEPENDENT ON DOSE LEVEL BUT HAS BEEN SHOWN TO VARY WITH SPECIES

Parke D V The Biochemistry of Foreign Compounds Oxford Pergamon Press 1968 p 118

from HSDB

INITIAL STEPS IN OXIDATION OF ETHYLENE GLYCOL TO DIALDEHYDE (GLYOXAL) amp TO GLYOXYLICACID SEEM TO BE MEDIATED BY ALC DEHYDROGENASE DECARBOXYLATION OF GLYOXYLIC ACIDYIELDS CARBON DIOXIDE amp FORMIC ACID GLYOXYLIC ACID IS ALSO OXIDIZED TO OXALIC ACID

Gilman AG LSGoodman and A Gilman (eds) Goodman and Gilmans The Pharmacological Basis of Therapeutics 7th edNew York Macmillan Publishing Co Inc 1985 p 1637

83 MetabolismMetabolites

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4961

may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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from HSDB

Piridoxilate is an association of glyoxylic acid and pyridoxine in which pyridoxine is supposed to facilitate in vivotransformation of glyoxylic acid to glycine rather than to oxalic acid However it has recently been shown that longterm treatment with piridoxilate may result in over production of oxalic acid and in calcium oxalate nephrolithiasis Apatient in whom piridoxilate induced both oxalate nephrolithiasis and chronic oxalate nephropathy with renalinsufficiency an association that has not been previously described was reported Therefore piridoxilate should beadded to the list of chemicals responsible for chronic oxalate nephropathy Abstract PubMed

Vigeral P et al Nephrol Dial Transplant 2 (4) 275shy8 (1987)

from HSDB

Cyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

Metabolically its toxicity is believed due to the capacity of oxalic acid to immobilize calcium and thus upset thecalciumshypotassium ratio in critical tissues

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

84 Mechanism of Action

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

1152015 oxalic acid | C2H2O4 shy PubChem

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

1152015 oxalic acid | C2H2O4 shy PubChem

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

1152015 oxalic acid | C2H2O4 shy PubChem

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

1152015 oxalic acid | C2H2O4 shy PubChem

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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9 Use and Manufacturing

91 Uses

1 Paint additives and coating additives not described by other categories2 Photosensitive chemicals3 Surface active agents

from EPA Chemical Data Report

911 Industry Uses

1 Cleaning and Furnishing Care Products2 Laundry and Dishwashing Products3 Paints and Coatings4 Photographic Supplies Film and Photochemicals

from EPA Chemical Data Report

912 Consumer Uses

MADE BY PASSING CARBON MONOXIDE INTO CONCENTRATED SODIUM HYDROXIDE OR BY HEATINGSODIUM FORMATE IN PRESENCE OF SODIUM HYDROXIDE OR SODIUM CARBONATE

Budavari S (ed) The Merck Index shy Encyclopedia of Chemicals Drugs and Biologicals Rahway NJ Merck and Co Inc1989 p 1093

from HSDB

OXALIC ACID IS PRODUCED COMMERCIALLY BY NITRIC ACID OXIDATION OF STARCH SUGAR ORETHYLENE GLYCOL

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

OXALIC ACID IS A COshyPRODUCT OF THE FERMENTATION OF MOLASSES TO CITRIC ACID OXALIC ACIDCAN BE MADE BY FUSING SAWDUST (OR OTHER FORMS OF CELLULOSE) WITH A MIXTURE OFSODIUM HYDROXIDE AND POTASSIUM HYDROXIDE TEXACO WAS GRANTED A PATENT IN 1973 FORTHE ELECTROLYTIC SYNTHESIS OF OXALIC ACID FROM CARBON DIOXIDE AND HYDROGEN

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

92 Methods of Manufacturing

Technical (crystals and powder) chemically pure a grade designation signifying a minimum of impurities but not100 purity

Sax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co

93 FormulationsPreparations

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

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141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5861

16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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1987 p 862

from HSDB

THE COMMERCIAL PRODUCT IS COMPRISED OF WHITE TO COLORLESS MONOCLINIC PRISMS ORGRANULES CONTAINING 7142 wt ANHYDROUS OXALIC ACID AND 2858 wt WATER

KirkshyOthmer Encyclopedia of Chemical Technology 3rd ed Volumes 1shy26 New York NY John Wiley and Sons 1978shy1984 pV16 618 (1981)

from HSDB

27 FOR TEXTILE FINISHING STRIPPING AND CLEANING 27 FOR METAL AND EQUIPMENTCLEANING 25 AS A CHEMICAL INTERMEDIATE 2 FOR LEATHER TANNING 19 FOR MISCAPPLICATIONS (1971)

SRI

from HSDB

33 FOR TEXTILE APPLICATIONS 20 FOR METAL 7 FOR LEATHER 20 FOR OXALATES AND 20FOR OTHER USE (1983)

CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

94 Consumption

(1972) 10X10+10 GSRI

from HSDB

(1974) 817X10+9 GSRI

from HSDB

(1982) 908X10+8 G (EST)CHEMICAL PRODUCTS SYNOPSIS OXALIC ACID 1984

from HSDB

95 US Production

(1972) 86X10+8 GSRI

from HSDB

(1975) 173X10+9 GSRI

from HSDB

(1984) 931X10+9 g

96 US Imports

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3661

Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

1152015 oxalic acid | C2H2O4 shy PubChem

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

CLICK TO LOAD

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 23: Oxalic Acid _ C2H2O4 - PubChem

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BUREAU OF THE CENSUS US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p1shy357

from HSDB

(1972) NEGLIGIBLESRI

from HSDB

168X10+8 gBUREAU OF THE CENSUS US EXPORTS SCHEDULE E 1984 p2shy79

from HSDB

97 US Exports

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3661

Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3761

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

1152015 oxalic acid | C2H2O4 shy PubChem

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4261

from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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10 Identification

VEGETABLE PRODUCTS TITRATION OR ATOMIC ABSORPTION SPECTROPHOTOMETRYAssociation of Official Analytical Chemists Official Methods of Analysis 15th ed and Supplements Washington DCAssociation of Analytical Chemists 1990 p 15994 97424

from HSDB

AIR SAMPLE PROCEDURE TITRATIONSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 649

from HSDB

101 Analytic Laboratory Methods

APPLICATION SERUM OR URINE METHOD FLUORESCENCE ANALYSISSunshine I (ed) CRC Handbook of Analytical Toxicology Cleveland The Chemical Rubber Co 1969 p 927

from HSDB

102 Clinical Laboratory Methods

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3661

Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3761

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3961

12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4261

from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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11 Safety and Hazards

111 Hazards Identification

Signal DangerHarmful if swallowedCauses severe skin burns and eye damageMay cause respiratory irritation

from ILOshyICSC

Signal Wng H312 shy Harmful in contact with skinH302 shy Harmful if swallowed

from REGULATION (EC) No 12722008

1111 GHS Classification

CLP Hazard Classs and Category CodesAcute Tox 4 Acute Tox 4

from REGULATION (EC) No 12722008

1112 CLP Hazard Class and Category Codes

As dust or as a solution can cause severe burns of eyes skin or mucous membranes Ingestion of 5 grams hascaused death with symptoms of nausea shock collapse and convulsions coming on rapidly Repeated orprolonged skin exposure can cause dermatitis and slowshyhealing ulcers (USCG 1999)

from CAMEO Chemicals

Corrosive

from NJDOH RTK Hazardous Substance List

1113 Health Hazard

1114 Fire Hazard

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3561

Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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Combustible Gives off irritating or toxic fumes (or gases) in a fire

from ILOshyICSC

Redness Pain Skin burns

from ILOshyICSC

1115 Skin Hazard

Cough Sore throat Burning sensation Shortness of breath Laboured breathing Headache

from ILOshyICSC

1116 Inhalation Hazard

Redness Pain Blurred vision Burns

from ILOshyICSC

1117 Eye Hazard

Sore throat Burning sensation Abdominal pain Laboured breathing Convulsions Paralysis Cardiac dysrhythmiaShock or collapse

from ILOshyICSC

1118 Ingestion Hazard

The chief effects of inhalation of the dust or vapor are irritation of the eyes and upper respiratory tractSax NI Dangerous Properties of Industrial Materials 6th ed New York NY Van Nostrand Reinhold 1984 p 2098

from HSDB

1119 Skin Eye and Respiratory Irritations

112 Safety and Hazard Properties

Combustible Solid

from NIOSHshyPocketGuide

1121 Flammability

Health 3 3= Materials that on short exposure could cause serious temporary or residual injury including thoserequiring protection from all bodily contact Fire fighters may enter the area only if they are protected from allcontact with the material Full protective clothing including selfshycontained breathing apparatus coat pants gloves

1122 NFPA Hazard Classification

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3761

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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boots and bands around legs arms and waist should be provided No skin surface should be exposedFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Flammability 1 1= This degree includes materials that must be preheated before ignition will occur such as ClassIIIB combustible liquids and solids and semishysolids whose flash point exceeds 200 deg F (934 deg C) as well asmost ordinary combustible materials Water may cause frothing if it sinks below the surface of the burning liquidand turns to steam However a water fog that is gently applied to the surface of the liquid will cause frothing thatwill extinguish the fire

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

Reactivity 0 0= This degree includes materials that are normally stable even under fire exposure conditions andthat do not react with water Normal fire fighting procedures may be used

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

1

from OSHA Occupational Chemical DB CAMEO Chemicals

1123 NFPA Fire Rating

0

from OSHA Occupational Chemical DB

1124 NFPA Reactivity Rating

2

from OSHA Occupational Chemical DB

3

from CAMEO Chemicals

1125 NFPA Health Rating

No data

from ILOshyICSC

1126 Physical Danger

500 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

1127 Chemical Danger

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

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LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

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1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

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1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

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PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

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1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

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AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

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ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 28: Oxalic Acid _ C2H2O4 - PubChem

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from HSDB

Decomposes on contact with hot surfaces or flames This produces formic acid and carbon monoxide The solutionin water is a medium strong acid Reacts violently with strong oxidants This generates fire and explosion hazardReacts with some silver compounds This produces explosive silver oxalate Attacks some forms of plastic

from ILOshyICSC

Permissible Exposure Limit Table Zshy1 8shyhr Time Weighted Avg 1 mgcu m29 CFR 19101000 (7198)

from HSDB

Vacated 1989 OSHA PEL TWA 1 mgcu m STEL 2 mgcu m is still enforced in some statesNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 369

from HSDB

1128 OSHA Standards

Recommended Exposure Limit 10 Hr TimeshyWeighted Avg 1 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Recommended Exposure Limit 15 Min ShortshyTerm Exposure Limit 2 mgcu mNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

