Potent Bacterial Mutagens Produced by Chlorination of Simulated Poultry Chiller Water

Hypochlorite treatment of a simulated food-processing mixture produces 3,4-dichloromaleimide and 3,3-dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione (C5HCl4NO2). The tetrachloro compound and two analogs, which can be synthesized from citraconic anhydride and itaconic anhydride, are direct-acting...

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Veröffentlicht in:Journal of agricultural and food chemistry 1996-01, Vol.44 (1), p.256-263
Hauptverfasser: Haddon, William F, Binder, Ronald G, Wong, Rosalind Y, Harden, Leslie A, Wilson, Robert E, Benson, Mabry, Stevens, Kenneth L
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container_end_page 263
container_issue 1
container_start_page 256
container_title Journal of agricultural and food chemistry
container_volume 44
creator Haddon, William F
Binder, Ronald G
Wong, Rosalind Y
Harden, Leslie A
Wilson, Robert E
Benson, Mabry
Stevens, Kenneth L
description Hypochlorite treatment of a simulated food-processing mixture produces 3,4-dichloromaleimide and 3,3-dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione (C5HCl4NO2). The tetrachloro compound and two analogs, which can be synthesized from citraconic anhydride and itaconic anhydride, are direct-acting Ames mutagens in Salmonella typhimurium TA100 tester strain. These novel five-carbon cyclic imides are structurally similar to 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), the principal mutagenic compound present in paper pulp bleaching liquors. Molecular structure analysis of the mutagens was based on X-ray crystallography, 13C NMR, and mass spectrometry of synthetic chlorinated imides with identical mass spectra and gas chromatographic retention indices. The tetrachloroimide accounts for much of the mutagenicity of the dichloromethane-extractable pH 2 fraction from chlorination of a simulated food-processing system consisting of chicken frankfurters. In the Ames TA100 tester strain it has a molecular mutagenicity of 1450 revertants/nmol without microsomal activation, making it the second most potent mutagen reported from a chlorination process. Keywords: Poultry chiller water; bacterial mutagens; chlorine disinfection byproducts; chlorinated imides
doi_str_mv 10.1021/jf950076s
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The tetrachloro compound and two analogs, which can be synthesized from citraconic anhydride and itaconic anhydride, are direct-acting Ames mutagens in Salmonella typhimurium TA100 tester strain. These novel five-carbon cyclic imides are structurally similar to 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), the principal mutagenic compound present in paper pulp bleaching liquors. Molecular structure analysis of the mutagens was based on X-ray crystallography, 13C NMR, and mass spectrometry of synthetic chlorinated imides with identical mass spectra and gas chromatographic retention indices. The tetrachloroimide accounts for much of the mutagenicity of the dichloromethane-extractable pH 2 fraction from chlorination of a simulated food-processing system consisting of chicken frankfurters. In the Ames TA100 tester strain it has a molecular mutagenicity of 1450 revertants/nmol without microsomal activation, making it the second most potent mutagen reported from a chlorination process. Keywords: Poultry chiller water; bacterial mutagens; chlorine disinfection byproducts; chlorinated imides</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf950076s</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>AGUA ; AVES DE CORRAL ; Biological and medical sciences ; BYPRODUCTS ; Chemical mutagenesis ; CHLORE ; CHLORINATED IMIDES ; CHLORINE ; CHLORINE DISINFECTION ; CLORO ; COMPOSE ORGANOAZOTE ; COMPUESTO ORGANICO DEL NITROGENO ; DESINFECCION ; DESINFECTION ; DISINFECTION ; EAU ; Fish and seafood industries ; Food industries ; Fundamental and applied biological sciences. Psychology ; IMIDES ; INDUSTRIA ; INDUSTRIE ; INDUSTRY ; Medical sciences ; MUTAGENICIDAD ; MUTAGENICITE ; MUTAGENICITY ; ORGANIC NITROGEN COMPOUNDS ; POULTRY ; PROCESAMIENTO ; PROCESSING ; SALMONELLA TYPHIMURIUM ; SOUS PRODUIT ; SUBPRODUCTOS ; Toxicology ; TRAITEMENT ; VOLAILLE ; WATER</subject><ispartof>Journal of agricultural and food chemistry, 1996-01, Vol.44 (1), p.256-263</ispartof><rights>Copyright © 1996 American Chemical Society</rights><rights>1996 