Androstenone

Androstenone
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	18339-16-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:37894 ;
ChEMBL	ChEMBL1309552 ;
ChemSpider	5254715 ;
ECHA InfoCard	100.038.367
PubChem CID	6852393;
UNII	BWD3D5941J ;
CompTox Dashboard (EPA)	DTXSID0040965 ;
	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 Key: HFVMLYAGWXSTQI-QYXZOKGRSA-N ; 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;
	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;
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). verify (what is ?) 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]

^ 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.
^ 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.
^ 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.

[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.

[2] 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.

[Wysocki_et_al_1989-3] 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.

[Wysocki_&_Beauchamp_1984-4] 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.

[5] 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.

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