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HomeProduct name listALPHA-ZEARALENOL

ALPHA-ZEARALENOL

Synonym(s):2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone;2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone solution

  • CAS NO.:36455-72-8
  • Empirical Formula: C18H24O5
  • Molecular Weight: 320.38
  • MDL number: MFCD16657008
  • EINECS: 828-728-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 20:33:22
ALPHA-ZEARALENOL Structural

What is ALPHA-ZEARALENOL?

Description

α-Zearalenol is a major 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, α-zearalenol has pronounced effects on uterotropic activity, sperm motility, and preimplantation embryonic development.

Chemical properties

Off-White Solid

The Uses of ALPHA-ZEARALENOL

The major metabolites of Zearalenone

The Uses of ALPHA-ZEARALENOL

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.

The Uses of ALPHA-ZEARALENOL

α- Zearalenol may be used as an analytical reference standard for the determination of the analyte in traditional medicinal herbs, human and animal urine by various chromatography techniques.

What are the applications of Application

α-Zearalenol is an estrogenic synthetic derivative of the Zeralenone mycotoxin

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.

Properties of ALPHA-ZEARALENOL

Melting point: 158-161°C
Boiling point: 599.0±50.0 °C(Predicted)
Density  1.174±0.06 g/cm3(Predicted)
Flash point: 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

Safety information for ALPHA-ZEARALENOL

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Health Hazard
GHS08
GHS Hazard Statements H314:Skin corrosion/irritation
H351:Carcinogenicity
H371:Specific target organ toxicity, single exposure
H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P273:Avoid release to the environment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for ALPHA-ZEARALENOL

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