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a346t-c9bcf98391d89814d30dfaf2b1f10e1b688e4d260ae70796f78738e887284f313</citedby><cites>FETCH-LOGICAL-a346t-c9bcf98391d89814d30dfaf2b1f10e1b688e4d260ae70796f78738e887284f313</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf950076s$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf950076s$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=2966405$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Haddon, William F</creatorcontrib><creatorcontrib>Binder, Ronald G</creatorcontrib><creatorcontrib>Wong, Rosalind Y</creatorcontrib><creatorcontrib>Harden, Leslie A</creatorcontrib><creatorcontrib>Wilson, Robert E</creatorcontrib><creatorcontrib>Benson, Mabry</creatorcontrib><creatorcontrib>Stevens, Kenneth L</creatorcontrib><title>Potent Bacterial Mutagens Produced by Chlorination of Simulated Poultry Chiller Water</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Hypochlorite treatment of a simulated food-processing mixture produces 3,4-dichloromaleimide and 3,3-dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione (C5HCl4NO2). The tetrachloro compound and two analogs, which can be synthesized from citraconic anhydride and itaconic anhydride, are direct-acting Ames mutagens in Salmonella typhimurium TA100 tester strain. These novel five-carbon cyclic imides are structurally similar to 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), the principal mutagenic compound present in paper pulp bleaching liquors. Molecular structure analysis of the mutagens was based on X-ray crystallography, 13C NMR, and mass spectrometry of synthetic chlorinated imides with identical mass spectra and gas chromatographic retention indices. The tetrachloroimide accounts for much of the mutagenicity of the dichloromethane-extractable pH 2 fraction from chlorination of a simulated food-processing system consisting of chicken frankfurters. In the Ames TA100 tester strain it has a molecular mutagenicity of 1450 revertants/nmol without microsomal activation, making it the second most potent mutagen reported from a chlorination process. Keywords: Poultry chiller water; bacterial mutagens; chlorine disinfection byproducts; chlorinated imides</description><subject>AGUA</subject><subject>AVES DE CORRAL</subject><subject>Biological and medical sciences</subject><subject>BYPRODUCTS</subject><subject>Chemical mutagenesis</subject><subject>CHLORE</subject><subject>CHLORINATED IMIDES</subject><subject>CHLORINE</subject><subject>CHLORINE DISINFECTION</subject><subject>CLORO</subject><subject>COMPOSE ORGANOAZOTE</subject><subject>COMPUESTO ORGANICO DEL NITROGENO</subject><subject>DESINFECCION</subject><subject>DESINFECTION</subject><subject>DISINFECTION</subject><subject>EAU</subject><subject>Fish and seafood industries</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>IMIDES</subject><subject>INDUSTRIA</subject><subject>INDUSTRIE</subject><subject>INDUSTRY</subject><subject>Medical sciences</subject><subject>MUTAGENICIDAD</subject><subject>MUTAGENICITE</subject><subject>MUTAGENICITY</subject><subject>ORGANIC NITROGEN COMPOUNDS</subject><subject>POULTRY</subject><subject>PROCESAMIENTO</subject><subject>PROCESSING</subject><subject>SALMONELLA TYPHIMURIUM</subject><subject>SOUS PRODUIT</subject><subject>SUBPRODUCTOS</subject><subject>Toxicology</subject><subject>TRAITEMENT</subject><subject>VOLAILLE</subject><subject>WATER</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><recordid>eNptkE1LAzEQhoMoWKsHf4CwBz14WE32Ix9HXbUKVQttKXgJ092kbl03JcmC_femrPTkaWCeZ16GF6Fzgm8ITsjtWoscY0bdARqQPMFxTgg_RAMcYMxzSo7RiXNrjDHPGR6g-cR41froHkqvbA1N9Np5WKnWRRNrqq5UVbTcRsVnY2zdgq9NGxkdTevvrgEf4MR0jbc7o24aZaNF2NpTdKShcersbw7R_OlxVjzH4_fRS3E3jiHNqI9LsSy14KkgFRecZFWKKw06WRJNsCJLyrnKqoRiUAwzQTXjLOWKc5bwTKckHaLrPre0xjmrtNzY-hvsVhIsd33IfR_BvezdDbgSGm2hLWu3P0gEpRnOgxb3Wu28-tljsF-SspTlcjaZylExHi3GDx_yLfgXva_BSFjZEDmfEiFYyOIiCfyq51A6uTadbUMh_7z3C5IUg7w</recordid><startdate>19960101</startdate><enddate>19960101</enddate><creator>Haddon, William F</creator><creator>Binder, Ronald G</creator><creator>Wong, Rosalind Y</creator><creator>Harden, Leslie A</creator><creator>Wilson, Robert E</creator><creator>Benson, Mabry</creator><creator>Stevens, Kenneth L</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19960101</creationdate><title>Potent Bacterial Mutagens Produced by Chlorination of Simulated Poultry Chiller Water</title><author>Haddon, William F ; Binder, Ronald G ; Wong, Rosalind Y ; Harden, Leslie A ; Wilson, Robert E ; Benson, Mabry ; Stevens, Kenneth