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α-Zearalenol

From Wikipedia, the free encyclopedia
(Redirected fromΑ-zearalenol)
Chemical compound
Pharmaceutical compound
α-Zearalenol
Clinical data
Other namesalpha-Zearalenol;trans-Zearalenol; 2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone
Identifiers
  • (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
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.264.264Edit this at Wikidata
Chemical and physical data
FormulaC18H24O5
Molar mass320.385 g·mol−1
3D model (JSmol)
  • C[C@H]1CCC[C@@H](CCC/C=C/C2=CC(=CC(=C2C(=O)O1)O)O)O
  • 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 anonsteroidalestrogen of theresorcylic acid lactone group related tomycoestrogens found inFusarium spp.[1] It is the α-epimer ofβ-zearalenol.[2] Along with β-zearalenol, it is a majormetabolite ofzearalenone formed mainly in theliver but also to a lesser extent in theintestines duringfirst-pass metabolism.[2][3] A relatively low proportion of β-zearalenol is metabolized from zearalenone compared to α-zearalenol in humans.[3] α-Zearalenol is about three to four times more potent as an estrogen relative to zearalenone.[1]

See also

[edit]

References

[edit]
  1. ^abChelkowski J (28 June 2014).Fusarium: Mycotoxins, Taxonomy, Pathogenicity. Elsevier Science. pp. 85–.ISBN 978-1-4832-9785-9.
  2. ^abMagan N, Olsen M (2004).Mycotoxins in Food: Detection and Control. Woodhead Publishing. pp. 356–.ISBN 978-1-85573-733-4.
  3. ^abEriksen GS (1998).Fusarium Toxins in Cereals: A Risk Assessment. Nordic Council of Ministers. pp. 61–.ISBN 978-92-893-0149-7.
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
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