Androsterone

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Androsterone
200px
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
Identifiers
CAS Number 53-41-8
ATC code none
PubChem CID 5879
ChemSpider 5668
Chemical data
Formula C19H30O2
Molar mass 290.440 g/mol[[Script error: No such module "String".]]
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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.[1]

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.[citation needed]

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 the 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

References

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External links


de:Androsteron

es:Androsterona fr:Androstérone it:Androsterone he:אנדרוסטרון nl:Androsteron oc:Androsterona pl:Androsteron pt:Androsterona

fi:Androsteroni
  1. FOLIA HISTOCHEMICA ET CYTOBIOLOGICA Vol. 43, No. 2, 2005 pp. 71-79 Mammalian sex hormones in plants Anna Janeczko and Andrzej Skoczowski Institute of Plant Physiology, Polish Academy of Sciences, Kraków, Poland