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{{chembox |
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{{chembox |
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| verifiedrevid = 414050757 |
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| verifiedrevid = 443829709 |
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|ImageFile=Furylfuramide.png |
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| ImageFile = Furylfuramide.svg |
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|ImageSize=200px |
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| ImageSize = 225px |
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|IUPACName=(Z)-2-(2-furyl)-3-(5-nitro-2-furyl)prop-2-enamide |
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| PIN = (2''Z'')-2-(Furan-2-yl)-3-(5-nitrofuran-2-yl)prop-2-enamide |
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|OtherNames=Tofuron,<br>Alpha-2-furyl-5-nitro-2-furanacrylamide, <br> |
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| OtherNames = (''Z'')-2-(2-Furyl)-3-(5-nitro-2-furyl)prop-2-enamide<br />AF-2,<ref name="nature"/> Tofuron,<br>Alpha-2-furyl-5-nitro-2-furanacrylamide,<br> |
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2-(2-Furyl)-3-(5-nitro-2-furyl)acrylic acid amide, <br> |
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2-(2-Furyl)-3-(5-nitro-2-furyl)acrylic acid amide, <br> |
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a-(Furyl)-b-(5-nitro-2-furyl)acrylic amide, <br> |
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a-(Furyl)-b-(5-nitro-2-furyl)acrylic amide, <br> |
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trans-2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamide,<br> |
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''trans''-2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamide,<br> |
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2-(2-furyl)-3-(5-nitro-2-furyl) acrylamide, <br> |
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2-(2-furyl)-3-(5-nitro-2-furyl) acrylamide, <br> |
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2-Furanacetamide, alpha-((5-nitro-2-furanyl)methylene)-,<ref></ref><ref name="who"/> |
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2-Furanacetamide, alpha-((5-nitro-2-furanyl)methylene)-,<ref></ref><ref name="who"/> |
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| Abbreviations=AF-2, FF |
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|Section1= {{Chembox Identifiers |
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|Section1 = {{Chembox Identifiers |
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| Abbreviations = AF-2, FF |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4444292 |
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| ChemSpiderID = 4444292 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LYAHJFZLDZDIOH-VURMDHGXSA-N |
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| StdInChIKey = LYAHJFZLDZDIOH-VURMDHGXSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=3688-53-7 |
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| CASNo=3688-53-7 |
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| PubChem=5280707 |
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| PubChem=5280707 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 054NR2135Y |
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| UNII = 054NR2135Y |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 15660 |
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| ChEBI = 15660 |
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| SMILES = O=()c2oc(/C=C(/c1occc1)C(=O)N)cc2 |
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| SMILES = O=()c2oc(/C=C(/c1occc1)C(=O)N)cc2 |
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|Section2= {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula=C<sub>11</sub>H<sub>8</sub>N<sub>2</sub>O<sub>5</sub> |
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| Formula = C<sub>11</sub>H<sub>8</sub>N<sub>2</sub>O<sub>5</sub> |
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| MolarMass=248.19162 |
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| MolarMass = 248.19162 |
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| Appearance= |
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|Section3= {{Chembox Hazards |
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|Section3 = {{Chembox Hazards |
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| MainHazards= |
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'''Furylfuramide''' is a synthetic ] derivative which was widely used as a ] in ] since at least 1965, but withdrawn from the market in 1974 when it was observed to be ]ic to ] '']'' and thus suspected of ]icity. This was confirmed later when ]<ref> |
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'''Furylfuramide''' (also known as '''AF-2''')<ref name="nature">{{cite journal|last1=Nomura|first1=Taisei|title=Carcinogenicity of the food additive furylfuramide in foetal and young mice|journal=Nature|volume=258|issue=5536|year=1975|pages=610–611|issn=0028-0836|doi=10.1038/258610a0|pmid=1239666|bibcode=1975Natur.258..610N|s2cid=4217389}}</ref> is a synthetic ] derivative which was widely used as a ] in ] since at least 1965, but withdrawn from the market in 1974 when it was observed to be ]ic to ] '']'' and thus suspected of ]icity. This was confirmed later when ]<ref> |
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{{Citation |
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{{Citation |
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| last = Hayatsu |
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| last = Hayatsu |
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| first = Hiroka |
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| first = Hiroka |
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| authorlink = |
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| author-link = |
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| coauthors = |
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| title = Mutagens in Food: Detection and Prevention |
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| title = Mutagens in Food: Detection and Prevention |
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| publisher = ] |
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| publisher = ] |
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| location = |
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| location = |
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| pages = 286 pages |
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| pages = 286 pages |
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| url = http://books.google.com/?id=eQyMCWRIVf4C&pg=RA1-PA1&lpg=RA1-PA1&dq=carcinogen+preservative+(furylfuramide%7Caf2) |
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| url = https://books.google.com/books?id=eQyMCWRIVf4C&q=carcinogen+preservative+(furylfuramide%7Caf2)&pg=RA1-PA1 |
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|isbn = 0849358779 }}</ref> found it to cause ] and ]s in the ]s, ]s, ], and ]s of ]s of both ]es, although insufficient evidence exists in human exposure.<ref name="who"> |
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| isbn = 0-8493-5877-9 }}</ref> found it to cause ] and ]s in the ]s, ]s, ], and ]s of ]s of both ]es, although insufficient evidence exists in human exposure.<ref name="who"> |
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{{Citation |
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{{Citation |
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|title=IARC Monographs on the Evaluation of Carcinogenic Risks to Humans |
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| last = |
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|publisher=], ] |
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| first = |
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|date=1998-04-16 |
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| author-link = |
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|volume=31 Some Food Additives, Feed Additives and Naturally Occurring Substances: Summary of Data Reported and Evaluation |
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| last2 = |
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|url=http://monographs.iarc.fr/ENG/Monographs/vol31/volume31.pdf |
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| first2 = |
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|url-status=dead |
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| author2-link = |
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|archiveurl=https://web.archive.org/web/20070929132025/http://monographs.iarc.fr/ENG/Monographs/vol31/volume31.pdf |
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| title = IARC Monographs on the Evaluation of Carcinogenic Risks to Humans |
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|archivedate=2007-09-29 |
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| place= |
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| publisher = ], ] |
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| date = 1998-04-16 |
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| location = |
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| volume = 31 Some Food Additives, Feed Additives and Naturally Occurring Substances: Summary of Data Reported and Evaluation |
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| edition = |
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| url = http://monographs.iarc.fr/ENG/Monographs/vol31/volume31.pdf |
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}}</ref> |
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}}</ref> |
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| first = Y |
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| first = Y |
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| author-link = |
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| last2 = |
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| first2 = |
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| author2-link = |
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| title = Consequences of the AF-2 incident in Japan |
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| title = Consequences of the AF-2 incident in Japan |
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| journal = Environmental Health Perspectives |
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| journal = Environmental Health Perspectives |
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| publisher = Environmental Health Perspectives, Vol. 29 |
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| place= |
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| date = April 1979 |
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| publisher =Environmental Health Perspectives, Vol. 29 |
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| date = April, 1979 |
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| pages = 183–87 |
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| location = |
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| pages = 183–187 |
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| volume = 29 |
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| volume = 29 |
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| edition = |
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| edition = |
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| doi =10.2307/3429062 |
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| doi = 10.2307/3429062 |
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| id = |
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| id = |
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| pmid = 389620 |
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| pmid = 389620 |
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