Zeranol

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Zeranol
Zeranol.png
Names
IUPAC name
(3S,7R)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one
Other names
α-Zearalanol
Identifiers
26538-44-3 N
ChEMBL ChEMBL371463 YesY
ChemSpider 2271133 N
Jmol-3D images Image
PubChem 2999413
UNII 76LO2L2V39 YesY
Properties
C18H26O5
Molar mass 322.40 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Zeranol (α-zearalanol) is a non-steroidal estrogen agonist. It is a mycotoxin, derived from fungi in the Fusarium family, and may be found as a contaminant in fungus-infected crops. It is 3-4x more potent as an estrogen agonist than the related compound zearalenone.[1]

Zeranol is approved for use as a growth promoter in livestock, including beef cattle, in the United States. In Canada, it is approved for use in beef cattle only.[2] Its application is not approved for use in the European Union.

Zeranol increases cancer cell proliferation in already existing breast cancer.[3] There are mixed results to whether zeranol has anticancer or carcinogenic properties in non cancer containing breast cells depending on dose.[3] Overall evidence points to zeranol being a risk factor and promoter for cancer.[3] However, dietary exposure from the use of zeranol-containing implants in cattle is insignificant.[4]

References[edit]

  1. ^ Mirocha, CJ; Schauerhamer, B; Christensen, CM; Niku-Paavola, ML; Nummi, M (1979). "Incidence of zearalenol (Fusarium mycotoxin) in animal feed". Applied and environmental microbiology 38 (4): 749–50. PMC 243572. PMID 161492. 
  2. ^ Health Canada, Questions and Answers - Hormonal Growth Promoters
  3. ^ a b c Ye, Weiping et al. (February 2011). "Zeranol Down-Regulates p53 Expression in Primary Cultured Human Breast Cancer Epithelial Cells through Epigenetic Modification". Int J Mol Sci 12 (3): 1519–1532. doi:10.3390/ijms12031519. PMC 3111616. PMID 21673905. 
  4. ^ Lindsay DG (August 1985). "Zeranol--a 'nature-identical' oestrogen?". Food Chem Toxicol 23 (8). pp. 767–74.