[CAS NO. 17924-92-4] Zearalenone

Name: Zearalenone
Brand: Arctom Scientific
SKU: SLK-S5676

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PRODUCTS SPECIFICATIONS [17924-92-4]

Store

Catalog

SLK-S5676

Brand

Selleck

CAS

17924-92-4

DESCRIPTION [17924-92-4]

Overview

MDL	MFCD00133085
Molecular Weight	318.36
Molecular Formula	C18H22O5
SMILES	OC1=C2C(=CC(O)=C1)/C=C/CCCC(=O)CCC[C@H](C)OC2=O

For research use only.

Storage

3 years,-20°C,powder
1 years,-80°C,in solvent

Shipping

Room temperature shipping(Stability testing shows this product can be shipped without any cooling measures.)

Description

Zearalenone (F2 toxin, RAL) is a non-steroidal estrogenic mycotoxin that acts by binding the (ER).

Targets

ERβ ^[1]	ERα ^[1]
165.7 nM	240.4 nM

In vitro

Zearalenone is able to occupy the active site of ERs in a strikingly similar manner as E2. Zearalenone disrupts genome stability and inhibits growth of porcine granulosa cells via the estrogen receptors which may promote granulosa cell apoptosis when the DNA repair system is not enough to rescue this serious damage. At low concentrations, ZEN enhances cell proliferation, increases colony formation and fastens cell migration after wound healing. Zearalenone exhibits carcinogenesis-like properties.

In vivo

In ovariectomized female ICR mice, s.c. administration of ZEN at doses ≥2 mg/kg/day for 3 consecutive days significantly increased uterine wet weight compared with the control group. Zearalenone is an immunotoxic compound similar to estrogen and some endocrine disruptors. After oral exposure, ZEA is rapidly absorbed and initially metabolized by the intestinal tissue and hepatocytes; this initiates the biotransformation of the compound into its major biologically active reductive metabolites, α- and β-zearalenol (α- and β-ZOL). The estrogenic activity of ZEA and its metabolites is mediated by their binding affinity to estrogen receptors (ER), and they are as potent as coumestrol and genistein, two endocrine-disrupting phytestrogens.

References

[1] Takemura H, et al. J Steroid Biochem Mol Biol. 2007, 103(2):170-7.
[2] Isis M. Hueza, et al. Toxins (Basel). 2014, 6(3): 1080–1095.
[3] Xue-Lian Liu, et al. Int J Biol Sci. 2018, 14(3): 294–305.
[4] Abassi H, et al. Toxicol Lett. 2016, 254:1-7.

Synonyms

1H-2-Benzoxacyclotetradecin-1,7(8H)-dione, 3,4,5,6,9,10-hexahydro-14,16-dihydroxy-3-methyl-, (3S,11E)-

1H-2-Benzoxacyclotetradecin-1,7(8H)-dione, 3,4,5,6,9,10-hexahydro-14,16-dihydroxy-3-methyl-, (S)-(-)-

Zearalenone

1H-2-Benzoxacyclotetradecin-1,7(8H)-dione, 3,4,5,6,9,10-hexahydro-14,16-dihydroxy-3-methyl-, [S-(E)]-

(3S,11E)-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione

(-)-Zearalenone

trans-Zearalenone

Mycotoxin F 2

6-(10-Hydroxy-6-oxo-trans-1-undecenyl)-β-resorcylic acid lactone

(S)-Zearalenone

Toxin F₂

(10S)-Zearalenone

Zenone

(S)-(-)-Zearalenone