Detail of "93490-31-4"

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4-Chloro-6-methoxyindole is the precursor of a potent mutagen (4-chloro-6-methoxy-2-hydroxy-1-nitroso-indolin-3-one oxime) that forms during nitrosation of the fava bean (Vicia faba)

4-Chloro-6-methoxyindole is the precursor of a potent mutagen (4-chloro-6-methoxy-2-hydroxy-1-nitroso-indolin-3-one oxime) that forms during nitrosation of the fava bean (Vicia faba). Yang, David; Tannenbaum, Steven R.; Buchi, George; Lee, Gary C. M. (Dep. Nutr. Food Sci., Massachusetts Inst. Technol., Cambridge, MA 02139, USA). Carcinogenesis (London), 5(10), 1219-24 (English) 1984. CODEN: CRNGDP. ISSN: 0143-3334. DOCUMENT TYPE: Journal CA Section: 17 (Food and Feed Chemistry) Section cross-reference(s): 4 Fava beans upon treatment with NO2- under simulated gastric conditions form a direct-acting bacterial mutagen, comparable in specific activity to the most potent known mutagens for several strains of Salmonella typhimurium. The precursor of the mutagen was isolated and identified as 4-chloro-6-methoxyindole (I) [93490-31-4] by UV, IR, NMR and mass spectrometry. The precursor was dechlorinated with NaBH4 and PdCl2 as the catalyst and the product obtained from this reaction was identified as 6-methoxyindole. Since synthetic I was not available, structure-activity studies were conducted on substituted indoles. Nitrosation of 4-chloroindole closely follows the results for nitrosation of 4-chloro-6-methoxyindole. The major product of nitrosation of 4-chloroindole is 4-chloro-2-hydroxy-N1-nitrosoindolin-3-one oxime [93490-32-5]. Thus, it appears that the major nitrosation product of 4-chloroindole and of I is a stable a-hydroxy N-nitroso compd. This is the 1st reported case of stable a-hydroxy N-nitroso compds. In the presence of N-(1-naphthyl)ethylenediamine-2HCl (NEDD) [1465-25-4], the a-hydroxy N-nitroso compd. rearranges to an arom. diazonium ion which couples with the diamine to form an azo dye. Studies on nitrosation kinetics indicate that the nitrosation of indoles are relatively fast reactions. Both the structural and rate studies give strong support to the hypothesis that intragastric nitrosation of fava beans yield the putative gastric carcinogen in the high-risk area in Colombia.