Natural Product Chemistry

1. STRUCTURAL ELUCIDATION
OF CAMPHOR
Submitted by:
T. RAMKUMAR
19PGCH10
1styr, M.Sc Chemistry
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2. CAMPHOR
 Camphor is derived from the wood of camphor
laurel(Cinnamomum camphora) and other releated trees of laurel
family.
 Camphor is a bicyclic mono terpenoid.
 Camphor is a white, crystalline substance with strong odour and
pangent taste.
 It is waxy and flammable substance.
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3.  It is obtained through steam distillation, purification and sub limation
of wood, twigs &bark of the tree.
 Melting point:180
0
c and boiling point is 2040
c
 It is optically active.
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4. General structure of camphor :
IUPAC Name :1,7,7-Trimethyl bicyclo[2.2.1]heptan-2-one
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5. STRUCTURAL ELUCIDATION OF CAMPHOR:
 Camphor molecular formula C10H16O.
Presence of keto group :
Camphor as it forms oxime with NH2OH & phenyl hydrazine.
C10H16O+ H2NOH
Camphor Hydroximine
C10H16=NOH
camphor oxime
Presence of bicyclic ring system:
The parent hydrocarbon of camphor has molecular formula C10H18
which correspond to the molecular formula of bicyclic compounds(CnH2n-2).
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6. Presence of –COCH2 group :
Camphor C8H14
camphor is confirmed by its formation to isonitroso derivativewith
amylnitrile and hydrochloride.
NOHO
O
Iso nitrso camphor
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Amylnitrile
HCl

7. Presence of six membered ring:
when distilled with ZnCl2/P2O5 it forms p-cymene.
P-cymene
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ZnCl2, P2O5
Camphor

8. Nature of the Carbon-Frame in Camphor
 Camphor on oxidation with HNO3 gives camphoric acid and camphoronic acid.
𝐶10 𝐻16O 𝐶10 𝐻16 𝑂4 𝐶9 𝐻14 𝑂6
Camphoric acid Camphoronic acid
𝐻𝑁𝑂3 𝐻𝑁𝑂3
(O) (O)

9. Structure of Camphoronic acid.
• The Molecular formula of camphoronic acid is 𝐶9 𝐻14 𝑂6.
• As camphoronic acid has been shown to be saturated tricarboxylic acid, its
molecular formula as 𝐶6 𝐻11(𝐶𝑂𝑂𝐻)3, so general formula (𝐶 𝑛 𝐻2𝑛+2) for
acyclic compound.
• That camphoronic acid is a acyclic compound.
• Camphoronic acid does not undergo decarboxylation reaction. It means that its
three carboxyl groups sholud be attached to three different carbon atoms.
•
COOHCOOHCOOH
C C C
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10. Structure of Camphoric acid
 The molecular formula of camphoric acid is 𝐶10 𝐻16 𝑂4.
 It is saturated dicarboxlic acid.
 Modify the molecular formula of camphoric acid,
(𝐶𝐻3)3 𝐶5 𝐻5(𝐶𝑂𝑂𝐻)2 . Which corresponds to general formula of 𝐶 𝑛 𝐻2𝑛 for a
monocyclic derivative.
 Camphoric acid is able to monoester to form shows that the two carboxyl
groups but not similar.
C C COOH C C COOH
C C
𝐵𝑟2
BrH
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11. Synthesis of Camphor by Haller (1896)
c a m p h o r ic a c id
C O O H ( C H 3 C O ) 2
C O
C O
O
N a - H g
C O
C H 2
O
K C N
C O O K
C H 2 C N
H y d r o ly s isC O O H
C O O H
H e a t w ith
C a s a lt
O
C O O H
C a m p h o r ic a n h y d r id e
C a m p o lid e
H o m o C a m p h o r ic a c id
C a m p h o r

12. Uses:
 Topical analgesic
 Antiseptic
 Muscle relaxant
 Anti inflammatory
 Contraceptive
 Cough suppressant
 Insect repellant
 Flavour in soaps & cosmetics
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13. Conclusion :
 we concluded in the camphor it presence of six membered
ring , ketone group, oxene group and it oxidized to form
camphoric acid &camphoronic acid .
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14. Reference:
 Organic chemistry of natural products :by O.P.Agrawal.
 Chemistry of natural products :by Gurdeep .R.Chatwal
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