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. 1972 Aug;128(5):1285–1291. doi: 10.1042/bj1281285

Ring hydroxylation of di-t-butylhydroxytoluene by rat liver microsomal preparations

Yon-Shong Shaw 1, Chiadao Chen 1
PMCID: PMC1174016  PMID: 4404965

Abstract

3,5-Di-t-butylhydroxytoluene (compound I) was converted into 4-hydroperoxy-4-methyl-2,6-di-t-butylcyclohexa-2,5-dienone (compound II), 4-hydroxy-4-methyl-2,6-di-t-butylcyclohexa-2,5-dienone (compound III) and 2,6-di-t-butyl-4-hydroxymethylphenol (compound IV) by rat liver microsomal preparations in the presence of NADPH and air. The oxidation of compound (I) by m-chloroperbenzoic acid also produced the same compounds. These results suggest that hydroperoxide can be an intermediate in aromatic hydroxylation and that biological oxygenations resemble per-acid reactions.

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Selected References

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