-CAROTENOIDS

INTRODUCTION:- It is carotenoids which occurs along with -carotene in vegetable

and animal material. It is isomeric with -carotene. It is optically active and
dextrorotatory due to the presence of an asymmetric carbon atom (*) in the -ionone
ring. In the respect, it is differs from -carotene which is optically inactive. - carotene is
isolated and separated by the same method as -carotene.

STRUCTURE OF -CAROTENOIDS

CONSTITUENT:-It is elucidated on the basis of following facts.

(1)Molecular formula:-Form analytical data, the molecular formula of - carotene has
been found to be C40H56.

(2)Presence of eleven unsaturation:-When - carotene is hydrogenated

catalytically (platinum), it yields C40H78, inducing that - carotene contains eleven double
bonds.

The molecular formula of full saturated -carotene is C40H56.Which corresponds to the

general formula CnH2n-2 for bicyclic compound and hence -carotene contains two rings.
(3)Presence of five conjugated double bonds:- As -carotene add on 5 molecular
of maleic anhydride to form crystalline adduct, this indicates that it contains five
conjugated double bonds.

(4)Presence of -ionone nucleus:-When -carotene is exposed to air it develop the

odour of violet but it this is less intense than that of -carotene. But this odour is
characteristics of -ionone. Therefore, -carotene must contain -ionone nucleus.
(5)Structure of -carotene:-When -carotene is ozonolysed, it is yields geronic acid
as well as isogeronic acid. But the former product, i.e. , geronic acid is an oxidation
products of -carotene. Therefore, -carotene musr contain -ionone nucleus. However,
as the latter product, i.e., isogeronic acid, is an oxidation product of -ionone, this
indicates that -carotene must contain a -ionone nucleus.
From the above facts, it follows that -carotene contains one ring -ionone ring and ionone ring.

On the basic of the above observations of structure of -carotene may be

written as follows:

-carotene is optically active due to the presence of chiral central (*) I the -ionone ring.

(6)Synthesis:-The structural of -carotene given above has been confirmed by its

varies synthesis as above:
(a)Karrer et al. (1950). In this synthesis, one mole of the acetylenic alcohol (I) is used
together with one molecule of the corresponding -ionone derivative (II)
(C16+H8+C16combination)

(b) Isler et al. (1961). According to this synthesis, -carotene is synthesized by using
Writing reaction as follows: