Zeranol

Zeranol

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
CAS Number	26538-44-3 N
ChEMBL	ChEMBL371463 Y
ChemSpider	2271133 N
Jmol 3D model	Interactive image
PubChem	2999413
UNII	76LO2L2V39 Y
InChI InChI=1S/C18H26O5/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/h10-12,14,19-21H,2-9H2,1H3/t12-,14+/m0/s1 N Key: DWTTZBARDOXEAM-GXTWGEPZSA-N N InChI=1/C18H26O5/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/h10-12,14,19-21H,2-9H2,1H3/t12-,14+/m0/s1 Key: DWTTZBARDOXEAM-GXTWGEPZBO
SMILES C[C@H]1CCC[C@@H](CCCCCC2=C(C(=CC(=C2)O)O)C(=O)O1)O
Properties
Chemical formula	C18H26O5
Molar mass	322.40 g·mol−1
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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.

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. Its application is not approved for use in the European Union.

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