Beruflich Dokumente
Kultur Dokumente
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Classification of sterols
1. Zoosterols: obtained from animals
E.g: Cholesterol, Cholestanol and coprostanol
2. Phytosterols: obtained from plants
E.g: Stigmasterol
3. Mycosterol: Obtained from yeast and fungi
E.g: Ergosterol
4. Miscellaneous: Occur naturally
This is not a rigid classification, because some of
the sterols obtained from more than one source.
E.g: Ergosterols obtained from plants as well as
from yeast and fungi. 2
Structural Elucidation of Cholesterol
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I. Structure of the nucleus
1. Molecular formula: C27H46O
2. Presence of one hydroxyl group:
on acetylation it forms monoacetate
3. Presence of one double bond:
It adds up two bromine atoms
4. Presence of Diel’s hydrocarbon:
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5. Reduction and oxidation
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2. Cholestanone III, on treatment with methyl
magnesium iodide followed by Se
dehydrogenation yields 3’, 7-dimethyl
cyclopentanophenanthrene VII, the structure of
which is proved by its synthesis.
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i. Conversion of I to VIII represents the
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14
4. The position of the double bond is further by the
following set of reactions.
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IV. Position of the angular methyl groups
The cyclopentanophenanthrene nucleus and the
side-chain of the cholesterol account for 17 and
8 carbon atoms respectively; thus 25 out of 27
carbon atoms of cholesterol have been
accounted for , the rest two carbon atoms are
found to be present as angular methyl groups by
the following facts.
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IV. Position of the angular methyl groups
i. The keto-acid XII, on clemmensen reduction
followed by twice B-W degradations gives a
tertiary acid, so one of the angular methyl
groups must be present on C10.
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IV. Position of the angular methyl groups
ii. Cholesterol on selenium dehydrogenation yields
Diel’s hydrocarbon and chrysene; the formation of the
latter is explained by the fact that there is an angular
methyl group at either C-13 or C-14 which enters the
five membered ring (D) of cholesterol to form a six
membered ring of chrysene.
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IV. Position of the angular methyl groups
iii. Upon distillation with Se aetiobilianic
formed.
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Synthesis of cholesterol (Woodward, 1951)
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Ergosterol
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