Radical addition of linoleic hydroperoxides to α-tocopherol or the analogous hydroxychroman
作者： H. W. Gardner , K. Eskins , G. W. Grams , G. E. Inglett
DOI: 10.1007/BF02532650
关键词:
摘要: Either linoleic acid hydroperoxide (LOOH) or methyl linoleate react anaerobically with either α-tocopherol (TOH) its model compound-2,2,5,7,8-pentamethyl-6-hydroxychroman (COH)-to form principally an addition compound of the two reactants. The reaction can be catalyzed by 1.28 X 10−5 M Fe(III) proflavin (0.01%) sensitized visible light. presence air in terminates addition, and quinones become major products from TOH compound. synthesized COH LOOH (a 4.9∶1 ratio 13-hydroperoxy-cis-9,trans-12-octadecadienoic 9-hydroperoxy-trans-10,cis-12-octadecadienoic acid) was used to solve structural details bridging function. Three isomers (methyl esterified) were isolated identified as 11-(2,2,5,7,8-pentamethyl-6-oxychroman)-cis-12,13-epoxy-trans-9-octadecenoate; 11-(2,2,5,7,8-pentamethyl-6-oxychroman)-trans-12,13-epoxy-trans-9-octadecenoate; 11-(2,2,5,7,8-pentamethyl-6-oxychroman)-cis-9,10-epoxy-trans-12-octadecenoate order decreasing abundance. mechanism appears free radical brought about catalytic formation alkoxy radicals chromanoxy model.
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