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

• ChemBase ID: 1657
• Molecular Formular: C19H30O
• Molecular Mass: 274.4409
• Monoisotopic Mass: 274.22966558
• SMILES: O[C@@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC=C2)C)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC=C2)C)C
• InChI: InChI=1S/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/m0/s1
• InChIKey: KRVXMNNRSSQZJP-PHFHYRSDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-13-en-5-ol; (1S,2S,5R,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol
• IUPAC Traditional name: androstenol
• Synonyms: 5α-Androst-16-en-3α-ol; 16,17-Androstene-3-Ol; 16-(5α)Androsten-3α-ol; 3α-Hydroxy-5α-androst-16-ene; 16-(5α)雄甾烯-3α-醇; 3α-羟基-5α-雄甾-16-烯; 5α-雄甾-16-烯-3α-醇

Database IDs

• CAS Number: 7148-51-8; 1153-51-1
• EC Number: 214-573-1
• MDL Number: MFCD00051224
• PubChem SID: 46505452; 160965114; 24891288; 24902057
• PubChem CID: 101989

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.296396
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.072646
• LogD (pH = 7.4): 4.072646
• Log P: 4.072646
• Molar Refractivity: 84.2323 cm^3
• Polarizability: 33.20933 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 5.13
• LOG S: -5.89
• Solubility (Water): 3.55e-04 g/l

PROPERTIES

Physical Property

• Melting Point: 140-141 °C(lit.)
• Optical Rotation: [α]20/D +19°, c = 1 in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥98%
• Empirical Formula (Hill Notation): C19H30O

DETAILS

DrugBank - DB01889

Drug information: experimental

Sigma Aldrich - A7883

Biochem/physiol Actions
5alpha-androst-16-en-3alpha-ol (androstenol), is an androgen believed to act as a pheromone.
Application
5-α-androst-16-en-3-α-ol (androstenol) is an androgen believed to act as a pheromone. Androstenol has been used in a study to develop a combined gas chromatography/thermal conversion/isotope ratio mass spectrometry (GC/TC/IRMS) method for D/H ratio determination of endogenous urinary steroids.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A7883.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.