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(3 R,5 S,8 R,9 S,10 S,13 S,14 S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[ a]phenanthren-17-one
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ATC code None
C 19 H 30 O 2
Mol. mass 290.440 g/mol
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Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone and weak androgen with a potency that is approximately 1/7 that of testosterone. In addition, it can be converted to [1 ] dihydrotestosterone (DHT) from 17-hydroxyprogesterone, bypassing conventional intermediates such as androstenedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right. [2 ] [3 ]
isomer is epiandrosterone.
History [ edit ]
It was first isolated in 1931, by
Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 liters (3,700 imp gal; 4,500 US gal) of male urine, from which they got 50 milligrams (0.77 gr) of crystalline androsterone, which was sufficient to find that the chemical formula was very similar to estrone.
Sources [ edit ]
Androsterone has been shown to naturally occur in
pine pollen and is well known in many animal species. [4 ]
Effects [ edit ]
Androsterone is often advertised as influencing human behavior, but there is little data to substantiate its use as a
pheromone. [ ] citation needed
Synthesis [ edit ]
Androsterone, its 3β-isomer,
epiandrosterone, and its 5β-isomer, etiocholanolone, are produced in the body from 5α-reduced metabolites of dehydroepiandrosterone (DHEA), androstenediol, and androstenedione such as, in the case of androsterone, 5α-androstanediol via 17β-hydroxysteroid dehydrogenase and 5α-androstanedione via 3α-hydroxysteroid dehydrogenase. [ ] citation needed
See also [ edit ]
References [ edit ]
^ Thomas Scott (1996). . Walter de Gruyter. p. 49. Concise Encyclopedia Biology ISBN 978-3-11-010661-9 . Retrieved 25 May 2012.
^ Brian E. Henderson; Bruce A. J. Ponder; Ronald Keith Ross (13 March 2003). . Oxford University Press. p. 23. Hormones, Genes, and Cancer ISBN 978-0-19-513576-3 . Retrieved 25 May 2012.
^ Kamrath C, Hochberg Z, Hartmann MF, Remer T, Wudy SA (March 2012). "Increased activation of the alternative "backdoor" pathway in patients with 21-hydroxylase deficiency: evidence from urinary steroid hormone analysis". The Journal of Clinical Endocrinology and Metabolism 97 (3): E367–75. doi: 10.1210/jc.2011-1997. PMID 22170725.
^ 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
External links [ edit ]