Oxidation of cholesterol by dioxygen species

Leland L. Smith, Martin J. Kulig, Denis Miiller, Ghulam Ansari

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Abstract

Reaction between cholesterol in aqueous sodium stearate dispersions and H2O2 yielded many products of which 12 were isolated and identified. Products included 5,6α-epoxy-5α-cholestan-3β-ol and 5,6β-epoxy-5β-cholestan-3β-ol in 1:8 ratio representing direct reaction between cholesterol and H2O2 and 5α-cholestane-3β,5,6β-triol formed by hydration of the 5,6-epoxides; epimeric cholesterol 7-hydroperoxides, epimeric cholest-5-ene-3β,7-diols, and 3β-hydroxycholest-5-en-7-one representing free-radical oxidation of cholesterol by molecular oxygen derived by H2O2 disproportionation; 5α-cholest-6-ene-3β,5-diol, cholest-4,6-dien-3-one, and 7α-stearatoxycholest-5-en-3β-ol possibly derived from singlet molecular oxygen released in H2O2 disproportionation; and 5α-cholestane-3β,6β-diol. These results complete our studies of reactions between cholesterol and dioxygen species, revealing for the first time the several pathways of oxidation of a biologically important substrate by dioxygen species.

Original languageEnglish (US)
Pages (from-to)6206-6211
Number of pages6
JournalJournal of the American Chemical Society
Volume100
Issue number19
StatePublished - 1978

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Smith, L. L., Kulig, M. J., Miiller, D., & Ansari, G. (1978). Oxidation of cholesterol by dioxygen species. Journal of the American Chemical Society, 100(19), 6206-6211.