Zeranol
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| 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  | |
| ChEMBL | ChEMBL371463  |
| ChemSpider | 2271133 |
| Jmol interactive 3D | Image |
| PubChem | 2999413 |
| UNII | 76LO2L2V39 |
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| Properties | |
| C18H26O5 | |
| Molar mass | 322.40 g·mol−1 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| 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
- ↑ 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.
- ↑ Health Canada, Questions and Answers - Hormonal Growth Promoters
- 1 2 3 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.
- ↑ Lindsay DG (August 1985). "Zeranol--a 'nature-identical' oestrogen?". Food Chem Toxicol 23 (8): 767–74. PMID 2931335.
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