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| ECHA InfoCard | 100.006.877 |
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| Formula | C19H30O2 |
| Molar mass | 290.447 g·mol−1 |
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Epiandrosterone, or isoandrosterone, also known as 3β-androsterone, 3β-hydroxy-5α-androstan-17-one, or 5α-androstan-3β-ol-17-one, is a steroid hormone with weak androgenic activity. It is a metabolite of testosterone and dihydrotestosterone (DHT). It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystalline androsterone (most likely mixed isomers), which was sufficient to find that the chemical formula was very similar to estrone.
Epiandrosterone has been shown to naturally occur in most mammals including pigs.
Epiandrosterone is naturally produced by the enzyme 5α-reductase from the adrenal hormone DHEA. Epiandrosterone can also be produced from the natural steroids androstanediol via 17β-hydroxysteroid dehydrogenase or from androstanedione via 3β-hydroxysteroid dehydrogenase.
See also
Further reading
- Simons RG, Grinwich DL (February 1989). "Immunoreactive detection of four mammalian steroids in plants". Canadian Journal of Botany. 67 (2): 288–96. doi:10.1139/b89-042.
- Janeczko A, Skoczowski A (2005). "Mammalian sex hormones in plants". Folia Histochemica et Cytobiologica. 43 (2): 71–9. PMID 16044944.
- Labrie F, Bélanger A, Labrie C, Candas B, Cusan L, Gomez JL (October 2007). "Bioavailability and metabolism of oral and percutaneous dehydroepiandrosterone in postmenopausal women". The Journal of Steroid Biochemistry and Molecular Biology. 107 (1–2): 57–69. doi:10.1016/j.jsbmb.2007.02.007. PMID 17627814. S2CID 26410666.
- Uralets VP, Gillette PA (September 1999). "Over-the-counter anabolic steroids 4-androsten-3,17-dione; 4-androsten-3beta,17beta-diol; and 19-nor-4-androsten-3,17-dione: excretion studies in men". Journal of Analytical Toxicology. 23 (5): 357–66. doi:10.1093/jat/23.5.357. PMID 10488924.