SLB-IL111 for Fatty Acid Methyl Ester (FAME) Applications (1 MB )

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sigma-aldrich.com 595 North Harrison Road, Bellefonte, PA 16823-0048 USA Tel: (800) 247-6628 (814) 359-3441 Fax: (800) 447-3044 (814) 359-3044 sigma-aldrich.com Technical Report SLB-IL111 for Fatty Acid Methyl Ester (FAME) Applications Michael D. Buchanan, Katherine K. Stenerson, and Leonard M. Sidisky The extremely polar SLB™-IL111 column exhibits the highest polarity of any GC phase, allowing it to resolve key cis/trans fatty acid methyl ester (FAME) isomers that cannot be resolved on other columns. It also provides an alternative selectivity for FAME applications typically performed on highly polar cyanopropyl siloxane columns. Its maximum temperature of 270 °C is very impressive for such an extremely polar column. The chromatograms shown here demonstrate the utility of the SLB-IL111 as a great column choice for the analysis of FAMEs. Fatty Acid Chemistry The most commonly analyzed fatty acids consist of C4-C24+ hydrocarbon chains with a carboxyl group (-COOH) at one end. Many types of fatty acids exist, including: Saturated = all single bonds between carbon atoms. Unsaturated = at least one double bond. Polyunsaturated = at least two double bonds. cis = bonds on either side of the double bond are on the same side. trans = bonds on either side of the double bond are on opposite sides. Omega 3 = initial double bond located directly after the third carbon atom as measured from the methyl end. Omega 6 = initial double bond located directly after the sixth carbon atom as measured from the methyl end. It is important for food manufacturers to report the levels of each type of fatty acid, as each has known or suspected health effects. Figure 1 shows the structures of several varieties of fatty acids. Derivatization of Fatty Acids to Methyl Esters GC can be used to analyze fatty acids, either as free fatty acids or as fatty acid methyl esters. The primary reasons to analyze fatty acids as fatty acid methyl esters include: In their free, underivatized form, fatty acids may be difficult to analyze, because these highly polar compounds tend to form hydrogen bonds, leading to adsorption issues. Reducing their polarity may make them more amenable for analysis. To distinguish between the very slight differences exhibited by unsaturated fatty acids, the polar carboxyl functional groups must first be neutralized. This then allows column chemistry to perform separations by degree of unsaturation, position of unsaturation, and even the cis vs. trans configuration of unsaturation. The esterification of fatty acids to FAMEs is performed using an alkylation derivatization reagent. Methyl esters offer excellent stability, and provide quick and quantitative samples for GC analysis. As shown in Table 1, the esterification reaction involves the condensation of the carboxyl group of the fatty acid and the hydroxyl group of an alcohol. Esterification is best done in the presence of an acidic catalyst (such as boron trichloride). The catalyst protonates the oxygen atom of the carboxyl group, making the acid much more reactive. Nucleophilic attack by an alcohol then yields an ester with the loss of water. The catalyst is removed with the water. The alcohol used determines the alkyl chain length of the resulting esters; the use of methanol will result in the formation of methyl esters whereas the use of ethanol will result in ethyl esters. (1,2) Table 1. Typical Esterification Procedure 1. Weigh 1-25 mg of sample into a 5-10 mL Micro Reaction Vessel. 2. Add 2 mL BCl 3 -Methanol, 12% w/w. A water scavenger (such as 2,2-dimethoxypropane) can be added at this point. 3. Heat at 60 °C for 5-10 minutes. Derivatization times may vary, depending on the specific compound(s) being derivatized. 4. Cool, then add 1 mL water and 1 mL hexane. 5. Shake the reaction vessel (it is critical to get the esters into the non- polar solvent). 6. After allowing the layers to settle, carefully transfer the upper (organic) layer to a clean vial. Dry the organic layer either by passing through a bed of anhydrous sodium sulfate during the transfer step to the clean vial, or by adding anhydrous sodium sulfate to the clean vial and then shaking. 7. Proceed to the appropriate GC analysis procedure. Figure 1. Fatty Acid Structures Saturated Fatty Acid (C5:0) cis Unsaturated Fatty Acid (C9:1n5c) trans Unsaturated Fatty Acid (C5:1n3t) An Omega 3 Fatty Acid

