Characterization of aminoindamines and aminoindoanilines formed by oxidative hair dyeing and their mutagenicity.
2-Amino-5-methoxy-2'(or 3')-methylindamine and 2-amino-5-methoxy-2'(or 3')-methylindoaniline were isolated from a coloring matter formed by oxidative condensation of 2,5-diaminotoluene with 2,4-diaminoanisole, and their structures were elucidated on the basis of nuclear magnetic resonance and mass spectral data. These two main components of the oxidation product formed at the early stage exhibited a positive result in the mutagenicity test on the thin-layer chromatography plate. The mutagenic activities of purified aminoindamines and aminoindoanilines against Salmonella typhimurium TA 98 were as strong as that of 2-acetamidofluorene. It was also demonstrated that 5-methoxy-2'(or 3')-methylindamine was formed in 10% yield under the conditions used for hair dyeing and the yield was dependent upon the molar ratio of 2,5-diaminotoluene to 2,4-diaminoanisole.
D000814:Aniline Compounds / Q000032:analysis*; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D006202:Hair Dyes / Q000032:analysis* / Q000633:toxicity; D006203:Hair Preparations / Q000032:analysis*; D006861:Hydrogen Peroxide; D007211:Indoles / Q000032:analysis*; D008099:Liver / Q000502:physiology; D008297:Male; D009153:Mutagens; D010084:Oxidation-Reduction; D051381:Rats; D012486:Salmonella typhimurium / Q000235:genetics
D000814:Aniline Compounds; D006202:Hair Dyes; D006203:Hair Preparations; D007211:Indoles; D009153:Mutagens; D006861:Hydrogen Peroxide