Α-Zearalenol

{{Short description|Chemical compound}}

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| drug_name = α-Zearalenol

| 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

| image = Alpha Zearalenol.svg

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| CAS_number = 36455-72-8

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| PubChem = 5284645

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| ChemSpiderID = 4447689

| UNII = 59D4EVJ5KC

| KEGG = C14750

| ChEBI = 35065

| ChEMBL = 371463

| C=18 | H=24 | O=5

| SMILES = C[C@H]1CCC[C@@H](CCC/C=C/C2=CC(=CC(=C2C(=O)O1)O)O)O

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = FPQFYIAXQDXNOR-QDKLYSGJSA-N

| synonyms = alpha-Zearalenol; trans-Zearalenol; 2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone

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α-Zearalenol is a nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in Fusarium spp.{{cite book| vauthors = Chelkowski J |title=Fusarium: Mycotoxins, Taxonomy, Pathogenicity|url=https://books.google.com/books?id=_1KeBQAAQBAJ&pg=PA85|date=28 June 2014|publisher=Elsevier Science|isbn=978-1-4832-9785-9|pages=85–}} It is the α-epimer of β-zearalenol. Along with β-zearalenol, it is a major metabolite of zearalenone formed mainly in the liver but also to a lesser extent in the intestines during first-pass metabolism.{{cite book| vauthors = Magan N, Olsen M |title=Mycotoxins in Food: Detection and Control|url=https://books.google.com/books?id=CZ3iEhPeejoC&pg=PA356|year=2004|publisher=Woodhead Publishing|isbn=978-1-85573-733-4|pages=356–}}{{cite book| vauthors = Eriksen GS |title=Fusarium Toxins in Cereals: A Risk Assessment|url=https://books.google.com/books?id=jU5Wx8LkZHUC&pg=PA61|year=1998|publisher=Nordic Council of Ministers|isbn=978-92-893-0149-7|pages=61–}} A relatively low proportion of β-zearalenol is metabolized from zearalenone compared to α-zearalenol in humans. α-Zearalenol is about three to four times more potent as an estrogen relative to zearalenone.