Iron-catalyzed reaction products of α-tocopherol with methyl 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoate |
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Authors: | Ryo Yamauchi Norio Yamamoto Koji Kato |
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Affiliation: | (1) Department of Food Science, Faculty of Agriculture, Gifu University, 1-1 Yanagido, 501-11 Gifu City, Gifu, Japan |
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Abstract: | α-Tocopherol was reacted with methyl 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoate in the presence of an iron-chelate, Fe(III)-acetylacetonate, at 37°C in benzene. The reaction was carried
out either aerobically or anaerobically. The main products of α-tocopherol under air were isolated and identified as two stereoisomers
of 4a,5-epoxy-8a-hydroperoxy-α-tocopherone, four stereoisomers of methyl 9-(8a-dioxy-α-tocopherone)-12,13-epoxy-10(E)-octadecenoate, four stereoisomers of methyl 11-(8a-dioxy-α-tocopherone)-12,13-epoxy-9(Z)-octadecenoate, two stereoisomers of methyl 13(S)-(8a-dioxy-α-tocopherone)-9(Z),11(E)-octadecadinoate, and α-tocopherol dimer. Besides the 8a-(lipid-peroxy)-α-tocopherones, two stereoisomers of methyl 11-(α-tocopheroxy)-12(S),13(S)-epoxy-9(E)-octadecenoate, two stereoisomers of methyl 9-(α-tocopheroxy)-12(S),13(S)-epoxy-10(E)-octadecenoate, and two isomers of methyl (α-tocopheroxy)-octadecadienoate were obtained under nitrogen atmosphere. The results
indicate that the peroxyl radicals from lipid hydroperoxides prefer to react with the 8a-carbon radical of α-tocopherol and
the carbon-centered radicals react with the phenoxyl radical of α-tocopherol. |
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