Estrone

Estrone
Systematic (IUPAC) name
3-hydroxy-13-methyl- 6,7,8,9,11,12,13,14,15,16- decahydrocyclopenta[a]phenanthren- 17- one
Clinical data
Pregnancy cat.  ?
Legal status  ?
Pharmacokinetic data
Protein binding >95%
Half-life 19 hours
Identifiers
CAS number 53-16-7 Y
ATC code G03CA07 G03CC04
PubChem CID 5870
DrugBank DB00655
ChemSpider 5660 Y
UNII 2DI9HA706A Y
KEGG D00067 N
ChEBI CHEBI:17263 N
ChEMBL CHEMBL1405 N
Chemical data
Formula C18H22O2 
Mol. mass 270.366 g/mol
SMILES eMolecules & PubChem
Physical data
Melt. point 254.5 °C (490 °F)
 N(what is this?)  (verify)

Estrone (E1, and also oestrone) is an estrogenic hormone secreted by the ovary as well as adipose tissue.[1]

Estrone is one of several natural estrogens, which also include estriol and estradiol. Estrone is the least abundant of the three hormones; estradiol is present almost always in the reproductive female body, and estriol is abundant primarily during pregnancy.

Estrone is relevant to health and disease states because of its conversion to estrone sulfate, a long-lived derivative. Estrone sulfate acts as a reservoir that can be converted as needed to the more active estradiol.

Estrone is the predominant estrogen in postmenopausal women.[2]

Biosynthesis

Estrone is synthesized via aromatase from androstenedione, a derivative of progesterone. The conversion consists of the de-methylation of C-19 and the aromaticity of the 'A' ring. This reaction is similar to the conversion of testosterone to estradiol.

Additional images

References

  1. ^ "Estrone -PubChem". National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5870&loc=ec_rcs. Retrieved 2009-09-06. 
  2. ^ Helen Varney, Jan M. Kriebs, Carolyn L. Gegor. Varney's midwifery, Fourth Edition. Jones and Bartlett Publishers, 2004, p. 340.