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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

signalword

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, 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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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% =
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)
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