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Mechanism of microsomal metabolism of benzene to phenol

Hinson, J.A.; Freeman, J.P.; Potter, D.W.; Mitchum, R.K.; Evans, F.E.

Molecular Pharmacology 27(5): 574-577

1985

ISSN/ISBN: 0026-895X
PMID: 3990679
Document Number: 261623
The mechanism of microsomal hydroxylation of benzene to phenol has been studied by examining the microsomal metabolism of the specifically deuterated derivative 1,3,5-[2H3]benzene. Evidence for the formation of the following four products was obtained: 2,3,5-[2H3]phenol, 3,5-[2H2]phenol, 2,4,6-[2H3]phenol, and 2,4-[2H2]phenol. The presence of 2,3,5-[2H3]phenol and 2,4-[2H2]phenol shows that, in the microsomal metabolism of benzene to phenol, a NIH shift had occurred. A deuterium isotope effect (kH/kD) of approximately 4 was detected in both the meta- and para-deuterated phenols. This finding indicates that cyclohexadienone, formed either by isomerization of the epoxide or directly from the enzyme-substrate complex, is a major intermediate in the metabolism of benzene to phenol.

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