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Allylic hydroxylation of cyclohexene.
Fed Proc 1976 Jan; 36:666
Drugs containing cyclohexene (110838) rings (hexobarbital (56291), thiocarbanidin (92977)) are metabolically hydroxylated at the allyl position. This reaction was studied with cyclohexene (CH). Microsomes or 9000 g supernatant fractions of rats or rabbits catalyzed the conversion of CH to 2-cyclohexen-1-o1 in the presence of a reduced nicotinamide-adenine-dinucleotide-phosphate generating system; the latter could not be substituted by a reduced nicotinamide-adenine-dinucleotide generating system. Allylic hydroxylation was stimulated by magnesium ions. The product was identified by gas-liquid chromatography, direct and after formation of the trimethylsilyl-derivative, and by mass spectrometry. The reaction was induced over five-fold by phenobarbital (PB) treatment of rats. CH oxide was formed at a fraction of the rate of 2-CH-1-o1 in control preparations, but to a greater extent than the alcohol in preparations from PB treated rats. Cyclohexane-diol formation was also induced by PB. The formation of a small amount of 2-cyclohexen- 1-one could be detected in preparations from PB treated rats. SKF 525-A was a more potent inhibitor of allylic hydroxylation than was metyrapone, but both inhibitors caused greater inhibition of epoxidation than of hydroxylation. 2-CH-1-o1 or 1-one were not formed from CH oxide in-vitro. After feeding CH to rats, 2-CH-1-one was found in urine; no 2-CH-1-o1 was detected before or after hydrolysis with beta-glucuronidase.
NIOSH-Publication; Grants-other; Hydrocarbons; Organic-solvents; Hydroxylation-reactions; Chemical-reactions; Drugs-interactions; Metabolism
Pharmacology and Therapeutics Univ of Florida Coll of Med Dept of Pharma & Therapeutics Gainesville, Fla 32601
110-83-8; 56-29-1; 92-97-7
Other Occupational Concerns; Grants-other
University of Florida Gainesville, Gainesville, Florida
Page last reviewed: September 2, 2020
Content source: National Institute for Occupational Safety and Health Education and Information Division