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Antioxidant reactions of α‐tocopherolhydroquinone
Author(s) -
Liebler Daniel C.,
Burr Jeanne A.
Publication year - 2000
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-000-0617-8
Subject(s) - autoxidation , chemistry , radical , antioxidant , acetonitrile , photochemistry , organic chemistry , medicinal chemistry
Abstract α‐Tocopherolhydroquinone (TQH 2 ) is a product of α‐tocopherol oxidation/reduction that exerts antioxidant effects in biological systems. TQH 2 inhibited autoxidation of methyl linoleate initiated by peroxyl radicals derived from thermolysis of 2,2′‐azobis(2,4‐dimethylvaleronitrile) in acetonitrile. TQH 2 oxidation yielded α‐tocopherolquinone (TQ) as a major product and 2,3‐epoxy‐α‐tocopherolquinone and 5,6‐epoxy‐α‐tocopherolquinone as minor products. Each TQH 2 consumed approximately two peroxyl radicals in the course of the oxidation. The data suggest that TQH 2 scavenges peroxyl radicals primarily by electron transfer to form TQ and secondarily by addition‐elimination to form the epoxyquinones.