Jump to content
 







Main menu
   


Navigation  



Main page
Contents
Current events
Random article
About Wikipedia
Contact us
Donate
 




Contribute  



Help
Learn to edit
Community portal
Recent changes
Upload file
 








Search  

































Create account

Log in
 









Create account
 Log in
 




Pages for logged out editors learn more  



Contributions
Talk
 



















Contents

   



(Top)
 


1 Biosynthesis  





2 Properties  



2.1  Detectability as a pheromone  





2.2  Commercial use  







3 See also  





4 References  














Androstenone






تۆرکجه
Deutsch
فارسی
Français
Galego
Italiano

Polski
Русский
Српски / srpski
Srpskohrvatski / српскохрватски

 

Edit links
 









Article
Talk
 

















Read
Edit
View history
 








Tools
   


Actions  



Read
Edit
View history
 




General  



What links here
Related changes
Upload file
Special pages
Permanent link
Page information
Cite this page
Get shortened URL
Download QR code
Wikidata item
 




Print/export  



Download as PDF
Printable version
 




In other projects  



Wikimedia Commons
 
















Appearance
   

 






From Wikipedia, the free encyclopedia
 


Androstenone
Skeletal formula of androstenone
Ball-and-stick model of the androstenone molecule
Names
IUPAC name

5α-Androst-16-en-3-one

Systematic IUPAC name

(3aS,3bR,5aS,9aS,9bS,11aR)-9a,11a-Dimethyl-3,3a,3b,4,5,5a,6,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one

Identifiers

CAS Number

3D model (JSmol)

ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.038.367 Edit this at Wikidata

PubChem CID

UNII

CompTox Dashboard (EPA)

  • 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/h3,9,13,15-17H,4-8,10-12H2,1-2H3/t13-,15-,16-,17-,18-,19-/m0/s1 checkY

    Key: HFVMLYAGWXSTQI-QYXZOKGRSA-N checkY

  • InChI=1/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/h3,9,13,15-17H,4-8,10-12H2,1-2H3/t13-,15-,16-,17-,18-,19-/m0/s1

    Key: HFVMLYAGWXSTQI-QYXZOKGRBP

  • O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@@]1(/C=C\C[C@H]12)C)[C@@]3(C)CC4

Properties

Chemical formula

C19H28O
Molar mass 272.432 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

☒N verify (what is checkY☒N ?)

Infobox references

Androstenone (5α-androst-16-en-3-one) is a 16-androstene class steroidal pheromone. It is found in boar's saliva, celery cytoplasm,[citation needed] and truffle fungus.[citation needed] Androstenone was the first mammalian pheromone to be identified. It is found in high concentrations in the saliva of male pigs, and, when inhaled by a female pig that is in heat, results in the female assuming the mating stance. Androstenone is the active ingredient in 'Boarmate', a commercial product made by DuPont sold to pig farmers to test sows for timing of artificial insemination.[1][2][3][4][5]

Biosynthesis[edit]

Androstenone is synthesized from androstadienoneby5α-reductase, and can be converted into 3α-androstenolor3β-androstenolby3-ketosteroid reductase.[6]

Properties[edit]

Depending upon the subject, androstenone can have an unpleasant, sweaty, urinous smell, a woody smell, or even a pleasant floral smell.[3][7][8]

There are two different genotypes that allow an individual to smell androstenone. The first genotype, which consists of two fully functional copies of the gene, is the RT/RT allele, and the second is the RT/WM allele.[citation needed] The OR7D4 receptor[4] has two non-synonymous single nucleotide polymorphisms,[9] which cause the gene to have two amino acid substitutions, which in turn cause the receptor to act differently. Those in possession of the two proper genes, (RT/RT) for OR7D4 tend to describe the odor for the steroid as the odor of stale urine. Those with only one gene (RT/WM) typically described the odor as weak or were not able to detect it. They can also find the smell 'pleasant', 'sweet' or 'similar to vanilla'.[10]

In small amounts, the odor is hardly detectable by most people. This may be due to a polymorphism in the receptor gene that codes for the androstenone receptor.[11] However, the ability to detect the odor varies greatly. It has been shown that the odor can be detected by people down to levels of 0.2 parts per billion to 0.2 parts in 100 million.[12] Several groups report, however, that some individuals who initially cannot smell androstenone can learn to smell it by repeated exposures to it.[13]

Detectability as a pheromone[edit]

In humans, androstenone also has been suggested to be a pheromone; however, there is little scientific data to support this claim.[14][better source needed] The vomeronasal organ is an auxiliary olfactory sense organ responsible for the detection of pheromones as more than just an odor. Most adult humans possess something resembling this organ, but there is no active function. Humans lack the sensory cells that exist in other mammals needed to detect pheromones beyond a smell.[clarification needed][dubiousdiscuss] Humans also lack the genetic ability to produce these sensory cells actively.[citation needed]

There is also a specific anosmia to the odor in some humans; they are unable to smell specific odors, but have, otherwise, a normal sense of smell. However, this should, by no means, be regarded as indicative for being labeled as a pheromone, as it is true of over 80 olfactory compounds.[15]

To animals, the smell of androstenone can act as a social sign of dominance and can be a way of attracting a mate.[citation needed][dubiousdiscuss]

Commercial use[edit]

Some commercially available products are advertised using claims that they contain human sexual pheromones, including androstenone, and that they can act as an aphrodisiac.[citation needed]

See also[edit]

References[edit]

