Furylfuramide

Last updated
Furylfuramide
Furylfuramide.svg
Names
Preferred IUPAC name
(2Z)-2-(Furan-2-yl)-3-(5-nitrofuran-2-yl)prop-2-enamide
Other names
(Z)-2-(2-Furyl)-3-(5-nitro-2-furyl)prop-2-enamide
AF-2, [1] 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)-, [2] [3]
Identifiers
  • 3688-53-7 Yes check.svgY
3D model (JSmol)
AbbreviationsAF-2, FF
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C11H8N2O5/c12-11(14)8(9-2-1-5-17-9)6-7-3-4-10(18-7)13(15)16/h1-6H,(H2,12,14)/b8-6- Yes check.svgY
    Key: LYAHJFZLDZDIOH-VURMDHGXSA-N Yes check.svgY
  • InChI=1/C11H8N2O5/c12-11(14)8(9-2-1-5-17-9)6-7-3-4-10(18-7)13(15)16/h1-6H,(H2,12,14)/b8-6-
    Key: LYAHJFZLDZDIOH-VURMDHGXBB
  • O=[N+]([O-])c2oc(/C=C(/c1occc1)C(=O)N)cc2
Properties
C11H8N2O5
Molar mass 248.19162
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Furylfuramide (also known as AF-2) [1] is a synthetic nitrofuran derivative which was widely used as a food preservative in Japan since at least 1965, but withdrawn from the market in 1974 when it was observed to be mutagenic to bacteria in vitro and thus suspected of carcinogenicity.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 [4] 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. [3]

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. [5]

Related Research Articles

Ames test

The Ames test is a widely employed method that uses bacteria to test whether a given chemical can cause mutations in the DNA of the test organism. More formally, it is a biological assay to assess the mutagenic potential of chemical compounds. A positive test indicates that the chemical is mutagenic and therefore may act as a carcinogen, because cancer is often linked to mutation. The test serves as a quick and convenient assay to estimate the carcinogenic potential of a compound because standard carcinogen assays on mice and rats are time-consuming and expensive. However, false-positives and false-negatives are known.

Carcinogen Substance, radionuclide, or radiation directly involved in causing cancer

A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis, the formation of cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substances are considered carcinogens, but their carcinogenic activity is attributed to the radiation, for example gamma rays and alpha particles, which they emit. Common examples of non-radioactive carcinogens are inhaled asbestos, certain dioxins, and tobacco smoke. Although the public generally associates carcinogenicity with synthetic chemicals, it is equally likely to arise in both natural and synthetic substances. Carcinogens are not necessarily immediately toxic; thus, their effect can be insidious.

Mutagen

In genetics, a mutagen is a physical or chemical agent that permanently changes genetic material, usually DNA, in an organism and thus increases the frequency of mutations above the natural background level. As many mutations can cause cancer, such mutagens are therefore carcinogens, although not all necessarily are. All mutagens have characteristic mutational signatures with some chemicals becoming mutagenic through cellular processes. Not all mutations are caused by mutagens: so-called "spontaneous mutations" occur due to spontaneous hydrolysis, errors in DNA replication, repair and recombination.

Formaldehyde Widely used toxic organic compound

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Acesulfame potassium Calorie-free sugar substitute

Acesulfame potassium, also known as acesulfame K or Ace K, is a synthetic calorie-free sugar substitute often marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number E950. It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG. In chemical structure, acesulfame potassium is the potassium salt of 6-methyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide. It is a white crystalline powder with molecular formula C
4
H
4
KNO
4
S
and a molecular weight of 201.24 g/mol.

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Ochratoxin A Chemical compound

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Ractopamine animal feed additive

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<i>N</i>-Nitrosodiethylamine Chemical compound

N-Nitrosodiethylamine (NDEA) is an organic compound with the formula Et2NNO (Et = C2H5). A member of the nitrosamines, it is a light-sensitive, volatile, clear yellow oil that is soluble in water, lipids, and other organic solvents. It has an amine or aromatic odor. It is used as gasoline and lubricant additive, antioxidant, and stabilizer for industry materials. When heated to decomposition, N-nitrosodiethylamine emits toxic fumes of nitrogen oxides. N-Nitrosodiethylamine affects DNA integrity, probably by alkylation, and is used in experimental research to induce liver tumorigenesis. It is carcinogenic and mutagenic. NDEA has also been found to perturb amino acid biosynthesis including arginine, as well as DNA damage repair and mitochondrial genome maintenance in yeast.

Dioxins and dioxin-like compounds Class of chemical compounds

Dioxins and dioxin-like compounds (DLCs) are a group of chemical compounds that are persistent organic pollutants (POPs) in the environment. They are mostly by-products of burning or various industrial processes - or, in case of dioxin-like PCBs and PBBs, unwanted minor components of intentionally produced mixtures.

2,3,7,8-Tetrachlorodibenzodioxin Polychlorinated dibenzo-p-dioxin, chemical compound

2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) is a polychlorinated dibenzo-p-dioxin (sometimes shortened, though inaccurately, to simply 'dioxin') with the chemical formula C12H4Cl4O2. Pure TCDD is a colorless solid with no distinguishable odor at room temperature. It is usually formed as an unwanted product in burning processes of organic materials or as a side product in organic synthesis.

Bioassay


A bioassay is an analytical method to determine the concentration or potency of a substance by its effect on living animals or plants, or on living cells or tissues(in vitro). A bioassay can be either quantal or quantitative, direct or indirect. If the measured response is binary, the assay is quantal, if not, it is quantitative.

References

  1. 1 2 Nomura, Taisei (1975). "Carcinogenicity of the food additive furylfuramide in foetal and young mice". Nature. 258 (5536): 610–611. Bibcode:1975Natur.258..610N. doi:10.1038/258610a0. ISSN   0028-0836. PMID   1239666. S2CID   4217389.
  2. On-Line Medical Dictionary
  3. 1 2 IARC Monographs on the Evaluation of Carcinogenic Risks to Humans (PDF), 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, archived from the original (PDF) on 2007-09-29
  4. Hayatsu, Hiroka (1991), Mutagens in Food: Detection and Prevention, CRC Press, pp. 286 pages, ISBN   0-8493-5877-9
  5. Tazima, Y (April 1979), "Consequences of the AF-2 incident in Japan", Environmental Health Perspectives, Environmental Health Perspectives, Vol. 29, 29: 183–87, doi:10.2307/3429062, JSTOR   3429062, PMC   1637377 , PMID   389620