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 × 10 −4 (t-BQ) and 8.3 × 10 −5 (BBDQ).