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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.038.367
PubChem CID
UNII
  • 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
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
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 YN ?)
Infobox references
Not to be confused with Androsterone, Androstenedione, or 5α-Androst-2-ene-17-one.

Androstenone (5α-androst-16-en-3-one) is a 16-androstene class 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.

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