The reaction of butylated hydroxyanisole and its metabolites with some arylamines: investigations of product mutagenicity.
We examined t-butylhydroquinone (t-BHQ) and t-butylquinone (t-BuQ), two of the major microsomal metabolites of the synthetic antioxidant butylated hydroxyanisole (BHA), for their ability to react with the xenobiotic arylamines aniline and N-methylaniline. A number of substances were isolated by thin-layer chromatography. The main products were quantitatively evaluated and their structures assigned. BHA and t-BHQ yielded reaction products with anilines only in the presence of an oxidant such as iodate (KIO3). We used the Salmonella/microsome mutagenicity assay to test the new compounds for mutagenic activity. The reaction products gave no evidence of mutagenicity in the S. typhimurium strains TA98 and TA100, with or without metabolic activation. In some instances the substituted quinone products are less toxic than t-BuQ alone.
Federal Institute for Nutrition Research, Engesserstrasse 20, Karlsruhe, Germany.
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D000814:Aniline Compounds / Q000737:chemistry; D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity*; D016227:Benzoquinones / Q000737:chemistry; D002083:Butylated Hydroxyanisole / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity*; D002855:Chromatography, Thin Layer; D006873:Hydroquinones / Q000737:chemistry; D008861:Microsomes; D009152:Mutagenicity Tests; D012486:Salmonella typhimurium
D000814:Aniline Compounds; D000975:Antioxidants; D016227:Benzoquinones; D006873:Hydroquinones; D002083:Butylated Hydroxyanisole; C018855:2-tert-butylhydroquinone; C051290:2-tert-butyl-4-quinone; C023650:aniline; C021313:methylaniline