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CHEMISTRY OF LIPIDS
OBJECTIVES
• Define lipids and its occurrence
• State the biological significance of fats
• Define chemical composition of fats
• Define physical properties of fats
• Define chemical properties of fats
• Classify lipids into fatty acids, triglycerides, steroids
• Define phospholipids
• Describe the chemistry and functions of cholesterol
• Explain lipoproteins
2
What are Lipids?
• Group of naturally occurring substances
• Insoluble in water
3
What are Lipids?
• LIPIDS: Fatty acids, Triacylglycerols, Ketone
bodies, Cholesterol, Phospholipids &
Sphingolipids
• Food sources:
– Milk, Egg, Meat, Liver
– Fish oils, nuts, seeds and oils
6
OBJECTIVES
• Define lipids and its occurrence
7
Biological Significance of Fats
Acts as fuel in the body. (caloric value: 9
Kcals/gm)
Deposits of fats underneath the skin = exert
insulating effects.
The mesenteric fat around organs (kidney) =
padding and protecting internal organs.
Building materials. (cholesterol – hormone
synthesis)
8
Biological Significance of Fats
Lipids supply the essential fatty acids which
cannot be synthesized in the body..
The Nervous system is particularly rich in lipids.
Vitamins A, D, E and K are fat soluble.
( lipid/fat is needed for absorbing these
vitamins)
Lipoproteins and phospholipids are important
constituents of cell wall & mitochondria.
9
Biological Significance of Fats
10
Lipoprotein &
Acts as fuel in Insulating effect
Phospholipids (cell
wall & mitochondrion the body
constituents)
Padding &
protection of
internal organs
Vitamin
A,D,E,K fat
soluble Building
vitamins Materials
(hormones)
Supply essential
Nervous
fatty acids
system: Rich in
lipids
11
Classification of Lipids
LIPIDS
Simple Lipids
Compound Lipids
Derived Lipids
Substances Associated with Lipids
12
Classification of Lipids
Classification Definition Examples
Esters of fatty acids * Neutral fats (F.A. + alcohol)
Simple Lipids with various alcohols * Glycerol (alcohol in fats)
* Anything other than glycerol
(alcohol in waxes)
13
Classification of Lipids
Classification Description 4 Sub-Divisions
Contains other chemical •Phospholipids
Compound groups in addition to alcohol •Glycolipids
Lipids and fatty acids •Sulpholipids
•Lipoprotein
•Phospholipids •Contains fatty acids, glycerol, phosphoric acid
& nitrogenous compound (lecithin, cephalin)
14
Classification of Lipids
Classification Description
Derived Lipids Substances derived from simple &
compound by hydrolysis.
Examples
•Fatty acids
Derived Lipids •Alcohols other than glycerol
•Glycerides
•Bases (choline, serine)
15
Classification of Lipids
Classification Examples
•Carotenoids
Substances Associated •Tocopherols
with Lipids •Vitamins A, D, E and K
•Steroids (Cholesterol)
16
OBJECTIVES
• Define lipids and its occurrence
• State the biological significance of fats
17
Chemical Composition of Fats
ANIMALS AND VEGETABLE FATS
Complex Triglycerides
mixtures of (TAG)-
glycerides Neutral fats
18
Chemical composition of lipids
OBJECTIVES
• Define lipids and its occurrence
• State the biological significance of fats
• Define chemical composition of fats
20
Physical Properties of Fats
• Greasy to touch and leaves an oily impression on
paper.
• Are insoluble in water but soluble in organic
solvents.
• Have less specific gravity than water (solid fat=
0.86), (liquid fat = 0.95)
• Pure glycerides are tasteless, odorless, colorless
and neutral in reaction (acidic-yellow color
(hydrolysis & oxidation)
21
• Flavor of butter is due to the presence of
bacterial flora; color of butter, human fat and
egg yolk (due to presence of carotene &
xanthophil).
• Hardness and consistency depends on the
amount of saturated and unsaturated fatty
acids present. Saturated fatty acids are solid
(room temperature) while Unsaturated fatty
acids are liquid (room temperature) (e.g. oils)
22
• Fats have definite melting points.
• When liquid fat is placed on water- it spreads
uniformly over the surface of water. If the
quantity is small – it forms a layer of 1
molecule thickness (effect: to lower surface
tension- help transport fat)
• Though fat is insoluble in water- can be
broken down into minute droplets and
dispersed in water (emulsification)
23
OBJECTIVES
• Define lipids and its occurrence
• State the biological significance of fats
• Define chemical composition of fats
• Define physical properties of fats
24
Chemical Properties of Fats
• Acrolein Formation – glycerol heat + potassium
bisulphate
• Hydrogenation – unsaturated fats (+nickel-catalyst)
– saturated fats (“hardening”) e.g vegetable oil –
commercial cooking oil
• Saponification – hydrolysis of fat by alkali (glycerol +
alkali salts = soap)
• Rancidity – chemical change resulting in unpleasant
odor and taste on storage when fats are exposed to
light, heat, air and moisture.