Transcript of SLB-IL111 for Fatty Acid Methyl Ester (FAME) Applications (1 MB )

sigma-aldrich.com

595 North Harrison Road, Bellefonte, PA 16823-0048 USATel: (800) 247-6628 (814) 359-3441 Fax: (800) 447-3044 (814) 359-3044

sigma-aldrich.com

Technical Report

SLB-IL111 for Fatty Acid Methyl Ester (FAME) Applications

Michael D. Buchanan, Katherine K. Stenerson, and Leonard M. Sidisky

The extremely polar SLB™-IL111 column

exhibits the highest polarity of any GC

phase, allowing it to resolve key cis/trans

fatty acid methyl ester (FAME) isomers that

cannot be resolved on other columns. It

also provides an alternative selectivity for

FAME applications typically performed on

highly polar cyanopropyl siloxane columns.

Its maximum temperature of 270 °C is very

impressive for such an extremely polar

column. The chromatograms shown here demonstrate the utility of the

SLB-IL111 as a great column choice for the analysis of FAMEs.

Fatty Acid ChemistryThe most commonly analyzed fatty acids consist of C4-C24+

hydrocarbon chains with a carboxyl group (-COOH) at one end. Many

types of fatty acids exist, including:

● Saturated = all single bonds between carbon atoms.

● Unsaturated = at least one double bond.

● Polyunsaturated = at least two double bonds.

● cis = bonds on either side of the double bond are on the same side.

● trans = bonds on either side of the double bond are on opposite sides.

● Omega 3 = initial double bond located directly after the third carbon

atom as measured from the methyl end.

● Omega 6 = initial double bond located directly after the sixth carbon

atom as measured from the methyl end.

It is important for food manufacturers to report the levels of each type of

fatty acid, as each has known or suspected health eff ects. Figure 1 shows

the structures of several varieties of fatty acids.

Derivatization of Fatty Acids to Methyl EstersGC can be used to analyze fatty acids, either as free fatty acids or as fatty

acid methyl esters. The primary reasons to analyze fatty acids as fatty acid

methyl esters include:

● In their free, underivatized form, fatty acids may be diffi cult to analyze,

because these highly polar compounds tend to form hydrogen bonds,

leading to adsorption issues. Reducing their polarity may make them

more amenable for analysis.

● To distinguish between the very slight diff erences exhibited by

unsaturated fatty acids, the polar carboxyl functional groups must

fi rst be neutralized. This then allows column chemistry to perform

separations by degree of unsaturation, position of unsaturation, and

even the cis vs. trans confi guration of unsaturation.

The esterifi cation of fatty acids to FAMEs is performed using an alkylation

derivatization reagent. Methyl esters off er excellent stability, and provide

quick and quantitative samples for GC analysis. As shown in Table 1, the

esterifi cation reaction involves the condensation of the carboxyl group

of the fatty acid and the hydroxyl group of an alcohol. Esterifi cation

is best done in the presence of an acidic catalyst (such as boron

trichloride). The catalyst protonates the oxygen atom of the carboxyl

group, making the acid much more reactive. Nucleophilic attack by

an alcohol then yields an ester with the loss of water. The catalyst is

removed with the water. The alcohol used determines the alkyl chain

length of the resulting esters; the use of methanol will result in the

formation of methyl esters whereas the use of ethanol will result in ethyl

esters. (1,2)

Table 1. Typical Esterifi cation Procedure

1. Weigh 1-25 mg of sample into a 5-10 mL Micro Reaction Vessel.

2. Add 2 mL BCl3-Methanol, 12% w/w. A water scavenger (such as

2,2-dimethoxypropane) can be added at this point.

