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W.H. Kalus,¹ R. Münzner,¹ and W.G. Filby²

¹Federal Institute for Nutrition Research, Engesserstr. 20, D-76131 Karlsruhe, Germany; ²Nuclear Research Center, 76344 Karlsruhe, Germany

Abstract
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. Key words: butylated hydroxyanisole, mutagenicity testing, structural assignment, substituted anilines, t-butylhydroquinone, t-butylquinone. Environ Health Perspect 102:96-99(1994)

Address correspondence to W.H. Kalus, Federal Institute for Nutrition Research, Engesserstr. 20, D-76131 Karlsruhe, Germany.

We thank L. Stieglitz and W. Roth, Institut für Heiße Chemie, Kernforschungszentrum Karlsruhe, Germany, for running the mass spectra. We thank A. Markowetz, Fa. Bruker, Rheinstetten, Germany and H. Röttele, Institut für Organische Chemie der Universität Karlsruhe, for the ¹H-NMR analyses. We are grateful to B. L. Pool-Zobel for her comments on the original manuscript. The technical assistance of G. Dubberke and R. Eysler is also greatly appreciated.

Received 3 March 1993 ; accepted 16 November 1993.