1129 NIOSH Recommendations

113 First Aid Measures

Eye Irrigate immediatelySkin Water flush promptlyBreathing Respiratory supportSwallow Medical attention immediately More information

from NIOSHshyPocketGuide

EYES First check the victim for contact lenses and remove if present Flush victims eyes with water or normalsaline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center Do not put anyointments oils or medication in the victims eyes without specific instructions from a physician IMMEDIATELYtransport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) developSKIN IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing Gentlywash all affected skin areas thoroughly with soap and water IMMEDIATELY call a hospital or poison control centereven if no symptoms (such as redness or irritation) develop IMMEDIATELY transport the victim to a hospital fortreatment after washing the affected areas INHALATION IMMEDIATELY leave the contaminated area take deepbreaths of fresh air If symptoms (such as wheezing coughing shortness of Breathing or burning in the mouth

1131 First Aid

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

1152015 oxalic acid | C2H2O4 shy PubChem

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

1152015 oxalic acid | C2H2O4 shy PubChem

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

1152015 oxalic acid | C2H2O4 shy PubChem

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

1152015 oxalic acid | C2H2O4 shy PubChem

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

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141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5861

16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 29: Oxalic Acid _ C2H2O4 - PubChem

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throat or chest) develop call a physician and be prepared to transport the victim to a hospital Provide properrespiratory protection to rescuers entering an unknown atmosphere Whenever possible SelfshyContained BreathingApparatus (SCBA) should be used if not available use a level of protection greater than or equal to that advisedunder Protective Clothing INGESTION DO NOT INDUCE VOMITING Corrosive chemicals will destroy themembranes of the mouth throat and esophagus and in addition have a high risk of being aspirated into thevictims lungs during vomiting which increases the medical problems If the victim is conscious and not convulsinggive 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control centerIMMEDIATELY transport the victim to a hospital If the victim is convulsing or unconscious do not give anything bymouth ensure that the victims airway is open and lay the victim on hisher side with the Headache lower than thebody DO NOT INDUCE VOMITING Transport the victim IMMEDIATELY to a hospital (NTP 1992)

from OSHA Occupational Chemical DB

Use water spray powder foam carbon dioxide

from ILOshyICSC

1132 Fire First Aid

In case of fire keep drums etc cool by spraying with water

from ILOshyICSC

1133 Explosion First Aid

Fresh air rest Halfshyupright position Refer immediately for medical attention

from ILOshyICSC

1134 Inhalation First Aid

Remove contaminated clothes Rinse skin with plenty of water or shower for at least 15 minutes Refer for medicalattention

from ILOshyICSC

1135 Skin First Aid

Rinse with plenty of water (remove contact lenses if easily possible) Refer immediately for medical attention

from ILOshyICSC

1136 Eye First Aid

Rinse mouth Do NOT induce vomiting Refer immediately for medical attention

from ILOshyICSC

1137 Ingestion First Aid

1152015 oxalic acid | C2H2O4 shy PubChem

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USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 30: Oxalic Acid _ C2H2O4 - PubChem

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3061

USE WATER SPRAY DRY CHEM ALC RESISTANT FOAM OR CARBON DIOXIDE DUST MAY BEREDUCED WITH WATER SPRAY AQUEOUS SOLUTION MUST BE CONTAINED FOR DISPOSAL USEWATER TO KEEP FIREshyEXPOSED CONTAINERS COOL WATER MAY CAUSE FOAMING OF MOLTENMATERIAL OXALIC ACID DIHYDRATE

Fire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

114 Fire Fighting Measures

Fires involving this compound may be controlled with a dry chemical carbon dioxide or Halon extinguisher (NTP1992)

from OSHA Occupational Chemical DB

1141 Fire Fighting

115 Accidental Release Measures

Personal protection particulate filter respirator adapted to the airborne concentration of the substance protectivegloves and safety goggles Sweep spilled substance into covered plastic containers If appropriate moisten first toprevent dusting Wash away remainder with plenty of water

from ILOshyICSC

1151 Spillage Disposal

Cover with soda ash or sodium bicarbonate Mix and add water Neutralize and drain into a drain with sufficientwater

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

from HSDB

1152 Cleanup Methods

Oxalic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlledincineration Pretreatment involves chemical reaction with limestone or calcium oxide forming calcium oxalate Thismay then be incinerated utilizing particulate collection equipment to collect calcium oxide for recycling

USEPA Engineering Handbook for Hazardous Waste Incineration p2shy18 (1981) EPA 68shy03shy3025

from HSDB

1153 Disposal Methods

Adequate ventilationITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 389

1154 Other Preventative Measures

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3161

from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3361

TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3461

NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3561

Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3661

Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4961

may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5061

hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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from HSDB

The worker should immediately wash the skin when it becomes contaminatedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Work clothing that becomes wet or significantly contaminated should be removed and replacedNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Workers whose clothing may have become contaminated should change into uncontaminated clothing beforeleaving the work premises

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

SRP Contaminated protective clothing should be segregated in such a manner so that there is no direct personalcontact by personnel who handle dispose or clean the clothing Quality assurance to ascertain the completeness ofthe cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuseby the workers Contaminated clothing should not be taken home at end of shift but should remain at employeesplace of work for cleaning

from HSDB

SRP The scientific literature for the use of contact lenses in industry is conflicting The benefit or detrimentaleffects of wearing contact lenses depend not only upon the substance but also on factors including the form of thesubstance characteristics and duration of the exposure the uses of other eye protection equipment and thehygiene of the lenses However there may be individual substances whose irritating or corrosive properties are suchthat the wearing of contact lenses would be harmful to the eye In those specific cases contact lenses should notbe worn In any event the usual eye protection equipment should be worn even when contact lenses are in place

from HSDB

116 Handling and Storage

Neutralizing Agents for Acids and Caustics Lime or soda ash (USCG 1999)

from OSHA Occupational Chemical DB

1161 Nonfire Spill Response

Separated from strong oxidants and food and feedstuffs Dry Well closed

from ILOshyICSC

1162 Safe Storage

STORE IN COOL DRY WELLshyVENTILATED LOCATION OXALIC ACID DIHYDRATE

1163 Storage Conditions

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3761

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3961

12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4061

Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5361

contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5761

References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 32: Oxalic Acid _ C2H2O4 - PubChem

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Reynolds JEF Prasad AB (eds) MartindaleshyThe Extra Pharmacopoeia 28th ed London The Pharmaceutical Press 1982p 49shy131

from HSDB

117 Exposure Control and Personal Protection

TWA 1 mgm ST 2 mgm

from NIOSHshyPocketGuide

1171 REL3 3

TWA 1 mgm

from NIOSHshyPocketGuide

1172 PEL3

1 mgm3

from OSHA Occupational Chemical DB

1173 PELshyTWA

1 mgm3

from OSHA Occupational Chemical DB

1174 RELshyTWA

2 mgm3

from OSHA Occupational Chemical DB

1175 RELshySTEL

500 mgm

from NIOSHshyPocketGuide

1176 IDLH3

8 hr Time Weighted Avg (TWA) 1 mgcu m 15 min Short Term Exposure Limit (STEL) 2 mgcu mAmerican Conference of Governmental Industrial Hygienists TLVs and BEIs Threshold Limit Values for Chemical Substancesand Physical Agents and Biological Exposure Indices Cincinnati OH 2008 p 45

from HSDB

1177 Threshold Limit Values

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TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3461

NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 33: Oxalic Acid _ C2H2O4 - PubChem

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3361

TLV 1mgmsup3 as TWA (ACGIH 2009)EU OEL ( selected) 1mgmsup3 as TWA

from ILOshyICSC

1178 Occupational Exposure Limits

Evaporation at 20degC is negligible a harmful concentration of airborne particles can however be reached quicklywhen dispersed

from ILOshyICSC

1179 Inhalation Risk

The substance is corrosive to the eyes skin and respiratory tract Corrosive on ingestion The substance may causeeffects on the calcium balance after ingestion Exposure at high levels could cause death

from ILOshyICSC

11710 Effects of Short Term Exposure

Repeated or prolonged contact with skin may cause dermatitis Exposure may result in kidney stones slowshyhealingulcers and black finger nails

from ILOshyICSC

11711 Effects of Long Term Exposure

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11712 Allowable Tolerances

Skin Prevent skin contactEyes Prevent eye contactWash skin When contaminatedRemove When wet or contaminatedChange DailyProvide Eyewash More information

from NIOSHshyPocketGuide

11713 Personal Protection

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3461

NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3561

Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3661

Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3761

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4061

Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4261

from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4461

contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4561

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5161

from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5261

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 34: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3461

NIOSHOSHA Up to 25 mgm (APF = 25) Any suppliedshyair respirator operated in a continuousshyflow mode (APF = 25) Anypowered airshypurifying respirator with a highshyefficiency particulate filter Up to 50 mgm (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Clickhere for information on selection of N R or P filters (APF = 50) Any selfshycontained breathing apparatus with a fullfacepiece (APF = 50) Any suppliedshyair respirator with a full facepiece Up to 500 mgm (APF = 2000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode Emergency or planned entry into unknown concentrations or IDLH conditions (APF = 10000) Any selfshycontainedbreathing apparatus that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode(APF = 10000) Any suppliedshyair respirator that has a full facepiece and is operated in a pressureshydemand or otherpositiveshypressure mode in combination with an auxiliary selfshycontained positiveshypressure breathing apparatus Escape (APF = 50) Any airshypurifying fullshyfacepiece respirator with an N100 R100 or P100 filter Click here forinformation on selection of N R or P filters Any appropriate escapeshytype selfshycontained breathing apparatusMore information

from NIOSHshyPocketGuide

11714 Respirator Recommendations

3 poundpound

3

3

NO open flames

from ILOshyICSC

11715 Fire Prevention

PREVENT DISPERSION OF DUST

from ILOshyICSC

11716 Exposure Prevention

Use ventilation (not if powder) local exhaust or breathing protection

from ILOshyICSC

11717 Inhalation Prevention

Protective gloves Protective clothing

from ILOshyICSC

11718 Skin Prevention

Wear face shield or eye protection in combination with breathing protection

from ILOshyICSC

11719 Eye Prevention

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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Do not eat drink or smoke during work Wash hands before eating

from ILOshyICSC

11720 Ingestion Prevention

EYE amp SKIN PROTECTION MUST BE PROVIDED FOR PERSONS WORKING WITH OXALIC ACIDInternational Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 984

from HSDB

Wear special protective clothing and positive pressure selfshycontained breathing apparatus Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

If mists of oxalic acid should be encountered from hot solutions adequate ventilation should be provided orproper respiratory protective devices worn

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

Respirator for dust or mist protection rubber neoprene or vinyl gloves chemical safety glasses rubbers overleather or rubber safety shoes apron or impervious clothing for splash protection

US Coast Guard Department of Transportation CHRIS shy Hazardous Chemical Data Volume II Washington DC USGovernment Printing Office 1984shy5

from HSDB

Wear appropriate personal protective clothing to prevent skin contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Wear appropriate eye protection to prevent eye contactNIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to thesubstance this is irrespective of the recommendation involving the wearing of eye protection

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 25 mgcu m Respirator Class(es) Any suppliedshyairrespirator operated in a continuous flow mode Eye protection needed Any powered airshypurifying respirator with adust and mist filter Eye protection needed