3. Heat at 60 °C for 5-10 minutes. Derivatization times may vary,

depending on the specifi c compound(s) being derivatized.

4. Cool, then add 1 mL water and 1 mL hexane.

5. Shake the reaction vessel (it is critical to get the esters into the non-

polar solvent).

6. After allowing the layers to settle, carefully transfer the upper (organic)

layer to a clean vial. Dry the organic layer either by passing through a

bed of anhydrous sodium sulfate during the transfer step to the clean

vial, or by adding anhydrous sodium sulfate to the clean vial and then

shaking.

7. Proceed to the appropriate GC analysis procedure.

Figure 1. Fatty Acid Structures

Saturated Fatty Acid (C5:0)

cis Unsaturated Fatty Acid (C9:1n5c)

trans Unsaturated Fatty Acid (C5:1n3t)An Omega 3 Fatty Acid

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GC Column Polarity ScaleA visual depiction of our GC column polarity scale is shown in Figure 2,

showing the relationship of several columns to one another. The

positions/maximum temperatures of several non-ionic liquid capillary

GC columns are shown to the left of the scale. Listed to the right of the

scale are the positions/maximum temperatures of Supelco® ionic liquid

capillary GC columns. All polarity number values are relative to both

squalane (0 on the scale) and SLB-IL100 (100 on the scale). This simple

but useful scale allows multiple columns to be quickly compared.

Detailed information concerning the scientifi c basis used to generate

this scale can be found at sigma-aldrich.com/il-gc

Figure 2. GC Column Polarity Scale, Positions/Maximum

Temperatures of Columns

Standard: 37-Component FAME MixTo properly identify fatty acid composition, standards of known reference

must be used. One such standard is the Supelco 37-Component FAME

Mix (47885-U). This standard contains methyl esters of fatty acids ranging

from C4 to C24, including key monounsaturated and polyunsaturated

fatty acids; making this standard very useful to food analysts since it can

be used to identify fatty acids in many diff erent types of foods. This mix

was analyzed on the SP™-2560, a popular cyanopropyl siloxane column,

and the SLB-IL111. Optimized chromatograms are shown in Figure 3.

Observations are:

● Baseline and Peak Shape. Both columns produced chromatograms

with minimal bleed and sharp peaks. Signal-to-noise ratios for the later

eluting peaks are slightly better with the SLB-IL111 column.

● Run Time. Dispersive interaction is weaker on the SLB-IL111; therefore,

overall analysis time is shorter than on the SP-2560 (22 minutes

compared to 26 minutes).

● Selectivity. Dipole-induced dipole interactions are stronger on the

SLB-IL111 than on the SP-2560. These interactions result in increased

retention of polarizable analytes (those with double bonds) relative to

non-polarizable analytes. In fact, the higher the degree of unsaturation

(the greater the number of double bonds), the stronger the retention

is. Overall, this results in alternative selectivity to the SP-2560. A

comparison of elution orders and elution locations are summarized in

Table 2 and Table 3, respectively.

Table 2. Comparison of Elution Orders

Peak ID Isomer SP-2560* SLB-IL111*

19 C18:2n6c C18:0 C20:021 C18:3n6 C20:0 C21:022 C18:3n3 C20:0 C21:025 C20:2 C21:0 C22:026 C20:3n6 C22:0 C23:027 C20:3n3 C22:0 C23:033 C22:2 C23:0 C24:0* On this column, this isomer elutes after this saturated FAME.

