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Z0166

Sigma-Aldrich

α-Zearalenol

Synonym(s):

2,4-Dihydroxy-6-(6α,10-dihydroxy-trans-1-undecenyl)benzoic acid μ-lactone

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About This Item

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

signalword

Danger

Hazard Classifications

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

Storage Class

8B - Non-combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Oestrogenic potencies of Zeranol, oestradiol, diethylstilboestrol, Bisphenol-A and genistein: implications for exposure assessment of potential endocrine disrupters
Leffers H, et al.
Human Reproduction, 16(5), 1037-1045 (2001)
The level of zearalenone and alpha-zearalenol in the blood of gilts after feeding them of feed with a low content of zearalenone
Obremski K, et al.
Journal of Animal and feed sciences, 12, 529-538 (2003)
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)
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