The effect of alkoxy substituents on the mutagenicity of some aminoazobenzene dyes and their reductive-cleavage products.
15 aminoazobenzene dyes and 7 of their reductive-cleavage products were examined in the Salmonella/microsome assay with strains TA98, TA100, TA1535, TA1537 and TA1538. Dyes tested included 5 derivatives of 4-aminoazobenzene with different alkoxy substituents (-OCH3, -OCH2CH3, -OCH2CH2 CH3, -OCH2CH2CH2CH3 or -OCH2CH2OH) in the 8-position as well as the corresponding derivatives of 4-[(4-aminophenyl)azo]-N,N-diethylaniline and 4-[(4-aminophenyl)azo]-N,N-bis(2-hydroxyethyl)aniline. In general, as the size of the substituent ortho to the primary amino group of the dyes was increased, the mutagenicity decreased. A similar trend was observed for the reductive-cleavage products. The results from the latter aspect of this study suggest that the mutagenicity of aminoazobenzene dyes can not be accounted for solely from the properties of their reductive-cleavage products.
Department of Textile Engineering, Chemistry and Science, North Carolina State University, Raleigh 27695-8302.
J F
JF
Esancy
H S
HS
Freeman
L D
LD
Claxton
D001391:Azo Compounds / Q000633:toxicity*; D055598:Chemical Phenomena; D002621:Chemistry; D004396:Coloring Agents / Q000633:toxicity*; D009152:Mutagenicity Tests; D009153:Mutagens; D010084:Oxidation-Reduction; D012486:Salmonella typhimurium / Q000235:genetics; D010128:p-Aminoazobenzene / Q000031:analogs & derivatives / Q000633:toxicity*
D001391:Azo Compounds; D004396:Coloring Agents; D009153:Mutagens; D010128:p-Aminoazobenzene