5alpha-Androst-16-en-3-one

Base Information

• Chemical Name: 5alpha-Androst-16-en-3-one
• CAS No.: 18339-16-7
• Molecular Formula: C19H28O
• Molecular Weight: 272.431
• European Community (EC) Number: 242-220-1
• UNII: BWD3D5941J
• DSSTox Substance ID: DTXSID0040965
• Nikkaji Number: J47.318I
• Wikipedia: Androstenone
• Wikidata: Q416745
• NCI Thesaurus Code: C95969
• Metabolomics Workbench ID: 35358
• ChEMBL ID: CHEMBL1309552
• Mol file: 18339-16-7.mol

Synonyms:5 alpha-androst-16-en-3-one;5alpha-androst-16-en-3-one;AEON steroid;androst-16-en-3-one;androst-16-en-3-one, (5beta)-isomer

Chemical Property of 5alpha-Androst-16-en-3-one

Chemical Property:

• Appearance/Colour: white crystals
• Vapor Pressure: 1.02E-05mmHg at 25°C
• Melting Point: 140-145 °C(lit.)
• Refractive Index: 1.529
• Boiling Point: 371.6 °C at 760 mmHg
• Flash Point: 157.7 °C
• PSA: 17.07000
• Density: 1.032 g/cm³
• LogP: 4.76430
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 272.214015512
• Heavy Atom Count: 20
• Complexity: 464

Purity/Quality:

99%, ^*data from raw suppliers

5α-Androstenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CC=C2)CCC4C3(CCC(=O)C4)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CC[C@@H]4[C@@]3(CCC(=O)C4)C
• Uses: 5α-Androst-16-en-3-one 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. 5α-Androst-16-en-3-one has been used: to quantify its concentration in various fat tissues to study its trigeminal percept and implications on the rate of specific anosmiato study the effects of immunocastration on meat quality and sensory properties of pork bellies

Technology Process of 5alpha-Androst-16-en-3-one

There total 17 articles about 5alpha-Androst-16-en-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

17β-methoxycarbonyloxy-5α-androstan-3-one (19291-29-3) → 5α-androst-16-en-3-one (18339-16-7)

Guidance literature:

In toluene; at 480 ℃;

DOI:10.1002/hlca.19830660121

Reference yield: 85.0%

[5,6,7-(2)H3]-3β-hydroxy5α-androst-16-en (1328881-12-4) → 5α-androst-16-en-3-one (18339-16-7)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1002/jlcr.1895

Reference yield: 81.0%

5α-androst-16-en-3β-ol (103615-90-3) → 5α-androst-16-en-3-one (18339-16-7)

Guidance literature:

With pyridine; chromium(VI) oxide; In dichloromethane; at 22 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)82442-X

upstream raw materials:

androstenol

5α-androst-16-en-3β-ol

17β-methoxycarbonyloxy-5α-androstan-3-one

3-oxo-5α-androstan-17α-yl cyclohexanecarboxylate

Downstream raw materials:

5α-androst-16-en-3β-ol

androstenol

androstan-3-one

5α-androstan-3β-ol

Refernces

• 1、 Fischer, Jochen,Elsinghorst, Paul W.,Wuest, Matthias. "Synthesis of deuterium-labeled d3-androstenone and d 3-skatole for boar taint analysis". . p. 591 - 596. Retrieved 2011/12/03.
• 2、 -. "Fragrance compositions and other compositions which contain human pheromones". . . Retrieved 2008/06/13.