Zearalenone

From DrugPedia: A Wikipedia for Drug discovery

Contents 1 Description 2 Chemical and physical properties 3 Sampling and analysis 4 General Properties 5 PhysioChemical Properties 6 External Links

[edit] Description

Show 3-D Structure

(S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacy clotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.Zearalenone (ZEA), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Fusarium species.

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<ref>Kuiper-Goodman et al., 1987; Tanaka et al., 1988a</ref> and also in bread.

[edit] Chemical and physical properties

Zearalenone is a white crystalline solid. It exhibits blue-green fluorescence when excited by long wavelength UV light (360) 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 (e =6,020). Maximum fluorescence in ethanol occurs with irradiation at 314nm and with emission at 450nm. Solubility in water is about 0.002g/100ml. 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.

[edit] 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 in not sufficient as it may often yield false positive results.

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.<ref>Zearalenone, fermentek.co.il</ref>

[edit] General Properties

*Molecular Weight

318.36

*Molecular Formula

C₁₈H₂₂O₅

*IUPAC NAME

(4S,12E)-15,17-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione

*Canonical Smiles

CC1CCCC(=O)CCCC=CC2=C(C=C(C=C2C(=O)O1)O)O

*Isomeric Smiles

C[C@H]1CCCC(=O)CCCC=CC2=C(C=C(C=C2C(=O)O1)O)O

[edit] PhysioChemical Properties

*Melting Point

164.5(EXP)

*LogP

3.58(EST)

*Water Solubility

[edit] External Links

• [1]Pubchem
• Detailed information about mycotoxins
• INTERNATIONAL PROGRAMME ON CHEMICAL SAFETY review on Zearalenone
• MSDS Zearalenone safety data sheet