Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

3β-Androstenol

From Wikipedia, the free encyclopedia
Chemical compound
3β-Androstenol
Names
IUPAC name
5α-Androst-16-en-3β-ol
Systematic 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
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 mass274.448 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Not to be confused with3α-Androstenol.

3β-Androstenol, also known as5α-androst-16-en-3β-ol, is anaturally occurringmammalianpheromone known to be present inhumans andpigs.[1][2][3] It is thought to play a role inaxillaryodor.[3] It is produced fromandrostenone via theenzyme3β-hydroxysteroid dehydrogenase.[1] Unlike its C3αepimer3α-androstenol, 3β-androstenol shows nopotentiation of theGABAA receptor oranticonvulsant activity.[4]

See also

[edit]

References

[edit]
  1. ^abKanlayavattanakul 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. ^abFischer 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.
Pheromones
Steroids
Volatileamines
Pherines
Precursors
Corticosteroids
Glucocorticoids
Mineralocorticoids
Sex steroids
Androgens
Estrogens
Progestogens
Neurosteroids
Others
Retrieved from "https://en.wikipedia.org/w/index.php?title=3β-Androstenol&oldid=1329036237"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2026 Movatter.jp