Chapter 3 Lipids
Chapter 3 Lipids
LIPIDS
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Introduction
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Definition:
Lipids are organic compounds formed
mainly from alcohol and fatty acids
combined together by ester linkage.
O
H2O O
R CH 2 OH
+ HO C R R CH 2 O C R
Fatty alcohol Fatty acid Esterase (lipase) ester (lipid)
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Fatty alcohols
1-Glycerol:
It is a trihydric alcohol (i.e., containing three OH
groups) and has the popular name glycerin.
It is synthesized in the body from glucose.
Properties:
1. Colorless, viscous oily, liquid with sweet taste.
2. On heating with sulfuric acid or it gives acrolein
that has a bad odour.
This reaction is used for detection of free
glycerol or any compound containing
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glycerol.
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CH 2 OH 2 H 2O CHO
HO CH CH
Heating, KHSO4
CH 2 OH CH 2
Glycerol Acrolein
2-Sphingosine:
- It is the alcohol present in sphingolipids.
- It is synthesized in the body from serine and
palmitic acid.
It is not positive with acrolein test.
OH
CH 3 (CH 2)12 CH CH CH CH NH 2
CH 2 OH
Sphingosine
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Fatty Acids
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Fatty acids are classified according to several
bases as follows:
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I. According to presence or absence of double
bonds
A-Saturated Fatty Acids
contain no double bonds with 2-24 or
more carbons.
solid at room temperature except if
they are short chained.
may be even or odd numbered.
have the molecular formula,
CnH2n+1COOH. 01/31/2025
Saturated fatty acids
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Caprylic (8 C ) CH3-(CH2)6-
COOH.
Capric (10 C ) CH 3-(CH2)8-
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B-Long-chain fatty acids:
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They contain more than 10 carbon atoms.
They occur in hydrogenated oils, animal fats,
butter and coconut and palm oils.
They are non-volatile and water-insoluble
Include palmitic, stearic, and lignoceric F.A.
Palmitic(16C) CH3-(CH2)14-COOH
Stearic (18 C ) CH3-(CH2)16-COOH
lignoceric (24C ) CH3-(CH2)22-
COOH 01/31/2025
B-Unsaturated Fatty Acids:
Based on Degree of Unsaturation they are
17 Monoethenoid acids: They contain one double bonds .
Molecular Formula :(CnH2n-1 COOH) Ex: Oleic acid.
Diethenoid acids : They contain two double bonds .
Molecular Formula :(CnH2n-3 COOH) Ex: Linoleic acid.
Triethenoid acids : They contain three double bonds .
Molecular Formula :(CnH2n-5 COOH) Ex: Linolenic acid.
Tetraethenoid acids : They contain four double bonds .
Molecular Formula :(CnH2n-7 COOH) Ex: Arachidonic acid.
Monoethenoid acids are commonly called as
monounsaturated fatty acids (MUFAs) and the remaining
ones as polyunsaturated fatty acids (PUFAs).
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linoleic, linolenic and arachidonic acid - On account
of the important physiological role, these 3 acids
are collectively called as essential fatty acids (EFA)
1-Monounsaturated fatty acids:
1-Palmitoleic acid :
It is found in all fats.
It is C16:1∆9, i.e., has 16 carbons and one double
bond located at carbon number 9 and involving
carbon 10.
Definition:
They are essential fatty acids that
can not be synthesized in the
human body and must be taken in
adequate amounts in the diet.
C18:29, 12.
It is the most important since other essential
fatty acids can be synthesized from it in the
body.
CH3-(CH2)4-CH = CH-CH2-CH=CH-
(CH2)7-COOH
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2-Linolenic acid:
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CH3-CH2-CH=CH-CH2-CH=CH-CH2-
CH=CH-(CH2)7-COOH
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3-Arachidonic acid:
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CH3-(CH2)4-CH=CH-CH2-CH=CH-CH2-
CH=CH-CH2-CH=CH-(CH2)3-COOH
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I. Simple Lipids
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O O
HO C R 1 CH 2 OH H 2C O C R1
O
O
HO C R 2 + HO C H R2 C O C H
O
O
CH 2 OH 3 H 2O H 2C O C R3
HO C R 3
Glycerol Triglycerides
Fatty acids (Triacylglycerol)
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Types of triglycerides
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Physical properties of fats and
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oils:
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3-Halogenation
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O O
C 15 H 31 C OH + C 30 H 61 OH C 15 H 31 C O C 30 H 61
B-Wax-like compounds:
Cholesterol esters: Lanolin (or wool fat) is
prepared from the wool-associated skin
glands and is secreted by sebaceous glands
of the skin.
It is very complex mixture, contains both
free and esterified cholesterol, e.g.,
cholesterol-palmitate and other sterols.
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Differences between neutral lipids and waxes:
3-Type of fatty Fatty acid mainly palmitic or Long and short chain fatty acids.
acids: stearic acid.
Definition:
They are lipids that contain additional substances,
e.g., sulfur, phosphorus, amino group, carbohydrate,
or proteins beside fatty acid and alcohol.
Compound or conjugated lipids are classified into the
following types according to the nature of the
additional group:
1. Phospholipids
2. Glycolipids.
3. Lipoproteins
Importance:
1. They are present in large amounts in the liver and brain as well as
blood. Every animal and plant cell contains phospholipids.
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2-Glycolipids
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Definition: They are lipids that contain
carbohydrate residues with sphingosine as the
alcohol and a very long-chain fatty acid (24 carbon
series).
They are present in cerebral tissue, therefore are
called cerebrosides
Classification: According to the number and nature
of the carbohydrate residue(s) present in the
glycolipids the following are
Cerebrosides. They have one galactose molecule
(galactosides).
Sulfatides. They are cerebrosides with sulfate on the
sugar (sulfated cerebrosides).
Gangliosides. They have several sugar and sugar-
amine residues. 01/31/2025
3-Lipoproteins
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2. Transport lipoproteins:
These are the forms present in blood
plasma.
They are composed of a protein called
Grp-2 01/31/2025
Plasma lipoproteins can be separated by
two methods:
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Prostaglandins
Synthesized from arachidonic acid
Several metabolic functions
Steroids
Cholesterol, ergosterol, bile acids
Terpenes
Made by plants
Carotenoids, xanthophylls
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Cholesterol Vitamin D3
(a sterol) (cholecalciferol)
Testosterone
(a steroid hormone) Stigmasterol
(a phytosterol)
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Cholesterol:
Importance: -
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19 17 16 CH 3
11 13
CH 3 C D CH 3
1 9 14 15
2
A 5 10 B 8
HO 3 4 6 7
HO
Steroid ring
Cholesterol
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Ergosterol
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HO HO
7-dehydrocholesterol Ergosterol 01/31/2025
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Steroids
Steroids constitute an important class of biological
compounds.
Steroids are usually found in association with fat.
They can be separated from fats after saponification
since they occur in the unsaponifiable residue.
They are derivatives of cholesterol that is formed of
steroid ring or nucleus.
Biologically important groups of substances, which
contain this ring, are:
1. Sterols.
2. Adrenal cortical hormones.
3. Male and female sex hormones.
4. Vitamin D group.
5. Bile acids.
6. Cardiac glycosides. 01/31/2025
General consideration about naturally occurring
steroids:
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