(1S,2S,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-13-en-5-one

• ChemBase ID: 125860
• Molecular Formular: C19H28O
• Molecular Mass: 272.42502
• Monoisotopic Mass: 272.21401552
• SMILES: O=C1C[C@@H]2CC[C@@H]3[C@H](CC[C@@]4(C=CC[C@@H]34)C)[C@@]2(C)CC1
• Canonical SMILES: O=C1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC=C2)C)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-13-en-5-one
• IUPAC Traditional name: androstenone
• Synonyms: 5α-Androst-16-en-3-one; Androstenone; 5α-Androst-16-en-3-one; 16-(5α)Androsten-3-one; 3-Keto-5α,16-androstene; Androstenone; 16-(5α)雄甾烯-3-酮; 3-酮-5α,16-雄甾烯; 雄烯酮; 5α-雄甾-16-烯-3-酮

Database IDs

• CAS Number: 18339-16-7
• EC Number: 242-220-1
• MDL Number: MFCD00010479
• PubChem SID: 24902025; 24891306; 162220205
• PubChem CID: 6852393
• CHEBI ID: 37894
• CHEMBL: 1309552
• Chemspider ID: 5254715
• Wikipedia Title: Androstenone

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.280147
• LogD (pH = 7.4): 4.280147
• Log P: 4.280147
• Molar Refractivity: 83.2042 cm^3
• Polarizability: 32.6592 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 140-145 °C(lit.)
• Optical Rotation: [α]20/D +38°, c = 2 in chloroform

Safety Information

• German water hazard class: -; 3

Product Information

• Purity: ≥98%
• Empirical Formula (Hill Notation): C19H28O

DETAILS

Sigma Aldrich - A8008

Application
5α-Androst-16-en-3-one (Androstenone) is a mammalian pheromone found in boar saliva, human sweat, and human urine.