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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:
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

Signal Word

Danger

Hazard Statements

H314,H361d

Hazard Classifications

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

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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
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
Yu Tian et al.
Theranostics, 11(11), 5197-5213 (2021-04-17)
Rationale: Zearalenone (ZEN), a pollutant in our daily diet, seriously threatens the reproductive health of humans and animals. The primordial follicle (PF) assembly in the mouse occurs during the perinatal period, which determines the whole ovarian reserve in reproductive lifespan.
Abdellah Zinedine et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 45(1), 1-18 (2006-10-19)
Zearalenone (ZEA) is a mycotoxin produced mainly by fungi belonging to the genus Fusarium in foods and feeds. It is frequently implicated in reproductive disorders of farm animals and occasionally in hyperoestrogenic syndromes in humans. There is evidence that ZEA
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