title: Metabolism of 2- and 3-tert-butyl-4-hydroxyanisole in the rat (III): Metabolites in the urine and feces.
abstract: The urinary and fecal metabolites of orally administered 2-tert-butyl-4-hydroxyanisole (2-BHA) and 3-tert-butyl-4-hydroxyanisole (3-BHA) in rats were identified. Samples of 2-day pooled urine and feces of rats given a single intragastric dose of 1 g/kg body wt of tert[butyl-14C]3-BHA (*Bu-3-BHA). tert[butyl-14C]2-BHA (*Bu-2-BHA), [methyl-14C]3-BHA (*Me-3-BHA) or [methyl-14C]-2-BHA (*Me-2-BHA) were analyzed by comparing thin-layer chromatography (TLC) retentions with authentic standards. Conjugated metabolites were identified after enzymatic hydrolysis. Proton magnetic resonance spectroscopy and electron impact mass spectrometry were used for confirmation of the authentic standards. In rats given 3-BHA, a major metabolite in the urine was 3-BHA-glucuronide with a smaller amount of tert-butylhydroquinone (TBHQ)-sulfate, while unchanged 3-BHA and 3-BHA-glucuronide were detected in the feces. In rats given 2-BHA, the main metabolites were the sulfate conjugates of 2-BHA, 4-tert-butyl-5-methoxy-1,2-benzoquinone (2-TBOQ) and the glucuronide of 2-BHA in the urine, while unchanged 2-BHA was found in the feces.
authors.affiliation: First Department of Pathology, Nagoya City University Medical School, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Hirose
authors.forename: A
authors.initials: A
authors.lastname: Hagiwara
authors.forename: K
authors.initials: K
authors.lastname: Inoue
authors.forename: N
authors.initials: N
authors.lastname: Ito
authors.forename: H
authors.initials: H
authors.lastname: Kaneko
authors.forename: K
authors.initials: K
authors.lastname: Saito
authors.forename: H
authors.initials: H
authors.lastname: Matsunaga
authors.forename: N
authors.initials: N
authors.lastname: Isobe
authors.forename: A
authors.initials: A
authors.lastname: Yoshitake
authors.forename: J
authors.initials: J
authors.lastname: Miyamoto
mesh_terms: D000284:Administration, Oral; D000818:Animals; D001345:Autoradiography; D001711:Biotransformation; D002083:Butylated Hydroxyanisole / Q000378:metabolism* / Q000652:urine; D002855:Chromatography, Thin Layer; D005243:Feces / Q000032:analysis; D008297:Male; D051381:Rats; D011916:Rats, Inbred F344; D013997:Time Factors
chemical_list: D002083:Butylated Hydroxyanisole; C051362:3-tert-butyl-4-hydroxyanisole; C051361:2-tert-butyl-4-hydroxyanisole