Chapter 15 Lipids

15.1
Lipids

Copyright 2007 by Pearson Education, Inc.

Publishing as Benjamin Cummings

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

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15.2 Fatty Acids

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Fatty Acids
Fatty acids
Are long-chain
carboxylic acids.
Typically contain 12-18
carbon atoms.
Are insoluble in water.
Can be saturated or
unsaturated.

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Fatty Acid Formulas

The formulas for fatty acids are written as
Condensed formulas.
Line-bond formulas.
For example caprylic acid with 8 carbon atoms.
CH3(CH2)6COOH
CH3CH2CH2CH2CH2CH2CH2COOH
O
OH
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Saturated Fatty Acids

Saturated fatty acids have
Single CC bonds.
Molecules that fit closely together
in a regular pattern.
Strong attractions between fatty
acid chains.
High melting points that make
them solids at room temperature.

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Some Saturated Fatty Acids

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Unsaturated Fatty Acids

Unsaturated fatty acids
Have one or more double C=C bond
Typically contain cis double bonds.

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Properties of Unsaturated Fatty

Acids
Unsaturated fatty acids
Have kinks in the fatty
acid chains.
Do not pack closely.
Have few attractions
between chains.
Have low melting points.
Are liquids at room
temperature.

kinks in
chain

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Unsaturated Fatty Acids

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Comparing Melting Points of

Some Fatty Acids

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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

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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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Prostaglandins
Prostaglandins have
20 carbon atoms in their fatty acid chains.
An OH on carbon 11 and 15.
A trans double bond at carbon 13.

C 11
C 13

C 15

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Prostaglandins in the Body

Prostaglandins are
Produced by injured
tissues.
Involved in pain,
fever, and
inflammation.
Not produced when
anti-inflammatory
drugs such as aspirin
inhibit their synthesis.
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17

Omega-6 and Omega 3- Fatty

Acids
Fatty acids
In vegetable oils are mostly omega-6 with
the first C=C at C6.
linoleic acid
CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH
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In fish oils are mostly omega-3 with the

first C=C at C3.
linolenic acid
CH3CH2(CH=CHCH2)3(CH2)6COOH
3
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Some Omega-6 and Omega-3

Fatty Acids

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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, Fats, and Oils

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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

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

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Fats and Oils: Triacylglycerols

Fats and oils are
Also called triacylglycerols.
Esters of glycerol.
Produced by esterification.
Formed when the hydroxyl
groups of glycerol react with the
carboxyl groups of fatty acids.

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Triacylglycerols
In a triacylglycerol,
Glycerol forms ester bonds with three fatty acids.

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Formation of a Triacylglycerol
glycerol

three fatty acids

triacylglycerol

O
CH2

OH

HO C
O

(CH2)14CH3

CH

OH +

HO C
O

(CH2)14CH3

CH2

OH

HO C

(CH2)14CH3 CH2 O C

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

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Solution
O
CH2

(CH2)16CH3

Stearic acid

O
CH

CH2

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

(CH2)12CH3

Oleic acid

Myristic acid

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Melting Points of Fats and Oils

A triacylglycerol that is a fat
Is solid at room temperature.
Is prevalent in meats, whole milk, butter, and cheese.

A triacylglycerol that is an oil

Is liquid at room temperature.
Is prevalent in plants such as olive and safflower.

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Oils with Unsaturated Fatty Acids

Oils

Have more unsaturated fats.

Have cis double bonds that cause kinks in the
fatty acid chains.
Cannot pack triacylglycerol molecules as close
together as in fats.
Have lower melting points than saturated fats.
Are liquids at room temperature.

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Diagram of Triacylglycerol with

Unsaturated Fatty Acids

Unsaturated fatty acid

chains have kinks that
do not allow close
packing.
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Saturated and Unsaturated Fatty

Acids In Fats and Oils

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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 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.

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Hydrogenation
O
CH2

(CH2)5CH CH(CH2)7CH3

Ni

O
CH
CH2

O
O

+ 3H2

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

(CH2)5CH CH(CH2)7CH3 CH2

(CH2)14CH3

O
glyceryl tripalmitoleate
(tripalmitolean)

CH

CH2

C (CH2)14CH3
O
C

(CH2)14CH3

glyceryl tripalmitate
(tripalmitin)

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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.

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

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Cis and Trans Fatty Acids

Unsaturated fatty acids can be
Cis with bulky groups on same side of C=C.
CH3 (CH2)5
(CH2)7 COOH cis
C=C

Trans have bulky groups on opposite sides of C=C.

CH3 (CH2)5
H

C=C
H

trans
(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 2-4% of our total

Calories.
Are reported in several studies reported to raise
LDL-cholesterol and lower HDL-cholesterol.

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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 +3H2O
O
C

(CH2)14CH3

H+
CH2 OH
CH

OH

+ 3 HO C

(CH2)14CH3

CH2 OH
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