Zearalenone

Preparation

benzene solution of AlI3 was prepared by stirring the reaction mixture of Al and I2. The methoxy reactant was then dissolved in anhydrous benzene and added to the AlI3 benzene solution. After the reaction was complete, an aqueous solution of NH4Cl and an aqueous solution of sodium metabisulfite were added to quench the reaction. The reaction mixture was then extracted with ethyl acetate, and the combined organic layers were dried over anhydrous Na2SO4. The desiccant was removed by filtration, and the resulting filtrate was concentrated under vacuum. The residue was then purified by silica gel (EtOAc/PE, 30:70) column chromatography to obtain the target product molecule, Zearalenone.

Chemical Properties

Crystalline Solid

Uses

A phytoestrogenic mycotoxin and ER activator

Uses

Estrogenic mycotoxin produced by Fusarium fungi commonly found in grains. One of a group of compounds known as resorcylic acid lactones

Uses

Zearalenone is a resorcylic acid lactone produced by a number of Fusarium sp.. Zearalenone acts as a non-steroidal estrogen, binding to estrogen receptor and is uterotropic. Zearalenone induces reproductive problems in animals and, in some animal models, is thought to be a primary initiator of hepatic tumours. In vivo, zearalenone undergoes metabolic reduction to the more estrogenic zearalenol. Contamination of grains, notably maize, by Fusarium species gives rise to high levels of zearalenone and is regarded as an important food quality issue for both humans and animal health.

Definition

ChEBI: A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.

General Description

White microcrystals or white powder.

Air & Water Reactions

Zearalenone may be sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

Zearalenone is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Zearalenone may be incompatible with alkalis.

Fire Hazard

Flash point data for Zearalenone are not available. Zearalenone is probably combustible.

Biochem/physiol Actions

Zearalenone, a fungal mycotoxin produced by Fusarium, binds the estrogen receptor (ER) and is uterotropic in the newborn rat. It is a common contaminant in cereal grain used for animal and human food, and exerts an estrogenic activity that modulates/disrupts endocrine function in animals and possibly humans.

Metabolic pathway

When zearalenone is subjected to microbial transformation by a fungus, Gliocladium roseum, it is converted to a 1 : 1 mixture of 1-(3,5-dihydroxyphenyl)- 10 0 -hydroxy-1-undecen-6'-one and 1-(3,5- dihydroxyphenyl)-6'-hydroxy-1-undecen-10'-one.

storage

-20°C