Facile synthesis of mutagen X (MX): 3-chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one

DRAFT: Evidence on the carcinogenicity of MX (3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone

Carcinogenicity of the drinking water mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone in the rat.

BACKGROUND Several epidemiologic studies have suggested that the consumption of chlorinated drinking water may be associated with the development of certain cancers in humans. 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), a byproduct of the chemical reactions that occur in chlorinated drinking water, has been found to be mutagenic in bacteria and mammalian cells; however, its poten...

3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) and mutagenic activity in Massachusetts drinking water.

There is limited information on the prevalence of the potent mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) in U.S. water supplies. We measured MX concentrations and mutagenic activity in tap water samples from 36 surface water systems throughout Massachusetts. We found MX levels much higher (up to 80 ng/L) than previously reported in the United States. We also evaluated the ...

3-Chloro-4-dimethyl­amino-5-[(1R,2S,5R)-2-isopropyl-5-methyl­cyclo­hex­yloxy]furan-2(5H)-one

The title compound, C(16)H(26)ClNO(3) contains one almost planar furan-one ring [maximum deviation of 0.021 (2) Å for the O atom] with a stereogenic center (S) and one cyclo-hexane ring which displays a chair conformation and has three stereogenic centers [S at the C atom bearing the isopropyl group, R at the C atom attached to the O atom and R at the C atom bearing the methyl group].

(S)-3-Chloro-4-(4-ethyl­piperazin-1-yl)-5-[(1R,2S,5R)-2-isopropyl-5-methyl­cyclo­hex­yloxy]furan-2(5H)-one

The title compound, C(20)H(33)ClN(2)O(3), was obtained via a tandem asymmetric Michael addition-elimination reaction of 3,4-dichloro-5-(S)-(l-menth-yloxy)furan-2(5H)-one and 1-ethyl-piperazine in the presence of potassium fluoride. The mol-ecular structure contains an approximately planar five-membered furan-one ring [maximum atomic deviation = 0.024 (2) Å] and two six-membered rings adopting c...