Androsterone
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| 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".]] |
| Script error: No such module "collapsible list". | |
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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.
Contents
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
- Androstadienone
- Androstatrione
- Androstenol
- Androstenone
- Adrenosterone
- Dehydroepiandrosterone
- Estratetraenol
References
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es:Androsterona fr:Androstérone it:Androsterone he:אנדרוסטרון nl:Androsteron oc:Androsterona pl:Androsteron pt:Androsterona
fi:Androsteroni- ↑ 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
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- Androgens
- Hormones of the liver
- Steroid hormones
- Pheromones
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