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

11721 Protective Equipment and Clothing

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5161

from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5261

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 36: Oxalic Acid _ C2H2O4 - PubChem

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Recommendations for respirator selection Max concn for use 50 mgcu m Respirator Class(es) Any airshypurifyingfullshyfacepiece respirator with a highshyefficiency particulate filter Any selfshycontained breathing apparatus with a fullfacepiece Any suppliedshyair respirator with a full facepiece

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Max concn for use 500 mgcu m Respirator Class(es) Any suppliedshyairrespirator that has a full facepiece and is operated in a pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Emergency or planned entry into unknown concn or IDLHconditions Respirator Class(es) Any selfshycontained breathing apparatus that has a full facepiece and is operated ina pressureshydemand or other positiveshypressure mode Any suppliedshyair respirator that has a full facepiece and isoperated in a pressureshydemand or other positiveshypressure mode in combination with an auxiliary selfshycontainedbreathing apparatus operated in pressureshydemand or other positiveshypressure mode

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

Recommendations for respirator selection Condition Escape from suddenly occurring respiratory hazardsRespirator Class(es) Any airshypurifying fullshyfacepiece respirator with a highshyefficiency particulate filter Anyappropriate escapeshytype selfshycontained breathing apparatus

NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 239

from HSDB

118 Stability and Reactivity

Water soluble Hygroscopic

from CAMEO Chemicals

1181 Air and Water Reactions

Acids Carboxylic

from CAMEO Chemicals

1182 Reactive Group

Reacts with strong alkalies strong oxidizing materials chlorites and hypochlorites Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy122

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215 degreesF and begins to sublime]

1183 Reactivities and Incompatibilities

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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NIOSH NIOSH Pocket Guide to Chemical Hazards DHHS (NIOSH) Publication No 97shy140 Washington DC US GovernmentPrinting Office 1997 p 238

from HSDB

Strong oxidizers silver compounds strong alkalis chlorites [Note Gives off water of crystallization at 215degF andbegins to sublime]

from NIOSHshyPocketGuide

STABILITY This chemical is hygroscopic and sensitive to heat Solutions of this chemical should be stable for 24hours under normal lab conditionsREACTIVITY This compound may react violently with furfuryl alcohol silversodium perchlorate sodium hypochlorite strong oxidizers sodium chlorite acid chlorides metals and alkali metals(NTP 1992)

from OSHA Occupational Chemical DB

119 Transport Information

Corrosive

from CAMEO Chemicals

1191 DOT Label

Do not transport with food and feedstuffs

from ILOshyICSC

1192 Packaging and Labelling

Symbol Xn R 2122 S (2)shy2425

from ILOshyICSC

1193 EC Classification

UN Hazard Class 8 UN Pack Group III

from ILOshyICSC

1194 UN Classification

NFPA Code H3 F1 R0

from ILOshyICSC

1195 Emergency Response

1110 Regulatory Information

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5161

from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5461

13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 38: Oxalic Acid _ C2H2O4 - PubChem

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 3861

Residues of oxalic acid are exempted from the requirement of a tolerance when used as a calcium chelating hardwater inhibitor in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticideformulations applied to growing crops or to raw agricultural commodities after harvest Limits No more oxalic acidshould be used than is necessary to chelate calcium and in no case should more than 2 lb oxalic acid per acre beused

40 CFR 1801001(c) (7190)

from HSDB

11101 FIFRA Requirements

1111 Other Safety Information

Combustion may produce irritants and toxic gases including formic acid Oxalic acid dihydrateFire Protection Guide to Hazardous Materials 12 ed Quincy MA National Fire Protection Association 1997 p 49shy99

from HSDB

11111 Toxic Combustion Products

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4061

Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4561

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5261

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 39: Oxalic Acid _ C2H2O4 - PubChem

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12 Toxicity

121 Toxicological Information

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion Serious local effects byall routes of exposure

from ILOshyICSC

inhalation ingestion skin andor eye contact

from NIOSHshyPocketGuide

1211 Exposure Routes

irritation eyes skin mucous membrane eye burns localized pain cyanosis shock collapse convulsions kidneydamage

from NIOSHshyPocketGuide

1212 Symptoms

Eyes skin respiratory system kidneys

from NIOSHshyPocketGuide

1213 Target Organs

A number of sulfhydryl compounds were shown to inhibit CO2 and oxalate formation from glyoxylate by rat liverhomogenates and hepatocytes The most significant inhibition occurred with cysteine and this inhibition wasconcentration dependent In rats made hyperoxaluric by administering ethylene glycol in their drinking water dailyintraperitoneal injections of cysteine caused a rapid and marked decrease in urinary oxalate excretion which wasmaintained over the duration of the treatment (28 days) Over this time period the level of urinary oxalate excretioninthese ethylene glycol treated rats was reduced to that of the controlsIt is postulated that the decrease is due tothe formation of acysteineshyglyoxylate adduct 2shycarboxyshy4shythiazolidine carboxylate which prevents glyoxylate beingfurther oxidized to oxalate Cysteine or similar sulphydryl compounds may therefore have potential as therapeuticagents in the prevention of renal stones Abstract PubMed

Bais R et al J Urol 145 (6) 1302shy5 (1991)

from HSDB

The study was conducted to investigate the effect of vitamin A B1 and B6 deficiency on oxalate metabolism inrats A significant hyperoxaluria was the common observation in all the three vitamin deficiencies (vitamin B6greater than vitamin A greater than vitamin B1) The activities of hepatic glycolate oxidase and glycolatedehydrogenase were markedly enhanced in vitamin A and vitamin B6 deficient rats However lactatedehydrogenase levels remained unaltered in these deficiencies as compared to their respective pair fed controlsVitamin B1 deficiency of 4 weeks duration could augment the activity of glycolate oxidase only with no alterationsin the glycolate dehydrogenase and lactate dehydrogenase levels Intestinal oxalate uptake studies revealedincreased bioavailability of oxalate from the gut in vitamin A and vitamin B6 deficient rats Thus the results suggestthe relative contribution of both exogenous as well as endogenous oxalate in the process of calculogenesis undervarious nutritional stress conditions in rat Abstract PubMed

1214 Interactions

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 40: Oxalic Acid _ C2H2O4 - PubChem

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Sharma S et al Ann Nutr Metab 34 (2) 104shy11 (1990)

from HSDB

Hyperoxalemia can be aggravated by vitamin C supplementation in regular hemodialysis patients The presentstudy was undertaken to examine the validity of this observation in an experimental setting Fifty fiveshysixthsnephrectomized rats were divided into two groups 30 rats were allowed free access to water containing 8 mgml ofvitamin C (100shy160 mg100 g24 hr) and the remainder given tap water without vitamin C The serum creatinineincreased and the hematocrit decreased gradually however there was no difference between the two groupsPlasma vitamin C oxalate and urinary oxalate levels were higher in the vitamin treated group than the nontreatedrats Histological examination revealed glomerular and interstitial fibrosis and round cell infiltration as well as tubularcyst formation Oxalate deposits in renal tubules were found only in vitamin Cshytreated rats with advanced renalfailure Nontreated animals with equally advanced renal impairment showed no oxalate deposits These resultsconfirm previous clinical findings that vitamin C supplementation aggravates the secondary oxalosis of chronic renalfailure Abstract PubMed

Ono K et al Nephron 51 (4) 536shy9 (1989)

from HSDB

Male Wistar strain rats which had been fed a glycolic acid diet developed severe nephrocalcinosis with urinarycalculi within 4 weeks Rats fed the same diet with citrate salts added had however either slight or nonephrocalcinosis without any stones in the urinary system Nephrocalcinosis intermediate between those in thecitrate groups and the glycolic acid group with some urinary calculi was observed in the citric acid group Duringthe experiment the urinary oxalate concentration increased markedly and was higher in the citrate and citric acidthan in the glycolic acid group The urinary citrate concentration was significantly higher in the citrate groups andlower in the citric acid and glycolic acid groups Therefore citrate salts can be concluded to inhibit nephrocalcinosisand calculi formation as a result of decreased urinary saturation by means of increase in urinary citrate in spite of aslight increase in the urinary oxalate Abstract PubMed

Ogawa Y et al Hinyokika Kiyo 33 (11) 1772shy7 (1987)

from HSDB

The addition of oxalate to blood stored in citrate phosphate dextrose produces a marked improvement in 23shydiphosphoglycerate preservation an increase in 23shydiphosphoglycerate levels can also be documented in shortshyterm incubation studies Oxalate is a potent in vitro inhibitor of red cell lactate dehydrogenasemonophosphoglycerate mutase and pyruvatekinase In the presence of fructose 16shydiphosphate the latterinhibitory effect is competitive with phospho(enol)pyruvate Determination of the levels of intermediate compoundsin red cells incubated with oxalate suggest the presence of inhibition at the pyruvatekinase step indicating that thisis the site of oxalate action Apparent inhibitionat the glyceraldehyde phosphate dehydrogenase step is apparentlydue to an increase in the NADHNAD ratio Oxalate had no effect on the in vivo viability of rabbit red cells stored incitrateshy phosphateshydextrose preservatives for 21 days Greater understanding of the toxicity of oxalate is requiredbefore it can be considered suitable as a component of preservative media but appreciation of the mechanism bywhich it affects 23shydiphosphoglycerate levels may be important in design of other blood additives Malonate the 3shycarbon dicarboxylic acid analog of oxalate did not inhibit pyruvatekinase nor affect 23shydiphosphoglycerate levelsAbstract PubMedBeutler E et al Blood 70 (5) 1389shy93 (1987)

from HSDB

Twenty two recurrent calcium stone formers had 24 hr urinary oxalate excretions on their home diets which weresignificantly greater than those of 30 normal subjects (048 + or shy 023 mmolday mean + or shy standard deviationcompared with 031 + or shy 011 p lt 001) The stone formers also demonstrated marked day to day variability inoxalate excretion indicating that a single normal urinary oxalate measurement did not exclude significanthyperoxaluria at other times On a hospital diet containing 1000 mg calcium per day urinary oxalate excretion fellsignificantly from 048 + or shy 023 mmolday to 032 + or shy 012 (p lt 001) As the urinary calcium excretion in andout of hospital was similar it seems unlikely that low calcium intake at home was responsible for the hyperoxaluriaAll patients had recurrent symptomatic stone disease and had been advised to avoid foods rich in oxalate Whilstpoor compliance is a possible explanation for the variability in oxalate excretion it is more likely that there is aninadvertent intake of oxalogenic precursors in their diet As normal subjects do not demonstrate hyperoxaluria onsimilar home diets stone formers may have a metabolic defect in the handling of these precursors AbstractPubMed

