Zearalanone

Zearalanone is a mycotoxin, an estrogen receptor (ER) agonist, and an active metabolite of alpha-zearalanol (Cay-23424) and the mycotoxin zearalenone (Cay-11353). Zearalanone induces reporter gene expression in S. cerevisiae expressing human ER (EC50 = 110 nM). It is also an androgen receptor antagonist (IC50 = 1,540 nM for the human receptor). It induces delayed maturation of primary bovine oocytes when used at a concentration of 30 µg/ml. 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. Zearalanone has been found as a contaminant in harvested maize, sorghum, and wheat.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: 320.4. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. lambdamax: 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.