Furylfuramide

Furylfuramide
IUPAC name

(Z)-2-(2-furyl)-3-(5-nitro-2-furyl)prop-2-enamide
Other names

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)-,[1][2]
Identifiers
CAS number 3688-53-7 Y
PubChem 5280707
ChemSpider 4444292 Y
UNII 054NR2135Y Y
KEGG D02528 Y
ChEBI CHEBI:15660 Y
ChEMBL CHEMBL259747 Y
Jmol-3D images Image 1
Properties
Molecular formula C11H8N2O5
Molar mass 248.19162
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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is a synthetic nitrofuran derivative which was widely used as a food preservative in Japan since at least 1965, but withdrawn from the market in 1974 when it was observed to be mutagenic to bacteria in vitro and thus suspected of carcinogenicity.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[3] 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.[2]

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.[4]

References

  1. ^ On-Line Medical Dictionary
  2. ^ a b IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, 31 Some Food Additives, Feed Additives and Naturally Occurring Substances: Summary of Data Reported and Evaluation, World Health Organization, International Agency for Research on Cancer, 1998-04-16, http://monographs.iarc.fr/ENG/Monographs/vol31/volume31.pdf 
  3. ^ Hayatsu, Hiroka (1991), Mutagens in Food: Detection and Prevention, CRC Press, pp. 286 pages, ISBN 0849358779, http://books.google.com/?id=eQyMCWRIVf4C&pg=RA1-PA1&lpg=RA1-PA1&dq=carcinogen+preservative+(furylfuramide%7Caf2) 
  4. ^ Tazima, Y (April, 1979), "Consequences of the AF-2 incident in Japan", Environmental Health Perspectives (Environmental Health Perspectives, Vol. 29) 29: 183–187, doi:10.2307/3429062, JSTOR 3429062, PMC 1637377, PMID 389620, http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1637377