| Identification | Back Directory | [Name]
BETA-ZEARALENOL | [CAS]
71030-11-0 | [Synonyms]
B-zearalenol
(3S,7S,11E)-
β-Zearalenol
BETA-ZEARALENOL
Zearalenol, beta-
beta Zearalenol from Giberella zeae
(-)-beta-Zearalenol, beta-Trans-Zearalenol
2,4-DIHYDROXY-6-[6BETA,10-DIHYDROXY-TRANS-1-UNDECENYL]BENZOIC ACID MICRO-LACTONE
(3S,7S,11E)-3,4,5,6,7,8,9,10-Octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one
1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S,7S,11E)-
1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S-(3R*,7R*,11E))- | [EINECS(EC#)]
664-283-8 | [Molecular Formula]
C18H24O5 | [MDL Number]
MFCD00151078 | [MOL File]
71030-11-0.mol | [Molecular Weight]
320.38 |
| Chemical Properties | Back Directory | [Melting point ]
137-139°C | [Fp ]
2℃ | [storage temp. ]
−20°C
| [solubility ]
Acetone: Slightly Soluble; Methanol: Slightly Soluble | [form ]
powder | [color ]
White to off-white | [BRN ]
3653579 | [Stability:]
Light Sensitive | [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 | [InChIKey]
FPQFYIAXQDXNOR-PMRAARRBSA-N | [SMILES]
C[C@H]1CCC[C@@H](O)CCC\C=C\c2cc(O)cc(O)c2C(=O)O1 |
| Hazard Information | Back Directory | [Description]
β-Zearalenol is a hepatic metabolite of zearalenone , a mycotoxin produced by fungi in food and animal feeds. It is a less potent agonist of estrogen receptors than the parent compound. However, β-zearalenol has pronounced effects on uterotropic activity and sperm acrosome reaction. | [Chemical Properties]
White Solid | [Uses]
Reactant involved in biological studies including:• ;Synthesis of amino glycoside nucleotides1• ;Enzymatic synthesis of glucuronides of zearalenone2• ;Derivatization of Zearalenone3,4,5 | [Uses]
The more active Zearalenone (Z270500) metabolite. | [Uses]
β-Zearalenol is a mycotoxin produced by several species of Fusarium. β-Zearalenol exhibits pronounced estrogenic activity, like other zearalenones. Contamination of grains by Fusarium species, notably maize, gives rise to high levels of zearalenol and is regarded as an important food quality issue for both human and animal health. | [Definition]
ChEBI: Beta-Zearalenol is a macrolide. | [References]
[1] Y UENO F T. alpha-Zearalenol, a major hepatic metabolite in rats of zearalenone, an estrogenic mycotoxin of Fusarium species.[J]. Journal of biochemistry, 1981, 89 2: 563-571. DOI: 10.1093/oxfordjournals.jbchem.a133232
[2] JOSé-MANUEL MOLINA-MOLINA . Assessment of estrogenic and anti-androgenic activities of the mycotoxin zearalenone and its metabolites using in vitro receptor-specific bioassays[J]. Food and Chemical Toxicology, 2014, 74: Pages 233-239. DOI: 10.1016/j.fct.2014.10.008
[3] ANGELA FILANNINO. Dose-response effects of estrogenic mycotoxins (zearalenone, alpha- and beta-zearalenol) on motility, hyperactivation and the acrosome reaction of stallion sperm.[J]. Reproductive Biology and Endocrinology, 2011, 9: 134. DOI: 10.1186/1477-7827-9-134
[4] DANIELA E. MARIN . Effects of zearalenone and its derivatives on the innate immune response of swine[J]. Toxicon, 2010, 56 6: Pages 956-963. DOI: 10.1016/j.toxicon.2010.06.020 |
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