Estrone

Estrone
Clinical data


ATC code	G03CA07 (WHO) G03CC04 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Protein binding	>95%
Biological half-life	19 hours
Identifiers
IUPAC name (8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
CAS Number	53-16-7^Y
PubChem CID	5870
IUPHAR/BPS	2818
DrugBank	DB00655^N
ChemSpider	5660^Y
UNII	2DI9HA706A
KEGG	D00067^N
ChEBI	CHEBI:17263^N
ChEMBL	CHEMBL1405^N
ECHA InfoCard	100.000.150
Chemical and physical data
Formula	C₁₈H₂₂O₂
Molar mass	270.366 g/mol
3D model (Jmol)	Interactive image
Melting point	254.5 °C (490.1 °F)
SMILES O=C4[C@]3(CC[C@@H]2c1ccc(O)cc1CC[C@H]2[C@@H]3CC4)C
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
^NY (what is this?)

Estrone (American English) (abbreviated as E1), or oestrone (British English), also known as estra-1,3,5(10)-trien-3-ol-17-one, is an estrogenic hormone secreted by the ovary as well as adipose tissue. It 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 was discovered and isolated by German chemist Adolf Butenandt. It was formerly marketed under the brand name Theelin in the United States for intramuscular injection, but this formulation is no longer available.

Estrone is synthesized via aromatase from 4-androstenedione. The conversion consists of the demethylation of the C19 position and the aromatization of the A ring. This reaction is similar to the conversion of testosterone to estradiol via aromatase. Estrone is also reversibly produced from estradiol via 17β-hydroxysteroid dehydrogenase.

Estrone has the chemical name 3-hydroxyestra-1,3,5(10)-triene-17-one or estra-1,3,5(10)-triene-3-ol-17-one and the chemical formula C₁₈H₂₂O₂. It is an odorless, solid crystalline powder, white in color with a melting point of 254.5 °C (490 °F) and a specific gravity of 1.23. At high temperatures estrone is combustible and the products of combusting estrone are carbon monoxide (CO) and carbon dioxide (CO₂).

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