5α-Androstenone

• CAT Number: R060103
• CAS Number: 18339-16-7
• Molecular Formula: C19H28O
• Molecular Weight: 272.432
• Purity: ≥95%
• Storage: -20°C
• 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
• 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
• InChIKey: HFVMLYAGWXSTQI-QYXZOKGRSA-N
• SMILES: CC12CCC3C(C1CC=C2)CCC4C3(CCC(=O)C4)C

5α-Androstenone(CAS 18339-16-7) is a mammalian pheromone released as a volatile chemical cue in boar saliva to facilitate social and sexual interactions. It has been used to prime sexual behavior of sows in estrus for mating or artificial insemination. 5α-androst-16-en-3-one is also found in human sweat and urine and has been used to study receptor-mediated odorant detection and the genetic basis for anosmias.

Reference

1: Andresen O. 5 alpha-androstenone and testosterone in peripheral plasma of the boar during and following copulation. Acta Vet Scand. 1976;17(4):475-87. PubMed PMID: 1015480.
2: Andresen O. 5alpha-androstenone in peripheral plasma of pigs, diurnal variation in boars, effects of intravenous HCG administration and castration. Acta Endocrinol (Copenh). 1975 Feb;78(2):385-91. PubMed PMID: 1172907.
3: Andresen O, Bakke H. 5alpha-androstenone in fat from boars selected for rate of gain and thickness of back fat, and from boars used in artificial insemination service. Acta Vet Scand. 1975;16(4):492-502. PubMed PMID: 1211326.