Determination of the strong mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone in chlorinated drinking and humic waters

Hemming, Jarl; Holmbom, Bjarne; Reunanen, Markku; Krönberg, Leif

doi:10.1016/0045-6535(86)90003-2

Cited by 203 publications

(98 citation statements)

References 10 publications

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“…The most known halogenated 292 furanone formed by chlorination of drinking water is the highly mutagenic MX and its analogues 293 (Hemming et al, 1986;Kronberg and Vartiaine, 1988;Meier et al, 1986). In a previous study on 294 chlorination of phenolic compounds, resorcinol was found to produce MX, but in low concentration at 295 acidic pH (i.e., 0.01 mmol/mol, pH 2) (Långvik et al, 1991).…”

Section: Hydroxy-2-pyridone With Four Chlorine Atoms (Text S3) 271mentioning

confidence: 99%

“…Based on the fragmentation 258 pattern and accurate mass of fragments obtained from EI and PCI modes (Table S2), the proposed 259 molecular structure of this compound is 3-chloro-5-hydroxy-1H-pyrrole-2-one with dichloromethyl 260 group. It is structurally very similar to MX (3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone), 261 the strong mutagen found from chlorinated drinking water and humic water (Hemming et al, 1986;after derivatization of the MTBE extract using acidic methanol, with a molecular formula of 264 C6H6NO2Cl3 (9.52ppm). The corresponding EI and PCI mass spectra presented a loss of 31 Da (-265…”

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confidence: 99%

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Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds

Nihemaiti

Roux

Hoppe‐Jones

et al. 2016

Environ. Sci. Technol.

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18The potential formation of nitrogenous disinfection by-products (N-DBPs) was investigated from the 19 chloramination of nitrogenous and non-nitrogenous aromatic compounds. All molecules led to the 20 formation of known N-DBPs (e.g., dichloroacetonitrile, dichloroacetamide) with various production 21 yields. Resorcinol, a major precursor of chloroform, also formed di-/tri-chloroacetonitrile, di-/tri-22 chloroacetamide, and haloacetic acids, indicating that it is a precursor of both N-DBPs and 23carbonaceous DBPs (C-DBPs) upon chloramination. More detailed experiments were conducted on 24 resorcinol to understand N-DBPs formation mechanisms and to identify reaction intermediates. Based 25 on the accurate mass from high resolution Quadrupole Time-of-Flight GC-MS (GC-QTOF) and 26 fragmentation patterns from electronic impact and positive chemical ionization modes, several 27 products were tentatively identified as nitrogenous heterocyclic compounds (e.g., 3-chloro-5-hydroxy-28 1H-pyrrole-2-one with dichloromethyl group, 3-chloro-2,5-pyrroledione). These products were 29 structurally similar to the heterocyclic compounds formed during chlorination, such as the highly 30 mutagenic MX (3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone) or halogenated pyrroles. To 31 our knowledge, this is the first time that the formation of halogenated nitrogenous heterocyclic 32 compounds is reported from chloramination process. The formation of these nitrogenous by-products 33 during chloramination might be of concern considering their potential toxicity. 34 ABSTRACT ART35 36 37 INTRODUCTION 38

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Section: Hydroxy-2-pyridone With Four Chlorine Atoms (Text S3) 271mentioning

confidence: 99%

mentioning

confidence: 99%

Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds

Nihemaiti

Roux

Hoppe‐Jones

et al. 2016

Environ. Sci. Technol.

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“…MCA (1) is a chlorinated hydroxyfuranone (CHFs), a distinctive class of compounds renowned for their mutagenicity 6−8 and their ominous presence in domestic waters as a consequence of the practice of chlorination. 6,8,9 The reactions of CHFs with purine bases are of interest and concern because of the damage they can inflict upon DNA and other biomolecules.…”

Section: Introductionmentioning

confidence: 99%

Regioisomeric α-hydroxy chlorohydrins from the reaction of mucochloric acid and guanosine

