An approach to the design of non-mutagenic azo dyes

Determination of aromatic amines originating from azo dyes by chemical reduction combined with liquid chromatography/mass spectrometry

“…One acid dye [Acid Orange 10 ( 16)] was included in this evaluation to determine if the reduction methodology could aid in developing MS screening procedures for this type of dye. PB determination of this acid dye only detected the volatile reductive cleavage product, (10) 4 Solvent Orange 7 2,4-dimethylaniline6 151 22.1 151 (11); 121 (100); 106 (78); 77 (15) (10); 108 (100); 80 (48); 64 (7) 10 1,4-diamino-naphthalene 158 10.7 158 (100); 109 (50); 80 (37) 8-amino-7-hydroxynaphthalene-1,3-363 16.6 not detected^48 disulfonic acid, disodium salt6>d 1 (r = retention time in TIC chromatogram (min); m/z (relative intensity) reports the major peaks (>5%) of each product down to m/z 50. A maximum of 18 ions are reported in descending m/z UV (%) = peak area of identified reduction product/ of the peak areas in the chromatogram of the reduced sample at a wavelength of 254 nm.…”

“…For instance, 2-naphthylamine, 4-aminobiphenyl, 4,4/-diaminobiphenyl (benzidine) (4), and Acid Red 27 (FD&C Red 2, a food, drug, and cosmetic colorant) have been identified as actual or potential carcinogens, although evidence suggests that metabolites of some of the azo compounds are the actual genotoxic agents (5). Also, certain aromatic amines used in the past as precursors of synthetic dyes pose a potential risk to the health of man (6,7). This point was initially thought to be important only if workers were exposed to a genotoxic precursor during dye manufacture or when handling an impure dye containing the unreacted genotoxic parent arylamine.…”