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 model Interactive image
PubChem 2999413
UNII 76LO2L2V39 YesY
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).
N verify (what is YesYN ?)
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. Merck Animal Health markets zeranol under the brand name Relgro.[3]

Although zeranol may increase cancer cell proliferation in already existing breast cancer,[4] dietary exposure from the use of zeranol-containing implants in cattle is insignificant.[5]

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. ^ Nichols, Wade; Hutcheson, John; Streeter, Marshall; Corrigan, Mark; Nuttelman, Brandon. "Implant Strategies for Finishing Cattle using Revalor® (trenbolone acetate and estradiol), Finaplix® (trenbolone) and/or Ralgro® (zeranol)" (PDF). Merck Animal Health. 
  4. ^ Xu, Pingping; Ye, Weiping; Jen, Robert; Lin, Shu-Hong; Kuo, Chieh-Ti; Lin, Young C. (2009-11-01). "Mitogenic activity of zeranol in human breast cancer cells is enhanced by leptin and suppressed by gossypol". Anticancer Research 29 (11): 4621–4628. ISSN 1791-7530. PMID 20032412. 
  5. ^ Lindsay DG (August 1985). "Zeranol--a 'nature-identical' oestrogen?". Food Chem Toxicol 23 (8): 767–74. PMID 2931335.