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Short Communication : Contribution of the 5‐hydroxyl group to the mutagenicity of mucochloric acid
Author(s) -
LaLonde Robert T.,
Perakyla Hannu,
Cook Gary P.,
Dence Carlton W.
Publication year - 1990
Publication title -
environmental toxicology and chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.1
H-Index - 171
eISSN - 1552-8618
pISSN - 0730-7268
DOI - 10.1002/etc.5620090601
Subject(s) - sodium borohydride , chemistry , salmonella , sodium , medicinal chemistry , organic chemistry , stereochemistry , toxicology , bacteria , biology , genetics , catalysis
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.