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Z2125

Sigma-Aldrich

Zearalenone

fungal mycotoxin

Synonym(s):

F-2 toxin

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About This Item

Empirical Formula (Hill Notation):
C18H22O5
CAS Number:
17924-92-4
Molecular Weight:
318.36
Beilstein/REAXYS Number:
1350216
MDL number:
MFCD00133085
UNSPSC Code:
12191503
PubChem Substance ID:
24902175
NACRES:
NA.77

Quality Level

300

storage temp.

−20°C

SMILES string

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

InChI

1S/C18H22O5/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/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3+/t12-/m0/s1

InChI key

MBMQEIFVQACCCH-QBODLPLBSA-N

Gene Information

mouse ... Esr1(13982)

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Biochem/physiol Actions

Zearalenone, a fungal mycotoxin produced by Fusarium, binds the estrogen receptor (ER) and is uterotropic in the newborn rat. It is a common contaminant in cereal grain used for animal and human food, and exerts an estrogenic activity that modulates/disrupts endocrine function in animals and possibly humans.

pictograms

Health hazardCorrosion
GHS08,GHS05

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Repr. 2 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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D M Sheehan et al.
Teratology, 29(3), 383-392 (1984-06-01)
Fusarium sp. contaminated feedstuffs elicit adverse estrogenic effects in several commercially important animal species via the mycotoxin zearalenone. An estrogenically active synthetic derivative, zearalanol, is used as an anabolic agent in cattle. Since estrogens can irreversibly alter target tissue development
Katarzyna Cieplińska et al.
Toxins, 11(5) (2019-05-30)
Zearalenone is a frequent contaminant of cereals and their by-products in regions with a temperate climate. This toxic molecule is produced naturally by Fusarium fungi in crops. The aim of this study was to determine the influence of low zearalenone
H Leffers et al.
Human reproduction (Oxford, England), 16(5), 1037-1045 (2001-05-02)
We have compared the oestrogenic potency of the synthetic oestrogen Zeranol, used as a growth promoter in meat production, and five related compounds, with the potency of 17beta-oestradiol, diethylstilboestrol (DES), genistein, and Bisphenol-A. The potency was assayed by analysing differences
Kazimierz Obremski et al.
Toxins, 12(6) (2020-05-31)
The aim of the present study was to determine the effect of zearalenone (ZEN), administered per os to gilts at doses equivalent to 50%, 100%, and 150% of no-observed-adverse-effect level (NOAEL) values for 14, 28, and 42 days during weaning
Cristina Juan et al.
Food chemistry, 134(4), 2389-2397 (2013-02-28)
Although analytical methods have been already reported for legislated mycotoxins as trichothecenes and zearalenone (ZON) separately, we describe the optimization of a simple and rapid multimycotoxin method for the determination of a total of 12 mycotoxins simultaneously, nine trichothecenes (NIV
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