POTENT BACTERIAL MUTAGENS PRODUCED BY CHLORINATION OF SIMULATED POULTRY CHILLER WATER

Hypochlorite treatment of a simulated food-processing mixture produces 3,4-dichloromaleimide and ichloro-4-(dichloromethylene)-2,5-pyrrolidi nedione (C5HCl4NO2). The tetrachloro compound and two analogs, which c an be synthesized from citraconic anhydride and itaconic anhydride, ar e direct-acting Ames mutagens in Salmonella typhimurium TA100 tester s train. These novel five-carbon cyclic imides are structurally similar to chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), the princi pal mutagenic compound present in paper pulp bleaching liquors. Molecu lar structure analysis of the mutagens was based on X-ray crystallogra phy, C-13 NMR, and mass spectrometry of synthetic chlorinated imides w ith identical. mass spectra and gas chromatographic retention indices. The tetrachloroimide accounts for much of the mutagenicity of the dic hloromethane-extractable pH 2 fraction from chlorination of a simulate d food-processing system consisting of chicken frankfurters. In the Am es TA100 tester strain it has a molecular mutagenicity of 1450 reverta nts/nmol without microsomal activation, making it the second most pote nt mutagen reported from a chlorination process.