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Z0166

Sigma-Aldrich

α-Zearalenol

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Synonym(s):
2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone
Empirical Formula (Hill Notation):
C18H24O5
CAS Number:
36455-72-8
Molecular Weight:
320.38
MDL number:
MFCD16657008
UNSPSC Code:
12352200
PubChem Substance ID:
24902159
NACRES:
NA.77

Assay

≥98% (HPLC)

Quality Level

200

form

powder

solubility

methanol: 9.80-10.20 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

SMILES string

C[C@H]1CCC[C@H](O)CCC\C=C\c2cc(O)cc(O)c2C(=O)O1

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

InChI key

FPQFYIAXQDXNOR-QDKLYSGJSA-N

Gene Information

rat ... Ar(24208)

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Application

α-Zearalenol has been used:
  • as an analytical standard in the quantification of mycotoxins from animal feed
  • to evaluate its oestrogenic activity on boar sperm motility , as an anti-oestrogen control in MCF7 cells
  • as a reference standard in a liquid chromatography-negative ion electrospray tandem mass spectrometry with atmospheric pressure chemical ionization (LCAPCI/MS/MS) for bovine follicular fluids (FFs) quantification

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.

Pictograms

CorrosionHealth hazard
GHS05,GHS08

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Carc. 2 - Eye Dam. 1 - Repr. 2 - Skin Corr. 1B - STOT SE 2

Storage Class Code

8B - Non-combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

高风险级别生物产品--毒素类产品

Certificates of Analysis (COA)

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Effects of zearalenone, alpha-zearalenol, and genistein on boar sperm motility in vitro
Krejcarkova A, et al.
Czech Journal of Animal Science, 62(10), 435-445 (2017)
Detection of zearalenone and its metabolites in naturally contaminated follicular fluids by using LC/MS/MS and in vitro effects of zearalenone on oocyte maturation in cattle
Takagi M, et al,
Reproductive Toxicology, 26(2), 164-169 (2008)
Dose-response effects of estrogenic mycotoxins (zearalenone, alpha-and beta-zearalenol) on motility, hyperactivation and the acrosome reaction of stallion sperm
Filannino A, et al.
Reproductive Biology and Endocrinology, 9(1), 134-134 (2011)
Zearalenone and its derivatives alpha-zearalenol and beta-zearalenol decontamination by Saccharomyces cerevisiae strains isolated from bovine forage
Keller L, et al.
Toxins, 7(8), 3297-3308 (2015)
Chemical assessment of mycotoxin contaminants and veterinary residues in Costa Rican animal feed
Leiva A, et al.
International Journal of Food Contamination, 6(1), 5-5 (2019)

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