Chemistry of lipids

Learning objectives
Classify lipids based on the physical and chemical
properties
List the components of Phospholipids and Glycolipids
Describe the Functions of phospholipase A2 and C
Classify the types of Phospholipids and Glycolipids
Analyze the Composition of surfactant and its
importance
Describe the structure of lipoproteins and their uses

Definition
Heterogenous group of compounds
Insoluble in water
Soluble in non- polar solvents:
Chloroform/ Ether.

BIOMEDICAL IMPORTANCE
Energy source stored in adipose tissue
Thermal insulator maintains body
temperature
Electrical insulator myelin sheath of nerves
Biomembranes phospholipids and
cholesterol
Steroid hormones cortisol, aldosterone

 Fat soluble vitamins vitamin A, D, E,

K.
Emulsifying agents bile salts
Essential FA (EFA) linoleic and
linolenic acid

Classification of lipids
Simple lipids : esters of fatty acids with
various alcohols
1. Fats/ oils esters of fatty acids with
glycerol
2. Waxes esters of fatty acids with
higher molecular weight monohydric
alcohols.

Fats /oils

 Complex lipids : fatty acids +

glycerol with additional groups;
a) Phospholipids : phosphoric acid
1. Glycerophospholipids - Glycerol
2. Sphingophospholipids sphingosine
(sphingomyelin)

b) Glycolipids fattyacid + sphingosine

+ carbohydrate ;
C) Sulfolipids and aminolipids;
D) Lipoproteins HDL, LDL , VLDL;

 Derived lipids : Fatty acids, Glycerol,

steroids, alcohols, sterols, fatty
aldehydes, ketone bodies, lipid
soluble vitamins.

FATTY ACIDS
Aliphatic carboxylic acids
Saturated or unsaturated
Unbranched
Even numbered (reflects the mode of
synthesis)
Cis double bonds

Classification of fatty acids based on chain

length:
Short-chain fatty acids - fewer than sixcarbons;
Medium-chain fatty acids (MCFA) - 612Carbons;
Long-chain fatty acids (LCFA) longer than
12Carbons;
Very-Long-chain fatty acids(VLCFA) longer than
22Carbons;
Eicosanoids derived and modified from 20 C
Arachidonic acid.

Trans fat
Trans fat : Not
digested by LIPASE
Deposition in the
blood vessels.
Partial hydrogenation
of unsaturated oils
leads to trans fats.
Free radical
generation.

Nomenclature
Saturated anoic . Ex : octanoic acid.
no double bonds
mostly solids
Unsaturated enoic . Ex:
octadecaenoic acid
double bonds mostly
liquids
PUFA Essential fatty acids.

Nomenclature of fatty acids:

1. Delta () naming; carbon 1 is carboxyl,
2 is called carbon, 3 is carbon, etc.
2. # of carbons: # of double bonds (carbons
at which double bonds occur)i.e. oleic
acid is 18:1(9)
carbon numbering - terminal methyl
group is always the omega carbon one.
Number in the bracket is first double
bond from omega i.e.

Essential fatty acids

-3 fatty acids: -Linolenic acidor ALA
(18:3) 9, 12, 15;
-6 fatty acids: Linoleic acidor LA
(18:2)9,12.
Why essential?
Lack the ability to introduce double bonds
in fatty acids beyond carbon 9 and 10.
9desaturase, 6desaturase, 5desaturase,
and 4desaturase are present in the body.

OTHER FATTY ACIDS

CYCLIC FATTY ACIDS:
1. Chaulmoogric acid
2. Hydnocarpic acid
BRANCHED CHAIN FATTY ACIDS:
1. Phytanic acid in butter
2. Sebaceous glands
Refsum disease: deficiency of enzyme phytanic
acid oxidase leading to accumulation of
branched chain phytanic acid.

PHYSICAL PROPERTIES
1. Melting point: Directly proportional to
(a) chain length
(b) saturation
2. Solubility: Inversely proportional to
(a) chain length
(b) saturation
3. Membrane fluidity: Inversely proportional to
(a) chain length
(b) saturation particle
fraction