Androstenone

Androstenone
IUPAC name (5S,8R,9S,10S,13R,14S)-10, 13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15- dodecahydrocyclopenta[a]phenanthren-3-one
Other names 5α-Androst-16-en-3-one
Identifiers
CAS number	18339-16-7 Y
PubChem	6852393
ChemSpider	5254715 Y
ChEBI	CHEBI:37894 Y
ChEMBL	CHEMBL1309552 N
Jmol-3D images	Image 1
SMILES O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@@]1(/C=C\C[C@H]12)C)[C@@]3(C)CC4
InChI 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 Y Key: HFVMLYAGWXSTQI-QYXZOKGRSA-N Y 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
Properties
Molecular formula	C19H28O
Molar mass	272.42502
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Androstenone (5α-androst-16-en-3-one) is a steroid found in both male and female sweat and urine. It is also found in boar's saliva, and in celery cytoplasm. Androstenone was the first mammalian pheromone to be identified. It is found in high concentrations in the saliva of male pigs, and, when sniffed 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.

Properties

Depending upon the subject, it is reported to be an unpleasant, sweaty, urinous smell, a woody smell, or even a pleasant floral smell.^[1][2][3]

There are two different genotypes that cause androstenone to smell. 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.^[4] The OR7D4 receptor has two non-synonymous single nucleotide polymorphisms,^[5] 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'. ^[6]

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.^[7] 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.^[8] Several groups report, however, that some individuals who initially cannot smell androstenone can learn to smell it by repeated exposures to it.^[9]

Detectability as a pheromone

In humans, androstenone also has been suggested to be a pheromone; however, scientific data to support these claims are scant.^[10] 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. Humans also lack the genetic ability to produce these sensory cells actively.^[11]

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.^[12] There are more promising data for a closely related compound, androstadienone.

To animals, the smell of androstenone can act as a social sign of dominance,^{[citation needed]} or it can be a way of attracting a mate.^{[citation needed]} This smell, to some animals, has a huge impact on behavioral patterns in the specimen.^[specify]

Commercial use

This section does not cite any references or sources. Please help improve this section by adding citations to reliable sources. Unsourced material may be challenged and removed. (January 2010)

Some commercially available substances are advertised using claims that the products contain human sexual pheromones and can act as an aphrodisiac. These products are the subject of marketing by mass unsolicited e-mail and typically contain deceitful claims.

See also

• Androstadienone
• Androstenol
• Androsterone
• Dehydroepiandrosterone
• Estratetraenol
• McClintock effect

References

1. ^ "Ability to perceive androstenone can be acquired by ostensibly anosmic people.". Proc Natl Acad Sci U S A. 1989 October. http://www.ncbi.nlm.nih.gov/sites/entrez?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=2813372&query_hl=4&itool=pubmed_docsum. Retrieved 2007-09-25. 
2. ^ "Sniffers' genes dictate if sweat smells sweet". New Scientist. 2007-09-22. http://www.newscientist.com/channel/being-human/mg19526225.600-sniffers-genes-dictate-if-sweat-smells-sweet.html. Retrieved 2007-09-25. 
3. ^ Steenhuysen, Julie (2007-09-16). "Stinky? It's not his sweat, it's your nose". Scientific American. http://www.sciam.com/article.cfm?alias=stinky-its-not-his-sweat. Retrieved 2007-09-25. ^{[dead link]}
4. ^ ^{[dead link]} http://web.ebscohost.com/src/pdf?vid=9&hid=13&sid=802c875e-0200-4687-8e68-25dd33572ceb%40sessionmgr10
5. ^ http://newswire.rockefeller.edu/?id=660&page=engine
6. ^ Swaminathan, Nikhil (2007-09-18). "The Scent of a Man". Scientific American. http://www.sciam.com/article.cfm?articleID=19CCCAFF-E7F2-99DF-394B61DF5ECC42B3&sc=I100322. Retrieved 2007-09-25. 
7. ^ Lundström, Johan N.; Suzi Seven, Mats J. Olsson, Benoist Schaal and Thomas Hummel (2006-07-14). "Olfactory Event-Related Potentials Reflect Individual Differences in Odor Valence Perception". Chemical senses 31 (8): 705–11. doi:10.1093/chemse/bjl012. PMID 16844768. http://chemse.oxfordjournals.org/cgi/content/abstract/31/8/705. Retrieved 2007-09-25. 
8. ^ Birchall, Annabelle (1990-08-25). "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. http://www.newscientist.com/article/mg12717314.700-a-whiff-of-happiness-can-smelling-a-molecule-contained-inhuman-sweat-ease-anxiety-and-stress-some-scientists-think-so-and-arguethat-osmotherapy-may-also-help-people-to-slim-or-stop-smoking-.html. Retrieved 2007-09-25. 
9. ^ Graham, Sarah (2002-10-23). "Nostrils Share Information for Recognizing Scents". Scientific American. http://www.sciam.com/article.cfm?articleID=0004E938-FE5B-1DB6-94E2809EC5880108&sc=I100322. Retrieved 2007-09-25. 
10. ^ Kirk-Smith, M.D., and Booth, D.A. (1980) "Effect of androstenone on choice of location in others' presence". In H. van der Starre (Ed.), Olfaction and Taste VII, London: Information Retrieval Ltd., pp.397-400.
11. ^ Spinney, Laura. "Five things humans no longer need". New Scientist. http://www.newscientist.com/article/dn13927-five-things-humans-no-longer-need.html. Retrieved 2008-05-20. 
12. ^ Araneda, RC; Ricardo C. Araneda and Stuart Firestein (2004). "The scents of androstenone in humans". The Journal of physiology 554 (Pt 1): 1. doi:10.1113/jphysiol.2003.057075. PMC 1664751. PMID 14678483. http://jp.physoc.org/cgi/content/full/554/1/1. Retrieved 2007-09-25. 

External links

• Pheromones and smells, youramazingbrain.org.uk