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
InChI InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1 N Key:DNXHEGUUPJUMQT-CBZIJGRNSA-N N
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.

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.

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

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  Androstenedione converting to estrone.

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  Steroidogenesis