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Z0167

Sigma-Aldrich

Zearalanone

Synonym(s):

2,4-Dihydroxy-6-(10-hydroxy-6-oxoundecyl)benzoic acid μ-lactone

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About This Item

Empirical Formula (Hill Notation):
C18H24O5
CAS Number:
5975-78-0
Molecular Weight:
320.38
MDL number:
MFCD00135821
UNSPSC Code:
12352200
PubChem Substance ID:
24902160
NACRES:
NA.77

sterility

non-sterile

Quality Level

200

Assay

≥98% (TLC)

form

powder

solubility

methanol: 9.80-10.20 mg/mL, clear, colorless

shipped in

ambient

storage temp.

−20°C

SMILES string

C[C@H]1CCCC(=O)CCCCCc2cc(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/h10-12,20-21H,2-9H2,1H3/t12-/m0/s1

InChI key

APJDQUGPCJRQRJ-LBPRGKRZSA-N

Gene Information

rat ... Ar(24208)

General description

Zearalanone (ZEA) or F-2 toxin, a nonsteroidal estrogenic mycotoxin is produced by various Fusarium species. Fusarium graminearum is considered as the primary producer of zearalanone. It is usually seen in moldy hay, high-moisture corn, corn infected before harvest etc.

Application

Zearalanone has been used:
  • as mycotoxin to study its effects on the histology of ovaries in pre-pubertal bitches
  • as a mycotoxin to investigate its influence on selected immunological, haematological and biochemical indexes in bitches
  • as a standard to develop calibration curves in order to study its effects on progesterone and 17β-estradiol concentrations in peripheral blood and body weights of pre-pubertal female Beagle dogs
  • as a standard to develop calibration curves to study its level of intoxication in women with neoplastic lesions in the reproductive tract

Biochem/physiol Actions

Zearalanone is believed to cause vulvovaginitis and estrogenic responses in swine.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Influence of zearalenone micotoxicosis on selected immunological, haematological and biochemical indexes of blood plasma in bitches
Polak M, et al.
Polish Journal of Veterinary Sciences, 7(3), 175-180 (2004)
The effect of low doses of zearalenone and its metabolites on progesterone and 17b-estradiol concentrations in peripheral blood and body weights of pre-pubertal female Beagle dogs
Gajecka M, et al.
Toxicon, 76, 260-269 (2013)
Łukasz Zielonka et al.
Toxins, 12(3) (2020-03-01)
The objective of this study was to determine the effect of long-term (48 days), per os administration of specific zearalenone (ZEN) doses (20 and 40 μg ZEN/kg BW in experimental groups EI and EII, which were equivalent to 200% and
Toxigenic fungi and mycotoxins in the barley-to-beer chain
Brewing Microbiology, 107-139 (2015)
Mathias Devreese et al.
Journal of agricultural and food chemistry, 63(20), 5092-5098 (2015-05-08)
After oral (PO) and intravenous (IV) administration of zearalenone (ZEN) to broiler chickens, laying hens, and turkey poults, the mycotoxin was rapidly absorbed (Tmax = 0.32-0.97 h) in all three species; however, the absolute oral bioavailability was low (F% =
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