Chapter 17 Lipids

17.4
Chemical Properties
of Triacylglycerols

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 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.
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Hydrogenation of Glyceryl
Trioleate

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Hydrogenation of Oils
The hydrogenation of oils
 converts double bonds to single bonds
 adds hydrogen (H2) to the carbon atoms of double
bonds
 increases the melting point
 produces solids such as margarine and shortening

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 Learning Check
What product(s) is obtained from the complete
hydrogenation of glyceryl trioleate?

1) glycerol and 3 oleic acids

2) glyceryltristearate
3) glycerol and 3 stearic acids

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 Solution
What product(s) is obtained from the complete
hydrogenation of glyceryl trioleate?

2) glyceryltristearate

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Olestra, A Fat Substitute
Olestra is
 used in foods as an artificial fat
 sucrose linked by ester bonds to several long-chain
fatty chains
 not broken down in the intestinal tract

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 Cis and Trans Fatty Acids
Unsaturated fatty acids can be
 Cis with bulky groups on the same side of C═C
CH3─ (CH2)5 (CH2)7─ COOH cis

C═C
H H
 Trans have bulky groups on opposite sides of C═C
CH3─ (CH2)5 H

C═C trans
H (CH2)7─ COOH

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 Trans Fatty Acids and
Hydrogenation
Trans fatty acids
 are formed during hydrogenation when cis double
bonds are converted to trans double bonds
 in the body behave like saturated fatty acids
 are estimated to make up 2 to 4% of our total
calories
 in several studies are reported to raise LDL-
cholesterol and lower HDL-cholesterol

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Trans Fats
In vegetable oils,
 the unsaturated fats usually contain cis double
bonds
 during hydrogenation, some cis double bonds are
converted to trans double bonds (more stable),
causing a change in the fatty acid structure
 a label states “partially” or “fully hydrogenated” if the
fats contain trans fatty acids

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Formation of Trans Fats

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 Learning Check
Identify each statement as true (T) or false (F).

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
Identify each statement as true (T) or false (F).

T A. There are more unsaturated fats in vegetable oils.

F B. Vegetable oils have higher melting points than
fats.
T C. Hydrogenation of oils converts some cis-double
bonds to trans-double bonds.
T D. Animal fats have more saturated fats.

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Hydrolysis
In acid or enzyme hydrolysis,
 water adds to the ester bonds
 triacylglycerols split into glycerol and three fatty acids
 an acid or enzyme catalyst is required

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 Base Hydrolysis (Saponification )
In base hydrolysis (saponification),
 a triacylglycerol reacts with a strong base
 a triacylglycerol splits into glycerol and the salts of
fatty acids
 soaps (salts of fatty acids) form

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Saponification

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 Learning Check
What products are obtained from the complete
hydrolysis of glyceryl trioleate?
1) glycerol and 3 oleic acids
2) glyceryl tristearate
3) glycerol and 3 stearic acids

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 Solution
What products are obtained from the complete
hydrolysis of glyceryl trioleate?
1) glycerol and 3 oleic acids

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 Learning Check
Draw the condensed structural formula of the
product of the following reaction.

CH2 O C (CH2)7 CH CH (CH2)5 CH3

O
Ni
CH O C (CH2)7 CH CH (CH2)5 CH3 + 3H2
O
CH2 O C (CH2)7 CH CH (CH2)5 CH3

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 Solution
O

CH2 O C (CH2)14 CH3

O

CH O C (CH2)14 CH3

CH2 O C (CH2)14 CH3

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