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4461

contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4561

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4961

may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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Brown JM et al Ann Clin Biochem 24 ( Pt 4) 385shy90 (1987)

from HSDB

Treatment should be rapidly instituted by giving a dilute solution of calcium lactate lime water finely pulverizedchalk plaster andor milk to supply large amounts of calcium to inactivate oxalate by forming an insoluble calciumsalt in the stomach Gastric lavage is controversial since this may compound an already severe corrosive lesion inthe esophagus or stomach However if used gastric lavage should be done with limewater (calcium hydroxide)Intravenous gluconate or calcium chloride solutions should be given to prevent hypocalcemic tetany in severe casesparathyroid extract also has been given Additionally acute renal failure should be anticipated and careful fluidmanagement is necessary Oxalates

Haddad LM Clinical Management of Poisoning and Drug Overdose 2nd ed Philadelphia PA WB Saunders Co 1990 p702

from HSDB

Metabolically its toxicity is believed to be due to the capacity of oxalic acid to immobilize calcium and thus upsetthe calciumshypotassium ratio in critical tissues Effective therapy against burns from oxalic acid involves replacementof calcium

American Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

1215 Antidote and Emergency Treatment

CAREFUL CONSIDERATION SHOULD BE GIVEN TO PLACEMENT OF ANY INDIVIDUALS WHO HAVEPERIPHERAL VASCULAR DISEASE OF THE HANDS amp IT WOULD SEEM BEST TO AVOID EXPOSURE OFSUCH PERSONS TO OXALIC ACID

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

from HSDB

1216 Medical Surveillance

SYMPTOMATOLOGY 1 BURNING PAIN IN THROAT ESOPHAGUS amp STOMACH EXPOSED AREAS OFMUCOUS MEMBRANE TURN OPAQUE WHITE 2 VOMITING (OFTEN BLOODY OR WITH COFFEEshyGROUND APPEARANCE) INTENSE BURNING PAIN SEVERE PURGING 3 PULSE BECOMES WEAKIRREGULAR SOMETIMES IMPERCEPTIBLE HYPOTENSION AND USUAL SIGNS OF CARDIOVASCULARCOLLAPSE APPEAR 4 IF DEATH IS DELAYED FOR FEW HR NERVOUS OR NEUROMUSCULARSYMPTOMS DEVELOP HEADACHE TETANY SOMETIMES CONVULSIONS STUPOR COMA ANDDEATH 5 RENAL DAMAGE AS EVIDENCED BY OLIGURIA ALBUMINURIA AND HEMATURIA MAYPERSIST FOR WEEKS ORAL OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy327

from HSDB

CHRONIC SKIN EXPOSURE TO SOLN OF OXALIC ACID HAS BEEN REPORTED TO HAVE CAUSEDLOCALIZED PAIN amp CYANOSIS IN FINGERS OR EVEN GANGRENOUS CHANGES APPARENTLY DUETO LOCALIZED ABSORPTION amp RESULTANT ARTERITIS

International Labour Office Encyclopedia of Occupational Health and Safety Vols IampII Geneva Switzerland InternationalLabour Office 1983 p 1574

1217 Human Toxicity Excerpts

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

1152015 oxalic acid | C2H2O4 shy PubChem

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4961

may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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from HSDB

THE NEUROMUSCULAR EFFECTS CAN BE EXPLAINED LARGELY BY CALCIUMshyCOMPLEXING ACTION OFOXALATE WHICH DEPRESSES THE LEVEL OF IONIZED CALCIUM IN BODY FLUIDS THISHYPOCALCEMIA PRODUCES SEVERE DISTURBANCES IN ACTIONS OF HEART amp NERVOUS SYSTEMDEATH MAY RESULT OXALATE

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIshy71

from HSDB

HAS CAUSED BURNS OF HUMAN EYE WHEN SOLN ACCIDENTALLY CAME IN CONTACT WITH EYEGrant WM Toxicology of the Eye 3rd ed Springfield IL Charles C Thomas Publisher 1986 p 685

from HSDB

TOXIC BY INHALATION AND INGESTION STRONG IRRITANTSax NI and RJ Lewis Sr (eds) Hawleys Condensed Chemical Dictionary 11th ed New York Van Nostrand Reinhold Co1987 p 862

from HSDB

Oxalic acid is regarded as a strong poison when taken internally as little as 5 grams have proved fatalAmerican Conference of Governmental Industrial Hygienists Documentation of the Threshold Limit Values and BiologicalExposure Indices 5th ed Cincinnati OH American Conference of Governmental Industrial Hygienists 1986 p 451

from HSDB

Oxalate production by molds infecting maize silage are believed to have caused intoxication in a horse OxalatesHumphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 200

from HSDB

Symptoms Local Conjunctivitis corneal damage gangrenous ulcerations of skin Inhalation Irritation of respiratorytract ulceration of mucous membranes epistaxis headache nausea vomiting muscular irritability weaknessalbuminuria Swallowing Burning amp corrosion of the mouth esophagus stomach nausea amp vomiting withhematemesis abdominal pain diarrhea bloody stool numbness amp tingling of fingers amp toes muscular irritabilitytetany convulsions shock oliguria anuria hematuria albuminuria cardiac irregularities amp circulatory collapse

ITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

Studies with both unlabeled and labeled agents in humans have provided both strong circumstantial and directevidence for the existence of minor pathways of carbohydrate metabolism and of oxidative dealkylation anddehalogenation reactions in drug biotransformations that link xylitol glycerol polysorbate emulsifiersmethoxyflurane and possibly dichloroacetate to endogenous oxalate production Because urinary oxalate is nowconsidered to be a critical factor in stone formation and because it is increasingly accepted that 80shy90 of urinaryoxalate is produced endogenously it is now possible to formulate pathways that link oxalate production with dietarymacronutrients Therapeutic modifications of diet in vivo hormonal milieu and intracellular metabolic controls inrelation to endogenous oxalate production may provide new forms of treatment for urolithiasis Abstract PubMed

Conyers RA et al Clin Chem 36 (10) 1717shy30 (1990)

from HSDB

Patients with chronic renal failure who undergo hemodialysis experience accelerated atherosclerosis and prematuredeath Since the end metabolite oxalic acid accumulates in plasma in proportion to the severity of renal failure astudy was conducted to determine whether sodium oxalate (0 to 300 uM) is an endothelial toxin and thereforemight enhance atherogenesis Exposure to uremic levels of oxalate (greater than 30 uM) for 9 to 28 days depressedendothelial cell replication by 33 to 84 (mean + or shy standard deviation 54 + or shy 157 n = 17 experiments p= 0002) In contrast replication of fibroblasts exposed to 200 uM oxalate for 45 days was not inhibited The

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4461

contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4561

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4961

may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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inhibitory effect of oxalate on endothelial cell replication was both dose and time dependent (both p lt 00001) andwas first detected 3 to 7 days after the initial exposure to oxalate Further the inhibitory effect was fully reversibleupon removal of oxalate but only if exposure was limited to 5 days or less Sodium salts of other carboxylic acids(citric succinic glyoxylic and malonic 200 uM) as well as hydrochloric acid (200 uM) did not suppress endothelialcell replication Oxalate also inhibited endothelial cell migration but had no effect on basal thrombin induced orarachidonate induced prostacyclin production by endothelial cells Exposure of endothelial cells to sodium oxalate(200 uM) for as little as 24 hr a time period sufficient to induce delayed transient inhibition of replication notdetectable until approximately 1 week after exposure inhibited incorporation of (3)Hshyleucine into protein by 40 (p=0009) It was concluded that sodium oxalate acts as a uremic toxin inhibiting endothelial cell replication andmigration functions which may be important for constitutive inhibition of atherosclerosis Abstract PubMed

Levin RI et al Arteriosclerosis 10 (2) 198shy207 (1990)

from HSDB

The efficacy of long term therapy with allopurinol 100 mg 3 times daily in the prevention of recurrent calciumoxalate calculi of the kidney was evaluated in a double blind placebo controlled study in 60 patients After the studythe placebo group had 634 fewer calculi whereas the allopurinol group had 812 fewer calculi During the studyperiod the mean rate of calculous events was 026 per patient per year in the placebo group and 012 in theallopurinol group When the treatment groups were compared by actuarial analysis the allopurinol group was foundto have a significantly longer time before recurrence of calculi It was concluded that allopurinol is effective in theprevention of calcium oxalate stones in patients with hyperuricosuria Abstract PubMed

Ettinger B et al N Engl J Med 315 (27) 1386shy9 (1986)

from HSDB

The effects of long term treatment with oral potassium citrate 30shy80 meqday were studied in 37 patients (aged28shy68 yr) with idiopathic hypocitraturic calcium oxalate neprholithiasis for a period of 2 yr Potassium citratetreatment produced a sustained increase in urinary citrate excretion from initially low values to within normal limitsUrinary pH rose significantly and was maintained at 65 to 70 Along with these changes urinary saturation ofcalcium oxalate declined significantly to normal limits Further stone formation ceased in 892 of patients duringtreatment and the stone formation rate declined from 211 to 028 stonespatient yr It was concluded thatpotassium citrate represents a rational treatment for patients with idiopathi hypocitraturic calcium oxalatenephrolithiasis because it provides physiologic correction (restoration of normal urinary citrate) and inhibits newstone formation Calcium oxalate Abstract PubMed

Pak CYC Fuller C Ann Intern Med 104 (Jan) 33shy7 (1986)

from HSDB

A 145 year old boy with end stage renal failure due to familial primary hyperoxaluria underwent cadaver donor renaltransplantation The graft function was stable for a period of 22 months while he was on conventionalimmunosuppressive therapy (prednisolone and azathioprine) and additional oral pyridoxine phosphorus andmagnesium supplementation When Cyclosporin A was introduced instead of azathioprine the blood levels ofoxalate rose and oxalate deposition in the renal tubuli became evident These observations suggest thatCyclosporin A interferes with oxalate metabolism and therefore should be given with utmost caution in patientswith primary hyperoxaluria Abstract PubMed

Drachman R et al Child Nephrol Urol 9 (1shy2) 90shy2 (1988)

from HSDB

A 34 year old woman developed a crystalline retinopathy after 2 yr of inhalational abuse of methoxyflurane Afterthe woman developed renal failure a renal biopsy showed multiple birefringent crystals in the renal tubular lumensepithelial cells and interstitium compatible with calcium oxalate Multiple bright yellow white crystals weredeposited throughout the retina and at the level of the retinal pigment epithelium with a retinal arterial andperiarterial predilection Calcium oxalate Abstract PubMed

Novak MA et al Retina 8 (4) 230shy6 (1988)

from HSDB

During the last 4 yr 27 specimens of calcium oxalate nephrolithiasis in patients receiving longshyterm treatment withpiridoxilate a drug composed of an equimolar combination of glyoxylate and pyridoxine were collected The meanduration of treatment was 36 yr (range 4 months to 10 yr) and the mean daily dose was 580 mg piridoxilate which

