alpha-Zearalenol

alpha-Zearalenol is a mycotoxin, an agonist of estrogen receptor alpha (ERalpha), and an active metabolite of zearalenone (Cay-11353). alpha-Zearalenol increases the proliferation of MCF-7 cells that endogenously express ERalpha (EC50 = 0.06 nM). It is also an androgen receptor antagonist (IC50 = 4,170 nM for the human receptor). alpha-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. 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. alpha-Zearalenol (1 mg/kg) increases uterine weight in immature female mice when administered at a dose of 1 mg/kg.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: alpha-ZEL. Molecular Formula: C18H24O5. Formula Weight: 320.4. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/ml, DMSO: 30 mg/ml, DMSO:PBS (pH 7.2) (1:7): 0.1 mg/ml, Ethanol: 20 mg/ml. lambdamax: 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.