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Unsaturated Alcohols

Among the unsaturated alcohols found in fats, many of them are pigments.
These include:

(a) Phytol (Phytyl alcohol): A constituent of chlorophyll. (b) Lycophyll: A


polyunsaturated dihydroxy alcohol

which occurs in tomatoes as a purple pigment.

(c) Carotene: Easily split in the body at the central point of the chain to give two
molecules of alcohol, vitamin A.

(d) Sphingosine or sphingol: An unsaturated amino alcohol present in body as a


constituent of phospho- lipid, sphingomyelin and various glycolipids.

Steroids and Sterols

1.The steroids are often found in association with fat.

2.They may be separated from the fat, after the fat is saponified, since they occur 
in unsaponifiable residue. 

3.All of the steroids have a similar cyclic nucleus resembling phenanthrene (ring A,


B and C) to which a cyclopentane ring (ring D) is attached. It is designated as
cyclopentano perhydro-phenanthrene nucleus (Fig. 4.3).

4.Methyl side chains occur typically at positions 10 and 13 (constituting carbon


atoms 19 and 18 respectively).

5.A side chain at position 17 is usual. If the compound has one or more –OH groups 


and no carbonyl or carboxyl groups, it is called a ‘sterol’ and the name terminates 
in –”ol”. Most important sterol in human body is cholesterol. 

Fig. 4.4: Cholesterol CHOLESTEROL


Structure: Cholesterol is the most important sterol in human body. Its molecular
formula is C27H45OH. Its structural formula is given in Figure 4.4.

• It possesses “cyclopentanoperhydrophenan- threne nucleus”.


• It has an –OH group at C3.• It has an unsaturated double bond between C5 and

C6.• It has two –CH3 groups at C10 and C13.• It has an eight carbon side chain
attached to C17.

Properties: The name cholesterol is derived from the Greek word meaning solid
bile. It occurs as a white or faintly yellow, almost odourless, pearly leaflets or
granules. It is insoluble in water, sparingly soluble in alcohol and soluble in
ether, chloroform, hot alcohol, ethyl acetate and vegetable oils. It easily
crystallises from such solutions in colourless, rhombic plates with one or more
characteristic notches in the corner (Fig. 4.5). It is not saponifiable. Its melting point
is 147 to 150o C. Since it has an unsaturated bond, it can take up two halogen
atoms.

Source• Exogenous: Dietary cholesterol, approximately

0.3 gm/day. Diet rich in cholesterol are butter, cream, milk, egg yolk, meat, etc. A 
hen’s egg weighing 2 oz gives 250 mg cholesterol 

• Endogenous: Synthesised in the body from acetyl CoA, approximately 1.0 gm/day.

Occurrence: It is widely present in body tissues. Choleste- rol is found in largest


amounts in normal human a