Zearalenone

Zearalenone

Names
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 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:10106 Y
ChEMBL	ChEMBL454173 Y
ChemSpider	4444897 Y
ECHA InfoCard	100.038.043
KEGG	C09981 Y
PubChem	5281576
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 Y Key: MBMQEIFVQACCCH-QBODLPLBSA-N Y 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	318.364 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Zearalenone (ZEN), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Fusarium and Gibberella species. Particularly is produced by Fusarium graminearum, Fusarium culmorum, Fusarium cerealis, Fusarium equiseti, Fusarium verticillioides, and Fusarium incarnatum

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. Zearalenone is the primary toxin, causing infertility, abortion or other breeding problems, especially in swine.

Zearalenone is heat-stable and is found worldwide in a number of cereal crops, such as maize, barley, oats, wheat, rice, and sorghum.

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

Zearalenone is a white crystalline solid. It exhibits blue-green fluorescence when excited by long wavelength ultraviolet (UV) light (360 nm) and a more intense green fluorescence when excited with short wavelength UV light (260 nm). In methanol, UV absorption maxima occur at 236 (e = 29,700), 274 (e = 13,909) and 316 nm (e = 6,020). Maximum fluorescence in ethanol occurs with irradiation at 314 nm and with emission at 450 nm. Solubility in water is about 0.002 g/100 mL. It is slightly soluble in hexane and progressively more so in benzene, acetonitrile, methylene chloride, methanol, ethanol, and acetone. It is also soluble in aqueous alkali.