Zearalenone

Zearalenone
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	Y
PubChem
ChemSpider	Y
KEGG	Y
ChEBI	Y
ChEMBL	Y
Jmol-3D images	Image 1
SMILES C[C@H]1CCCC(=O)CCC/C=C/c2cc(cc(c2C(=O)O1)O)O
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
Properties
Molecular formula	C18H22O5
Molar mass	318.36 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y   Y/N?)

Zearalenone (ZEA), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Fusarium and Gibberella species.^[1]

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^[2][3] and also in bread.

Chemical and physical properties

Zearalenone is a white crystalline solid. It exhibits blue-green fluorescence when excited by long wavelength 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.

Dermal exposure

Zearalenone can permeate through the human skin.^[4] However, no significant hormonal effects are expected after dermal contact in normal agricultural or residential environments.

Sampling and analysis

In common with other mycotoxins, sampling food commodities for zearalenone must be carried out to obtain samples representative of the consignment under test. Commonly used extraction solvents are aqueous mixtures of methanol, acetonitrile, or ethyl acetate followed by a range of different clean-up procedures that depend in part on the food and on the detection method in use. TLC methods and HPLC are commonly used. HPLC alone is not sufficient, as it may often yield false positive results. Today, HPLC-MSMS analysis is used to quantify and confirm the presence of zearalenone.

The TLC method for zearalenone is: normal phase silica gel plates, the eluent: 90% dichloromethane, 10% v/v acetone; or reverse phase C18 silica plates; the eluent: 90% v/v methanol, 10% water. Zearalenone gives unmistakable blue luminiscence under UV.^[1]

See also

• Zeranol
• Zearalanone

References

External links

• Eriksen, G. S.; Pennington, J.; Schlatter, J. (2000). "Zearalenone". WHO International Programme on Chemical Safety - Safety Evaluation of Certain Food Additives and Contaminants. Inchem. WHO Food Additives Series: 44. 
• "MSDS for Zearalenone". Fermentek.