3β-Androstenol

From Wikipedia, the free encyclopedia
3β-Androstenol
3β-Androstenol.svg
Names
Preferred IUPAC name
(3aS,3bR,5aS,7S,9aS,9bS,11aR)-9a,11a-Dimethyl-3a,3b,4,5,5a,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-3H-cyclopenta[a]phenanthren-7-ol
Other names
5α-Androst-16-en-3β-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
    Key: KRVXMNNRSSQZJP-LOVVWNRFSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CC[C@@H]4[C@@]3(CC[C@@H](C4)O)C
Properties
C19H30O
Molar mass 274.448 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3β-Androstenol, also known as 5α-androst-16-en-3β-ol, is a naturally occurring mammalian pheromone known to be present in humans and pigs.[1][2][3] It is thought to play a role in axillary odor.[3] It is produced from androstenone via the enzyme 3β-hydroxysteroid dehydrogenase.[1] Unlike its C3α epimer 3α-androstenol, 3β-androstenol shows no potentiation of the GABAA receptor or anticonvulsant activity.[4]

See also[edit]

References[edit]

  1. ^ a b Kanlayavattanakul M, Lourith N (2011). "Body malodours and their topical treatment agents". International Journal of Cosmetic Science. 33 (4): 298–311. doi:10.1111/j.1468-2494.2011.00649.x. PMID 21401651. S2CID 11235250.
  2. ^ Richard L. Doty (27 January 2010). The Great Pheromone Myth. JHU Press. pp. 139–. ISBN 978-0-8018-9347-6.
  3. ^ a b Fischer J, Elsinghorst PW, Bücking M, Tholen E, Petersen B, Wüst M (2011). "Development of a candidate reference method for the simultaneous quantitation of the boar taint compounds androstenone, 3α-androstenol, 3β-androstenol, skatole, and indole in pig fat by means of stable isotope dilution analysis-headspace solid-phase microextraction-gas chromatography/mass spectrometry". Anal. Chem. 83 (17): 6785–91. doi:10.1021/ac201465q. PMID 21800819.
  4. ^ Sinclair PA, Hancock S, Gilmore WJ, Squires EJ (2005). "Metabolism of the 16-androstene steroids in primary cultured porcine hepatocytes". J. Steroid Biochem. Mol. Biol. 96 (1): 79–87. doi:10.1016/j.jsbmb.2005.01.030. PMID 15896952. S2CID 9435153.