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Lipids
By
Assoc. prof. Hesham Haffez
2022

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Lipids
• Lipids are a heterogeneous class of naturally
occurring organic compounds classified together
on the basis of common solubility properties
– they are insoluble in water, but soluble in aprotic
organic solvents, including diethyl ether, methylene
chloride, and acetone

• Lipids include
– triglycerides, phospholipids, prostaglandins,
prostacyclins, and fat-soluble vitamins
– cholesterol, steroid hormones, and bile acids

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Lipids

ARE LIPIDS BAD? DO THEY HAVE ANY FUNCTION?

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Fatty Acids
• Fatty acid: a long, unbranched chain
carboxylic acid, most commonly of 12 to 20
carbons, derived from hydrolysis of animal
fats, vegetable oils, or the phospholipids of
biological membranes

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Fatty Acids
• Among the fatty acids most abundant in plants and
animals
– nearly all have an even number of carbon atoms, most
between 12 and 20, in an unbranched chain
– the three most abundant are palmitic, stearic acid, and
oleic acid
– in most unsaturated fatty acids, the cis isomer
predominates; the trans isomer is rare
– unsaturated fatty acids have lower melting points than
their saturated counterparts; the greater the degree of
unsaturation, the lower the melting point

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Unsaturated FA

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Contains
one double Contains
bond more than
one double
bond

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Triglycerides
• Triglyceride: an ester of glycerol with three
fatty acids
O
O CH2 OCR
1 . NaOH, H 2O
R'CO CH O
2 . HCl, H 2O
CH2 OCR''
A triacylglycerol CH2 OH RCO 2 H
(a triglyceride)
HOCH + R'CO 2 H
CH2 OH R''CO 2 H
1,2,3-Propanetri ol Fatty acids
(Gl ycerol, gl yceri n)

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Triglycerides
• Physical properties depend on the fatty acid
components
– melting point increases as the number of carbons in its
hydrocarbon chains increases and as the number of
double bonds decreases
– triglycerides rich in unsaturated fatty acids are
generally liquid at room temperature and are called oils
– triglycerides rich in saturated fatty acids are generally
semisolids or solids at room temperature and are called
fats

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Triglycerides
• The lower melting points of triglycerides rich in
unsaturated fatty acids are related to differences in their
three-dimensional shape
– hydrocarbon chains of saturated fatty acids can lie parallel,
there are strong dispersion forces between their chains; these
triglycerides pack into well-ordered, compact crystalline
forms and have melting points above room temperature
– because of the cis configuration of the double bonds in
unsaturated fatty acids, their hydrocarbon chains have a less
ordered structure and dispersion forces between hydrocarbon
chains are weaker; these triglycerides have melting points
below room temperature

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Soaps and Detergents

• Natural soaps are prepared by boiling lard
or other animal fat with NaOH, in a reaction
called saponification (Latin, sapo, soap)
O
O CH2 OCR
saponification
RCOCH + 3 NaOH
O
CH2 OCR CH2 OH O
A trigl yceri de - +
CHOH + 3 RCO Na
(a triester of glycerol)
Sodi um soaps
CH2 OH
1,2,3-Propanetriol
(Gl ycerol; Gl yceri n)
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Soaps and Detergents

• Soaps clean by acting as emulsifying agents
– the long hydrophobic hydrocarbon chains of soaps are
insoluble in water and tend to cluster in such a way as
to minimize their contact with water
– the polar hydrophilic carboxylate groups, on the other
hand, tend to remain in contact with the surrounding
water molecules
– driven by these two forces, soap molecules
spontaneously cluster into micelles

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Soaps and Detergents

• Micelle: a spherical arrangement of organic
molecules in water clustered so that their
hydrophobic parts are buried inside the sphere and
their hydrophilic parts are on the surface of the
sphere and in contact with water

• When soap is mixed with water-insoluble grease,

oil, and fat stains, the nonpolar parts of the soap
micelles “dissolve” these nonpolar dirt molecules
and they are carried away in the polar wash water

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Property-Rancidity
Definition:
- It is a physico-chemical change in the natural
properties of the fat leading to the development of
unpleasant odour or taste or abnormal color particularly
on aging after exposure to atmospheric oxygen, light,
moisture, bacterial or fungal contamination and/or heat.
Types and causes of Rancidity:
1.Hydrolytic rancidity
2.Oxidative rancidity
3.Ketonic rancidity

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1-Hydrolytic rancidity:
Due to hydrolysis of the fat
by lipase from bacterial contamination
at high temperature and moisture.
2-Oxidative Rancidity:
oxidation of fat or oil
Due to exposure to oxygen, light and/or heat
producing peroxide derivatives
that are toxic and have bad odor.
3-Ketonic Rancidity:
due to contamination with fungi
Moisture accelerates ketonic rancidity.

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Prevention of rancidity is achieved by:

1.Avoidance of the causes (exposure to light, oxygen,
moisture, high temperature and bacteria or fungal
contamination).
2.By keeping fats or oils in well-closed containers in
cold, dark and dry place.
3.Addition of anti-oxidants. The most common natural
antioxidant is vitamin E.

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Hazards of Rancid Fats:

1.The products of rancidity are toxic, i.e., causes
food poisoning and cancer.
2.Rancidity destroys the fat-soluble vitamins
(vitamins A, D, K and E).
3.Rancidity destroys the polyunsaturated
essential fatty acids.
4.Rancidity causes economical loss because
rancid fat is inedible(Unfit to eat).

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