Table 3. Comparison of Elution Locations

Peak ID Isomer SP-2560 SLB-IL111

28 C20:4n6 Right after C23:0 Right before C24:029 C20:5n3 Right after C24:0 >1 min. after C24:032 C22:1n9 Between C22:0 and C23:0 Right before C23:034 C22:6n3 ~2.5 min. after C24:0 ~3.2 min. after C24:0

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Figure 3. 37-Component FAME Mix

SP-2560 Conditions column: SP-2560, 100 m x 0.25 mm I.D., 0.20 μm (24056) oven: 140 °C (5 min.), 8 °C/min. to 180 °C, 4 °C/min. to 210 °C, 20 °C/min. to 250 °C (7 min.) inj.: 250 °C det.: FID, 250 °C carrier gas: hydrogen, 40 cm/sec injection: 1 μL, 100:1 split liner: 4 mm I.D., cup design sample: Supelco 37-Component FAME Mix (47885-U), analytes at concentrations indicated in methylene chlorideSLB-IL111 Conditions column: SLB-IL111, 100 m x 0.25 mm I.D., 0.20 μm (29647-U) oven: 140 °C (5 min.), 8 °C/min. to 180 °C, 5 °C/min. to 260 °C det.: FID, 260 °C

All other conditions the same as those used for the SP-2560

1. Butyric Acid Methyl Ester (C4:0) at 4 wt % 2. Caproic Acid Methyl Ester (C6:0) at 4 wt % 3. Caprylic Acid Methyl Ester (C8:0) at 4 wt % 4. Capric Acid Methyl Ester (C10:0) at 4 wt % 5. Undecanoic Acid Methyl Ester (C11:0) at 2 wt % 6. Lauric Acid Methyl Ester (C12:0) at 4 wt % 7. Tridecanoic Acid Methyl Ester (C13:0) at 2 wt % 8. Myristic Acid Methyl Ester (C14:0) at 4 wt % 9. Myristoleic Acid Methyl Ester (C14:1) at 2 wt %

10. Pentadecanoic Acid Methyl Ester (C15:0) at 2 wt % 11. cis-10-Pentadecenoic Acid Methyl Ester (C15:1) at 2 wt % 12. Palmitic Acid Methyl Ester (C16:0) at 6 wt % 13. Palmitoleic Acid Methyl Ester (C16:1) at 2 wt % 14. Heptadecanoic Acid Methyl Ester (C17:0) at 2 wt % 15. cis-10-Heptadecenoic Acid Methyl Ester (C17:1) at 2 wt % 16. Stearic Acid Methyl Ester (C18:0) at 4 wt % 17. Oleic Acid Methyl Ester (C18:1n9c) at 4 wt % 18. Elaidic Acid Methyl Ester (C18:1n9t) at 2 wt %

SLB-IL111

SP-2560

10 20Min

19. Linoleic Acid Methyl Ester (C18:2n6c) at 2 wt % 20. Linolelaidic Acid Methyl Ester (C18:2n6t) at 2 wt % 21. γ-Linolenic Acid Methyl Ester (C18:3n6) at 2 wt % 22. -Linolenic Acid Methyl Ester (C18:3n3) at 2 wt % 23. Arachidic Acid Methyl Ester (C20:0) at 4 wt % 24. cis-11-Eicosenoic Acid Methyl Ester (C20:1n9) at 2 wt % 25. cis-11,14-Eicosadienoic Acid Methyl Ester (C20:2) at 2 wt % 26. cis-8,11,14-Eicosatrienoic Acid Methyl Ester (C20:3n6)

at 2 wt % 27. cis-11,14,17-Eicosatrienoic Acid Methyl Ester (C20:3n3)

at 2 wt % 28. Arachidonic Acid Methyl Ester (C20:4n6) at 2 wt % 29. cis-5,8,11,14,17-Eicosapentaenoic Acid Methyl Ester

(C20:5n3) at 2 wt % 30. Heneicosanoic Acid Methyl Ester (C21:0) at 2 wt % 31. Behenic Acid Methyl Ester (C22:0) at 4 wt % 32. Erucic Acid Methyl Ester (C22:1n9) at 2 wt % 33. cis-13,16-Docosadienoic Acid Methyl Ester (C22:2)

at 2 wt % 34. cis-4,7,10,13,16,19-Docosahexaenoic Acid Methyl Ester

(C22:6n3) at 2 wt % 35. Tricosanoic Acid Methyl Ester (C23:0) at 2 wt % 36. Lignoceric Acid Methyl Ester (C24:0) at 4 wt % 37. Nervonic Acid Methyl Ester (C24:1n9) at 2 wt %

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Application: Trans FatsFatty acids in the cis confi guration are the dominant form in nature.

