Zearalenone
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Category | Mycotoxins |
Catalog number | BBF-03998 |
CAS | 17924-92-4 |
Molecular Weight | 318.37 |
Molecular Formula | C18H22O5 |
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Description
Zearalenone is a mycotoxin produced by Fusarium. The 100 ppm acetonitrile solution of Zearalenone, a kind of natural estrogen, could be used as standard solution.
Specification
Synonyms | (3S,11E)-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2 -benzoxacyclotetradecin-1,7(8H)-dione; (-)-Zearalenone; Mycotoxin F 2; Toxin F2; Zenone; trans-Zearalenone |
Storage | Store at -20°C (dark) |
IUPAC Name | (4S,12E)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione |
Canonical SMILES | CC1CCCC(=O)CCCC=CC2=CC(=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 |
InChI Key | MBMQEIFVQACCCH-QBODLPLBSA-N |
Source | Zearalenone (ZEA), also known as RAL and F-2 mycotoxin, is produced by some Giberella species. Several Fusarium species also produce zearalenone as their primary toxin. It can be found worldwide in a number of cereal crops, such as maize, barley, oats, wheat, rice, and sorghum, and also in bread. |
Properties
Appearance | White to Pale Beige Solid |
Application | Estrogens, Non-Steroidal |
Boiling Point | 600.4°C at 760 mmHg |
Melting Point | 160-161°C |
Density | 1.168 g/cm3 |
Solubility | less than 0.1 mg/mL at 64 °F |
Toxicity
Carcinogenicity | 3, not classifiable as to its carcinogenicity to humans. |
Mechanism Of Toxicity | Zearalenone's genotoxicity results from it's ability to cause DNA fragmentation, chromosome aberrations, and DNA adduct formation. It exerts cytotoxic effects by enhancing lipid peroxidation, increasing oxidative stress, and inducing apoptosis. Zearalenone also has significant estrogenic activity, causing severe reproductive problems in animals. In humans, Zearalenone has been shown to cause an earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia and breast cancer in women. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. |
Toxicity | LD50 > 2000 mg/kg (Oral, Mouse); LD50 > 500 mg/kg (Intraperitoneal, Mouse). |
Reference Reading
Spectrum
LC-MS/MS Spectrum - 20V, Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2