Substituent effects on the mutagenicity of phenyl glycidyl ethers in Salmonella typhimurium

Phenyl glycidyl ether and 6 para-subst i tuted derivatives, the methoxy, tert-butyl, methyl, chloro, bromo and nitro compounds, were tested in the Ames' test for mutagenicity. With the exception of the tert-butyl derivative in TA1535, all 7 compounds were mutagenic in both strains TA100 and TA1535. Electron-donating groups in the para position decreased mutagenicity while electron-withdrawing groups increased this mutagenicity. The mutagenicity of the series of compounds in both strains could be correlated to the Hammett substituent constants for the para-subst i tuent groups. The glycidyl ether results might best be considered in terms of a normal reaction with bionucleophiles as compared to the literature report for the correlation of mutagenicity with abnormal product formation for a styrene oxide series.