A mycotoxin
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Zearalenone

Item No. 11353

Technical Information
Formal Name
(3S,11E)-3,4,5,6,9,10-hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione
CAS Number
17924-92-4
Synonyms
  • FES
  • Mycotoxin F2
  • Toxin F2
  • Zenone
Molecular Formula
C18H22O5
Formula Weight
Purity
≥98%
Formulation
A crystalline solid
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:7): 0.12 mg/mlEthanol: 20 mg/ml
λmax
236, 274, 316 nm
SMILES
OC1=C(C(O[C@@H](C)CCCC(CCC/C=C/2)=O)=O)C2=CC(O)=C1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Zearalenone is a mycotoxin that has been found in Fusarium and has estrogenic activities.1 It binds to human estrogen receptor α (ERα) and ERβ (IC50s = 9 and 5.8 nM, respectively).2 Zearalenone induces precocious development of mammary tissues in young female pigs and prepucial enlargement in young male pigs.3 Zearalenone (1.5-5 mg/kg of diet) induces hyperestrogenism in pigs. It also induces degeneration of meiotic chromatin in oocytes and reduces fertility in pigs when administered at a dose of 200 µg/kg.4 Zearalenone has been found as a contaminant in wheat, maize, and barley and livestock feeds.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zinedine, A., Soriano, J.M., Moltó, J.C., et alReview on the toxicity, occurrence, metabolism, detoxification, regulations and intake of zearalenone: An oestrogenic mycotoxin. Food Chem. Toxicol. 45(1), 1-18 (2007).

    2. Kuiper, G.G.J.M., Lemmen, J.G., Carlsson, B., et alInteraction of estrogenic chemicals and phytoestrogens with estrogen receptor β. Endocrinology 139(10), 4252-4263 (1998).

    3. Richard, J.L. Some major mycotoxins and their mycotoxicoses—an overview. Int. J. Food Microbiol. 119(1-2), 3-10 (2007).

    4. Tiemann, U., and Dänicke, S. In vivo and in vitro effects of the mycotoxins zearalenone and deoxynivalenol on different non-reproductive and reproductive organs in female pigs: A review. Food Addit. Contam. 24(3), 306-314 (2007).