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Lipids
5 Maret 2013
Lipids
Lipids are
Biomolecules that contain fatty acids or a steroid
nucleus.
Soluble in organic solvents but not in water.
Named for the Greek word lipos, which means fat.
Extracted from cells using organic solvents.
Types of Lipids
The types of lipids containing fatty acids are
Waxes.
Fats and oils (triacylglycerols).
Glycerophospholipids.
Prostaglandins.
Not steroids, as they do not contain fatty acids.
Structures of Lipids
Fatty Acids
Fatty Acids
Fatty acids
Are long-chain
carboxylic acids.
Typically contain 12-18
carbon atoms.
Are insoluble in water.
Can be saturated or
unsaturated.
CLASSIFICATION AND
NOMENCLATURE
8
10
11
12
13
14
15
17
18
19
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BIOCHEMISTRY
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22
23
24
trans
(CH2)7 COOH
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26
kinks in
chain
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28
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Learning Check
Assign the melting points of 17C, 13C, and 69C
to the correct fatty acid. Explain.
stearic acid (18 C) saturated
oleic acid (18 C) one double bond
linoleic acid (18 C) two double bonds
30
Solution
Stearic acid is saturated and would have a higher
melting point than the unsaturated fatty acids.
Because linoleic has two double bonds, it would have
a lower mp than oleic acid, which has one double
bond.
stearic acid mp 69C saturated
oleic acid mp 13C
linoleic acid mp -17C most unsaturated
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33
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Learning Check
Write a fatty acid with 10 carbon atoms that is:
A. saturated
B. monounsaturated omega-3
C. monounsaturated omega-6
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Solution
Write a fatty acid with 10 carbon atoms that is:
A. saturated
CH3CH2CH2CH2CH2CH2CH2CH2CH2COOH
B. monounsaturated omega-3
CH3CH2CH=CHCH2CH2CH2CH2CH2COOH
C. monounsaturated omega-6
CH3CH2CH2CH2CH2CH=CHCH2CH2COOH
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Waxes
Waxes are
Esters of saturated fatty acids and long-chain alcohols.
Coatings that prevent loss of water by leaves of plants.
TABLE 17.2
Triacylglycerols
In a triacylglycerol,
Glycerol forms ester bonds with three fatty acids.
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Formation of a Triacylglycerol
glycerol
triacylglycerol
CH2
OH
HO C
O
(CH2)14CH3
CH
OH
HO C
O
(CH2)14CH3
HO C
(CH2)14CH3 CH2 O C
CH2
OH
O
(CH2)14CH3
O
CH O C
(CH2)14CH3
+ 3H2O
O
CH2 O C
(CH2)14CH3
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Olive Oil
Olive oil
Contains a high
percentage of oleic
acid, which is a
monounsaturated fatty
acid with one cis
double bond.
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Learning Check
What are the fatty acids in the following triacylglycerol?
O
CH2
(CH2)16CH3
O
CH
CH2
C (CH2)7CH CH(CH2)7CH3
O
C
(CH2)12CH3
43
Solution
O
CH2
(CH2)16CH3
O
CH
CH2
Stearic acid
C (CH2)7CH CH(CH2)7CH3
O
C
(CH2)12CH3
Oleic acid
Myristic acid
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Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Chemical Properties of
Triacylglycerols
49
Chemical Properties of
Triacylglycerols
The chemical reactions of triacylglycerols are similar
to those of alkenes and esters.
In hydrogenation, double bonds in unsaturated
fatty acids react with H2 in the presence of a Ni or
Pt catalyst.
In hydrolysis, ester bonds are split by water in the
presence of an acid, a base, or an enzyme.
50
Hydrogenation of Oils
The hydrogenation of oils
Adds hydrogen (H2) to the carbon atoms of double bonds.
Converts double bonds to single bonds.
Increases the melting point.
Produces solids such as margarine and shortening.
51
Copyright 2007 by Pearson Education, Inc Publishing as Benjamin Cummings
Hydrogenation
O
CH2
(CH2)5CH CH(CH2)7CH3
O
CH
CH2
Ni
C (CH2)5CH CH(CH2)7CH3
O
C
+ 3HO
2
(CH2)14CH3
O
glyceryl tripalmitoleate
(tripalmitolean)
CH
CH2
C (CH2)14CH3
O
C
(CH2)14CH3
glyceryl tripalmitate
(tripalmitin)
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Learning Check
(1) True or (2) False
A. There are more unsaturated fats in vegetable oils.
B. Vegetable oils have higher melting points than fats.
C. Hydrogenation of oils converts some cis-double
bonds to trans- double bonds.
