Flavin-sensitized photo-oxidation of unsaturated fatty acids

Shunichi Fukuzumi, Kumiko Tanii, Toshio Tanaka

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27 Scopus citations


Photo-oxidation of unsaturated fatty acids or esters (LH = oleic acid, linoleic acid, methyl linoleate, and linolenic acid) by oxygen proceeds efficiently in the presence of a riboflavin derivative, riboflavin - 2′,3′,4′,5′-tetra-acetate (Fl), in acetonitrile by a type II (singlet oxygen) mechanism with a limiting quantum yield (φ = 0.65) which corresponds to the quantum yield of the intersystem crossing of the flavin. The addition of HClO4 - by which Fl is protonated to FlH + - showed a remarkable inhibitory effect on the Fl-sensitized photo-oxidation of LH, since FlH+ is photo-reduced by LH to yield the dihydroflavin radical cation FlH2+. which has no ability to sensitize the energy transfer to oxygen in its ground state.

Original languageEnglish
Pages (from-to)2103-2108
Number of pages6
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number12
StatePublished - 1989


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