A mycotoxin, an ERα agonist, and an active metabolite of zearalenone
Related Products
Active Metabolite(s)
23424α-Zearalanol
Isomer(s)
19460β-Zearalenol
Parent Compound(s)
11353Zearalenone
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α-Zearalenol

Item No. 16549

Technical Information
Formal Name
(3S,7R,11E)-3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one
CAS Number
36455-72-8
Synonyms
  • α-ZEL
Molecular Formula
C18H24O5
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:7): 0.1 mg/mlEthanol: 20 mg/ml
λmax
235, 275, 315 nm
SMILES
OC1=C(C(O[C@@H](C)CCC[C@H](O)CCC/C=C/2)=O)C2=CC(O)=C1
InChi Code
InChI=1S/C18H24O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,14,19-21H,2,4-6,8-9H2,1H3/b7-3+/t12-,14+/m0/s1
InChi Key
FPQFYIAXQDXNOR-QDKLYSGJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    α-Zearalenol is a mycotoxin, an agonist of estrogen receptor α (ERα), and an active metabolite of zearalenone (Item No. 11353).1,2 α-Zearalenol increases the proliferation of MCF-7 cells that endogenously express ERα (EC50 = 0.06 nM).2 It is also an androgen receptor antagonist (IC50 = 4,170 nM for the human receptor). α-Zearalenol induces cytotoxicity in isolated phorbol 12-myristate 13-acetate-stimulated pig neutrophils (IC50 = 59.0 µM). It increases intracellular superoxide levels when used at a concentration of 1 µM and decreases IL-8 supernatant levels in the same cells at 10 µM.3 It increases total and progressive motility and the levels of acrosome-reacted sperm, as well as decreases path and straight-line velocity and cell linearity, in isolated stallion sperm when used at a concentration of 100 µM.4 α-Zearalenol (1 mg/kg) increases uterine weight in immature female mice when administered at a dose of 1 mg/kg.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ueno, Y., and Tashiro, F. α-Zearalenol, a major hepatic metabolite in rats of zearalenone, an estrogenic mycotoxin of Fusarium species. J. Biochem. 89(2), 563-571 (1981).

    2. Molina-Molina, J.M., Real, M., Jimenez-Diaz, I., et alAssessment of estrogenic and anti-androgenic activities of the mycotoxin zearalenone and its metabolites using in vitro receptor-specific bioassays. Food Chem. Toxicol. 74, 233-239 (2014).

    3. Marin, D.E., Taranu, I., Burlacu, R., et alEffects of zearalenone and its derivatives on the innate immune response of swine. Toxicon 56(6), 956-953 (2010).

    4. Filannino, A., Stout, T.A.E., Gadella, B.M., et alDose-response effects of estrogenic mycotoxins (zearalenone, alpha- and beta-zearalenol) on motility, hyperactivation and the acrosome reaction of stallion sperm. Reprod. Biol. Endocrinol. 9, 134 (2011).