Α-zearalenol

α-Zearalenol

Identifiers
IUPAC name (2E,7R,11S)-7,15,17-trihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,15,17-tetraen-13-one
Synonyms	alpha-Zearalenol; trans-Zearalenol; 2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone
CAS Number	36455-72-8
PubChem CID	5284645
ChemSpider	4447689
UNII	59D4EVJ5KC
KEGG	C14750
ChEBI	CHEBI:35065
ChEMBL	CHEMBL371463
Chemical and physical data
Formula	C18H24O5
Molar mass	320.3802 g/mol
3D model (JSmol)	Interactive image
SMILES C[C@H]1CCC[C@@H](CCC/C=C/C2=CC(=CC(=C2C(=O)O1)O)O)O
InChI 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 Key:FPQFYIAXQDXNOR-QDKLYSGJSA-N

α-Zearalenol is a nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in Fusarium spp. It is the α epimer of β-zearalenol and along with β-zearalenol is a major metabolite of zearalenone formed mainly in the liver but also to a lesser extent in the intestines during first-pass metabolism. A relatively low proportion of β-zearalenol is formed from zearalenone compared to α-zearalenol in humans. α-Zearalenol is about 3- to 4-fold more potent as an estrogen relative to zearalenone.