  1. ^ Pierce, John D.; Cohen, Adam B.; Ulrich, Patricia M. (March 2004). "Responsivity to Two Odorants, Androstenone and Amyl Acetate, and the Affective Impact of Odors on Interpersonal Relationships". Journal of Comparative Psychology. 118 (1): 14–19. doi:10.1037/0735-7036.118.1.14. PMID 15008668.
  • ^ Dorries, Kathleen M.; Adkins-Regan, Elizabeth; Halpern, Bruce P. (1997). "Sensitivity and Behavioral Responses to the Pheromone Androstenone Are Not Mediated by the Vomeronasal Organ in Domestic Pigs". Brain, Behavior and Evolution. 49 (1): 53–62. doi:10.1159/000112981. PMID 8980852.
  • ^ a b Wysocki, C. J.; Dorries, K. M.; Beauchamp, G. K. (1 October 1989). "Ability to perceive androstenone can be acquired by ostensibly anosmic people". Proceedings of the National Academy of Sciences. 86 (20): 7976–7978. Bibcode:1989PNAS...86.7976W. doi:10.1073/pnas.86.20.7976. PMC 298195. PMID 2813372.
  • ^ a b Wysocki, C. J.; Beauchamp, G. K. (1 August 1984). "Ability to smell androstenone is genetically determined". Proceedings of the National Academy of Sciences. 81 (15): 4899–4902. Bibcode:1984PNAS...81.4899W. doi:10.1073/pnas.81.15.4899. PMC 391599. PMID 6589634.
  • ^ Bonneau, M.; Walstra, P.; Claudi-Magnussen, C.; Kempster, A.J.; Tornberg, E.; Fischer, K.; Diestre, A.; Siret, F.; Chevillon, P.; Claus, R.; Dijksterhuis, G.; Punter, P.; Matthews, K.R.; Agerhem, H.; Béague, M.P.; Oliver, M.A.; Gispert, M.; Weiler, U.; von Seth, G.; Leask, H.; Font i Furnols, M.; Homer, D.B.; Cook, G.L. (March 2000). "An international study on the importance of androstenone and skatole for boar taint: IV. Simulation studies on consumer dissatisfaction with entire male pork and the effect of sorting carcasses on the slaughter line, main conclusions and recommendations". Meat Science. 54 (3): 285–295. doi:10.1016/s0309-1740(99)00105-9. PMID 22060698.
  • ^ Weusten, J. J. A. M. (1989). Biochemical pathways in human testicular steroidogenesis (Thesis). hdl:2066/113615.
  • ^ "Sniffers' genes dictate if sweat smells sweet". New Scientist. 19 September 2007.
  • ^ Steenhuysen, Julie (16 September 2007). "Stinky? It's not his sweat, it's your nose". Reuters.
  • ^ Keller, Andreas; Zhuang, Hanyi; Chi, Qiuyi; Vosshall, Leslie B.; Matsunami, Hiroaki (September 2007). "Genetic variation in a human odorant receptor alters odour perception". Nature. 449 (7161): 468–472. Bibcode:2007Natur.449..468K. doi:10.1038/nature06162. PMID 17873857. S2CID 4417235.
  • ^ Swaminathan, Nikhil (18 September 2007). "The Scent of a Man". Scientific American.
  • ^ Lundstrom, J. N.; Seven, S.; Olsson, M. J.; Schaal, B.; Hummel, T. (1 October 2006). "Olfactory Event-Related Potentials Reflect Individual Differences in Odor Valence Perception". Chemical Senses. 31 (8): 705–711. doi:10.1093/chemse/bjl012. PMID 16844768.
  • ^ Birchall, Annabelle (25 August 1990). "A whiff of happiness: Can smelling a molecule contained in human sweat ease anxiety and stress? Some scientists think so, and argue that 'osmotherapy' may also help people to slim or stop smoking". New Scientist.
  • ^ Graham, Sarah (23 October 2002). "Nostrils Share Information for Recognizing Scents". Scientific American.
  • ^ Kirk-Smith, M.D.; Booth, D.A. (1980). "Effect of androstenone on choice of location in others' presence". In van der Starre, H (ed.). Proceedings of the 7th International Symposium on Olfaction and Taste (ISOT VII) and of the 4th Congress of the European Chemoreception Research Organization (ECRO IV): joint meeting held at 'de Leeuwenhorst' Congress Centre, Noordwijkerhout, the Netherlands, 22nd-25th July, 1980. IRL Press. pp. 397–400. ISBN 978-0-904147-20-9. OCLC 63367504.{{cite book}}: CS1 maint: date and year (link)
  • ^ Araneda, Ricardo C.; Firestein, Stuart (1 January 2004). "The scents of androstenone in humans". The Journal of Physiology. 554 (1): 1. doi:10.1113/jphysiol.2003.057075. PMC 1664751. PMID 14678483.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Androstenone&oldid=1217132562"

    Categories: 
    Androstanes
    Human pheromones
    Mammalian pheromones
    Neurosteroids
    Hidden categories: 
    CS1 maint: date and year
    Use dmy dates from November 2023
    Articles without KEGG source
    Articles with changed EBI identifier
    ECHA InfoCard ID from Wikidata
    Articles containing unverified chemical infoboxes
    Chembox image size set
    Articles with short description
    Short description matches Wikidata
    All articles with unsourced statements
    Articles with unsourced statements from September 2016
    Articles with unsourced statements from April 2021
    All articles lacking reliable references
    Articles lacking reliable references from February 2023
    Wikipedia articles needing clarification from February 2023
    All accuracy disputes
    Articles with disputed statements from February 2023
    Articles with unsourced statements from March 2014
    Articles with unsourced statements from September 2023
    Articles with disputed statements from September 2023
    Articles with unsourced statements from November 2023
     



    This page was last edited on 4 April 2024, at 01:06 (UTC).

    Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.



    Privacy policy

    About Wikipedia

    Disclaimers

    Contact Wikipedia

    Code of Conduct

    Developers

    Statistics

    Cookie statement

    Mobile view



    Wikimedia Foundation
    Powered by MediaWiki