Roles of Oxygen in Photochemical Reaction of Naphthols in Aqueous Nitrite Solution and Mutagen Formation

概要

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Naphthols were irradiated with ultraviolet light in aqueous nitrite solution under air, oxygen and nitrogen atmospheres. 2-Naphthol gave a mutagenic product in an amount proportional to the irradiation time under air. The mutagen formation was greatly accelerated under oxygen, whereas irradiation under nitrogen gave no mutagen. 1-Naphthol gave scarcely any mutagen under any conditions. The photoreactions of naphthols in the presence and absence of nitrite under the three conditions were analyzed by high performance liquid chromatography in terms of degradation of naphthols and production of nitrosonaphthols, nitronaphthols, quinones and isocoumarin. It was proved that the reactions of nitration and naphthoquinone production both require oxygen. Consequently, the oxygen requirement for mutagen formation was attributable to those for nitration and quinone production from 2-naphthol. Nitronaphthols were presumed to be produced directly by the reaction of photo-induced naphthoxy radical with NO_2 radical formed by oxidation of photo-induced NO radical. Both 1,2- and 1,4-naphthoquinones were found to be converted photochemically to photo-stable isocoumarin, which exhibited only ambiguous mutagenicity, at different rates. 1-Naphthol, compared with 2-naphthol, was hardly nitrated and was easily converted to isocoumarin, and such reactivity was presumed to be the main reason for the lack of mutagen formation.
社団法人日本薬学会の論文
1988-11-25