Correspondingly, enzymes have evolved to effi ciently digest and

metabolize them with a high degree of specifi city. Conversely, trans

fatty acids are relatively rare in nature. However, they have become

predominant synthetic additives to processed foods, especially fried

foods and baked goods, because they can increase the shelf life and

fl avor stability of foods containing them. It is now known that trans

fatty acids, formed by partial hydrogenation of vegetable oil, interfere

with natural metabolic process. Studies have linked their nutritional

contribution to be similar to that of saturated fatty acids, possibly

playing a role in the heightened risk of coronary artery disease. (3-5)

Because of this, consumer groups have pressured manufacturers and

restaurants for the elimination of trans fats. Many regulatory agencies

worldwide now require content labeling, to inform buyers of ‘trans fat’

levels of foods and some dietary supplements.

The analysis of nutritionally signifi cant C18 cis and trans fatty acids,

as their methyl esters requires the use of a highly polar column to

resolve the geometric positional isomers. The 100 m SP-2560 column is

extremely useful for this type of analysis. Based on the results seen with

analysis of the 37-component FAME mix, the SLB-IL111 was expected

to off er selectivity for this application that is complementary to the SP-

2560. To compare the two columns, a partially hydrogenated vegetable

oil (PHVO) sample containing various C18:1 geometric positional isomers

was analyzed on both. The PHVO extract was graciously provided by Dr.

Pierluigi Delmonte at the United States Food and Drug Administration

(US FDA). A trans fraction extract and a cis fraction extract, both prepared

from PHVO using an Ag-ion fractionation procedure, were also supplied

by Dr. Delmonte. The PHVO extract contains thirteen C18:1 trans FAME

isomers (from C18:14t to C18:116t), and thirteen C18:1 cis FAME

isomers (from C18:14c to C18:116c). Complete details of the PHVO

extract preparation and Ag-ion fractionation can be found in Reference 6.

The established AOCS method for determining fat content requires

an SP-2560 column to be operated with a 180 °C isothermal oven

temperature. (7) To determine the optimal oven temperature for these

analytes on the SLB-IL111, the PHVO extract was analyzed at several

diff erent oven temperatures. We determined that 168 °C isothermal

was optimal, the same temperature reported by Delmonte et al. as

being optimal for these analytes on this column. (6)

Once optimal conditions were established, the PHVO, trans fraction,

and cis fraction extracts were sequentially analyzed on each column.

Figure 4

shows the resulting chromatograms; on the SP-2560 at 180 °C

isothermal, the method-specifi ed oven temperature, and the SLB-IL111

at 168 °C isothermal, the experimentally-determined optimal oven

temperature. Following the completion of these analyses and a review

of Reference 6, several observations were made.

● Elution Temperature. Even at a lower oven temperature, analytes eluted

faster from the SLB-IL111 than the SP-2560. This is due to the higher

polarity of the SLB-IL111 phase.

● Elution Order. The SLB-IL111 resulted in a diff erent elution order than

that obtained with the SP-2560. This was predicted due to the diff erent

selectivities of the columns observed during the analysis of the

37-component FAME mix, and based on the data used to generate our

GC column polarity scale.

● C18:1 Isomers. The SLB-IL111 was able to provide resolution of

C18:115t from C18:19c, a separation not possible with the SP-2560.

