Reaction products of alpha-tocopherol with a free radical initiator, 2,2'-Azobis(2,4-dimethylvaleronitrile).

alpha-Tocopherol was reacted with an alkylperoxyl radical at 37 degrees C in ethanol. 2,2'-Azobis(2,4-dimethylvaleronitrile) was used to generate the alkylperoxyl radicals. The reaction products of alpha-tocopherol were isolated by reverse-phase and normal-phase high performance liquid chromatography, and their structures were characterized by infrared, ultraviolet, 1H and 13C nuclear magnetic resonances and mass spectrometry. They were 8aS-hydroperoxy-alpha-tocopherone, 8aR-hydroperoxy-alpha-tocopherone, a mixture of 7,8-epoxy-8aS-ethoxy-alpha-tocopherone and 7,8-epoxy-8aR-ethoxy-alpha-tocopherone, 8aS-(1R-cyano-1,3-dimethyl)butylperoxy-alpha-tocopherone+ ++, 8aS-(1S-cyano-1,3-dimethyl)butylperoxy-alpha-tocopherone+ ++, a mixture of 8aR-(1R-cyano-1,3-dimethyl)butylperoxy-alpha-tocopherone+ ++ and 8aR-(1S-cyano-1,3-dimethyl)butyl-peroxy-alpha-tocopherone, 4aS,5R-epoxy-8aR-ethoxy-alpha-tocopherone, 4aR,5S-epoxy-8aS-ethoxy-alpha-tocopherone, 4aS,5R-epoxy-8aS-ethoxy-alpha-tocopherone and 4aR,5S-epoxy-8aR-ethoxy-alpha-tocopherone.