Androstenone

Chembox new
ImageFile=Androstenone.pngImageSize=200px
IUPACName= (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
OtherNames=5α-Androst-16-en-4-one
Section1= Chembox Identifiers
CASNo=18339-16-7
PubChem=6852393
SMILES=CC12CCC3C(C1CC=C2)CCC4C3(CCC(=O)C4)C
Section2= Chembox Properties
Formula=C₁₉H₂₈O
MolarMass=272.42502
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Section3= Chembox Hazards
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Androstenone (5α-androst-16-en-4-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 who is in heat, results in the female assuming the mating stance. Androstenone is the active ingredient in BoarTaint, a commercial product sold to pig farmers to test sows for timing of artificial insemination.

Properties

Depending upon who is doing the smelling, it is reported to be an unpleasant, sweaty, urinous smell, a woody smell, or even a pleasant floral smell. [cite web | coauthors = Wysocki CJ, Dorries KM, Beauchamp GK. | title = Ability to perceive androstenone can be acquired by ostensibly anosmic people. | publisher = Proc Natl Acad Sci U S A. | date = 1989 Oct | url = http://www.ncbi.nlm.nih.gov/sites/entrez?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=2813372&query_hl=4&itool=pubmed_docsum | accessdate = 2007-09-25 ] [cite web | title = Sniffers' genes dictate if sweat smells sweet | publisher = New Scientist | date = 2007-09-22 | url = http://www.newscientist.com/channel/being-human/mg19526225.600-sniffers-genes-dictate-if-sweat-smells-sweet.html | accessdate = 2007-09-25 ] [cite web | last = Steenhuysen | first = Julie | title = Stinky? It's not his sweat, it's your nose | publisher = Scientific American | date = 2007-09-16 | url = http://www.sciam.com/article.cfm?alias=stinky-its-not-his-sweat | accessdate = 2007-09-25 ] The differences in perceived odor can be accounted for by the genetic differences in the OR7D4 receptor which detects the chemical. People who possess 2 proper genes for OR7D4 tend to describe the odor for the steroid as likable to urine. Those with only 1 gene typically described the odor as weak or were not able to detect it. Those with mutated copies of the gene described the odor as pleasant or sweet. [cite web | last = Swaminathan | first = Nikhil | title = The Scent of a Man | publisher = Scientific American | date = 2007-09-18 | url = http://www.sciam.com/article.cfm?articleID=19CCCAFF-E7F2-99DF-394B61DF5ECC42B3&sc=I100322 | accessdate = 2007-09-25 ]

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. [cite web | last = Lundström | first = Johan N. | coauthors = Suzi Seven, Mats J. Olsson, Benoist Schaal and Thomas Hummel | title = Olfactory Event-Related Potentials Reflect Individual Differences in Odor Valence Perception | publisher = Oxford Journal | date = 2006-07-14 | url = http://chemse.oxfordjournals.org/cgi/content/abstract/31/8/705 | accessdate = 2007-09-25 ] However, the range of abilities to detect the odor vary greatly. It has been proven that the odor can be detected by people in levels in a range of 0.2 parts per billion and 0.2 parts in 100 million. [cite web | last = Birchall | first = Annabelle | title = 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 | publisher = New Scientist | date = 1990-08-25 | url = 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 | accessdate = 2007-09-25] Several groups report, however, that some individuals who initially cannot smell androstenone can learn to smell it by repeated exposures to it. [cite web | last = Graham | first = Sarah | title = Nostrils Share Information for Recognizing Scents | publisher = Scientific American | date = 2002-10-23 | url = http://www.sciam.com/article.cfm?articleID=0004E938-FE5B-1DB6-94E2809EC5880108&sc=I100322 | accessdate = 2007-09-25 ]

Detectability As a Pheromone

In humans androstenone also has been suggested to be a pheromone, however, scientific data to support these claims are scant. The vomeronasal organ is an auxiliary olfactory sense organ that is 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 mammalians needed to detect pheromones beyond a smell. Humans also lack the genetic ability to produce these sensory cells actively. [cite web | last = Spinney | first = Laura | title = Five things humans no longer need | publisher = New Scientist | url = http://www.newscientist.com/article/dn13927-five-things-humans-no-longer-need.html | accessdate = 2008-05-20] There is also a specific anosmia to the odor in some humans; they are unable to smell specific odors but have besides that a normal sense of smell. However, this should by no means be seen as indicative for being labeled as a pheromone, as it is true of over 80 olfactory compounds. [cite web | coauthors = Ricardo C. Araneda and Stuart Firestein | title = The scents of androstenone in humans | publisher = The Journal of Physiology | url = http://jp.physoc.org/cgi/content/full/554/1/1 | accessdate = 2007-09-25] There is more promising data for a closely related compound, androstadienone.

Commercial Use

Some commercially-available substances are advertised using claims that the products contain human sexual pheromones and can act as an aphrodisiac. However these often lack credibility due to an excessive marketing of pheromones by unsolicited e-mail.

See also

McClintock effect
Androstadienone

External links

*http://www.youramazingbrain.org.uk/supersenses/pheromones.htm

References