Androstadienol
Clinical data
Other names5,16-Androstadien-3β-ol
ATC code
  • None
Identifiers
  • (3S,8S,9S,10R,13R,14S)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H28O
Molar mass272.432 g·mol−1
3D model (JSmol)
  • C[C@@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@]34C)[C@@H]2CC=C1
  • InChI=1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,5,9,14-17,20H,4,6-8,10-12H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
  • Key:QVHPTAJAHUONLV-DYKIIFRCSA-N

Androstadienol, or androsta-5,16-dien-3β-ol, is a 16-androstene class endogenous steroid, pheromone, and chemical intermediate to several other pheromones that is found in the sweat of both men and women.[1][2]

Androstadienol and androstadienone are odorless compounds secreted by the apocrine glands, and via conversion into the more powerfully-odorous androstenone and androstenol (catalyzed by aerobic corynebacteria, particularly Corynebacterium xerosis, in men, and Micrococcaceae spp. in women), are considered to be mainly responsible for the "musky" component of axillary (underarm) odor.[1][2][3] Androstadienol is synthesized from pregnenolone by the 16-ene-synthetase activity of CYP17A1,[4] and is converted into androstadienone by 3β-hydroxysteroid dehydrogenase.[5] Male sweat contains approximately five times as much androstenone as does female sweat, which can be explained by sex differences in androstadienol and androstadienone production.[1][2]

Androstadienone, which is produced from androstadienol, has been found to affect brain activity.[6] Specifically, it has been found to activate the hypothalamus, most maximally the medial preoptic and anterior hypothalamic areas, in heterosexual women and homosexual men, but not in heterosexual men (who instead experienced hypothalamic activation in response to smelling estratetraenol, an estrogen-related pheromone, while heterosexual women and homosexual men did not).[6] It has also been found to activate the anterior area of the inferior lateral prefrontal cortex, the superior temporal cortex, and olfactory areas.[6] The affected brain areas are thought to be involved in sexual behavior, attention, visual perception/recognition, and social cognition.[6]

See also

References

  1. ^ a b c Gower DB (6 December 2012). "Human Phermones?". In Jellinek JS (ed.). The Psychological Basis of Perfumery. Springer Science & Business Media. pp. 179–. ISBN 978-94-009-1567-1.
  2. ^ a b c Mandal FB (17 January 2012). "Chapter 12: Human Behaviour". Textbook of Animal Behaviour. PHI Learning Pvt. Ltd. pp. 296–. ISBN 978-81-203-4519-5.
  3. ^ Wilson M (2005). "The Skin and Its Indigenous Microbiota". Microbial Inhabitants of Humans: Their Ecology and Role in Health and Disease. Cambridge University Press. pp. 51–106 (104). doi:10.1017/CBO9780511735080.003. ISBN 978-0-521-84158-0.
  4. ^ Kaminski RM, Marini H, Ortinski PI, Vicini S, Rogawski MA (May 2006). "The pheromone androstenol (5 alpha-androst-16-en-3 alpha-ol) is a neurosteroid positive modulator of GABAA receptors". The Journal of Pharmacology and Experimental Therapeutics. 317 (2): 694–703. doi:10.1124/jpet.105.098319. PMID 16415088. S2CID 95393004.
  5. ^ Johannes J, Weusten AM (1989). Biochemical pathways in human testicular steroidogenesis (PDF). Pressa Trajectina.
  6. ^ a b c d Hawkes CH, Doty RL (12 February 2009). "Anatomy and physiology: Factors that Influence Normal Function". The Neurology of Olfaction. Cambridge University Press. pp. 37–. ISBN 978-0-521-68216-9.
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