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.
Department of Agricultural Chemistry, Gifi University, Japan.
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R
Yamauchi
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T
Matsui
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Y
Satake
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Kato
Y
Y
Ueno
D000478:Alkylation; D001391:Azo Compounds; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D005609:Free Radicals; D006358:Hot Temperature; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009570:Nitriles; D010100:Oxygen; D010545:Peroxides / Q000138:chemical synthesis; D014810:Vitamin E
D001391:Azo Compounds; D005609:Free Radicals; D009570:Nitriles; D010545:Peroxides; C055792:2,2'-azobis(2,4-dimethylvaleronitrile); D014810:Vitamin E; D010100:Oxygen