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Androstadienol

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
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
  • 1224-94-8
PubChem CID
  • 150900
ChemSpider
  • 133002
CompTox Dashboard (EPA)
  • DTXSID40924155
Chemical and physical data
FormulaC19H28O
Molar mass272.432 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 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 Edit

References Edit

  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.

androstadienol, confused, with, androstanedione, androstanediol, androstenedione, androstenediol, androsta, dien, androstene, class, endogenous, steroid, pheromone, chemical, intermediate, several, other, pheromones, that, found, sweat, both, women, clinical, . Not to be confused with androstanedione androstanediol androstenedione or androstenediol Androstadienol or androsta 5 16 dien 3b 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 AndrostadienolClinical dataOther names5 16 Androstadien 3b olATC codeNoneIdentifiersIUPAC 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 olCAS Number1224 94 8PubChem CID150900ChemSpider133002CompTox Dashboard EPA DTXSID40924155Chemical and physical dataFormulaC 19H 28OMolar mass272 432 g mol 13D model JSmol Interactive imageSMILES C C 12CC C H 3 C H CC C4C C H O CC C 34C C H 2CC C1InChI 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 s1Key QVHPTAJAHUONLV DYKIIFRCSA NAndrostadienol 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 3b 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 EditList of neurosteroids Pheromones and pherinesReferences Edit a b c Gower DB 6 December 2012 Human Phermones In Jellinek JS ed The Psychological Basis of Perfumery Springer Science amp Business Media pp 179 ISBN 978 94 009 1567 1 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 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 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 Johannes J Weusten AM 1989 Biochemical pathways in human testicular steroidogenesis PDF Pressa Trajectina 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 Retrieved from https en wikipedia org w index php title Androstadienol amp oldid 1176355033, wikipedia, wiki, book, books, library,

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