Additionally, the SLB-IL111 off ered improved resolution of some

isomers that cannot be completely resolved with the SP-2560, such

as C18:110t from C18:111t, and the pair C18:113t/C18:114t

from other isomers.

● C18:2 Isomers. Delmonte et al. reported that the SLB-IL111 is able

to resolve C18:29c,11t from C18:27t,9c. These are the two most

abundant conjugated linoleic acid (CLA) isomers found in ruminant

fats. These two important isomers cannot be resolved using any

other GC column without fi rst performing time-consuming Ag-ion

fractionation. (6)

Based on the data presented here and the work reported by

Delmonte et al., it appears the SP-2560 and SLB-IL111 can be used in

a complementary fashion, to provide more complete and accurate

fatty acid identifi cation and composition information than currently

possible. It requires less time and labor to inject one extract on two

diff erent columns, than to perform Ag-ion fractionation of an extract

prior to injecting multiple fractions on a single column.

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Figure 4. PHVO Sample and cis/trans Fractions on SP-2560 and SLB-IL111

SP-2560 Conditions column: SP-2560, 100 m x 0.25 mm I.D., 0.20 μm (24056) oven: 180 °C isothermal inj.: 250 °C det.: FID, 250 °C carrier gas: hydrogen, 1 mL/min. injection: 1 μL, 100:1 split liner: 4 mm I.D., split liner with cup (2051001)

PHVO (trans fraction)

PHVO (cis fraction)

t4 t5

t6-8 t9

t10

t11

t12t13-14

t15 t16

c4-5c6-8

c9

c10

c11

c12

c13 c14 c15 c16

PHVO (trans fraction)

PHVO (cis fraction)

t4 t5

t6

t8-9t10

t11

t12t13-14

t15t16

t7

c4 c5c6-7

c8

c9

c10c11

c12

c13c15 c16

c14

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Min

PHVO total

t4 t5

t6-8 t9

t10

t11

t12t13-14

t15, c9

t16

c4-5

c6-8

c10

c11

c12

c14 c15 c16c13

PHVO total

t4

t6,c5

t8-9t10

t11t12,c6-7t15,c8

t13-14

t16

t7

c9

c10c11

c12

c13 c14

c15 c16t5c4

SLB-IL111 Conditions column: SLB-IL111, 100 m x 0.25 mm I.D., 0.20 μm (29647-U) oven: 168 °C isothermal

All other conditions the same as those used for the SP-2560. All peak IDs as labeled

6 sigma-aldrich.com/il-gc

Application: Edible OilsThe edible oil industry boasts revenue measured in the tens of billions

of dollars. As such, it can be subject to criminal acts of fraud aimed

at increasing profi ts. A GC fi ngerprinting technique can be used to

monitor product for adulteration (adding a cheaper, inferior oil to

boost the volume of a premium, higher priced oil), and also identify

the source of oils in unknown samples.

To properly identify an edible oil through pattern recognition, it

is necessary to have standards of known reference; such as, our

Characterized Reference Oils. These can be used as part of a quality

control program, providing an excellent means of standardizing

procedures and comparing results between facilities.

The esterifi cation of fatty acids to FAMEs is performed using an alkylation

derivatization reagent. Methyl esters off er excellent stability, and provide

quick and quantitative samples for GC analysis. The esterifi cation reaction

involves the condensation of the carboxyl group of the fatty acid and the

hydroxyl group of an alcohol. Esterifi cation is best done in the presence

of an acidic catalyst (such as boron trichloride). The catalyst protonates

the oxygen atom of the carboxyl group, making the acid much more

reactive. Nucleophilic attack by an alcohol then yields an ester with the

loss of water. The catalyst is removed with the water. The alcohol used

determines the alkyl chain length of the resulting esters; the use of

methanol will result in the formation of methyl esters, whereas the use of

ethanol will result in ethyl esters. (6,7)

Following derivatization, fi ve of our Characterized Reference Oils were

analyzed on the SLB-IL111. The resulting chromatograms are shown in

Figure 5. A 30 m column was selected because the higher resolution

provided by a longer column was not necessary for this application.

