Androsterone

Androsterone

Systematic (IUPAC) name
(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	53-41-8 Y
ATC code	None
PubChem	CID 5879
ChemSpider	5668 Y
UNII	C24W7J5D5R Y
ChEBI	CHEBI:16032 Y
ChEMBL	CHEMBL87285 Y
Chemical data
Formula	C19H30O2
Mol. mass	290.440 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1 Y Key:QGXBDMJGAMFCBF-HLUDHZFRSA-N Y
Y(what is this?)  (verify)

Androsterone (ADT) is a steroid hormone with weak androgenic activity. It is made in the liver from the metabolism of testosterone. Its beta-isomer is Epiandrosterone.

History

It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17000 litres of male urine, from which they got 50 milligrams of crystalline androsterone, which was sufficient to find that the chemical formula was very similar to estrone.

Sources

Androsterone has been shown to naturally occur in pine pollen and is well known in many animal species.

Celery is claimed to contain androsterone; however, this is inaccurate. Celery actually contains androstenone, which has a different structure to androsterone and is otherwise unrelated.

Effects

Androsterone is often advertised as influencing human behavior, but there is little data to substantiate its use as a pheromone.^{[citation needed]}

Synthesis

Androsterone and its 3β isomer, epiandrosterone, are naturally produced by an enzyme 5α-reductase from the adrenal hormone dehydroepiandrosterone (DHEA).^{[citation needed]} Androsterone can also be converted from the natural steroids 5α-androstanediol via 17β-hydroxysteroid dehydrogenase or from 5α-androstanedione via 3α-hydroxysteroid dehydrogenase.^{[citation needed]}

Synonyms

Synonyms include 3α-hydroxy-17-androstanone; 3α-Hydroxy-5-α-androstan-17-one; 3α-hydroxyetioallocholan-17-one; 3α-hydroxy-17-androstanone; 3α-hydroxyetioallocholan-17-one; 3α-hydroxy-17-androstanone; 3α-hydroxy-5α-androstan-17-one; 3α-hydroxyetioallocholan-17-one

See also

• Androstadienone
• Androstatrione
• Androstenol
• Androstenone
• Adrenosterone
• Dehydroepiandrosterone
• Estratetraenol

External links

• Androsterone entry in the HMDB