alpha-Zearalenol

α-Zearalenol is a nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in Fusarium spp.[1] 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.[2][3] A relatively low proportion of β-zearalenol is formed from zearalenone compared to α-zearalenol in humans.[3] α-Zearalenol is about 3- to 4-fold more potent as an estrogen relative to zearalenone.[1]

α-Zearalenol
Clinical data
Other namesalpha-Zearalenol; trans-Zearalenol; 2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone
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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.264.264
Chemical and physical data
FormulaC18H24O5
Molar mass320.385 g·mol−1
3D model (JSmol)
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

See also

References
  1. Chelkowski J (28 June 2014). Fusarium: Mycotoxins, Taxonomy, Pathogenicity. Elsevier Science. pp. 85–. ISBN 978-1-4832-9785-9.
  2. Magan N, Olsen M (2004). Mycotoxins in Food: Detection and Control. Woodhead Publishing. pp. 356–. ISBN 978-1-85573-733-4.
  3. Eriksen GS (1998). Fusarium Toxins in Cereals: A Risk Assessment. Nordic Council of Ministers. pp. 61–. ISBN 978-92-893-0149-7.
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