Additionally, the shorter column resulted in shorter run times. The %

compositions, based on peak areas, agree with those listed on the

Certifi cate of Analysis for each mix.

Figure 5. Characterized Reference Oils

column: SLB-IL111, 30 m x 0.25 mm I.D., 0.20 μm (28927-U) oven: 180 °C inj.: 250 °C det.: FID, 260 °C carrier gas: helium, 25 cm/sec injection: 1 μL, 50:1 split liner: 4 mm I.D., split type, cup design samples: characterized reference oils, methylated using BF3-Methanol prior to analysis

1. Lauric Acid Methyl Ester (C12:0) 2. Myristic Acid Methyl Ester (C14:0) 3. Palmitic Acid Methyl Ester (C16:0) 4. Palmitoleic Acid Methyl Ester (C16:1) 5. Stearic Acid Methyl Ester (C18:0) 6. Oleic Acid Methyl Ester (C18:1n9c) 7. Linoleic Acid Methyl Ester (C18:2n6c) 8. Linolenic Acid Methyl Ester (C18:3n3) 9. Arachidic Acid Methyl Ester (C20:0) 10. cis-11-Eicosenoic Acid Methyl Ester (C20:1)

3 4 5 6

Min

Canola Oil

Lard Oil

Palm Oil

Soybean Oil

Sunfl ower Seed Oil

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ConclusionThe extreme polarity of the SLB-IL111 phase, in combination with a

270 °C maximum temperature, makes the SLB-IL111 useful for several

FAME applications. Specifi cally:

● cis/trans FAME isomers: when paired with the SP-2560, provides

more complete and accurate fatty acid identifi cation/composition

information than currently possible

● FAME profi le fi ngerprinting of edible oils: provides great resolution and

peak shapes in a quick analysis

Additionally, the SLB-IL111 provides alternative selectivity to

cyanopropyl siloxane columns for other applications. The extremely

polar SLB-IL111 exhibits weaker dispersive interactions than less polar

phases; which, in the applications shown here, results in lower elution

temperatures and shorter analysis times.

References

1. W. W. Christie, “Gas Chromatography and Lipids” The Lipid Library, http://www.lipidlibrary.co.uk/GC_lipid/gc_lip.html (accessed Jun 26, 2008).

2. W. W. Christie, “Why I Dislike Boron Trifl uoride-Methanol” Lipid Technology (1994) 6, 66-68.

3. A. Ascherio and W. Willett, “Health Eff ects of Trans Fatty Acids” Am. J. Clin. Nutr. (1997) 66 (supplement), p. 1006S.

4. S. Stender and J. Dyerberg, “Infl uence of Trans Fatty Acids on Health” An-nals of Nutrition and Metabolism (2004) 48 (2), p. 61.

5. American Heart Association Web Page, http://www.americanheart.org/presenter.jhtml?identifi er= 1728 (accessed Jan. 4, 2006).

6. P. Delmonte, A-R.F. Kia, J.K.G. Kramer, M.M. Mossoba, L. Sidisky, and J.I. Rader, “Separation Characteristics of Fatty Acid Methyl Esters Using SLB-IL111, A New Ionic Liquid Coated Capillary Gas Chromatographic Column” Journal of Chromatography A 1218 (2011) p. 545.

7. AOCS Method Ce 1h-05, “Determination of cis-, trans-, Saturated, Monoun-saturated and Polyunsaturated Fatty Acids in Vegetable or Non-ruminant Animal Oils and Fats by Capillary GLC” AOCS Offi cial Methods (2005) Ameri-can Oil Chemists Society.

Ordering InformationDescription Cat. No.

