Androstadienol

{{Short description|Chemical compound}}

{{Distinguish|androstanedione|androstanediol|androstenedione|androstenediol}}

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| IUPAC_name = (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

| image = 5,16-androstadien-3β-ol.svg

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| CAS_number = 1224-94-8

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| PubChem = 150900

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| ChemSpiderID = 133002

| synonyms = 5,16-Androstadien-3β-ol

| C=19 | H=28 | O=1

| SMILES = C[C@@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@]34C)[C@@H]2CC=C1

| StdInChI = 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

| StdInChIKey = QVHPTAJAHUONLV-DYKIIFRCSA-N

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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.{{cite book| vauthors = Gower DB | chapter = Human Phermones? | veditors = Jellinek JS |title=The Psychological Basis of Perfumery| chapter-url= https://books.google.com/books?id=iLv0CAAAQBAJ&pg=PA179|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-009-1567-1|pages=179–}}{{cite book| vauthors = Mandal FB | chapter = Chapter 12: Human Behaviour |title=Textbook of Animal Behaviour | chapter-url = https://books.google.com/books?id=FF-LDWalcqEC&pg=PA296 |date=17 January 2012|publisher=PHI Learning Pvt. Ltd.|isbn=978-81-203-4519-5|pages=296–}}

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.{{cite book| vauthors = Wilson M | chapter = The Skin and Its Indigenous Microbiota |title=Microbial Inhabitants of Humans: Their Ecology and Role in Health and Disease| chapter-url = https://books.google.com/books?id=q9Qx9oRKO_kC&pg=PA104 |year=2005|publisher=Cambridge University Press|isbn=978-0-521-84158-0|pages= 51–106 (104) | doi = 10.1017/CBO9780511735080.003 }} Androstadienol is synthesized from pregnenolone by the 16-ene-synthetase activity of CYP17A1,{{cite journal | vauthors = Kaminski RM, Marini H, Ortinski PI, Vicini S, Rogawski MA | title = The pheromone androstenol (5 alpha-androst-16-en-3 alpha-ol) is a neurosteroid positive modulator of GABAA receptors | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 317 | issue = 2 | pages = 694–703 | date = May 2006 | pmid = 16415088 | doi = 10.1124/jpet.105.098319 | s2cid = 95393004 }} and is converted into androstadienone by 3β-hydroxysteroid dehydrogenase.{{cite book|title=Biochemical pathways in human testicular steroidogenesis| vauthors = Johannes J, Weusten AM |year=1989|publisher=Pressa Trajectina|url=http://repository.ubn.ru.nl/bitstream/handle/2066/113615/mmubn000001_074818627.pdf?sequence=-1}} 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.

Androstadienone, which is produced from androstadienol, has been found to affect brain activity.{{cite book| vauthors = Hawkes CH, Doty RL | chapter = Anatomy and physiology: Factors that Influence Normal Function |title=The Neurology of Olfaction| chapter-url = https://books.google.com/books?id=aoE9-GKuhnIC&pg=PA37|date=12 February 2009|publisher=Cambridge University Press|isbn=978-0-521-68216-9|pages=37–}} 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). It has also been found to activate the anterior area of the inferior lateral prefrontal cortex, the superior temporal cortex, and olfactory areas. The affected brain areas are thought to be involved in sexual behavior, attention, visual perception/recognition, and social cognition.