<i>Short Communication</i>: Contribution of the 5-hydroxyl group to the mutagenicity of mucochloric acid

Abstract

Abstract The sodium borohydride reduction of 3,4-dichloro-5-hydroxy-2(5H)-furanone (mucochloric acid) resulted in the formation of 3,4-dichloro-2(5H)-furanone and 4-chloro-2(5H)-furanone formed in relative amounts of 98 and 2%, respectively. Mucochloric acid and 3,4-dichloro-2(5H)-furanone were assayed together against Salmonella typhimurium (TA100). Mucochloric acid was consistently more mutagenic than 3,4-dichloro-2(5H)-furanone by a factor ranging from 36 to 49 times as established from three determinations of relative mutagenicity. Thus, the hydroxyl group substituted at the 5 position is concluded to have a marked influence on the mutagenicity of a chlorinated 2(5H)-furanone.