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4561

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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contained 160 mg glyoxylate Calculi often recurred with an average number of 99 per patient and an openoperation shock wave lithotripsy or percutaneous nephrolithotomy was required in 22 patients (81) Oxalateexcretion was 727 + or shy 246 umole per day while on the drug and 382 + or shy 201 umole per day after the drug waswithdrawn Whewellite was the major component of calculi in all cases but the stones exhibited a peculiarmorphological arrangement with multiple small indentations and a fine mamillary structure Freshly voided urinespecimens contained unusual crystals which on infrared spectroscopy were composed of calcium oxalate trihydratea variety of crystal never observed previously in human urine Piridoxilate induced calcium oxalate nephrolithiasis isa new variety of metabolic drug induced nephrolithiasis Observations suggest that even large doses of pyridoxinemay be unable to prevent the excessive production of oxalate from glyoxylate Abstract PubMed

Daudon M et al J Urol 138 (2) 258shy61 (1987)

from HSDB

OXALATE MAY UPSET CALCIUM METABOLISM SUFFICIENTLY TO INTERFERE WITH MILKPRODUCTION AND BONE GROWTH IN LACTATING AND PREGNANT ANIMALS OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

MOST COMMON EFFECT OF OXALATES IS TO CAUSE KIDNEY DAMAGE OWING TO BLOCKING OFTUBULES BY CRYSTALS OF CALCIUM OXALATE OXALATES MAY CRYSTALLIZE OUT IN BRAINTISSUE amp CAUSE SYMPTOMS OF PARALYSIS amp OTHER DISORDERS OF CENTRAL NERVOUS SYSTEMOXALATES MAY LEAD TO BREAKDOWN OF RED BLOOD CELLS OXALATES

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 258

from HSDB

FIRST SYMPTOMS INCLUDE DULLNESS AND LOSS OF APPETITE HEAD IS LOWERED amp ANIMAL ISUNWILLING TO KEEP WITH FLOCK WITH ACUTE POISONING THERE MAY BE SALIVATION AND NASALDISCHARGE WITH PROGRESSIVE WEAKNESS RAPID SHALLOW BREATHING AND COLLAPSEOXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

AT POST MORTEM AN INVARIABLE FINDING IS ACCUMULATION OF CALCIUM OXALATE CRYSTALS INKIDNEYS AND URINARY TRACT LUNGS MAY BE DARK RED amp FILLED WITH BLOOD AND THERE MAY BEPETECHIAL OR LARGER HEMORRHAGES OXALATE

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

TOXIC DOSE OF OXALIC ACID TO THE DOG IS ABOUT 1 G amp TO THE CAT ABOUT 02 GClarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

IN ATTEMPTS TO INDUCE OXALATE POISONING IN HORSES 2 DOSES OF 454 G OF OXALIC ACIDSODIUM OXALATE OR AMMONIUM OXALATE HAD TO BE GIVEN WITHIN 24 HR OR 200 G OFAMMONIUM OXALATE DAILY FOR 5 DAYS IN ORDER TO KILL THE ANIMALS DOSE OF 200 G OF OXALICACIDDAY FOR 8 DAYS INDUCED NONshyFATAL POISONING

Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

DOSE OF 340 G OF HALOGETON OR 900 G OF GREASEWOOD BOTH OXALATEshyCONTAINING PLANTSIS A LETHAL DOSE FOR A FASTING SHEEP

1218 NonshyHuman Toxicity Excerpts

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

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141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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Clarke EG and M L Clarke Veterinary Toxicology Baltimore Maryland The Williams and Wilkins Company 1975 p 259

from HSDB

MALE amp FEMALE LONGshyEVANS RATS MAINTAINED FOR 70 DAYS ON DIETS CONTAINING 25 amp 50OXALIC ACID HAD DECR BODY WT amp RESTRICTED GROWTH RATES 50 DEPRESSED ABSOLUTEORGAN WT BUT ENHANCED ORGANBODY WT RATIO VAGINAL SMEARS INDICATED DISRUPTEDESTROUS CYCLES Abstract PubMed

GOLDMAN ET AL RES COMMUN CHEM PATHOL PHARMACOL 18 (2) 369 (1977)

from HSDB

SIGNIFICANT REDN IN THYROID WT 24 HR THYROID UPTAKE OF (125)I amp PLASMA RADIOACTIVITYOBSERVED WITH INCR IN PLASMA THYROIDshySTIMULATING HORMONE IN LONGshyEVANS RATSINGESTING DIETARY 50 OXALIC ACID 50 CAN LEAD TO HYPOTHYROIDISM INCR INTRIIODOTHYRONINE Abstract PubMed

GOLDMAN M DOERING GJ TOXICOL APPL PHARMACOL 48 (3) 409 (1979)

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 WTWT OXALIC ACID ADAPTEDANIMALS TOLERATED OXALATE WITHOUT SIGNS OF TOXICITY HOWEVER 2 OTHER SHEEP DIEDBECAUSE THEY WERE UNABLE TO TOLERATE THE INFUSION OF INCR AMT OF SODIUM OXALATEINTO THE RUMENS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5)1173 (1977)

from HSDB

Oxalis cernua (Oxalis pesshycaprae Bermuda buttercup soursob) has caused chronic oxalate poisoning in sheep inAustralia This plant often causes intoxication in sheep grazing in olive orchards in Sardinia where it grows freelyCalves fed exclusively on milk from cows given this plant have been reported to have developed catarrhal enteritismarked eosinophilia submucosal intestinal hemorrhages folliculitis of the mesenteric lymph nodes and nephrosiswith crystalline deposits Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 253

from HSDB

The oxalate content of plants is highest at the leafy stage of growth and plants which are normally not dangerousto stock may become so at certain times of the year Halogeton may contain as much as 345 of oxalatemangels up to 12 and soursob 59 (dry weight) Unfortunately most oxalateshycontaining plants are very palatableto stock Although sugar beet tops are harmful to animals when fresh they can be fed without ill effect once thetops have wilted This is said to be due to conversion of harmful soluble salts into harmless insoluble ones duringthe process but there is contrary evidence on this point and the question is complicated by the fact that oxalate isnot the only toxic substance in sugar beet tops they can contain lethal quantities of nitrate Oxalates

Humphreys DJ Veterinary Toxicology 3rd ed London England Bailliere Tindell 1988 p 199

from HSDB

2 SHEEP amp 1 COW CHANGED FROM ALFALFA HAY TO DIETS WITH 12 OXALIC ACID 10shyFOLD ampGREATER INCR IN IN VITRO RATE OF OXALATE METAB BY RUMINAL MICROBES OXALATEDEGRADING CAPACITY NEGLIGIBLE IN CELLshyFREE RUMINAL FLUID OF ADAPTED SHEEP BUT ASSOCWITH FRACTIONS WITH BACTERIAL CELLS Abstract PubMed

ALLISON ET AL J ANIM SCI 45 (5) 1173 (1977)

from HSDB

Ten of 100 mature ewes were afflicted with acute oxalate toxicosis within 40 hours after being temporarily pennedin a lot that contained considerable growing Rumex crispus (curly dock) Clinical signs of toxicosis included excesssalivation tremors ataxia and recumbency Affected ewes were markedly hypocalcemic and azotemic Oxalatecrystals were not observed in urine Gross postmortem lesions were minimal and nondiagnostic in 2 ewes that diedperacutely but perirenal edema andrenal tubular degeneration were clearly observable in ewes euthanatizedon the

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5061

hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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third day of toxicosis Diagnosis of oxalate toxicosis was confirmed by histopathologic findings Samples of Rumexspp contained 66 to 111 oxalic acid on a dry weight basis a concentration comparable with that in other oxalatecontaining plants that have caused acute oxalate toxicosis Abstract PubMed

Panciera RJ et al J Am Vet Med Assoc 196 (12) 1981shy4 (1990)

from HSDB

In a period of 21 days six subcutaneous injections of calcium chloride and dibutyloxalate solution produced aflecklike polymorphous cornealopacity and a slight stromal clouding in chinchilla rabbits as seen with the slit lampIn front of the endothelium opaque structures could be seen with the specular microscope New Zealand whiterabbits showed only a diffuse corneal clouding Light microscopy revealed a reticular alteration of the cytoplasm inthe basal layers of the corneal epithelium primarily in chinchilla bastard rabbits In central corneal areas an irregularstructure of the basal epithelial cells and a papilla like alteration of the stromalshyepithelial border was seen In theendotheliuman increased formation of vacuoles was observed in both species Scanning electron microscopydemonstrated endothelial cell loss Dibutyl oxalate Abstract PubMed

Weber U et al Graefes Arch Clin Exp Ophthalmol 224 (5) 447shy51 (1986)

from HSDB

Deposition of calcium oxalate is responsible for the pathologic manifestations of oxalosis and may contribute tomultiorgan dysfunction in uremia and to the progression of renal damage after renal failure is established A ratmodel of oxalosis using a single intravenous injection of sodium oxalate 03 mmolkg body weight in rats has beendeveloped Polarized light microscopy and section freeze dry auto radiography were used to identify (14)Cshyoxalatewithin the renal parenchyma and in extrarenal organs (14)Cshyoxalate crystals under 3 u in length were identifiedwithin one min of injection in proximal tubule lumens Section freeze dry autoradiography showed occasional minutecrystals within glomeruli heart lung and liver at one hr In contrast to concentrative cellular uptake demonstrated inrat renal cortical slices in vitro intracellular accumulation of (14)Cshyoxalate could not be detected in vivo Within thefirst 24 hr renal oxalate retention reached amaximum of 25 + or shy 4 of the injected dosegm kidney compared toa maximum of only 7 + or shy 3 gm kidney after ip administration Although less than 1 dosegm kidneyremained after one week crystal fragments were scattered throughout the cortex and medulla often surrounded byfoci of interstitial nephritis The retention of crystals in kidney and other body organs following iv oxalate provides amodel of oxalosis which stimulates pathophysiologic events in a variety of clinical situations characterized bytransiently or persistently elevated serum oxalate Abstract PubMed

Blumenfrucht MJ et al J Urol 135 (6) 1274shy9 (1986)

from HSDB

LDLo Dog oral 1000 mgkgITII Toxic and Hazardous Industrial Chemicals Safety Manual Tokyo Japan The International Technical Information Institute1988 p 388

from HSDB

1219 NonshyHuman Toxicity Values

Oxalic acid (OA) a metabolite of ethylene glycol was selected for testing in the RACB protocol based on thebiological activity of the parent compound Data collected on body weights clinical signs amp foodwaterconsumption during the doseshyrangeshyfinding segment (Task 1) were used to set concns for the main study (Task 2) at005 010 amp 02 OA in drinking water These concns reduced water consumption in the middle amp high dosegroups by approx 25 amp yielded calculated consumption estimates of nearly =89 162 amp 275 mg OAkgdayThere were no adverse clinical signs One female died in both the low amp middle dose groups At 02 OA thenumber of litterspair was reduced by 5 amp the pup weight adjusted for litter size was reduced by nearly =4 sireamp dam weights were not affected during Task 2 For the last litter born in Task 2 body weights amp pup number wererecorded for the controls amp 01 amp 02 OA groups there were no treatmentshyrelated changes in pup survival orweight gain to postnatal day 14 Because a modest degree of effect seen at the top dose group in Task 2 wasidentified only after summing all the Task 2 litter data it was predicted that the single litter produced in Task 3