L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a346t-c9bcf98391d89814d30dfaf2b1f10e1b688e4d260ae70796f78738e887284f313</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>AGUA</topic><topic>AVES DE CORRAL</topic><topic>Biological and medical sciences</topic><topic>BYPRODUCTS</topic><topic>Chemical mutagenesis</topic><topic>CHLORE</topic><topic>CHLORINATED IMIDES</topic><topic>CHLORINE</topic><topic>CHLORINE DISINFECTION</topic><topic>CLORO</topic><topic>COMPOSE ORGANOAZOTE</topic><topic>COMPUESTO ORGANICO DEL NITROGENO</topic><topic>DESINFECCION</topic><topic>DESINFECTION</topic><topic>DISINFECTION</topic><topic>EAU</topic><topic>Fish and seafood industries</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>IMIDES</topic><topic>INDUSTRIA</topic><topic>INDUSTRIE</topic><topic>INDUSTRY</topic><topic>Medical sciences</topic><topic>MUTAGENICIDAD</topic><topic>MUTAGENICITE</topic><topic>MUTAGENICITY</topic><topic>ORGANIC NITROGEN COMPOUNDS</topic><topic>POULTRY</topic><topic>PROCESAMIENTO</topic><topic>PROCESSING</topic><topic>SALMONELLA TYPHIMURIUM</topic><topic>SOUS PRODUIT</topic><topic>SUBPRODUCTOS</topic><topic>Toxicology</topic><topic>TRAITEMENT</topic><topic>VOLAILLE</topic><topic>WATER</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Haddon, William F</creatorcontrib><creatorcontrib>Binder, Ronald G</creatorcontrib><creatorcontrib>Wong, Rosalind Y</creatorcontrib><creatorcontrib>Harden, Leslie A</creatorcontrib><creatorcontrib>Wilson, Robert E</creatorcontrib><creatorcontrib>Benson, Mabry</creatorcontrib><creatorcontrib>Stevens, Kenneth L</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Haddon, William F</au><au>Binder, Ronald G</au><au>Wong, Rosalind Y</au><au>Harden, Leslie A</au><au>Wilson, Robert E</au><au>Benson, Mabry</au><au>Stevens, Kenneth L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Potent Bacterial Mutagens Produced by Chlorination of Simulated Poultry Chiller Water</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>1996-01-01</date><risdate>1996</risdate><volume>44</volume><issue>1</issue><spage>256</spage><epage>263</epage><pages>256-263</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Hypochlorite treatment of a simulated food-processing mixture produces 3,4-dichloromaleimide and 3,3-dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione (C5HCl4NO2). The tetrachloro compound and two analogs, which can be synthesized from citraconic anhydride and itaconic anhydride, are direct-acting Ames mutagens in Salmonella typhimurium TA100 tester strain. These novel five-carbon cyclic imides are structurally similar to 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), the principal mutagenic compound present in paper pulp bleaching liquors. Molecular structure analysis of the mutagens was based on X-ray crystallography, 13C NMR, and mass spectrometry of synthetic chlorinated imides with identical mass spectra and gas chromatographic retention indices. The tetrachloroimide accounts for much of the mutagenicity of the dichloromethane-extractable pH 2 fraction from chlorination of a simulated food-processing system consisting of chicken frankfurters. In the Ames TA100 tester strain it has a molecular mutagenicity of 1450 revertants/nmol without microsomal activation, making it the second most potent mutagen reported from a chlorination process. Keywords: Poultry chiller water; bacterial mutagens; chlorine disinfection byproducts; chlorinated imides</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/jf950076s</doi><tpages>8</tpages></addata></record>
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identifier ISSN: 0021-8561
ispartof Journal of agricultural and food chemistry, 1996-01, Vol.44 (1), p.256-263
issn 0021-8561
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language eng
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source American Chemical Society
subjects AGUA
AVES DE CORRAL
Biological and medical sciences
BYPRODUCTS
Chemical mutagenesis
CHLORE
CHLORINATED IMIDES
CHLORINE
CHLORINE DISINFECTION
CLORO
COMPOSE ORGANOAZOTE
COMPUESTO ORGANICO DEL NITROGENO
DESINFECCION
DESINFECTION
DISINFECTION
EAU
Fish and seafood industries
Food industries
Fundamental and applied biological sciences. Psychology
IMIDES
INDUSTRIA
INDUSTRIE
INDUSTRY
Medical sciences
MUTAGENICIDAD
MUTAGENICITE
MUTAGENICITY
ORGANIC NITROGEN COMPOUNDS
POULTRY
PROCESAMIENTO
PROCESSING
SALMONELLA TYPHIMURIUM
SOUS PRODUIT
SUBPRODUCTOS
Toxicology
TRAITEMENT
VOLAILLE
WATER
title Potent Bacterial Mutagens Produced by Chlorination of Simulated Poultry Chiller Water
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