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5-アセチルアミノフラン-2(5H)-オン

Butenolide

HCID 27790
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
16275-44-8
標準SMILES
CC(=O)NC1C=CC(=O)O1
InChIKey
HUSDLVGPEKVWAL-UHFFFAOYSA-N
分子式
C6H7NO3
平均分子量
141.12 g/mol
単同位体質量
141.04259309

概要

Butenolide is a mycotoxin found in various species of fungi of the genus Fusarium. It can often be found in contaminated agricultural products. Butenolide had been implicated as the causative agent of a livestock mycotoxicosis called “fescue foot”, a peripheral vascular disorder occurring in cattle grazing on tall fescue grass. Butenolide is also one of the mycotoxins which have been considered as a suspected etiological factor for Kaschin-Beck disease (an endemic osteoarthropathy) and Keshan disease (an endemic cardiomyopathy), prevailing in some regions of China, and several studies have also indicated that butenolide can cause cartilage damage. (A3036, A3039)

名称と識別子

優先名称
Butenolide
IUPAC
N-(5-oxo-2H-furan-2-yl)acetamide
現地名
5-アセチルアミノフラン-2(5H)-オン
英語名
2-Furanone,5-acetamido-
分子式
C6H7NO3
分子量
141.12

名称と別名

5-Acetamido-2(5)-furanoneYM5GCO381HNSC 114350NSC-114350BRN 1680823AI3-44725N-(2,5-Dihydro-5-oxo-2-furanyl)acetamideUNII-YM5GCO381HDTXSID4010174565-18-11-00344 (Beilstein Handbook Reference)Crotonic acid, 4-acetamido-4-hyroxy-, gamma-lactoneACETAMIDO-4-HYDROXY-2-BUTENOIC ACID-Y-LACTONE
名称をさらに表示
N-(2,5-ジヒドロ-5-オキソフラン-2-イル)アセトアミド5-アセチルアミノフラン-2(5H)-オンN-[(2,5-ジヒドロ-5-オキソフラン)-2-イル]アセトアミド5-アセチルアミノ-2(5H)-フラノンブテノライドN-(5-オキソ-2,5-ジヒドロフラン-2-イル)アセトアミド5-(アセチルアミノ)フラン-2(5H)-オン5-ACETAMIDO-2-FURANONE5-Acetamide-Butenolide5-Acetamido-Butenolide5-Acetylamino-2(5H)-furanoneN-(5-oxo-2H-furan-2-yl)acetamideN-(2,5-Dihydro-5-oxofuran-2-yl)acetamideAcetamide, N-(2,5-dihydro-5-oxo-2-furanyl)-4-ACETAMIDO-4-HYDROXY-2-BUTENOICACIDGAMMA-LACTONE
methyl 13-((2S)-2-hydroxy-3,4-dimethyl-5-oxofuran-2-yl)tridecanoatemethyl 13-[(2S)-2-hydroxy-3,4-dimethyl-5-oxofuran-2-yl]tridecanoateRefChem:122141CHEBI:50523DTXCID701475651N-(5-oxo-2,5-dihydrofuran-2-yl)ethanimidic acid2-B4O2-buten-4-olide

物性

構造計算による物性

XLogP
-0.3
極性表面積
55.4 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
1
重原子数
10
形式電荷
0
複雑度
197

物理化学的性質

融点
115 °C · 115 °C
沸点
471.7 · 471.7±44.0 °C(Predicted)
比重(密度)
1.26 · 1.26±0.1 g/cm3(Predicted)
溶解性
Dichloromethane: solubleDMSO: solubleEthanol: solubleMethanol: soluble
外見
solid
酸解離定数(Pka)
12.85 · 12.85±0.20(Predicted)
比重
1.185 · 1.185
色
White amorphous

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

毒性情報

Health Effects · 1 件

Butenolide is cardiotoxic and hepatotoxic. Fusarium mycotoxins has been associated with both alimentary toxic aleukia, and esophageal cancer. Consumption of Fusarium mycotoxins-contaminated foodstuffs has also been considered as a suspected etiological factor for Kashin–Beck disease and Keshan disease. (A3036, A3039)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 件

Butenolide causes lipid peroxidation, disrupting the membrane lipid bilayer and causing damage to membrane protiens. It also induces production of reactive oxygen species by impairing the activities of complexes I–IV of the mitochondrial respiratory chain, especially in the liver, leading to oxidative stress. In addition, butenolide disrupts the cation gradient by inhibiting the activity of Ca2+/Mg2+-ATPase and Na+/K+-ATPase, likely either as a side effect of lipid peroxidation or by binding to the sulfhydryl groups in the active sites of these enzymes. (A3036, A3037)

Signs and SymptomsButenolide irritates the eyes and skin. It may also cause weight loss and growth retardation. (A3036, A3038)
Carcinogen ClassificationNot listed by IARC.
Toxicity DataLD50: 44 mg/kg (Intraperitoneal, Mouse) (A3038) LD50: 275 mg/kg (Oral, Mouse) (A3038)

安全データ

毒性
mouse,LD50,intraperitoneal,43600ug/kg (43.6mg/kg),Phytochemistry. An International Journal of Plant Biochemistry. Vol. 7, Pg. 139, 1968.
hs_code
2931900090

化学と産業

薬理情報

MeSH Pharmacological Classification · 2 件

Agents that are used to suppress appetite.

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.

用途と製造

UsesButenolide is a mycotoxin found in various species of fungi of the genus Fusarium. It can often be found in contaminated agricultural products. (A3036)

応用分野

用途カビ毒定量標準品。

上流・下流製品情報

上流原料

5-Ethoxy-5H-furan-2-oneアセトアミド

サプライヤー3 社

Alfa Chemistry1-516-6625404 · [email protected]
ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD+8613676922317 · [email protected]
Alfa Chemistry+1-5166625404 · [email protected]

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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
16275-44-8
PubChem CID
27790
DTXSID
DTXSID401017456
ChEMBL
CHEMBL1094585
UNII
YM5GCO381H
Nikkaji
J53.984H