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Merck

Z2125

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
UNSPSC Code:
12191503
NACRES:
NA.77
PubChem Substance ID:
24902175
MDL number:
MFCD00133085
Beilstein/REAXYS Number:
1350216
Quality level:
300

Key Documents

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Product Name

Zearalenone, fungal mycotoxin

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

SMILES string

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

InChI key

MBMQEIFVQACCCH-QBODLPLBSA-N

storage temp.

−20°C

Quality Level

300

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000463722
0000463722
0000400767
0000400767
0000389387

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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
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
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
S De Baere et al.
Analytica chimica acta, 756, 37-48 (2012-11-28)
A sensitive and specific method for the quantitative determination of zearalenone (ZEN) and its major metabolites (α-zearalenol (α-ZEL), β-zearalenol (β-ZEL), α-zearalanol (α-ZAL), β-zearalanol (β-ZAL) and zearalanone (ZAN)) in animal plasma using liquid chromatography combined with heated electrospray ionization (h-ESI) tandem
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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