D. Animal fats have more saturated fats.
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Solution
(1) True or (2) False
A. T There are more unsaturated fats in vegetable oils.
B. F Vegetable oils have higher melting points than fats.
C. T Hydrogenation of oils converts some cis-double
bonds to trans- double bonds.
D. T Animal fats have more saturated fats.
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Hydrolysis
In hydrolysis,
Triacylglycerols split into glycerol and three fatty acids.
An acid or enzyme catalyst is required.
O
CH2
CH
CH2
C
O
(CH2)14CH3
C (CH2)14CH3
H2O
+3
O
C
(CH2)14CH3
H+
CH2 OH
CH
OH
CH2
OH
+3
HO C
(CH2)14CH3
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Saponification
O
CH2 O C
(CH2)14CH3
O
CH O C
(CH2)14CH3
O
CH2 O C
(CH2)14CH3
+ 3NaOH
CH2 OH
CH OH
+ 3
CH2 OH
O
Na+ -O C
(CH2)14CH3
soap
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Learning Check
Write the product of the following reaction.
O
CH2
O C
O
(CH2)5CH CH(CH2)7CH3
CH
C (CH2)5CH
O
CH2
(CH2)5CH
CH(CH2)7CH3
H2
+3
Ni
CH(CH2)7CH3
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Solution
O
CH2
C
O
CH
C (CH2)14CH3
O
CH2
(CH2)14CH3
(CH2)14CH3
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Cholesterol
Cholesterol
Is the most abundant steroid in the body.
Has methyl CH3- groups, alkyl chain, and -OH
attached to the steroid nucleus.
CH3
CH3
CH3
CH3
CH3
HO
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An artery clogged by
cholesterol plaque
Copyright 2007 by Pearson Education, Inc.
Publishing as Benjamin Cummings
63
Cholesterol in Foods
Cholesterol is
Synthesized in
the liver.
Obtained from
foods.
Considered
elevated if
plasma
cholesterol
exceeds 200
mg/dL.
TABLE 17.4
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Steroid Hormones
low solubility in water
transported by proteins,
can pass through
membranes
Vitamin A and D
Isoprene is a common
precursor for sterols, Vitamin
D and Vitamin A
CH2=C(CH3)-CH=CH2
LIPID OXIDATION
Introduction
Oxidative deterioration of lipids containing any
number of carbon-carbon double bonds
Fatty acids
Cholesterol
Produces various primary and secondary byproducts that influence food quality
Oxidized foods can cause oxidative stress in
biological systems and cause diseases
Types of Rancidity
Hydrolytic rancidity
Lipase
Free fatty acids provide aroma
Oxidative rancidity
Radical oxidation
Aldehydes and other compounds provide aroma
Oxidative Rancidity
Part 1: Form lipid hydroperoxides
Part 2: Break down lipid hydroperoxides
Oxidative Rancidity
Initiation
A radical is formed
Propagation
Radicals react and transfer their unpaired electron
to other compounds
Termination
Two radicals combine to stop the reaction
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H H H
C C C C C
H H H
RH
R
H
.
Radical Migration
Addition of Oxygen
- Propagation R
+O2
.
ROO +RH
ROO
ROOH
+R
Termination
(2)
18:0
18:19
18:29,12
18:39,12,15
1
100
1200
2500
Peroxide value
Iodine Value
TBA analysis
Oxidative Stress
phenolic antioxidants
2. Function as being preferentially oxidized:
ascorbate
3. Chelating agents for free iron
4. Changing environments: packaging
5. Dietary modification of fatty acids, vitamin E
enrichment
Synthetic antioxidants
TBHQ
PG
Natural antioxidants
Flavone
Isoflavone
Epicatechin
Quercetin
Tocopherol
Sesamol
Ideal Antioxidants
No harmful physiological effects
Not contribute an objectionable flavor, odor,
or color to the product
Effective in low concentration
Fat soluble
Carry-through effect no destruction during
processing
Readily available
Economical
Non-absorbable by the body