Formation of 1-nitropyrene by photolysis of pyrene in water containing nitrite ion

Abstract

The ether extract from the pyrene suspended in water containing nitrite ion, which was irradiated with a high-pressure mercury lamp, exhibited strong mutagenicity toward S. typhimurium TA98 in the absence of S9. The mutagenicity of the ether extract increased with increasing nitrite concentration and irradiation time and with lowering in pH of the solution. The major mutagen in the ether extract was isolated by means of silicagel column chromatography and identified to be 1-nitropyrene on the basis of the spectral data of MS and NMR. A pyrequinone as minor mutagen was also isolated and tentatively identified.