Mechanism of microsomal metabolism of benzene to phenol

Journal Article · Wed May 01 04:00:00 EDT 1985 · Mol. Pharmacol.; (United States)

OSTI ID:5253689

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

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-(/sub 2/H/sup 3/)benzene. Evidence for the formation of the following four products was obtained: 2,3,5-(/sub 2/H/sup 3/)phenol, 3,5-(/sub 2/H/sup 2/)phenol, 2,4,6-(/sub 2/H/sup 3/)phenol, and 2,4-(/sub 2/H/sup 2/)phenol. The presence of 2,3,5-(2H3)phenol and 2,4-(/sub 2/H/sup 2/)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.

• Research Organization: National Center for Toxicological Research, Jefferson, AR
• OSTI ID: 5253689
• Journal Information: Mol. Pharmacol.; (United States), Journal Name: Mol. Pharmacol.; (United States) Vol. 5; ISSN MOPMA
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
ANIMALS
AROMATICS
BENZENE
BODY
CELL CONSTITUENTS
DEUTERIUM
DEUTERIUM COMPOUNDS
DIGESTIVE SYSTEM
GLANDS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
HYDROXYLATION
ISOTOPES
LIGHT NUCLEI
LIVER
MAGNETIC RESONANCE
MAMMALS
METABOLISM
MICROSOMES
NUCLEAR MAGNETIC RESONANCE
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANOIDS
ORGANS
PHENOLS
RATS
RESONANCE
RODENTS
STABLE ISOTOPES
VERTEBRATES