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Butenolide

HCID 27790
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Basic information

CAS
16275-44-8
Standard SMILES
CC(=O)NC1C=CC(=O)O1
InChIKey
HUSDLVGPEKVWAL-UHFFFAOYSA-N
Molecular formula
C6H7NO3
Average molar mass
141.12 g/mol
Monoisotopic mass
141.04259309

Overview

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)

Names & identifiers

Preferred name
Butenolide
IUPAC
N-(5-oxo-2H-furan-2-yl)acetamide
English name
2-Furanone,5-acetamido-
Molecular formula
C6H7NO3
Molecular weight
141.12

Names & synonyms

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
Show more names
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

Properties

Computed structural properties

XLogP
-0.3
Topological polar surface area
55.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
10
Formal charge
0
Complexity
197

Physicochemical properties

Melting point
115 °C · 115 °C
Boiling point
471.7 · 471.7±44.0 °C(Predicted)
Density
1.26 · 1.26±0.1 g/cm3(Predicted)
solubility
Dichloromethane: solubleDMSO: solubleEthanol: solubleMethanol: soluble
form
solid
pka
12.85 · 12.85±0.20(Predicted)
Specific Gravity
1.185 · 1.185
color
White amorphous
FDA UNII
5 GCO381H · YM5GCO381H
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
271 · P271-P261
HS Code
2931900090 · 2931900090
Toxicity
50 · mouse,LD50,intraperitoneal,43600ug/kg (43.6mg/kg),Phytochemistry. An International Journal of Plant Biochemistry. Vol. 7, Pg. 139, 1968.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Health Effects · 1 item

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 item

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)

Safety data

hs_code
2931900090
Toxicity
mouse,LD50,intraperitoneal,43600ug/kg (43.6mg/kg),Phytochemistry. An International Journal of Plant Biochemistry. Vol. 7, Pg. 139, 1968.
Signal word
Warning
Symbol(GHS)

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

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.

Uses & manufacturing

UsesButenolide is a mycotoxin found in various species of fungi of the genus Fusarium. It can often be found in contaminated agricultural products. (A3036)
Applications · 1 item

Uses5-Acetamido-butenolide is a mycotoxin from Fusarium nivale and a related compound of Butenolide. Butenolide is known to induce oxidative damage to membrane lipids and proteins. 5-Acetamido-butenolide has been used to investigate mycardial damage and toxicosis by mycotoxins.

Upstream & downstream products

Upstream raw materials

5-Ethoxy-5H-furan-2-oneAcetamide

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Compound notes

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Database identifiers

CAS
16275-44-8
PubChem CID
27790
DTXSID
DTXSID401017456
ChEMBL
CHEMBL1094585
UNII
YM5GCO381H
Nikkaji
J53.984H
GHS07
Hazard statements
H315-H319-H335
Precautionary statements
P271-P261