Functions of Cholesterol:

• Cholesterol is required to build and maintain membranes.

• It modulates membrane fluidity over the range of
physiological temperatures.
• Cholesterol serves as a precursor for the biosynthesis of
steroids hormones, bile acids, and vitamin D.
• Cholesterol is the principal sterol synthesized by animals.
• Recent studies show that vitamin D is a potent
antioxidant, helping to detox the body and protect arteries
too.
Functions of Cholesterol:

• Cholesterol is an important precursor molecule for the

synthesis of Steroid hormones Including the adrenal gland
hormones
cortisol
aldosterone
• As well as the sex hormones
progesterone
estrogens
testosterone
Identification Tests for Cholesterol

• Modified Abell-Kendall method:

• Cholesterol is hydrolyzed with alcoholic KOH
• Unesterified cholesterol is extracted with petroleum jelly
• measured by using Libbermann-Burchardt reaction

Cholesterol + sulphuric acid + acetic anhydride

↓
bluish green colour
Synthesis of Cholesterol

• Robinson synthesis:
• The starting compound for
this synthesis is 1,6-
dihydroxy naphthalene.
• After 20 steps it is
converted into
androsterone
• Androsterone is then
converted into
androstenedione by
oxidation.

• androstenedione is
converted into
dehydroepiandrosterone
• Dehydroepiandrosterone
is converted pregnenolone
by multiple steps.

• Pregnenolone leads to a
compound known as
allopregnenolone
• The addition of acetate in
allopregnenolone leads to
cholestanol.
• The oxidation of
cholestanol gives ketone.
• In the next step
bromination of ketone
produces a bromo-ketone.
• After the formation of
enone by the elimination of
bromo-ketone, the final
product is cholesterol.
Over all reaction: