- Factors on the formation of strong mutagen [3-chloro-4-(dichloromethyl)- 5-hydroxy-2(5H)-furanone] MX by chlorination of syringaldehyde
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Syringaldehyde (4-hydroxy-3,5-dimethoxybenzaldehyde) was chlorinated in the laboratory at different reaction time, temperature, pH and chlorine dose, and MX was determined and quantified by GC/MS. The finding suggests that the optimal chlorination conditions are as follows: temperature = 298 K, pH = 5, Cl:syrin. (mol:mol) = 9:1. We also found that the formation of MX increased with the syringaldehyde concentration in a linear relationship. In addition, when syringaldehyde was chlorinated with a different chlorine dose in an alkaline condition, no MX was detected. This study will conduce to elucidating the kinetic process for the formation of MX from syringaldehyde and will be of great help for better control of MX in drinking water. Syringaldehyde (4-hydroxy-3,5-dimethoxybenzaldehyde) was chlorinated in the laboratory at different reaction time, temperature, pH and chlorine dose, and MX was determined and quantified by GC/MS. The finding suggests that the optimal chlorination conditions are as follows: temperature = 298 K, pH = 5, Cl:syrin. (mol:mol) = 9:1. We also found that the formation of MX increased with the syringaldehyde concentration in a linear relationship. In addition, when syringaldehyde was chlorinated with a different chlorine dose in an alkaline condition, no MX was detected. This study will conduce to elucidating the kinetic process for the formation of MX from syringaldehyde and will be of great help for better control of MX in drinking water. (C) 2000 Elsevier Science Ltd.
- Chengyong, Yang,Zhuo, Chen,Huixian, Zou,Junhe, Lu,Jinqi, Zhang
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- Screening the precursors of strong mutagen [3-chloro-4-(dichloromethyl)- 5-hydroxy-2(5H)-furanone] MX from chlorinated water
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In this study, 21 suspected precursors of MX were chlorinated in laboratory condition. Only 8 of selected compounds syringaldehyde, acetosyringone, ferulic acid, 3-ethoxy-4-hydroxy-benzaldehyde, 3,4,5- trimethoxy-benzaldehyde, vanillin, tryptophan, and tyrosine were screened as precursors of MX. The yields of MX by chlorination of syringaldehyde are the highest and decreased with chlorine dose, but the yields of MX by the other 7 compounds increased with chlorine dose. It may be possible to elucidate the reaction mechanism for the formation of MX in light of the reaction of these screened precursors with chlorine.
- Huixian, Zou,Junhe, Lu,Zhuo, Chen,Chengyong, Yang,Jinqi, Zhang,Wen, Zhou
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- Facile synthesis of mutagen X (MX): 3-chloro-4-(dichloromethyl)-5-hydroxy- 5H-furan-2-one
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3-Chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one (mutagen X, MX) was synthesized in six steps from commercially-available and inexpensive starting materials (27% overall yield). This synthesis enables the preparation of MX analogs and does not require the use of chlorine gas, as do previously reported methods.
- Velvadapu, Venkata,McDonnell, Mark E.,Jaffe, Eileen K.,Reitz, Allen B.
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p. 3144 - 3146
(2012/08/08)
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- Modification of Synthesis of 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX)
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Addition of chlorine to methyl 3-(dichloromethyl)-4,4-dichlorocrotonate (1), a critical procedure in the total synthesis of the title compound MX, was modified by using novel catalysts.A minor modification in the purification of MX was also described.
- Jinqi, Zhang,Zhen, Zhu,Huixian, Zou,Minmin, Yang
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p. 3402 - 3406
(2007/10/03)
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- Synthesis of chlorinated 5-hydroxy 4-methyl-2(5H)-furanones and mucochloric acid
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An improved procedure for the synthesis of chlorinated 5-hydroxy-4-methyl-2(5H)-furanones is described. By this method also carbon-labelled (13C and 14C at C-3) hydroxyfuranones, including mucochloric acid, can be prepared. Each step of the method was examined in an effort to optimize both the yield and the purity of the compounds.
- Franzen, Robert
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p. 3905 - 3908
(2007/10/02)
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- POSSIBLE REACTION PATHWAYS FOR THE FORMATION OF 3-CHLORO-4-(DICHLOROMETHYL)-5-HYDROXY-2(5H)-FURANONE (MX).
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Three compounds, 3,4,5-trimethoxybenzaldehyde (I), 1-dichloromethyl-3,4,5-trimethoxy-benzene (II) and 3,4,5-trimethoxyphenylacetic acid (III) were treated with aqueous chlorine at pH 2. Aqueous chlorination of the three compounds increased the formation of MX (3-chloro-4-dichloromethyl-5(2H)-hydroxyfuranone) and E-MX (E 2-chloro-3-dichloromethyl-4-oxo-butenoic acid) in the order I>II>III. By 1H-NMR spectroscopy and gas chromatography it was shown that II hydrolizes readily to I in water. It is known that III is converted to II in chlorination reactions. We suggest that the (formed) aldehyde group remains intact during the formation of MX and E-MX from these three compounds. They could thus form MX and E-MX, via similar mechanisms. This suggested mechanism may also occur when phenolic precursor structures present in humic material are treated with chlorine in the process of drinking water production.
- Langvik, Vivi-Ann,Hormi, Osmo
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p. 1111 - 1118
(2007/10/03)
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- Potentially Mutagenic, Chlorine-Substituted 2(5H)-Furanones: Studies of Their Synthesis and NMR Properties
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The mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), 1, and seven analogues of it were synthesized from 4-(hydroxymethyl)-2(5H)-furanone, 2.This investigation was untertaken to learn if 2 would serve as a versatile starting point for the preparation of MX analogues required for structure/activity studies of genotoxicity.Compound 2 was treated with thionyl chloride-pyridine to develop the C-4 chloromethyl group.Oxidation of 2 with pyridinium chlorochromate to the aldehyde, followed by treatment of the latter with phosphorus pentachloride, developed the C-4 dichloromethyl group.Thereafter, when attachment of chlorine at C-3 was desired, the aluminum chloride promoted chlorine addition to the C-3-C-4 double bond followed by the triethylamine-promoted elimination of hydrogen chloride resulted in the required 3-chloro-4-(chloromethyl) or 4-(dichloromethyl)-5-desoxy analogues of MX.Hydroxylation at C-5 was achieved in two steps, involving first bromine substitution employing NBS under free radical conditions followed by metal ion assisted hydrolysis of the bromide in aqueous acetone.Special regard was paid to the characterization of MX and its analogues by assessing the values of 13C NMR chemical shift, the consistency of substitution effects, and the occurrence and magnitude of direct and long-range couplings in the spectra of these compounds.
- LaLonde, Robert T.,Perakyla, Hannu,Hayes, Michael P.
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p. 2847 - 2855
(2007/10/02)
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- Synthesis of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone, a potent mutagen
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Starting from tetrachloroacetone 1 and (carbomethoxymethylene)triphenylphosphorane 4, the title compound 16 was prepared in five steps in 44percent yield.Spectroscopic and chromatographic data indicated that this material was identical to a potent mutagen isolated from kraft pulp chlorination effluent.Various mutant Salmonella typhimurium strains (TA 98, 100, and 1537) behaved similarly when incubated with either 16 or the isolated mutagen.
- Padmapriya, Abeysinghe A.,Just, George,Lewis, Norman G.
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p. 828 - 832
(2007/10/02)
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