β-Zearalenol
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Category | Mycotoxins |
Catalog number | BBF-04352 |
CAS | 71030-11-0 |
Molecular Weight | 320.38 |
Molecular Formula | C18H24O5 |
Purity | > 99 % by HPLC |
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Description
A mycotoxin produced by several species of fusarium. It exhibits pronounced estrogenic activity, like other zearalenones. It is an important food quality issue for both human and animal health.
Specification
Synonyms | 1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S-(3R*,7R*,11E))-; β-trans-Zearalenol; (-)-β-Zearalenol; (3S,7S,11E)-3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one |
Storage | Store at -20 °C |
IUPAC Name | (4S,8S,12E)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one |
Canonical SMILES | CC1CCCC(CCCC=CC2=C(C(=CC(=C2)O)O)C(=O)O1)O |
InChI | InChI=1S/C18H24O5/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/h3,7,10-12,14,19-21H,2,4-6,8-9H2,1H3/b7-3+/t12-,14-/m0/s1 |
InChI Key | FPQFYIAXQDXNOR-PMRAARRBSA-N |
Source | Fusarium sp. |
Properties
Appearance | White to pale beige solid |
Boiling Point | 599 °C at 760 mmHg |
Melting Point | 137-139 °C |
Density | 1.174 g/cm3 |
Solubility | Slightly soluble in Acetone, Methanol |
LogP | 3.37140 |
Toxicity
Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
Mechanism Of Toxicity | Mycotoxins, such as α-zearalenol (α-ZOL) and β-Zearalenol (β-ZOL), as contaminants of animal food can impair fertility and can cause abnormal fetal development in farm animals. The effects of mycotoxins on FSH receptor-dependent and receptor-independent pathways indicate that adenylate cyclase activity and/or regulatory pathways further downstream are targets of mycotoxin actions. The apparent dose-dependent reduction of p450scc and 3beta-HSD transcripts implies an effect of α- and β-ZOL on transcriptional regulation of these enzymes. The zearalenone metabolites induced loss of mitochondrial membrane potential (MMP), mitochondrial changes in Bcl-2 and Bax proteins, and cytoplasmic release of cytochrome c and apoptosis-inducing factor (AIF). Use of an inhibitor specific to c-Jun N-terminal kinase (JNK), p38 kinase or p53, but not pan-caspase or caspase-8, decreased the toxin-induced generation of reactive oxygen species (ROS) and also attenuated the α-ZOL- or β-ZOL-induced decrease of cell viability. |
Reference Reading
Spectrum
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