5α-Androst-2-ene-17-one

Not to be confused with Androstenone.

5α-Androst-2-ene-17-one
Names

IUPAC name (5S,8R,9S,10S,13S,14S)-10,13-Dimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
Other names 17-Oxo-5α-androst-2-ene; Delta-2-androst-17-one; (+)-Androst-2-en-17-one
Identifiers
CAS Number	963-75-7^Y
3D model (Jmol)	Interactive image
ChemSpider	92089^Y
ECHA InfoCard	100.012.289
PubChem	239425
InChI InChI==1S/C19H28O/c1-18-11-4-3-5-13(18)6-7-14-15-8-9-17(20)19(15,2)12-10-16(14)18/h3-4,13-16H,5-12H2,1-2H3/t13-,14+,15+,16+,18+,19+/m1/s1^Y Key: ISJVDMWNISUFRJ-HKQXQEGQSA-N^Y InChI=1S/C19H28O/c1-18-11-4-3-5-13(18)6-7-14-15-8-9-17(20)19(15,2)12-10-16(14)18/h3-4,13-16H,5-12H2,1-2H3/t13?,14-,15-,16-,18-,19-/m0/s1 Key: ISJVDMWNISUFRJ-HKQXQEGQBN
SMILES C[C@@]34CC[C@H]2[C@@H](CCC1C\C=C/C[C@@]12C)[C@@H]4CCC3=O
Properties
Chemical formula	C₁₉H₂₈O
Molar mass	272.43 g·mol⁻¹
Melting point	106 to 107 °C (223 to 225 °F; 379 to 380 K)^[1]
Pharmacology
Pregnancy category	X
Routes of administration	Oral
Pharmacokinetics:
Metabolism	Liver
Excretion	Urine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

5α-Androst-2-ene-17-one is a steroid. It is referred to commercially as delta-2-androst-17-one. This compound is a naturally occurring pheromone found in elephants and boars.^[2] 5α-Androst-2-ene-17-one is also a natural human metabolite of DHEA.^[3]^[4]

References

↑ Bockova, H. (1966). Collection of Czechoslovak Chemical Communications. 31 (9): P3790–3799. doi:10.1135/cccc19663790. CS1 maint: Untitled periodical (link)
↑ Marchlewska-Koj, A.; Lepri, J. J. (2001). "Chemical signals in vertebrates 9". Springer. 9: 131. ISBN 978-0-306-46682-3.
↑ Callies, F; Arlt, W; Siekmann, L; Hübler, D; Bidlingmaier, F; Allolio, B (2000). "Influence of oral dehydroepiandrosterone (DHEA) on urinary steroid metabolites in males and females.". Steroids. 65 (2): 98–102. doi:10.1016/S0039-128X(99)00090-2. PMID 10639021.
↑ Gower, DB; Mallet, AI; Watkins, WJ; Wallace, LM (1997). "Transformations of steroid sulphates by human axillary bacteria. A mechanism for human odour formation?". Biochemical Society Transactions. 25 (1): 16S. doi:10.1042/bst025016s. PMID 9056914.

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