12110 National Toxicology Program Reports

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would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 47: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4761

would be insufficient to help determine the affected sex Thus the last litter from the control amp high dose animalswere reared for testing in Task 4 amp Task 3 was not conducted After the Task 4 mice were weaned 10 F0 micefrom the control amp 02 groups were killed amp necropsied No changes were seen in body or organ weights fromfemales For males the only significant effect was a 19 decr in prostate weight at 02 OA Total calcium levelsin blood were measured for 10 mice of each sex in the control amp 02 OA groups the control level of 94 mgdlwas unchanged by OA consumption In the Task 4 oneshywk mating trial there was a 20 reduction in the number oflive pupslitter delivered by the 02 OA group No other differences were observed After 7 days of vaginal lavagethe F1 mice were killed amp necropsied While terminal body weight was unchanged in either sex female kidneyweight (adjusted for body weight) was increased by 10 in the OAshytreated females There were no other changes inorgan weights The of abnormal sperm forms increased from 22 in controls to 40 in the 02 OA groupSerum calcium levels in either sex were unchanged from control levels of 79 mgdl In summary in the F0 miceOA at these levels reduced water consumption amp reduced the number of litterspair adjusted pup weight ampprostate weight in the absence of detected somatic organ changes In F1 mice an incr in kidney weight occurredconcomitant with a reduction in the number of live pupslitter amp increased abnormal sperm forms If the kidneyweight effect is the result of reduced water consumption then it can be concluded that Oxalic Acid is a reproductivetoxicant in Swiss mice at concns that reduce parental water consumption but that cause few other somatic effects

Department of Health amp Human ServicesNational Institute of Environmental Health Sciences National Toxicology ProgramOxalic Acid (CAS 144shy62shy7) Reproduction and Fertility Assessment in CDshy1 Mice When Administered in Drinking Water NTPStudy No RACB84064 (September 1985) Available from as of August 14 2002 httpntpniehsnihgovindexcfmobjectid=0847F35Ashy0850shyD1E7shyB02ED4DDD150F990

from HSDB

122 Ecological Information

Oxalic acid is naturally contained as the potassium or calcium salt in plants vegetables human urine animal urineand kidney stones It is also the product of the metabolism of many molds Oxalic acid may be released to theenvironment in tobacco smoke automobile exhaust rendering in waste streams from pulp bleaching and byphotochemical oxidations of anthropogenic compounds during long range transport If released to soil oxalic acidunder environmental conditions (pH 5shy9) will be in the form of the oxalate ion (pKa1 and pKa2 of 125 and 428respectively) and is expected to leach in soil Photolysis is expected to be an important fate process the daytimepersistence of oxalic acid on soil surfaces is not expected to exceed a few hours Based upon screeningbiodegradation tests biodegradation in soil is expected to be important If released to water oxalic acid will notvolatilize adsorb to sediment bioconcentrate in aquatic organisms oxidize or hydrolyze The predominant aquaticfate processes are expected to be photolysis in surface waters and aerobic and anaerobic biodegradation Ifreleased to the atmosphere removal from air via wet deposition dry deposition and photolysis is likely to occurExposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater In occupationalsettings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin contact (SRC)

from HSDB

1221 Environmental FateExposure Summary

MANY PLANTS CONTAIN OXALATE NOTABLY RHUBARB LEAVES DIEFFENBACHIA OR DUMBCANEBEETS SPINACH MANGOLD HALOGETON SORREL PURSLANE DOCK GREASEWOOD amp RUSSIANTHISTLE OXALATES

Gosselin RE RP Smith HC Hodge Clinical Toxicology of Commercial Products 5th ed Baltimore Williams and Wilkins1984 p IIIshy326

from HSDB

PLANTS CONTAINING OXALATES ATRIPLEX SPECIES BETA VULGARIS CALANDRINIA SPECIESEMEX AUSTRALIS ENCHYLAENA TOMENTOSA HALOGETON GLOMERATUS OXALIS SPECIESPORTULACA SPECIES RHEUM RHAPONTICUM RUMEX SPECIES SALSOLA KALI SARCOBATUS

1222 Natural Occurring Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4861

VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 4961

may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5061

hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5161

from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

1152015 oxalic acid | C2H2O4 shy PubChem

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Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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VERMICULATUS THRELKELDIA PROCERIFLORA TRIANTHEMA SPECIES FROM TABLE OXALATESClarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 260

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) and these frequently colonize lakes and other aquaticenvironments Furthermore oxylate may constitute as much as 50 of the dry weight of some plant organs servingboth an excretory and a storage function by chelating and precipitating excess calcium ions(3) It is the product ofthe metabolism of many molds(1) Several species of Penicillium and Aspergillus convert sugar into calcium oxylatewith 90 yields under optimum conditions(1) It also occurs in human and animal urine and the calcium salt is amajor constituent of kidney stones(2)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

Oxalic acid may be released to the environment as emissions from rendering tobacco smoke(1) and automobileexhaust(2) Oxalic acid may be produced in the atmosphere by photochemical oxidations of anthropogeniccompounds during long range transport(3) Oxalic acid has been identified in pulp kraft mill effluents(4shy6) thereforeit may be released to the environment in waste streams resulting from pulp bleaching(SRC) The estimatedemission rate of oxalic acid in the South East Air Basin CA is 87 kgday(7)

(1) Graedel TE et al Atmospheric Chemical Compounds NY Academic Press p 346 (1986) (2) Kawamura K Kaplan IREnviron Sci Technol 21 105shy10 (1987) (3) Satsumabayashi H Kurita H Atmospheric Environ 24A 1443shy50 (1990) (4) Suntio LRet al Chemosphere 17 1249shy90 (1988) (5) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (6) Kringstad KPLindstrom K Environ Sci Technol 18 236Ashy48A (1984) (7) Grosjean D et al Measurements of Organic Acids in the South EastAir Basin State of California Air Resources Board NTIS PB89shy145411 p 43 (1988)

from HSDB

1223 Artificial Sources

TERRESTRIAL FATE An estimated Koc value of 5(1SRC) for oxalic acid indicates high mobility in soil(2) andoxalic acid has been detected in groundwater(3) Volatilization from moist soils is not expected to be rapid basedupon a low Henrys Law constant Several screening studies indicate rapid biodegradation of oxalic acid(4shy8)Although these studies are not specific to soil media they suggest that oxalic acid will readily biodegrade in soilThe oxalic acid concn in another study was determined to decrease from 30 mgkg on a soil surface to about 6mgkg 540 cm below the soil surface(3) which suggests that biodegradation may have occurred(SRC) Photolysis isexpected to be an important terrestrial fate process the daytime persistence of oxalic acid on soil surfaces is notexpected to exceed a few hours(9)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 7shy415shy15 to 15shy32 (1990) (2) Swann RL et al Res Rev 85 17shy28 (1983) (3) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (4)Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Grosjean D et al Measurements ofOrganic Acids in the South Coast Air Basin ARBshyRshy88375 PB89shy145441) Gov Rep Announce Index (US) 89(9) Abstr No921946 (1989)

from HSDB

AQUATIC FATE Several screening studies(4shy8) and grab sample tests(9) indicate that under aerobic andanaerobic conditions oxalic acid will readily biodegrade in aquatic ecosystems Based on an experimental HenrysLaw constant of 14X10shy10 atmshycu mmole at 25 deg C(2) oxalic acid is expected to be essentially nonvolatile fromwater(1) Adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processesfor oxalic acid in water systems Based on pKa1 and pKa2 values of 125 and 428(3) respectively oxalic acid willexist primarily as the oxalate ion under environmental conditions (pH 5shy9SRC) Aquatic oxidation is not likely to bean important fate process based on a halfshylife of 285 yrs in water under continuous sunlight(3SRC) Oxalic acid

1224 Environmental Fate

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5261

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

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contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5461

13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

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16 Biological Test Results

from PubChem

161 BioAssay Results

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17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

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may react slowly in water with photochemically produced OH radicals but it is expected to be removed rapidly fromsurface water by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a few hours(10)

(1) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy10 15shy415shy15 to 15shy32 (1990) (2) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (3) Buxton GV et al J Phys Chem Ref Data17(2) 517shy882 (1988) (4) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (5) Heukelekian H Rand MC J WaterPollut Contr Assoc 29 1040shy53 (1955) (6) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (7) Takemoto et alSuishitsu Odaku Kenkyu 4 80shy90 (1981) (8) Young et al J Water Pollut Contr Fed 40 354shy68 (1968) (9) Smith RL OremlandRS Appl Environ Microbiol 46 106shy113 (1983) (10) Grosjean D et al Measurements of Organic Acids in the South Coast AirBasin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

ATMOSPHERIC FATE Based on a measured vapor pressure of 23410shy4 mm Hg at 25 deg C(2) oxalic acid isexpected to exist almost entirely in the vapor phase in the ambient atmosphere(3) In the vapor phase oxalic acidin the ambient atmosphere is very slowly degraded by reaction with photochemically formed hydroxyl radicals thehalfshylife for this reaction in air can be estimated to be about 223 days(1) Oxalic acid in the ambient atmospheremay react slowly with OH radicals but it is removed rapidly by photolysis the daytime persistence of oxalic acid isnot expected to exceed a few hours(4) Based on its high water solubility removal from air via wet deposition islikely to occur(4SRC) Oxalic acid may also be removed from air via dry deposition with 11 of the total depositionbeing dry deposition(4)

(1) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (2) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley16 618shy36 (1981) (3) Eisenreich SJ et al Environ Sci Technol 15 30shy8 (1981) (4) Grosjean D et al Measurements of OrganicAcids in the South Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Six tests at oxalic acid initial concns of 33 to 10 ppm exhibited 75 to 202 BODT over an incubation period of 5days in an aerobic screening study using sewage inoculum(1) A 78 and 555 BODT for oxalic acid was measuredunder aerobic conditions over a period of 5 days in screening tests at 20 deg C using sewage inoculum(2) Oxalicacid at initial concns of 000375 00375 and 0375 ppm exhibited 95 99 and 100 degradation respectively inan aerobic screening study at 25 deg C using sewage inoculum(3) In another screening study using sewageinoculum 68 and 64 BODT were measured for oxalic acid at initial concns of 10 and 20 ppm respectively over a5 day incubation period(4) An 89 BODT was measured for oxalic acid (10 ppm initial concn) in an aerobicscreening study using sewage inoculum at 195shy205 deg C over an incubation period of 5 days(5)

