Rôle of a metabolite in allergenicity of Sudan I.
A metabolite of Sudan I (1-phenylazo-2-naphthol) was isolated after in vitro incubation with the supernatant of guinea pig liver homogenate (S-9). The metabolite was found to be 4'-hydroxy-1-phenylazo-2-naphthol by gas chromatography-mass spectrometry (GC-MS), and proton and carbon-13 nuclear magnetic resonance (NMR) analyses. It elicited positive reactions in guinea pigs sensitized to Sudan I. It was also shown to be allergenic. The results suggest that para-hydroxylation of the phenyl group of Sudan I may play an important rôle in its allergenicity.
D000818:Animals; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D003877:Dermatitis, Contact / Q000276:immunology*; D006168:Guinea Pigs; D006900:Hydroxylation; D009284:Naphthols / Q000276:immunology*; D010328:Patch Tests; D013329:Structure-Activity Relationship
D009284:Naphthols; C024336:1-phenylazo-2-naphthol