A mycotoxin, an ER agonist, and an active metabolite of α-zearalanol and zearalenone
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Zearalanone

Item No. 19459

Technical Information
Formal Name
(3S)-3,4,5,6,9,10,11,12-octahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione
CAS Number
5975-78-0
Synonyms
  • ZAN
  • Zanone
  • (S)-Zearalanone
Molecular Formula
C18H24O5
Formula Weight
Purity
≥98%
A crystalline solid
λmax
218, 265, 303 nm
SMILES
OC1=C(C(O[C@@H](C)CCCC(CCCCC2)=O)=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/h10-12,20-21H,2-9H2,1H3/t12-/m0/s1
InChi Key
APJDQUGPCJRQRJ-LBPRGKRZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Zearalanone is a mycotoxin, an estrogen receptor (ER) agonist, and an active metabolite of α-zearalanol (Item No. 23424) and the mycotoxin zearalenone (Item No. 11353).1,2 Zearalanone induces reporter gene expression in S. cerevisiae expressing human ER (EC50 = 110 nM).1 It is also an androgen receptor antagonist (IC50 = 1,540 nM for the human receptor).2 It induces delayed maturation of primary bovine oocytes when used at a concentration of 30 µg/ml.3 Zearalanone induces cytotoxicity in isolated phorbol 12-myristate 13-acetate-stimulated pig neutrophils (IC50 = 53.1 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.4 Zearalanone has been found as a contaminant in harvested maize, sorghum, and wheat.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Le Guevel, R., and Pakdel, F. Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods. Hum. Reprod. 16(5), 1030-1036 (2001).

    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. Minervini, F., Dell'Aquila, M.E., Maritato, F., et alToxic effects of the mycotoxin zearalenone and its derivatives on in vitro maturation of bovine oocytes and 17 beta-estradiol levels in mural granulosa cell cultures. Toxicol. In Vitro 15(4-5), 489-495 (2001).

    4. 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).

    5. Aoyama, K., Ishikuro, E., Noriduki, H., et alFormation ratios of zearalanone, zearalenols, and zearalanols versus zearalenone during incubation of Fusarium semitectum on sorghum and ratios in naturally contaminated sorghum. Food Hyg. Saf. Sci. 56(6), 247-251 (2015).