Furylfuramide

Chembox new
ImageFile=Furylfuramide.pngImageSize=200px
IUPACName=(Z)-2-(2-furyl)-3-(5-nitro-2-furyl)prop-2-enamide
OtherNames=Tofuron,
Alpha-2-furyl-5-nitro-2-furanacrylamide,
2-(2-Furyl)-3-(5-nitro-2-furyl)acrylic acid amide,
a-(Furyl)-b-(5-nitro-2-furyl)acrylic amide,
trans-2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamide,
2-(2-furyl)-3-(5-nitro-2-furyl) acrylamide,
2-Furanacetamide, alpha-((5-nitro-2-furanyl)methylene)- [ [http://cancerweb.ncl.ac.uk/cgi-bin/omd?furylfuramide On-Line Medical Dictionary] ] ,
Abbreviations=AF-2, FF
Section1= Chembox Identifiers
CASNo=3688-53-7
PubChem=5280707
SMILES=C1=COC(=C1)C(=CC2=CC=C(O2) [N+] (=O) [O-] )C(=O)N
Section2= Chembox Properties
Formula=C₁₁H₈N₂O₅
MolarMass=248.19162
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Section3= Chembox Hazards
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Furylfuramide is a synthetic nitrofuran derivative which was widely used as a food preservative in Japan since at least 1965, but withdrawn from the market in 1974 when it was observed to be mutagenic to bacteria "in vitro" and thus suspected of carcinogenicity. This was confirmed later when animal testing [cite book
last = Hayatsu
first = Hiroka
authorlink =
coauthors =
title = Mutagens in Food: Detection and Prevention
publisher = CRC Press
date = 1991
location =
pages = 286 pages
url = http://books.google.com/books?id=eQyMCWRIVf4C&pg=RA1-PA1&lpg=RA1-PA1&dq=carcinogen+preservative+(furylfuramide%7Caf2)&source=web&ots=SiwaUvBhTp&sig=qyZmYHDYJWdEu4Tqe99uol4ctFo#PRA1-PA1,M1
isbn = 0849358779 ] found it to cause benign and malignant tumors in the mammary glands, stomachs, esophagi, and lungs of rodents of both sexes, although insufficient evidence exists in human exposure.Citation
last =
first =
author-link =
last2 =
first2 =
author2-link =
title = IARC Monographs on the Evaluation of Carcinogenic Risks to Humans
place=
publisher = World Health Organization, International Agency for Research on Cancer
date = 1998-04-16
location =
volume = 31 Some Food Additives, Feed Additives and Naturally Occurring Substances: Summary of Data Reported and Evaluation
edition =
url = http://monographs.iarc.fr/ENG/Monographs/vol31/volume31.pdf
doi =
id = ]

This successful use of bacterial mutagenicity as a screen for carcinogenicity confirmed the use of this methodology as a rapid and efficient test, in comparison to animal testing alone, and led to its further development. The availability of such simpler tests in turn gave rise to greater government oversight and testing of compounds to which the public would be exposed. [ Citation
last = Tazima
first = Y
author-link =
last2 =
first2 =
author2-link =
title = Consequences of the AF-2 incident in Japan
journal = Environmental Health Perspectives
place=
publisher =
date = April, 1979
location =
pages = 183-187
volume = 29
edition =
url = http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1637377
doi =
id = ]

References