Oxidation of cholesterol by dioxygen species

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

Research output: Contribution to journalArticle

45 Citations (Scopus)

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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Cholesterol
Cholestanol
Oxygen
Oxidation
Molecular oxygen
Cholestanes
Singlet Oxygen
Epoxy Compounds
Dispersions
Hydration
Free Radicals
Free radicals
Sodium
Substrates

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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.

Oxidation of cholesterol by dioxygen species. / Smith, Leland L.; Kulig, Martin J.; Miiller, Denis; Ansari, Ghulam.

In: Journal of the American Chemical Society, Vol. 100, No. 19, 1978, p. 6206-6211.

Research output: Contribution to journalArticle

Smith, LL, Kulig, MJ, Miiller, D & Ansari, G 1978, 'Oxidation of cholesterol by dioxygen species', Journal of the American Chemical Society, vol. 100, no. 19, pp. 6206-6211.
Smith, Leland L. ; Kulig, Martin J. ; Miiller, Denis ; Ansari, Ghulam. / Oxidation of cholesterol by dioxygen species. In: Journal of the American Chemical Society. 1978 ; Vol. 100, No. 19. pp. 6206-6211.
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