Lipids

Composition of Lipids
Fatty Acids
Fats, and Oils
Chemical Properties of Triglycerides

Composition of Lipids
Lipids with fatty acids

Waxes
Fats and oils (trigycerides)
Glycerophospholipids
Sphingolipids
prostaglandins
Glycosphingolipids

Lipids without fatty acids (with steroid nucleus)

Cholesterol
Bile salts
Lipoproteins
Steroid hormones
2

Fatty Acids
Long-chain carboxylic acids
unbranched
Insoluble in water
Typically 12-18 carbon atoms (even
number)
Some contain double bonds
corn oil contains 86%
unsaturated fatty
acids and 14%
saturated fatty acids
3

Forms of Fatty Acids

a) Saturated - CC bonds
b) Unsaturated - one or more -C=C- bonds
c) Polyunsaturated more than 3 C=C bonds
COOH
palmitic acid, a saturated acid
COOH
palmitoleic acid, an unsaturated fatty acid4

Saturated fatty acids

Fit closely in regular pattern
COOH
COOH
COOH

Unsaturated fatty acids

Cis form

H
C C

cis double bond

COOH
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Properties of Saturated
Fatty Acids
Contain only single CC bonds
Closely packed
Strong attractions between chains
High melting points
Solids at room temperature
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Properties of Unsaturated
Fatty Acids
Contain one or more double C=C
bonds
Nonlinear chains do not allow
molecules to pack closely
Few interactions between chains
Low melting points
Liquids at room temperature
7

Prostaglandins
Hormone-like substance produced in low
amounts in most cells of the body
Formed from arachidonic acid (20 C)
A.k.a. eicosanoids
With potent physiological effectsin
BP
Uterine contraction
Produce inflammation and pain
Blood clotting
Bronchodilation
Inhibit secretion of acid

Arachidonic acid in the blood is converted to

prostaglandin when tissues are injured .
Prostaglandin cause inflammation and pain in
the area and fever.
NSAIDS (Nonsteroidal Anti-inflammatory drugs)
Antipyretics
Reduce pain and swelling
e.g. Ibuprofen, Naproxen, Ketoprofen, nabumeton
long term usage- liver, kidney an GI damage

Types of Fatty Acids

1)WAXES
An ester of a long chain FA and
alcohol (14-30 C atoms)
In plants prevent water loss and
damage from pests
In animal skin, fur and feathers
provide waterproof coating

Types of wax

Types of FattyAcids

2) TRIACYLGLYCEROLS
Fats and oils stored in the body
Aka triglycerides
Major form of energy storage for animals
Triesters of glycerol and fatty acids
Produced by esterification

Triglycerides (triacylglcerols)
Esters of glycerol and fatty acids
ester bonds
O
CH 2

(CH 2)14CH3 + H2O

O
CH
CH2

O
O

C (CH 2)14CH3
O
C

+ H2O

(CH 2)14CH3 +

H2O

13

O
CH2 OH
CH

OH

CH2

OH

glycerol

HO C
O
+

(CH2)14CH3

HO C (CH2)14CH3
O
HO C

(CH2)14CH3

palmitic acid (a fatty acid)

14

Learning Check
What are the fatty acids in the following
triglyceride?

O
CH2

(CH2)16CH3

O
CH
CH2

O
O

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

(CH2)12CH3

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Solutions L2
What are the fatty acids in the following
triglyceride?

O
CH2

C
O

CH
CH2

Stearic acid

(CH2)16CH3
Oleic acid

C (CH2)7CH CH(CH2)7CH3
O
Myristic acid
O C (CH2)12CH3
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Melting points of Fats and Oil

FAT TAG that is solid at

room temperature
- from animal
sources
E.g. fats in meat, whole
milk, butter and cheese

Melting points of Fats and Oil

OILS TAG that is liquid at room
temperature

- from plant sources

e.g. olive oil, peanut oil (monounsat)
oils from corn, cottonseed, safflower,
sunflower (polyunsat)

Chemical Properties of Triglycerides

Hydrogenation
Unsaturated compounds react with H2
Ni or Pt catalyst
C=C bonds
CC bonds

Hydrolysis
Split by water and acid or enzyme catalyst
Produce glycerol and 3 fatty acids
20

Hydrogenation

O
CH2

(CH2)5CH CH(CH2)7CH3

O
CH
CH2

O
O

C (CH2)5CH CH(CH2)7CH 3
O
C

+ 3 H2

Ni

(CH2)5CH CH(CH2)7CH3

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Product of Hydrogenation
O
CH2

(CH2)14CH3

O
CH

C (CH2)14CH 3
O
Hydrogenation converts double bonds in oils to single bonds.

The solid
products are usedCH
to makeO
margarine and other hydrogenated items .
C (CH2)14CH3
2

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Hydrolysis
Triglycerides split into glycerol and three
fatty acids (H+ or enzyme catalyst)
O

CH2

(CH2)14CH3

O
CH
CH2

O
O

C (CH2)14CH3
O
C

+3 H2O

(CH2)14CH3
CH2 OH
CH

OH

CH2

OH

O
+

3 HO C

(CH2)14CH3
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Saponification
Hydrolysis with a strong base
Triglycerides split into glycerol and the salts
of fatty acids
The salts of fatty acids are soaps
KOH gives softer soaps

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Saponification

Fat / oil + strong base -

glycerol + salts of fatty
acids (soaps)

Saponification

O
CH2

(CH2)16CH3

O
CH
CH 2

O
O

C
O
C

(CH2)16CH3 + 3 NaOH
(CH 2)16CH 3

CH2 OH
CH
CH2

+OH + 3 Na O C (CH2)14CH3
salts of fatty acids (soaps)
OH
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Learning Check L3
What are the products obtained from the
complete hydrogenation of glyceryl
trioleate?
(1) Glycerol and 3 oleic acids
(2) Glyceryltristearate
(3) Glycerol and 3 stearic acids

27

Solution L3
What are the products obtained from the
complete hydrogenation of glyceryl
trioleate?
2. Glyceryltristearate

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