A common mycotoxin food contaminant
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Product Type

Environmental Toxicology
Toxins
Mycotoxins

Research Area

Cancer

Tenuazonic Acid (copper salt)

Item No. 11443

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-acetyl-1,5-dihydro-4-hydroxy-5S-[(1S)-1-methylpropyl]-2H-pyrrol-2-one, hemicopper salt
Synonyms
  • AAC-toxin
Molecular Formula
C10H14NO3 • 1/2Cu
Formula Weight
228.0
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/ml
λmax
225, 291 nm
SMILES
CC[C@H](C)[C@@]1([H])C([O-])=C(C(C)=O)C(N1)=O.CC[C@H](C)[C@@]2([H])C([O-])=C(C(C)=O)C(N2)=O.[Cu+2]
InChi Code
InChI=1S/2C10H15NO3.Cu/c2*1-4-5(2)8-9(13)7(6(3)12)10(14)11-8;/h2*5,8,13H,4H2,1-3H3,(H,11,14);/q;;+2/p-2/t2*5-,8-;/m00./s1
InChi Key
IAHMFKOQYRRWFU-BDDFVKGKSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Tenuazonic acid is one of the major Alternaria mycotoxins commonly found as a natural contaminant in food (LD50 = 548 μg/egg in the chicken embryo toxicity assay).1 Tenuazonic acid contamination has been linked to esophageal cancer in human populations at risk of high exposure. Mice fed 100 mg/kg/day tenuazonic acid orally for 10 months developed precancerous lesions on the esophageal mucosa.2 Microscopic analysis of mucosal epithelial cells from these tenuazonic acid-treated animals reveal pyknosis and marked pleomorphisms in the nuclei, chromatin granulation and increased chromatin mass, irregularities in nuclear contours, and vacuolization in nucleoplasms.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Griffin, G.F., and Chu, F.S. Toxicity of the Alternaria metabolites alternariol, alternariol methyl ether, altenuene, and tenuazonic acid in the chicken embryo assay. Appl. Environ. Microbiol. 46(6), 1420-1422 (1983).

    2. Yekeler, H., Bitmis, K., Ozçelik, N., et al. Analysis of toxic effects of Alternaria toxins on esophagus of mice by light and electron microscopy. Toxicol. Pathol. 29(4), 492-497 (2001).