Α-Zearalenol: Difference between revisions

{{Short description|Chemical compound}}

{{Drugbox

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| drug_name = α-Zearalenol

| IUPAC_name = (2''E'',7''R'',11''S'')-7,15,17-trihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,15,17-tetraen-13-one

| image = Alpha Zearalenol.svg

| width =

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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->

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<!-- Identifiers -->

| CAS_number_Ref =

| CAS_number = 36455-72-8

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| PubChem = 5284645

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| DrugBank_Ref =

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| ChemSpiderID_Ref =

| ChemSpiderID = 4447689

| UNII = 59D4EVJ5KC

| KEGG = C14750

| ChEBI = 35065

| ChEMBL = 371463

<!--Chemical data-->

| 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 [[mycoestrogen]]s found in ''[[Fusarium|Fusarium spp]]''.<ref name="Chelkowski2014">{{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–}}</ref> 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 [[intestine]]s during [[first-pass metabolism]].<ref name="MaganOlsen2004">{{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–}}</ref><ref name="Eriksen1998">{{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–}}</ref> A relatively low proportion of β-zearalenol is formed from zearalenone compared to α-zearalenol in humans.<ref name="Eriksen1998" /> α-Zearalenol is about 3- to 4-fold more potent as an estrogen relative to zearalenone.<ref name="Chelkowski2014" />

==See also==

* [[Taleranol]] (β-zearalanol)

* [[Zeranol]] (α-zearalanol)

* [[Zearalanone]]

==References==

{{reflist|30em}}

{{Estrogen receptor modulators}}

{{DISPLAYTITLE:''alpha''-Zearalenol}}

{{DEFAULTSORT:Zearalenol, alpha-}}

[[Category:Lactones]]

[[Category:Mycoestrogens]]

[[Category:Mycotoxins]]

[[Category:Resorcinols]]