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Antioxidant Activity and Pungency of Synthetic Capsaicin Homologues

In the previous paper, the antioxidant effect of capsaicin, the pungent principle of red pepper, has been demonstrated. Capsaicin is a N-vanillylamide whose pungency has been known to depend upon the carbon chain length of the fatty acid moiety. In this paper, to obtain the pungent free N-vanillylamides, which are expected to be useful as antioxidants for foods, syntheses of N-vanillylamides of saturated C12 to C22 fatty acids were carried out, and their pungency and antioxidant activity were determined. As a result, their pungency reduced with the elongation of carbon chain of the fatty acid. That is, compared with C9 amide, the pungency of C14 amide was 1/100 and that of C18 amide decreased to 1/1000. On the other hand, the antioxygenic effect of each synthetic N-vanillylamide on methyl ester of safflower oil was almost equal to that of the natural pungent mixture extracted from red pepper. By addition of 0.02mol/kg of synthetic amides in the substrate, the antioxidant activity was equivalent to that of BHA in 0.02% level. In this level, pungency was not found in the sensory even for C12 amide.