ALPHA-ZEARALENOL Chemical Properties

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

Hazard Codes 

Xn,T,F

Risk Statements 

20/21/22-40-52/53-68/20/21/22-36-11-62-48/20-63-46-45

Safety Statements 

36/37-61-16-45-53

RIDADR 

UN 1648 3 / PGII

WGK Germany 

3

F 

8

HS Code 

29322090

MSDS

• Language:English Provider:SigmaAldrich

ALPHA-ZEARALENOL Usage And Synthesis

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

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.

Uses

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.

Uses

The major metabolites of Zearalenone

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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