| Identification | Back Directory | [Name]
ALPHA-ZEARALENOL | [CAS]
36455-72-8 | [Synonyms]
ZEARALENOL
Α-ZEARALENOL
A-ZEARALENOL
(3S,7R,11E)-
alfa-Zearalenol
ALPHA-ZEARALENOL
Zearalenol, alpha-
trans-α-Zearalenol
α-Zearalenol solution
alpha-Zearalenol solution
alpha Zearalenol from Giberella zeae
α-Zearalenol Solution in Acetonitrile, 100μg/mL
2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone
2,4-Dihydroxy-6-(6Alpha,10-dihydroxy-trans-1-undecenyl)benzoicacidμ-lactone
2,4-DIHYDROXY-6-[6ALPHA,10-DIHYDROXY-TRANS-1-UNDECENYL]BENZOIC ACID MICRO-LACTONE
2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone solution
α-Zearalenol,2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone
(2E,7R,11S)-7,15,17-trihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,15,17-tetraen-13-one
(3S,7R,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,7R,11E)-
1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S-(3R*,7S*,11E))- | [EINECS(EC#)]
828-728-1 | [Molecular Formula]
C18H24O5 | [MDL Number]
MFCD00079649 | [MOL File]
36455-72-8.mol | [Molecular Weight]
320.38 |
| Chemical Properties | Back Directory | [Melting point ]
158-161°C | [Boiling point ]
599.0±50.0 °C(Predicted) | [density ]
1.174±0.06 g/cm3(Predicted) | [Fp ]
2℃ | [storage temp. ]
-20°C | [solubility ]
≤20mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide | [form ]
crystalline solid | [pka]
7.61±0.60(Predicted) | [color ]
White to off-white | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Description]
α-Zearalenol is a major hepatic metabolite of zearalenone (Item No. 11353), a mycotoxin produced by fungi in food and animal feeds.1,2 It is a less potent agonist of estrogen receptors than the parent compound.3 However, α-zearalenol has pronounced effects on uterotropic activity, sperm motility, and preimplantation embryonic development.4,5,6 | [Chemical Properties]
Off-White Solid | [Uses]
The major metabolites of Zearalenone | [Uses]
α-Zearalenol is a mycotoxin produced by several species of Fusarium. α-Zearalenol exhibits pronounced estrogenic activity, being 3-fold more active than zearalenone. Contamination of grains, notably maize, by Fusarium species gives rise to high levels of zearalenol and is regarded as an important food quality issue for both humans and animal health. | [Definition]
ChEBI: Alpha-Zearalenol is a macrolide. | [Biochem/physiol Actions]
α-Zearalenol (α-ZOL) is a catabolite of zearalenone, synthesized majorly in granulosa cells, intestine and liver in pigs. It has estrogenic functionality. α-ZOL inhibits sperm motility in horse possibly by eliciting genotoxic effect. α-ZOL displays higher affinity towards estrogenic receptors. | [in vitro]
the binding characteristic of α-zea was less potent with estrogen receptors than the parent compound [2]. α-zearalenol showed pronounced effects on uterotropic activity [3]. α-zea inhibited normal sperm motility, but stimulated hyperactive motility in the remaining motile cells and simultaneously induced the acrosome reaction [4]. | [References]
[1]. zinedine a, soriano j m, molto j c, et al. review on the toxicity, occurrence, metabolism, detoxification, regulations and intake of zearalenone: an oestrogenic mycotoxin[j]. food and chemical toxicology, 2007, 45(1): 1-18.
[2]. kiang d t, kennedy b j, pathre s v, et al. binding characteristics of zearalenone analogs to estrogen receptors[j]. cancer research, 1978, 38(11 part 1): 3611-3615.
[3]. mirocha c j, pathre s v, behrens j, et al. uterotropic activity of cis and trans isomers of zearalenone and zearalenol[j]. applied and environmental microbiology, 1978, 35(5): 986-987.
[4]. filannino a, stout t a e, gadella b m, et al. 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(1): 134. |
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