SLB-IL111 Column 15 m x 0.10 mm I.D., 0.08 μm 28925-U

30 m x 0.25 mm I.D., 0.20 μm 28927-U

60 m x 0.25 mm I.D., 0.20 μm 28928-U

100 m x 0.25 mm I.D., 0.20 μm 29647-U

Supelco 37-Component FAME Mix 10 mg/mL (total wt.) in methylene chloride, 1 mL 47885-U

See Figure 3 for list of analytes and concentrations

Characterized Reference Oils Canola Oil, 1 g 46961

Coconut Oil, 1 g 46949

Corn Oil, 1 g 47112-U

Cottonseed Oil, 1 g 47113

Lard Oil, 1 g 47115-U

Linseed (Flaxseed) Oil, 1 g 47559-U

Menhaden Fish Oil, 1 g 47116

Olive Oil, 1 g 47118

Palm Oil, 1 g 46962

Peanut Oil, 1 g 47119

Saffl ower Oil, 1 g 47120-U

Soybean Oil, 1 g 47122

Sunfl ower Seed Oil, 1 g 47123

Derivatization Reagents BCl3-Methanol, 12% w/w, 20 x 1 mL 33353

BCl3-Methanol, 12% w/w, 20 x 2 mL 33089-U

BCl3-Methanol, 12% w/w, 400 mL 33033

BF3-Methanol, 10% w/w, 20 × 1 mL 33356

BF3-Methanol, 10% w/w, 19 × 2 mL 33020-U

BF3-Methanol, 10% w/w, 10 × 5 mL 33040-U

BF3-Methanol, 10% w/w, 400 mL 33021

Micro Reaction Vessels and Caps 5 mL Clear, with Hole Caps, 12 ea 33299

5 mL Clear, with Solid Caps, 12 ea 27039

5 mL Amber, with Hole Caps, 12 ea 27478-U

10 mL Clear, with Hole Caps, 12 ea 27479

Water Scavenger 2,2-Dimethoxypropane, 98%, 25 mL D136808-25ML

Sodium Sulfate, Anhydrous, >99.0% Granular, 500 g 239313-500G

Granular, 1 Kg 239313-1KG

Granular, 2.5 Kg 239313-2.5KG

Trademarks

SLB, SP, Supelco – Sigma-Aldrich Co. LLC

SLB-IL111

● Application: This extremely polar ionic liquid column was the

world’s fi rst commercial column to rate over 100 on our GC col-

umn polarity scale. As such, it has the most orthogonal selectivity

compared to commonly used non-polar and intermediate polar

columns, providing increased selectivity for polar and polarizable

analytes. Its temperature limit of 270 °C is very impressive for such

an extremely polar column. The 60 m version is excellent at resolv-

ing benzene and other aromatics in gasoline samples. The 100 m

version is suitable for detailed cis/trans FAME isomer analysis, and

is a great complementary column to the SP-2560. Launched in

2010.

● USP Code: None

● Phase: Non-bonded; proprietary

● Temperature Limits: 50 °C to 270 °C (isothermal or programmed)

Order/Customer Service (800) 325-3010 • Fax (800) 325-5052

Technical Service (800) 325-5832 • sigma-aldrich.com/techservice

Development/Custom Manufacturing Inquiries (800) 244-1173

Safety-related Information sigma-aldrich.com/safetycenter

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©2011 Sigma-Aldrich Co. All rights reserved. SIGMA, SAFC, SIGMA-ALDRICH, ALDRICH, FLUKA, and SUPELCO are trademarks belonging to Sigma-Aldrich Co. and its affiliate Sigma-Aldrich

Biotechnology, L.P. Sigma brand products are sold through Sigma-Aldrich, Inc. Sigma-Aldrich, Inc. warrants that its products conform to the information contained in this and other Sigma-Aldrich

publications. Purchaser must determine the suitability of the product(s) for their particular use. Additional terms and conditions may apply. Please see reverse side of the invoice or packing slip.

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