Dr.

Habib Nasir

Dr. Habib Nasir

School of Natural Sciences
National University of Sciences and Technology
Islamabad

Terpenoids
▪ Introduction
▪ Classification
▪ Isolation techniques and discussion with
particular reference to structure and synthesis and
biosynthesis of typical terpenoids such as:
▪ citral,
▪ α-terpineol,
▪ α-pinene,
▪ camphor and
▪ α-cadinene.
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 Dr. Habib Nasir

Camphor
▪ A waxy and transparent solid
with strong aroma.
▪ It is obtained from wood of the
camphor laurel (Cinnamomum
camphora), a large evergreen
tree found in East Asia.
▪ It has anti-bacterial, anti-
fungal, and anti-inflammatory
properties,
▪ It relieves pain and treats
skin ailments. C10H16O
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Camphor
▪ Camphor is a bicyclic
monoterpene ketone
bearing “Bornane,” a
fundamental terpenoid. Bornane

Cinnamomum camphora Mothballs 4

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 Dr. Habib Nasir

Establishment of structure by
degradation
▪ Molecular formula of camphor is C10H16O.
▪ Nature of Oxygen atom in camphor is found to be
ketonic as it forms oxime with hydroxyl amine.
▪ Camphor when oxidised with nitric acid yields a
dicarboxylic acid called camphoric.
▪ Molecular formula of saturated hydrocarbon of
camphor (C10H16O) corresponds to the general
formula of a bicyclic compound (CnH2n-2).
▪ When distilled with zinc Chloride or phosphorous
peroxide, it yields p-cymene. Formation of p-
cymene confirms the presence of six-membered
ring.
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▪ Oxidation of camphor with nitric acid gives

camphoric acid, C10H16O4, and
▪ further oxidation of camphoric acid gives
camphoronic acid, C9H14O6.
▪ Camphoric acid is saturated dicarboxylic acid with
the same number of carbon atoms as camphor,
▪ it suggest that keto group is present in one of ring
and ring contain keto group is opened in the
formation of camphoric acid .
▪ Thus, camphoric acid should be a monocyclic
compound.
▪ Camphoronic acid is tricarboxylic acid.
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COOH

Synthesis by Komppa (1903)

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Synthesis by Komppa …

Commercial synthesis of camphor

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Commercial synthesis of camphor

Isoborneol (II)
Alpha pinene (III)
Bornyl chloride (IV)
Camphene (V)
Isobornyl formate (VI)
Isobornyl acetate (VII) 11

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Thank you

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