(1) Gaffney PE Heukelekian H Sew Indust Wastes 30 503 (1958) (2) Heukelekian H Rand MC J Water Pollut Contr Assoc 291040shy53 (1955) (3) Madsen EL Alexander M Appl Environ Microbiol 50 342shy9 (1985) (4) Takemoto et al Suishitsu OdakuKenkyu 4 80shy90 (1981) (5) Young et al J Water Pollut Contr Fed 40 354shy68 (1968)

from HSDB

Ultimate anaerobic biodegradation rates were determined in a marinewatersediment grab sample taken from a saltmarsh in Palo Alto CA to be 041 092 and 076day which correspond to anaerobic degradation halfshylives of 17075 and 09 days respectively In another marinewatersediment grab sample from Big Soda Lake NV anaerobicbiodegradation rates of 0004 and 022day were determined which correspond to halfshylives of 173 and 315 daysrespectively Using the same method (14CO2 evolution GC) ultimate anaerobic biodegradation rates of 055 031545 173 and 196day (halfshylives of 126 223 013 04 and 035 days respectively) were measured infreshwatersediment grab samples taken from Searsville Lake Palo Alto CA In a freshwatersediment grabsample taken from Lake Tahoe CA ultimate anaerobic biodegradation rates were measured to be 001 and013day which correspond to respective halfshylives of 69 and 53 day(1)[(1) Smith RL Oremland RS Appl EnvironMicrobiol 46 106shy13 (1983)] Full text PMC239274 Abstract PubMed

from HSDB

1225 Biodegredation

The rate constant for the vaporshyphase reaction of oxalic acid with photochemically produced hydroxyl radicals can beestimated to be 72X10shy14 cu cmmoleculeshysec at 25 deg C which corresponds to an atmospheric halfshylife of about223 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1SRC) Acids are generally resistent to

1226 Abiotic Degredation

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

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from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5261

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5361

contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5461

13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

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15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5761

References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5861

16 Biological Test Results

from PubChem

161 BioAssay Results

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5961

17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6061

1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 50: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

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hydrolysis(4) therefore oxalic acid is not expected to hydrolyze in aquatic environments Based on dissociationconstant values pKa1 and pKa2 of 125 and 428(1) respectively oxalic acid is expected to exist as an ion underenvironmental conditions (pH 5shy9) The aquatic oxidation rate for the reaction of hydroxyl radicals in water with theoxalate ion has been experimentally determined to be 77X10+6 Lmoleshys at pH 6(1) Based on this rate and ahydroxyl radical concn of 1X10shy17 moleL in water under continuous sunlight(3) the halfshylife for the aquaticoxidation of oxalic acid can be estimated to be 285 yrs(SRC) Oxalic acid may react slowly with OH in water but itis removed rapidly by direct photolysis the daytime persistence of oxalic acid is not expected to exceed a fewhours(5)

(1) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988) (2) Atkinson R Environ Toxicol Chem 7 435shy42 (1988) (3) Mill Tet al Science 207 886shy7 (1980) (4) Lyman WJ et al Handbook of Chemical Property Estimation Methods Washington DCAmer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (5) Grosjean D et al Measurements of Organic Acids in theSouth Coast Air Basin ARBshyRshy88375 PB89shy145411 Gov Rep Announce Index (US) 89(9) Abstr No 921946 (1989)

from HSDB

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the BCF for oxalic acid can be estimated to be approximately 06(SRC) and therefore should not beexpected to bioconcentrate in aquatic organisms(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1227 Bioconcentration

Based on an average experimental water solubility of 220000 mgL at 25 deg C(1) and a regression derivedequation(2) the Koc for undissociated oxalic acid can be estimated to be approximately 5 This Koc value indicatesthat oxalic acid will have very high mobility in soil(3) therefore adsorption to soil and sediment may not be animportant fate process Based on pKa1 and pKa2 values of 125 and 428(4) respectively oxalic acid will existprimarily as the oxalate ion under environmental conditions (pH 5shy9) No experimental data are available todetermine whether the oxalate ion will adsorb to sediment or soil more strongly than its estimated Koc valueindicates(SRC)

(1) Yalkowsky SH et al Arizona Data Base of Water Solubility (1989) (2) Lyman WJ et al Handbook of Chemical PropertyEstimation Methods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990) (3) Swann RL et al ResRev 85 17shy28 (1983) (4) Buxton GV et al J Phys Chem Ref Data 17 517shy882 (1988)

from HSDB

1228 Soil AdsorptionMobility

Based on an experimental Henrys Law constant of 14X10shy10 atmshycu mmole at 25 deg C(1) oxalic acid isessentially nonvolatile from water(2)

(1) Gaffney JS et al Environ Sci Technol 21 519shy24 (1987) (2) Lyman WJ et al Handbook of Chemical Property EstimationMethods Washington DC Amer Chem Soc pp 4shy9 5shy4 5shy10 7shy4 7shy5 15shy15 to 15shy32 (1990)

from HSDB

1229 Volatilization from WaterSoil

GROUNDWATER Oxalic acid was detected at a site in Germany at a concn of about 1 mgkg in groundwater 610to 640 cm below the surface however it was not detected in groundwater 640 to 670 cm below the surface(1)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

12210 Water Concentrations

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5161

from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5261

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5361

contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5461

13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5561

14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5661

15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5761

References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5861

16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5961

17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6061

1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 51: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5161

from HSDB

RAINSNOW Oxalic acid was detected in two samples of mist collected in Los Angeles CA on June 9 1983 andJune 11 1983 at concns of 233 and 4 uM respectively(1) In the same study oxalic acid was detected in 4 fogsamples in June of 1983 at concns ranging from 173 to 187 uM at an average concn of 18 uM(1) Also oxalic acidwas detected in 8 rain samples collected in Los Angeles CA in August and September of 1983 at concns rangingfrom 28 to 207 uM at an average concn of 159 uM(1)

(1) Steinberg S et al Intern J Environ Anal Chem 19 251shy60 (1985)

from HSDB

Oxalic acid has been qualitatively detected in pulp mill effluents(1) Oxalic acid was identified in two prebleachingspent liquors of kraft pulp mill effluents at concns of 05 and 6 gton of pulp(2) It was detected during kraft pulpbleaching at a concn of 130 gton in a spent chlorination liquor and 590 gton in a spent alkali extraction liquor(3)Oxalic acid was identified in the automobile exhaust of a 1982 Toyota Corolla at a concn of 182 nmolecushym(4) Itwas also identified at a concn of 482 nmolecushym in automobile exhaust from a 1971 Mercedes Benz(4)

(1) Suntio LR et al Chemosphere 17 1249shy90 (1988) (2) Lindstrom K Osterberg F Environ Sci Technol 2 133shy8 (1986) (3)Kringstad KP Lindstrom K Environ Sci Technol 18 236Ashy48A (1984) (4) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12211 Effluents Concentrations

Oxalic acid was detected at concns ranging from 30 to 6 mgkg in soil 0 to 540 cm respectively below the surfaceat a site in Germany(1) Oxalic acid was identified in 2 soil samples taken from the UCLA campus (Los AngelesCA) at concns of 166 and 156 nmolg(2) Oxalic acid was detected in 2 fractions of bog sediment from the LosAngeles CA area at concns of 1410 (humic acid fraction) and 3350 (fulvic acid fraction) nmolg(2) Significantconcns of oxylate (dissolved plus particulate) were present in sediments taken from a diversity of aquaticenvironments ranging from 01 to 07 mmoll of sediment(3) These included pelagic and littoral sediments fromtwo freshwater lakes (Searsville Lake CA and Lake Tahoe CA) a hypersaline meromictic alkaline lake (Big SodaLake NV) and a south San Francisco Bay mud flat and salt marsh(3)

(1) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990) (2) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (3)Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12212 SedimentSoil Concentrations

URBANSUBURBAN Oxalic acid was the dominant species of dicarboxylic acids in the range C2shyC10 identified inthe Los Angeles CA ambient atmosphere(1) In June 1984 oxalic acid was detected in west Los Angeles air atconcns of 638 and 212 nmolcushym(1) Oxalic acid was detected in west Los Angeles ambient air in 6 samples at aconcn range of 340 to 865 nmolcushym and an average concn of 54 nmolcushym in October 1984(1) In the samestudy during October of 1984 it was detected in 2 samples taken from downtown Los Angeles at concns of 660and 831 nmolcushym(1) Oxalic acid was also detected in greenhouse air at UCLA (Los Angeles CA) in Decemberof 1984 at concns of 131 and 283 nmolcushym(1) Oxalic acid was detected in airborne aerosols above Takasakiand Karuizawa Japan at average concns of 51 and 38 ngcushym respectively during July of 1986(2) Oxalic acidwas detected at a concn of approximately 3 ngcushym in airborne particulate matter in a suburban area in Japan(3)In September of 1985 oxalic acid was detected in the ambient atmosphere of Claremont CA in 12 of 12 samplestaken at a concn range of lt012 to 094 ugcushym(4)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmos Environ 24A 1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)

from HSDB

12213 Atmospheric Concentrations

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5261

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5361

contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5461

13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

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14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

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httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5661

15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

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1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5761

References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5861

16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5961

17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

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1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6061

1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 52: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5261

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the sap of the plant as the potassium or calcium salt(2) Oxalic acid was qualitatively detected in rawcassava (Manihot esculenta Crantz) which is one of the major staple foods of the tropics(1) Gari and Farine(Farinha demandioca) both products of cassava were determine to be 004 and 02 oxalic acid respectively(1)

(1) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (2) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983)

from HSDB

12214 Food Survey Values

OXALATE CONTENT OF PLANTS IS HIGHEST AT LEAFY STAGE OF GROWTH amp PLANTS WHICH ARENORMALLY NOT DANGEROUS TO STOCK MAY BECOME SO CERTAIN TIMES OF YR HALOGETONMAY CONTAIN 345 OF OXALATE MANGELS UP TO 12 amp SOURSOB 59 (DRY WT) OXALATE

Clarke M L D G Harvey and D J Humphreys Veterinary Toxicology 2nd ed London Bailliere Tindall 1981 p 258

from HSDB

Oxalic acid is present in many plants and vegetables notably in those of the Oxalis and Rumex families where itoccurs in the leaves roots rhizomes and sap of the plant as the potassium or calcium salt(1shy2) For examplewaterlilies and duckweed are oxylateshycontaining plants(3) Furthermore oxylate may constitute as much as 50 ofthe dry weight of some plant organs serving both an excretory and a storage function by chelating and precipitatingexcess calcium ions(3) Oxylate concns ranged from 01 to 50 in several plant species that are potential sourcesof the oxylates in sediments of Searsville Lake CA Lake Tahoe CA Big Soda Lake NV and a south SanFrancisco Bay mud flat and salt marsh(3)

(1) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp Co Inc p 991 (1983) (2) Bernales CA et al KirkshyOthmerEncycl Chem Tech 3rd NY Wiley 16 618shy36 (1981) (3) Smith RL Oremland RS Appl Environ Microbiol 46 106shy13 (1983)

from HSDB

12215 Plant Concentrations

Oxalic acid occurs in human and animal urine and the calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12216 Animal Concentrations

Oxalic acid was identified in greenhouse dust and dust from downtown Los Angeles CA at a concns of 2330 and2510 nmolg respectively(1)

