title: Mutagens formed from butylated hydroxyanisole treated with nitrite under acidic conditions.
abstract: The reaction products from butylated hydroxyanisole treated with nitrite under acidic conditions were investigated for mutagenic activity in Salmonella typhimurium his reversion assay and for DNA-damaging activity using H17 Rec+ (wild) and M45 Rec- (recombinationless) of Bacillus subtilis. The chloroform extract of the reaction mixture showed 9 spots on thin-layer chromatography (TLC). Compounds from 2 spots on the TLC had high mutagenic activity in TA100 without S9 mix, with DNA-damaging activity. The 2 mutagens were then crystallized from the reaction mixture and identified to be 2-tert.-butyl-p-quinone (t-BQ) and the dimer of t-BQ; 3,3'-di-tert.-butyl-biphenyldiquinone-(2,5,2',5') (BBDQ), from their instrumental analysis. The mutagenic activities of t-BQ and BBDQ were determined by Ames test, and the induced mutation frequencies were about 1.9 X 10(-4) (t-BQ) and 8.3 X 10(-5) (BBDQ).
mesh_terms: D000818:Animals; D001412:Bacillus subtilis / Q000187:drug effects; D016227:Benzoquinones; D002083:Butylated Hydroxyanisole / Q000378:metabolism; D002855:Chromatography, Thin Layer; D004249:DNA Damage; D004269:DNA, Bacterial / Q000187:drug effects*; D004347:Drug Interactions; D005503:Food Additives / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D009152:Mutagenicity Tests; D009153:Mutagens / Q000138:chemical synthesis / Q000494:pharmacology*; D009573:Nitrites / Q000494:pharmacology*; D011809:Quinones / Q000138:chemical synthesis / Q000494:pharmacology*; D051381:Rats; D011919:Rats, Inbred Strains; D012486:Salmonella typhimurium / Q000187:drug effects*; D012977:Sodium Nitrite / Q000494:pharmacology*
chemical_list: D016227:Benzoquinones; D004269:DNA, Bacterial; D005503:Food Additives; D009153:Mutagens; D009573:Nitrites; D011809:Quinones; C051291:3,3'-di-tert-butylbiphenyldiquinone-(2,5,2',5'); D002083:Butylated Hydroxyanisole; C051290:2-tert-butyl-4-quinone; D012977:Sodium Nitrite