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ALPHA-ZEARALENOL

CAS No.
36455-72-8
Chemical Name:
ALPHA-ZEARALENOL
Synonyms
ZEARALENOL;Α-ZEARALENOL;A-ZEARALENOL;(3S,7R,11E)-;α-Zearalenol;alfa-Zearalenol;ALPHA-ZEARALENOL;trans-α-Zearalenol;Zearalenol, alpha-;α-Zearalenol solution
CBNumber:
CB8491950
Molecular Formula:
C18H24O5
Molecular Weight:
320.38
MDL Number:
MFCD16657008
MOL File:
36455-72-8.mol
Last updated:2023-06-08 09:02:17

ALPHA-ZEARALENOL 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)
Stability Hygroscopic
FDA UNII 59D4EVJ5KC

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS08
Signal word  Danger
Hazard statements  H314-H351-H361fd-H371-H412
Precautionary statements  P260-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
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
8
HS Code  29322090
NFPA 704
0
3 0

ALPHA-ZEARALENOL price More Price(17)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich Z0166 α-Zearalenol 36455-72-8 5mg $384 2024-03-01 Buy
Sigma-Aldrich 35406 α-Zearalenol solution 10 μg/mL in acetonitrile, analytical standard 36455-72-8 1ml $835 2024-03-01 Buy
Cayman Chemical 16549 α-Zearalenol ≥98% 36455-72-8 1mg $68 2024-03-01 Buy
Cayman Chemical 16549 α-Zearalenol ≥98% 36455-72-8 5mg $286 2024-03-01 Buy
Sigma-Aldrich Z0166 α-Zearalenol 36455-72-8 10mg $424.2 2024-03-01 Buy
Product number Packaging Price Buy
Z0166 5mg $384 Buy
35406 1ml $835 Buy
16549 1mg $68 Buy
16549 5mg $286 Buy
Z0166 10mg $424.2 Buy

ALPHA-ZEARALENOL Chemical Properties,Uses,Production

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

The major metabolites of Zearalenone

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

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.

17924-92-4
71030-11-0
36455-72-8
Synthesis of ALPHA-ZEARALENOL from Zearalenone

ALPHA-ZEARALENOL Preparation Products And Raw materials

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Zearalenol, alpha- 2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone solution α-Zearalenol solution Α-ZEARALENOL ZEARALENOL ALPHA-ZEARALENOL α-Zearalenol,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 A-ZEARALENOL (3S,7R,11E)-3,4,5,6,7,8,9,10-Octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one trans-α-Zearalenol 1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S-(3R*,7S*,11E))- 1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S,7R,11E)- (3S,7R,11E)- 2,4-DIHYDROXY-6-[6ALPHA,10-DIHYDROXY-TRANS-1-UNDECENYL]BENZOIC ACID MICRO-LACTONE (2E,7R,11S)-7,15,17-trihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,15,17-tetraen-13-one alpha Zearalenol from Giberella zeae alfa-Zearalenol alpha-Zearalenol solution α-Zearalenol Solution in Acetonitrile, 100μg/mL 2,4-Dihydroxy-6-(6Alpha,10-dihydroxy-trans-1-undecenyl)benzoicacidμ-lactone α-Zearalenol 36455-72-8 Chiral Reagents Heterocycles Intermediates & Fine Chemicals Metabolites & Impurities Pharmaceuticals