– E.g. Ascorbic acid (Vitamin C) and Vitamin E are
antioxidants (prevents rancidity)
25
OBJECTIVES
• Define lipids and its occurrence
• State the biological significance of fats
• Define chemical composition of fats
• Define physical properties of fats
• Define chemical properties of fats
26
Essential Fatty Acids (Polyunsaturated
Fatty Acids)
Lipids Examples Sources
•Linoleic acid •Linseed
•Cotton seeds
Polyunsaturated •Peanuts
Fatty Acids
•Linolenic acid •Corn oils
•Arachidonic acid
28
What are Steroids?
• Are non-saponifiable lipids
• Are biological compounds with diverse
physiological activities
• Are compounds having a
cyclopentanoperhydrophenanthrene ring
system
• Has only a hydroxyl group (-OH) as its
functional group (sterol, e.g. cholesterol)
29
OBJECTIVES
• Define lipids and its occurrence
• State the biological significance of fats
• Define chemical composition of fats
• Define physical properties of fats
• Define chemical properties of fats
• Classify lipids into fatty acids, triglycerides, steroids
• Define phospholipids
• Describe the chemistry and functions of cholesterol
• Explain lipoproteins
30
What are Phospholipids?
• Lipids containing phosphorus
31
OBJECTIVES
• Define lipids and its occurrence
• State the biological significance of fats
• Define chemical composition of fats
• Define physical properties of fats
• Define chemical properties of fats
• Classify lipids into fatty acids, triglycerides, steroids
• Define phospholipids
32
What is Cholesterol?
• Are light yellow Are synthesized in the liver,
crystalline solid adrenal cortex, intestines,
• Are soluble in testes and skin.
chloroform and other Play an important role as a
fat solvents component of biomembranes
• Polyunsaturated and has a modulating effect
acids – lower the on the fluid state of the
plasma cholesterol membrane.
level Can be estimated by color
• The most abundant reactions (e.g. Liebermann-
lipid in the human Burchard reaction) – blue or
body green color
33
Functions of Cholesterol
• An important tissue It neutralizes the
component hemolytic action of
(modulating effect, various agents such as
integrity &
permeability) venom, bacterial toxins
• Play an important It gives rise to “provitamin
role in insulating D”
nerves and brain It is a precursor of cholic
structure acid in the body as also
• For transport of fatty bile salts.
acids in the body
It gives rise to sex
• It is a part of hormones
lipoproteins
34
Functions of Cholesterol
Atherosclerosis Diabetes Mellitus
Plaque around
The artery Myxoedema
Hardening & (Hypothyroidism)
Narrowing
CHOLESTEROL
Hyperthyroidism Xanthomatosis
(fat storage
disorder)
Obstructive jaundice
Nephrotic syndrome
(kidney disorder) 35
OBJECTIVES
• Define lipids and its occurrence
• State the biological significance of fats
• Define chemical composition of fats
• Define physical properties of fats
• Define chemical properties of fats
• Classify lipids into fatty acids, triglycerides, steroids
• Define phospholipids
• Describe the chemistry and functions of cholesterol
• Explain lipoproteins
36
What are Lipoproteins?
• Are conjugated proteins involved in transport
and delivery of lipids to tissues.
E.g. Lipids (Cholesterol & triglycerides) + water
soluble carrier proteins
• It transport neutral lipids in the blood.
• It has lower density than the ordinary protein
molecule.
37
Distribution of Lipoproteins:
Body tissues
Cell membranes Plasma
Nucleus, Cholesterol,
Mitochondria Phospholipids, neutral
Microsome fat, traces of fat soluble
vitamins
Steroid hormone
LIPOPROTEINS Rhodopsin
Thromboplastin
(prothrombin- (combination of
thrombin) protein, opsin and
retinal aldehyde of
Vit. A
Egg yolk
(HDL & LDL) Fat droplets in milk 38
Lipoproteins according to Density
Type Density Protein Triglycerides Cholesterol Phospholipids
g/ml (TAG)
Free Ester
Chylomicrons < 0.95 1 85-95 1-2 1-2 3-6
Very low 0.95- 10 50-60 4-8 10 15-20
density 1.006
lipoprotein
VLDL