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 language||English (US)|
|Number of pages||6|
|Journal||Journal of the American Chemical Society|
|State||Published - 1978|
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