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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/05/27 19:27:00」(JST)

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is a synthetic nitrofuran derivative which was widely used as a food preservative in Japan since at least 1965, but withdrawn from the market in 1974 when it was observed to be mutagenic to bacteria in vitro and thus suspected of carcinogenicity.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

^ On-Line Medical Dictionary
^ ^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
^ Hayatsu, Hiroka (1991), Mutagens in Food: Detection and Prevention, CRC Press, pp. 286 pages, ISBN 0-8493-5877-9
^ 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

English Journal

The antimutagenic effect of mistletoe lectin (Viscum album L. var. coloratum agglutinin).

Hong CE1, Lyu SY.
Phytotherapy research : PTR.Phytother Res.2012 May;26(5):787-90. doi: 10.1002/ptr.3639. Epub 2011 Nov 14.
A galactose- and N-acetyl-D-galactosamine-specific lectin (Viscum album L. var. coloratum agglutinin, VCA), which is known for its anticancer activity, was isolated from mistletoe. In this study, we investigated the antimutagenic potentials of VCA by using the pre-incubation method of the Ames test
PMID 22084060

Facile synthesis of 4-O-β-N-acetylchitooligosyl 2-acetamido-2,3-dideoxydidehydro-gluconolactone based on the transformation of chitooligosaccharide and its suppressive effects against the furylfuramide-induced SOS response.

Ogata M1, Takeuchi R, Suzuki A, Hirai H, Usui T.
Bioscience, biotechnology, and biochemistry.Biosci Biotechnol Biochem.2012;76(7):1362-6. Epub 2012 Jul 7.
A facile synthesis method is described for transforming the reducing-end residue of chitooligosaccharides (DP 2-4) into lactone. The desired 4-O-β-N-acetylchitooligosyl lactones (GN(n)L) were conveniently prepared from chitooligosaccharides by consecutive dehydration and oxidation reactions to affo
PMID 22785478

Antigenotoxic activity of naturally occurring furanocoumarins.

Marumoto S1, Oda Y, Miyazawa M.
Environmental and molecular mutagenesis.Environ Mol Mutagen.2011 Oct;52(8):646-57. doi: 10.1002/em.20665. Epub 2011 Jul 22.
This study was designed to investigate the antigenotoxic effects of a series of naturally occurring furanocoumarins (NOFs) including isoimperatorin, imperatorin, (+)-oxypeucedanin, (+)-byakangelicol, and (+)-byakangelicine on antigenotoxic activities against genotoxicity induced by carcinogens [fury
PMID 21786339

Japanese Journal

Facile Synthesis of 4-O-β-N-Acetylchitooligosyl 2-acetamido-2,3-dideoxydidehydro-gluconolactone Based on the Transformation of Chitooligosaccharide and Its Suppressive Effects against the Furylfuramide-Induced SOS Response

OGATA Makoto,TAKEUCHI Ryota,SUZUKI Akari,HIRAI Hirofumi,USUI Taichi
Bioscience, biotechnology, and biochemistry 76(7), 1362-1366, 2012-07-23
NAID 10030982177

キチンオリゴ糖誘導体の合成とフリルフラミド誘発性SOS応答の抑制効果

尾形慎,竹内良太,鈴木亜日里,平井浩文,碓氷泰市
キチン・キトサン研究 = Chitin and chitosan research 18(2), 212, 2012-07-01
NAID 10030780613

Facile Synthesis of 4-O-β-N-Acetylchitooligosyl 2-acetamido-2,3-dideoxydidehydro-gluconolactone Based on the Transformation of Chitooligosaccharide and Its Suppressive Effects against the Furylfuramide-Induced SOS Response

OGATA Makoto,TAKEUCHI Ryota,SUZUKI Akari [他],HIRAI Hirofumi,USUI Taichi
Bioscience, Biotechnology, and Biochemistry 76(7), 1362-1366, 2012
A facile synthesis method is described for transforming the reducing-end residue of chitooligosaccharides (DP 2–4) into lactone. The desired 4-O-β-N-acetylchitooligosyl lactones (GNnL) were convenient …
NAID 130001862730

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リンク元	「フリルフルアミド」

「フリルフルアミド」

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)-,
Identifiers
CAS number	3688-53-7
PubChem	5280707
ChemSpider	4444292
UNII	054NR2135Y
KEGG	D02528
ChEBI	CHEBI:15660
ChEMBL	CHEMBL259747
Jmol-3D images	Image 1
	SMILES O=[N+]([O-])c2oc(/C=C(/c1occc1)C(=O)N)cc2 ;
	InChI 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- ; Key: LYAHJFZLDZDIOH-VURMDHGXSA-N 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 ;
Properties
Molecular formula	C11H8N2O5
Molar mass	248.19162
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: furylfuramide
同: フリルフラミド、AF-2, AF2、2-(2-furyl)‐3-(5-nitro-2-furyl)acrylamide, 2-(2-フリル)-3-(5-ニトロ-2-フリル)アクリル酸アミド

[show details]

フリルフルアミド : 40 件
フリルフラミド : 63 件

furylfuramide フリルフルアミド : 34 件
furylfuramide フリルフラミド : 33 件

C11H8N2O5。
発癌性のある防腐剤

[1] On-Line Medical Dictionary

[who-2] 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

[3] Hayatsu, Hiroka (1991), Mutagens in Food: Detection and Prevention, CRC Press, pp. 286 pages, ISBN 0-8493-5877-9

[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

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案内

furylfuramide