A mycotoxin with pro-oxidant activity
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5-Acetamide-Butenolide

Item No. 40867

Technical Information
Formal Name
N-(2,5-dihydro-5-oxo-2-furanyl)-acetamide
CAS Number
16275-44-8
Synonyms
  • 4-acetamido-4-hydroxy-2-Butenoic Acid γ-lactone
  • NSC 114350
Molecular Formula
C6H7NO3
Formula Weight
Purity
≥70%
Formulation
A solid
Dichloromethane: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
CC(NC1C=CC(O1)=O)=O
InChi Code
InChI=1S/C6H7NO3/c1-4(8)7-5-2-3-6(9)10-5/h2-3,5H,1H3,(H,7,8)
InChi Key
HUSDLVGPEKVWAL-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    5-Acetamide-butenolide is a mycotoxin that has been found in Fusarium and has pro-oxidant activity.1,2,3 It disrupts the mitochondrial membrane potential in primary neonatal rat cardiomyocytes when used at a concentration of 50 µg/ml.2 5-Acetamide-butenolide also induces the production of thiobarbituric acid reactive substances (TBARS) in isolated rat myocardial mitochondria in a concentration-dependent manner, an effect that can be reduced by glutathione (GSH). It increases the production of reactive oxygen species (ROS) and decreases the levels of GSH in, as well as reduces the viability of, HepG2 cells when used at concentrations ranging from 25 to 100 µg/ml.3 5-Acetamide-butenolide is toxic to mice (LD50 = 43.6 mg/kg, i.p.).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yates, A.S., Tookey, H.L., Ellis, J.J., et alMycotoxins produced by fusarium nivale isolated from tall fescue (festuca arundinacea schreb.). Phytochemistry 7(1), 139-146 (1968).

    2. Wang, Y.-M., Liu, J.-B., and Peng, S.-Q. Effects of Fusarium mycotoxin butenolide on myocardial mitochondria in vitro. Toxicol. Mech. Methods 19(2), 79-85 (2009).

    3. Wang, Y.-M., Peng, S.-Q., Zhou, Q., et alDepletion of intracellular glutathione mediates butenolide-induced cytotoxicity in HepG2 cells. Toxicol. Lett. 164(3), 231-239 (2006).