Klika¹,

Mäki²,

Sjöholm³

et al. 2006

Arkivoc

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The reaction of mucochloric acid with guanosine produces as the major product oxalyl ethenoguanosine together with a minor amount of its degradation product ethenoguanosine. Also present in trace amounts were two sets of regioisomeric α-hydroxy chlorohydrins consisting of interconverting C-6(7) epimers for both C-7(6) stereoisomers, i.e. a total of four stereoisomers were present for each regioisomeric set. Each regioisomeric set consisted of products where a newly-formed six-membered ring was fused onto the nucleobase, one set via N-1 and N-2 of guanosine, the other via N-2 and N-3. The structural elucidation of the compounds was based on NMR studies ( 1 H, 13 C, and 15 N NMR) and a plausible mechanism for their creation is also presented.

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“…Le chloroforme et les acides dichloro et trichloroacétiques sont les principaux sous-produits de chloration analysables formés par chloration de substances humiques aquatiques (JOHNSON et al, 1982 ;MILLER et UDEN, 1983 ;NOR -WOOD et ai, 1983 ;COLEMAN et al, 1984 ;RECKHOW, 1984 ;SEEGER et al, 1984;CROUE, 1987). Certains des composés organo-chlorés formés pré-sentent des propriétés mutagènes (DE GREEF et al, 1980 ;KRINGSTAD et al, 1983 ;COLEMAN et al, 1984 ;KOOL et al, 1984 ;MEIER et al, 1985) et en particulier le chloro-3 (dichloromethyl) -4 hydroxy -5 (5H) furanone -2 ou « MX » et son isomère « E-MX », récemment identifiés lors de la chloration des eaux et des solutions de substances humiques (HEMMING et al, 1986 ;KRONBERG et ai, 1987). L'essentiel des travaux de recherche sur les substances humiques aquatiques a été effectué par des laboratoires américains.…”

Section: Introductionunclassified

Etude sur les acides fulviques extraits d'eaux superficielles françaises - Extraction, caractérisation et réactivité avec le chlore

Légube¹,

Xiong²,

Croué³

et al. 2005

rseau

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Après avoir présenté quelques données bibliographiques sur les substances humiques aquatiques, l'extraction de plusieurs substances humiques issues de onze eaux de surface françaises, est discutée en terme de rendements d'extraction. Quelques paramètres de caractérisation des acides fulviques sont présentés et en particulier, l'analyse élémentaire, l'absorption UV, les fonctions carboxyles et les potentiels de réactivité avec le chlore. Concernant la chloration, une attention particulière a été portée d'une part sur la nature produits organo-chlorés formés et d'autre part sur les corrélations qui existent entre la nature des acides fulviques et leur potentiel de réactivité avec le chlore.Numerous procedure for the isolation of aquatic humic substances are described in literature. The first part of this study presents the extraction of fulvic and humic acids from eleven French surface waters, using XAD 8 macroreticular resin as developed by TRURMAN and MALCOLM (1981). The results are discussed in terms of extraction yield and fulvic acid/humic acid mass ratio.The second part of the paper presents some structural parameters of the extracted fulvic acids such as elemental analysis, UV-absorbance, carboxyle-function content and in some cases of fulvic acids, infrared spectrum and apparent molecular weight investigated by ultra filtration.The third part of the work concerns the study of fulvic acids chlorination. Firstly, the gas chromatography - mass spectrometry analysis of one chlorinated fulvic acid allowed us to identify some chlorination by-products and especially chloroform, dichloro-acetic and trichloroacetic acids and some other chlorinated aliphatic acids. Secondly, the chlorine reactivity potentials of each fulvic acids were determined and results are discussed in terms of chlorine consumption, chloroform and total organohalides formation potentials. Some relationships are established between the chlorine reactivity potentials and UV-absorbance of the extracted fulvic acids

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Determination of the strong mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone in chlorinated drinking and humic waters

Cited by 203 publications

References 10 publications

Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds

Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds

Regioisomeric α-hydroxy chlorohydrins from the reaction of mucochloric acid and guanosine

Etude sur les acides fulviques extraits d'eaux superficielles françaises - Extraction, caractérisation et réactivité avec le chlore

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