Ring hydroxylation of di-t-butylhydroxytoluene by rat liver microsomal preparations.
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.
D000388:Air; D000818:Animals; D001565:Benzoates; D055598:Chemical Phenomena; D002621:Chemistry; D002845:Chromatography; D003408:Cresols / Q000378:metabolism*; D006900:Hydroxylation; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism*; D009249:NADP; D010084:Oxidation-Reduction; D010545:Peroxides; D051381:Rats
D001565:Benzoates; D003408:Cresols; D007202:Indicators and Reagents; D010545:Peroxides; D009249:NADP