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| | Zearalenone Basic information |
| | Zearalenone Chemical Properties |
| Melting point | 164-165°C | | alpha | 25546 -170.5° (c = 1.0 in CH3OH) | | Boiling point | 377.53°C (rough estimate) | | density | 1.1270 (rough estimate) | | refractive index | 1.6120 (estimate) | | Fp | 6 °C | | storage temp. | 2-8°C | | solubility | DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:7): 0.12 mg/ml; Ethanol: 20 mg/ml | | pka | 7.58±0.40(Predicted) | | form | neat | | color | Off-white | | Merck | 13,10169 | | BRN | 1350216 | | InChIKey | MBMQEIFVQACCCH-QBODLPLBSA-N | | LogP | 3.830 (est) | | CAS DataBase Reference | 17924-92-4(CAS DataBase Reference) | | EPA Substance Registry System | Zearalenone (17924-92-4) |
| | Zearalenone Usage And Synthesis |
| Chemical Properties | Crystalline Solid | | 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. | | 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 | | 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 |
| | Zearalenone Preparation Products And Raw materials |
| Raw materials | 2,4-O-Dimethylzearalenone-->Benzoic acid, 2,4-dihydroxy-6-iodo-, methyl ester-->(2E,11S)-15-hydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione-->6-(tert-ButyldiMethylsilyloxy)-1-hexyne-->Methyl 2,4-dihydroxybenzoate-->(R)-(-)-PENTEN-2-OL-->5-HEXYN-1-OL | | Preparation Products | BETA-ZEARALENOL-->ZEARALANONE-->ALPHA-ZEARALENOL |
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