(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987)

from HSDB

12217 Other Environmental Concentrations

Exposure of the general population to oxalic acid is expected to occur through consumption of foods in which it isnaturally contained inhalation of contaminated air and consumption of contaminated groundwater(1shy7SRC) Inoccupational settings exposure to oxalic acid may occur through inhalation of vapors and through eye and skin

12218 Probable Routes of Human Exposure

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5361

contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5461

13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5561

14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5661

15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5761

References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5861

16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5961

17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6061

1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 53: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5361

contact(SRC)(1) Kawamura K Kaplan IR Environ Sci Technol 21 105shy10 (1987) (2) Satsumabayashi H Kurita H Atmospheric Environ 24A1443shy50 (1990) (3) Yokouchi Y Ambe Y Atmos Environ 20 1727shy34 (1986) (4) Grosjean D Atmos Environ 22 1637shy48 (1988)(5) Dougan J et al J Sci Food Agric 34 874shy84 (1983) (6) Windholz M et al The Merck Index 10th ed Rahway NJ Merck amp CoInc p 991 (1983) (7) Cordt T Kussmaul H Vom Wasser 74 287shy98 (1990)

from HSDB

NIOSH (NOHS Survey 1972shy1974) has statistically estimated that 705215 workers are potentially exposed to oxalicacid in the USA(1) NIOSH (NOES Survey 1981shy1983) has statistically estimated that 130128 workers arepotentially exposed to oxalic acid in the USA(2)

(1) NIOSH National Occupational Hazard Survey (NOHS) (1974) (2) NIOSH National Occupational Exposure Survey (NOES)(1983)

from HSDB

Oxalic acid calcium salt is a major constituent of kidney stones(1)(1) Bernales CA et al KirkshyOthmer Encycl Chem Tech 3rd NY Wiley 16 618shy36 (1981)

from HSDB

12219 Body Burdens

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5461

13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5561

14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5661

15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5761

References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5861

16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5961

17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6061

1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 54: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5461

13 Literature

Depositor Provided PubMedCitations 3531 records

from PubChem

131 Depositor Provided PubMed Citations

from PubChem

132 NLM Curated PubMed Citations

Giuseppe Messina Giovanni M Sechi Loreno Lorenzoni Giovanni Chessa Method of preparation of oxalic acidesters and amides US Patent US4981963 issued July 1971

from DrugBank

133 Synthesis References

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5561

14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5661

15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5761

References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5861

16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5961

17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6061

1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 55: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5561

14 Patents

from PubChem

141 DepositorshySupplied Patent Identifiers

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5661

15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5761

References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5861

16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5961

17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6061

1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 56: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5661

15 Biomolecular Interactions and Pathways

from PubChem

151 Protein Bound 3shyD Structures

from PubChem

152 Biosystems and Pathways

DrugBank Interactions 1 of 3

Target Protoshyoncogene tyrosineshyprotein kinase Src More information

General Function Involved in protein kinase activity

Gene Name SRC

GenBank Gene AL133293

GenBank Protein 10635153

1 Overington JP AlshyLazikani B Hopkins AL How many drug targets arethere Nat Rev Drug Discov 2006 Dec5(12)993shy6 Pubmed

2 Imming P Sinning C Meyer A Drugs their targets and the nature and

153 DrugBank Interactions

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5761

References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5861

16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5961

17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6061

1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 57: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5761

References number of drug targets Nat Rev Drug Discov 2006 Oct5(10)821shy34Pubmed

3 Berman HM Westbrook J Feng Z Gilliland G Bhat TN Weissig HShindyalov IN Bourne PE The Protein Data Bank Nucleic Acids Res2000 Jan 128(1)235shy42 Pubmed

from DrugBank

DrugBank Interactions 2 of 3

Transporter Solute carrier organic anion transporter family member 2B1

Action inhibitor

General Function Involved in anion transporter activity

Specific FunctionMediates the Na(+)shyindependent transport of organic anions such astaurocholate the prostaglandins PGD2 PGE1 PGE2 leukotriene C4thromboxane B2 and iloprost

Gene Name SLCO2B1

GenBank Gene AB026256

GenBank Protein 5006263

References

Kobayashi D Nozawa T Imai K Nezu J Tsuji A Tamai I Involvement ofhuman organic anion transporting polypeptide OATPshyB (SLC21A9) in pHshydependent transport across intestinal apical membrane J Pharmacol Exp Ther2003 Aug306(2)703shy8 Epub 2003 Apr 30 Pubmed

from DrugBank

DrugBank Interactions 3 of 3

Transporter Solute carrier family 22 member 8

Action substrate

General Function Carbohydrate transport and metabolism

Specific Function

Plays an important role in the excretiondetoxification of endogenous andexogenous organic anions especially from the brain and kidney Involved in thetransport basolateral of steviol fexofenadine Transports benzylpenicillin(PCG) estroneshy 3shysulfate (E1S) cimetidine (CMD) 24shydichloroshyphenoxyacetate (24shyD) pshyaminoshyhippurate (PAH) acyclovir (ACV) andochratoxin (OTA)

Gene Name SLC22A8

GenBank Gene AF097491

GenBank Protein 4378059

References

Race JE Grassl SM Williams WJ Holtzman EJ Molecular cloning andcharacterization of two novel human renal organic anion transporters (hOAT1and hOAT3) Biochem Biophys Res Commun 1999 Feb 16255(2)508shy14Pubmed

from DrugBank

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5861

16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5961

17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6061

1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 58: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5861

16 Biological Test Results

from PubChem

161 BioAssay Results

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5961

17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6061

1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 59: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 5961

17 Classification

171 Ontologies

from MeSH

1711 MeSH Tree

from ChEBI

1712 ChEBI Ontology

from Gene Ontology

1713 Gene Ontology Biological Process

from Gene Ontology

1714 Gene Ontology Molecular Function

from KEGG

1715 KEGG Metabolite

from WIPO

1716 WIPO IPC

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

CLICK TO LOAD

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6061

1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 60: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6061

1 OXALIC ACID from HSDB 1100 httptoxnetnlmnihgovcgishybinsissearchrdbs+hsdbterm+rn+rel+144shy62shy7

2 Oxalic Acid from DrugBank DB03902 httpwwwdrugbankcadrugsDB039023 OXALIC ACID from ILOshyICSC 0529 httpwwwiloorgdynicscshowcarddisplayp_card_id=0529

PeershyReview Status 24112009 Validated4 Oxalic acid from NIOSHshyPocketGuide npgd0474 httpwwwcdcgovnioshnpgnpgd0474html5 OXALIC ACID from OSHA Occupational Chemical DB 270

httpwwwoshagovchemicaldatachemResulthtmlRecNo=2706 Oxalic acid from CAMEO Chemicals CBNOAA00000000008966

httpcameochemicalsnoaagovchemical89667 EPA Chemical Data Report 144shy62shy7 httpwwwepagovcdr8 DrugBank DB03902 interaction 1 httpwwwdrugbankcadrugsDB03902targets9 DrugBank DB03902 interaction 2 httpwwwdrugbankcadrugsDB03902transporters10 DrugBank DB03902 interaction 3 httpwwwdrugbankcadrugsDB03902transporters11 oxalic acid from NJDOH RTK Hazardous Substance List 1445

httpnjgovhealtheohrtkwebdocumentsfs1445pdfNew Jersey Department of Health Right to Know Hazardous Substance List

12 ECHA 205shy634shy3 httpechaeuropaeu13 ECHA 208shy932shy1 httpechaeuropaeu14 ECHA 213shy950shy8 httpechaeuropaeu15 REGULATION (EC) No 12722008 607shy006shy00shy81 httpwwwreachshy

complianceeuenglishcomplianceCLPCLPshyInitialshyVersionhtml16 Wiki 772 httpenwikipediaorgwikiOxalic_acid17 FDASPL Indexing data 9E7R5L6H31

httpwwwfdagovForIndustryDataStandardsStructuredProductLabelingucm377913htm18 The Cambridge Structural Database CCDC 929767 httpwwwccdccamacukpagesHomeaspx

The Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

19 The Cambridge Structural Database CCDC 929768 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

20 The Cambridge Structural Database CCDC 929769 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

21 The Cambridge Structural Database CCDC 929770 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

22 The Cambridge Structural Database CCDC 929771 httpwwwccdccamacukpagesHomeaspxThe Cambridge Structural Database provides access to 3D structures of molecules determined experimentally using diffractiontechniques

23 Oxalic acid from NIST RI for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm24 Oxalic acid from NIST GCshyMS for MUBZPKHOEPUJKRshyUHFFFAOYSAshyN httpwwwnistgovsrdnist1acfm25 PubChem httppubchemncbinlmnihgov

Data deposited in or computed by PubChem26 Oxalic Acid from MeSH 68019815 httpwwwncbinlmnihgovmesh6801981527 MeSH Tree from MeSH DescTree httpwwwnlmnihgovmeshmeshhomehtml

MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for PubMed28 ChEBI Ontology from ChEBI OBO httpwwwebiacukchebiuserManualForwarddoChEBI20Ontology

The ChEBI Ontology is a structured classification of the entities contained within ChEBI

29 Metabolite from KEGG br08001 httpwwwgenomejpdbgetshybinwww_bgetbritebr08001

18 Information Sources

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems

Page 61: Oxalic Acid _ C2H2O4 - PubChem

1152015 oxalic acid | C2H2O4 shy PubChem

httppubchemncbinlmnihgovcompoundoxalic_acidsection=ChemicalshyandshyPhysicalshyProperties 6161

Compounds with biological roles30 biological process from Gene Ontology GO_ROOT_486550

httpamigogeneontologyorgamigotermGO0008150The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the biological processes domain shown hererepresents recognized series of events or a collection of molecular events with a defined beginning and end Mutantphenotypes often reflect disruptions in biological processes The terms below apply to the geneprotein target(s) tested bythe BioAssay

31 molecular function from Gene Ontology GO_ROOT_486552httpamigogeneontologyorgamigotermGO0003674The Gene Ontology (GO) httpwwwgeneontologyorg project provides a controlled vocabulary of terms for describing thefunctions of gene products and is divided into three domains Each term in the molecular functions domain shown hererepresent a proteins jobs or abilities These may include transporting things around binding to things holding things togetherand changing one thing into another This is different from the biological processes the gene product is involved in whichinvolve more than one activity The terms below apply to the geneprotein target(s) tested by the BioAssay

32 International Patent Classification 2015 from WIPO IPC httpwwwwipointclassificationsipcThe World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a hierarchicalsystem of language independent symbols for the classification of patents and utility models according to the different areas oftechnology to which they pertain

33 Reducing Agents from MeSH 68019163 httpwwwncbinlmnihgovmesh6801916334 NCBI LinkOut httpwwwncbinlmnihgovprojectslinkout

LinkOut is a service that allows one to link directly from NCBI databases to a wide range of information and services beyondNCBI systems