Chapter 5 - LIPIDS Triglycerides, Phospholipids, and Sterols.
5 lipids
13
Lipids
Transcript of 5 lipids
Lipids
Lipids
Complex
(hydrolysated)
-glycerides
(fats and oils)
- glycolipids
-phospholipids
- waxes
Simple
(nonhydrolysated)
-steroids
-terpenes
Unsaturated fatty acids
C17H33COOH C17H31COOHC17H29COOHC15H29COOHC19H31COOH
C17H33COOH
C17
H31
COOH
C17H29COOH
C15
H29
COOH
C19H31COOH
oleic
linolic
linoleic
palmitooleic
arachidonic
Saturated fatty acids
C15H31COOH C17H35COOHC11H23COOHC13H27COOHC19H39COOH
C15H31COOH
C17
H35
COOH
C11H23COOH
C13
H27
COOH
C19H39COOH
palmitic
stearic
lauric
myristic
arachidic
Waxes (alcohol + fatty acid)
H3C(CH
2)
14CH
2OHH
3C(CH
2)
29CH
2OH
H3C(CH
2)
14CH
2OH
H3C(CH
2)
29CH
2OH
OOH3C (CH2)14CH2 C15H31C
(CH2)29CH2 C C15H31H3C OO
Cetyl alcohol
Miritcyl alcohol
Cetylpalmitate
Miritcylpalmitate
C3H7COOHC17H33COOH
C3H7COOH
C17H33COOH
H3C (CH2)7 CH COOHCH (CH2)7
butiric acid
oleic acid
C C(CH2)7 COOH
(CH2)7H3C
H
HC C
(CH2)7 COOH(CH2)7H3C
H H
Trans-form
Oleic acid
Cis-form
Ellaidic acid
Isomerism
Lipids (glycerides)
Acidic hydrolysisTristearine
CH2
CH
OH
CH2 OH
OH OH CO
C17H35
OH CO
C17H35
OH CO
C17H35 CO
C17H35
CO
C17H35
CO
C17H35CH2
CH
O
CH2 O
O + 3 H2O
PropertiesAlkaline hydrolysis (saponification)
C15
H31
COOK
C15
H31
COOK
Solid soap
Liquid soap
CH2
CH
OH
CH2 OH
OH
CO
C17H35
CO
C17H35
CO
C17H35CH2
CH
O
CH2 O
O + 3 NaOH + C17H35COONa3
2C15
H31
COOH + MgO (C15
H31
COO)2Mg + H
2O2C
15H
31COOH +K
2CO
3 2C
15H
31COOK + CO
2 + H
2OC
17H
35COOH + NH
3 C
17H
35COONH
4
2C15
H31
COOH + MgO (C15
H31
COO)2Mg + H
2O
2C15
H31
COOH +K2CO
3 2C
15H
31COOK + CO
2 + H
2O
C17
H35
COOH + NH3 C
17H
35COONH
4
Acidic hydrolysis
H+H+
H+H+H+
H+
-3HOH
CH2
CH2
O
OO
CO
CO
COCHR1R2
R3
+ 3H2O
+ 3H2O
R1=C15H31 palmitic a. R.
R2=R3=C17H35 stearic a. R.
HydrationCH2
CH2
O
OO
CO
CO
COCHC17H33C17H33
C17H33
Ni t+ 3H2 Ni
Ni t
t Ni t
+ 3H2
Ni
Ni
t
t CH2
CH2
O
OO
CO
CO
COCHC17H35C17H35
C17H35
CH2
CH2
O
OO
CO
CO
CO RR
RCH
H2O H+
+ 3HOH H2O
H2O H+
H+ H2O H+
+ 3HOH
H2O
H2O
H+
H+
CH2
OH
CH2 OH
CH
OH
+ 3RCOOH
+ 3RCOOH
Test ReactionsCH2
CH2
O
OO
CO
CO
CO
CH3CH
CH(CH2)7
C17H33C17H33
CH (CH2)7
CH2
CH2
O
OO
CO
CO
CO
CH3CH
CH(CH2)7
C17H33C17H33
CH (CH2)7
KMnO4
KMnO4
KMnO4KMnO4
KMnO4
KMnO4
CH2
CH2
O
OO
CO
CO
CO
Br
BrCH3CH
CH(CH2)7
C17H33C17H33
CH (CH2)7
Br2Br2
CH2
CH2
O
OO
CO
CO
CO
CH3OHCH
OH
CH(CH2)7
C17H33C17H33
CH (CH2)7
(OH)2(OH)2
--H2O --H2O
--H2O--H2O
--H2O
--H2O
AlBr3
blue solution
OxidationH3C (CH2)7 CH COOHCH (CH2)7
ENZ.ENZ.
ENZ.ENZ.ENZ.
ENZ.
OH OHCOOHCH(CH2)7H3C CH (CH2)7
ENZ.ENZ.
ENZ.ENZ.ENZ.
ENZ.O
COOHCH(CH2)7H3COCH (CH2)7
1.
2.
1.
β-oxidation (in organizm)
OCH2
OHH3C C(CH2)x CH2
ENZ.ENZ.
ENZ.ENZ.ENZ.
ENZ. OOH
H3C C(CH2)xOH
OCH3C
Acetic acid
Peroxide Oxidation
R CH2 CH CH
OH ( - H2O)+
R CH CH CH
O2
R CH CH CH
HOH ( - OH)O O
R CH CH CH
O OH
R'
R'
R'
R'
R C + [CH CH - R']H
O
OH
C CH2 O
HR'
O2
R C + OH
O C CH2
O
HO
R'
Phospholipids.
Phosphotidilcholin (Lecitin)
