A mycotoxin
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Active Metabolite(s)
236364-hydroxy Alternariol
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Alternariol

Item No. 11306

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,7,9-trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one
CAS Number
641-38-3
Synonyms
  • AOH
  • NSC 638263
Molecular Formula
C14H10O5
Formula Weight
258.2
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 0.5 mg/ml
λmax
257, 289, 301, 342 nm
SMILES
CC1=C(C2=C(C(O3)=O)C(O)=CC(O)=C2)C3=CC(O)=C1
InChi Code
InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3
InChi Key
CEBXXEKPIIDJHL-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Alternariol is a mycotoxin, a toxic secondary fungal metabolite, produced by Alternaria molds. It is cytotoxic, fetotoxic, teratogenic, mutagenic, and genotoxic.1 It induces cytochrome P450 1A1 expression and apoptosis in mouse hepatoma cells (20-40 μM).2 Alternariol, whose synthesis is inhibited by light, naturally occurs on fruits, vegetables, and cereals, such as apples, tomatoes, and wheat.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Siegel, D., Troyanov, S., Noack, J., et al. Alternariol. Acta Crystallogr. Sect. E Struct. Rep. Online 66(Pt 6), o1366 (2010).

    2. Schreck, I., Deigendesch, U., Burkhardt, B., et al. The alternaria mycotoxins alternariol and alternariol methyl ether induce cytochrome P450 1A1 and apoptosis in murine hepatoma cells dependent on the aryl hydrocarbon receptor. Arch. Toxicol. 1-8 (2011).

    3. Häggblom, P., and Unestam, T. Blue light inhibits mycotoxin production and increases total lipids and pigmentation in Alternaria alternata. Appl. Environ. Microbiol. 38(6), 1074-1077 (1979).