Zearalenone

Zearalenone
Names
	Preferred IUPAC name (3S,11E)-14,16-Dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione
	Other names Mycotoxin F2
Identifiers
CAS Number	17924-92-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:10106 ;
ChEMBL	ChEMBL454173 ;
ChemSpider	4444897 ;
ECHA InfoCard	100.038.043
KEGG	C09981 ;
PubChem CID	5281576;
UNII	5W827M159J ;
CompTox Dashboard (EPA)	DTXSID0021460 ;
	InChI InChI=1S/C18H22O5/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/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3+/t12-/m0/s1 Key: MBMQEIFVQACCCH-QBODLPLBSA-N ; InChI=1/C18H22O5/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/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3+/t12-/m0/s1 Key: MBMQEIFVQACCCH-QBODLPLBBS;
	SMILES C[C@H]1CCCC(=O)CCC/C=C/c2cc(cc(c2C(=O)O1)O)O;
Properties
Chemical formula	C18H22O5
Molar mass	318.369 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Zearalenone (ZEN), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Fusarium and Gibberella species. Specifically, the Gibberella zeae, the fungal species where zearalenone was initially detected, in its asexual/anamorph stage is known as Fusarium graminearum. Several Fusarium species produce toxic substances of considerable concern to livestock and poultry producers, namely deoxynivalenol, T-2 toxin, HT-2 toxin, diacetoxyscirpenol (DAS) and zearalenone. Particularly, ZEN is produced by Fusarium graminearum, Fusarium culmorum, Fusarium cerealis, Fusarium equiseti, Fusarium verticillioides, and Fusarium incarnatum. Zearalenone is the primary toxin that binds to estrogen receptors, causing infertility, abortion or other breeding problems, especially in swine. Often, ZEN is detected together with deoxynivalenol in contaminated samples and its toxicity needs to be considered in combination with the presence of other toxins.

Zearalenone is heat-stable and is found worldwide in a number of cereal crops, such as maize, barley, oats, wheat, rice, and sorghum. Its production increases when the climate is warm with air humidity at or above twenty percent. The environmental pH plays also a role in the toxin's production. When temperatures fall to 15^oC, alkaline soils still support ZEN production. At the preferred Fusarium temperature, which ranges between 25^oC and 30^oC, neutral pH results in the greatest toxin production.

In addition to its actions on the classical estrogen receptors, zearalenone has been found to act as an agonist of the GPER (GPR30).