Preparation of the Addition Products of α-Tocopherol with Cholesteryl Linoleate-Peroxyl Radicals

Abstract

α-Tocopherol was reacted with cholesteryl linoleate hydroperoxides (Ch18:2-OOH) in the presence of an iron-chelate, Fe(III) acetylacetonate, at 37°C in benzene. The reaction products were isolated and identified as four positional isomers of cholesteryl (8a-dioxy-α-tocopherone)-epoxyoctadecenoates and two positional isomers of cholesteryl (8a-dioxy-α-tocopherone)- octadecadienoates. The result indicates that the peroxyl radicals from Ch18:2-OOH react with the 8a-carbon radical of α-tocopherol to form the addition products.

• α-tocopherol
• antioxidant
• cholesteryl ester hydroperoxide
• lipid peroxidation