Androstenone 5α-androst-16-en-3-one is a steroidal pheromone It is found in boar's saliva, celery cytoplasm, and truffle fungus 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 Biosynthesis
- 2 Properties
- 21 Detectability as a pheromone
- 22 Commercial use
- 3 See also
- 4 References
Androstenone is synthesized from androstadienone by 5α-reductase, and can be converted into 3α-androstenol or 3β-androstenol by 3-ketosteroid reductase
Depending upon the subject, it is reported to be an unpleasant, sweaty, urinous smell, a woody smell, or even a pleasant floral smell
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 The OR7D4 receptor has two non-synonymous single nucleotide polymorphisms, 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'
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 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 02 parts per billion to 02 parts in 100 million Several groups report, however, that some individuals who initially cannot smell androstenone can learn to smell it by repeated exposures to it
Detectability as a pheromone
In humans, androstenone also has been suggested to be a pheromone; however, there is little scientific data to support this claim 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
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
To animals, the smell of androstenone can act as a social sign of dominance, or it can be a way of attracting a mate
Some commercially available products are advertised using claims that they contain human sexual pheromones, including androstenone, and that they can act as an aphrodisiac These products are the subject of marketing by mass unsolicited e-mail
- List of neurosteroids § Pheromones and pherines
- ^ Pierce, J D, J; Cohen, A B; Ulrich, P M 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:101037/0735-7036118114 PMID 15008668
- ^ Dorries, K M; Adkins-Regan, E; Halpern, B 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: 53 doi:101159/000112981
- ^ a b Wysocki, C J; Dorries, K M; Beauchamp, G K 1989 "Ability to perceive androstenone can be acquired by ostensibly anosmic people" Proceedings of the National Academy of Sciences of the United States of America 86 20: 7976–7978 doi:101073/pnas86207976 PMC 298195 PMID 2813372
- ^ a b Wysocki, C J; Beauchamp, G K 1984 "Ability to smell androstenone is genetically determined" Proceedings of the National Academy of Sciences of the United States of America 81 15: 4899–4902 doi:101073/pnas81154899 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 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:101016/S0309-17409900105-9 PMID 22060698
- ^ Joseph Johannes; Agnes Maria Weusten 1989 Biochemical pathways in human testicular steroidogenesis PDF Pressa Trajectina
- ^ "Sniffers' genes dictate if sweat smells sweet" New Scientist 2007-09-22 Retrieved 2007-09-25
- ^ Steenhuysen, Julie 2007-09-16 "Stinky It's not his sweat, it's your nose" Chicago Reuters Archived from the original on July 2, 2016 Retrieved 2007-09-25
- ^ http://webebscohostcom/src/pdfvid=9&hid=13&sid=802c875e-0200-4687-8e68-25dd33572ceb%40sessionmgr10
- ^ "Archived copy" Archived from the original on 2010-10-17 Retrieved 2009-12-04
- ^ Swaminathan, Nikhil 2007-09-18 "The Scent of a Man" Scientific American Retrieved 2007-09-25
- ^ Lundstrom, J N; Seven, S; Olsson, M J; Schaal, B; Hummel, T 2006 "Olfactory Event-Related Potentials Reflect Individual Differences in Odor Valence Perception" Chemical Senses 31 8: 705–711 doi:101093/chemse/bjl012 PMID 16844768
- ^ 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 Retrieved 2007-09-25
- ^ Graham, Sarah 2002-10-23 "Nostrils Share Information for Recognizing Scents" Scientific American Retrieved 2007-09-25
- ^ Kirk-Smith, MD, and Booth, DA 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, pp397-400
- ^ Araneda, R C; Firestein, S 2003 "The scents of androstenone in humans" The Journal of Physiology 554 Pt 1: 1 doi:101113/jphysiol2003057075 PMC 1664751 PMID 14678483
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