TLC-Fractionation and GC/MS Characterization of Mutagenic Substances in Chlorinated 4-Alkylphenol Solutions.

The diethyl ether extracts from aqueous 4-alkylphenol solutions after treatment with chlorine were mutagenic to the Ames Salmonella tester strains TA98 and TA100 in the absence of rat liver homogenate. Gas chromatography/mass spectrometry (GC/MS) showed the occurrence of chlorinated products in the extracts; chloro-4-alkylphenols, chloro-4-alkylquinones and chlorinated 4-alkylphenol dimers. The diethyl ether extracts were fractionated into several fractions by polyamide thin-layer chromatography (TLC) . The fractionated components were examined for mutagenicity by means of Ames assay, and were identified by GC/MS. TLC fractionation of the extracts revealed that two components present in the extracts are mutagenic. GC/MS analyses indicated the presence of 2, 6 -dichloro-4-hydroxy-4-alkylcyclohexa-2, 5-dien-1-ones as the major mutagen and chlorinated 4-alkylphenol dimers as minor mutagenic compounds in the chlorinated 4-alkylphenol solutions.