AUTOXIDATION OF CAROTENOIDS AND THEIR RELATIVE POLARITY

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Abstract
The possible relation between the structural characteristics and the autoxidatiue susceptibility of seven carotenoids which differ among themselves in the type, number and positions of functional groups has been studied. It was possible to correlate the relative polarity and the autoxidative susceptibility only for five of them: β‐carotene, apo‐8′‐carotenol, cryptoxanthin, canthaxanthin and zeaxanthin. The basic structure in these pigments has one or more β‐ionine rings, and as the relative polarity increased, the oxygen uptake decreased. Capsanthin and capsorubin did not fit into the above category, and this is due to the five membered ring systems in their structures which is quite different from the β‐ionone ring. It was evident that an unsubstituted β‐ionone ring was the most susceptible structure for oxidative changes. Substitution in the 3‐position of the β‐ionone ring offered some stabilizing influence and zeaxanthin, which has hydroxyI groups in 3 and 3’positions, offered the greatest resistance to autoxidation.

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