16-Dehydropregnenolone acetate

Base Information

• Chemical Name: 16-Dehydropregnenolone acetate
• CAS No.: 979-02-2
• Molecular Formula: C23H32O3
• Molecular Weight: 356.505
• European Community (EC) Number: 213-558-7
• NSC Number: 37741
• UNII: 832VMW7ZGC
• DSSTox Substance ID: DTXSID8057857
• Nikkaji Number: J22.711K
• Wikipedia: 16-Dehydropregnenolone_acetate
• Wikidata: Q27115857
• Metabolomics Workbench ID: 110521
• ChEMBL ID: CHEMBL1761683
• Mol file: 979-02-2.mol

Synonyms:20-oxopregna-5,16-dien-3-β-yl acetate;16-Denyprasterone Acetate;16-Denyprasterone Acetate(16-DPA);16-Dehydropregnenolone Acetate(16-DPA);16 Dehydropregneninolone, Acetate;Pregna-5,16-dien-20-one, 3- (acetyloxy)-, (3.beta.)-;20-Oxopregna-5, 16-dien-3.beta.-yl acetate;Dehydropregnenolone acetate;Pregna-5,16-dien-20-one, 3-beta-hydroxy-, acetate;Pregna-5,16-dien-20-one, 3beta-hydroxy-, acetate (8CI);4-08-00-01125 (Beilstein Handbook Reference);16,17-Didehydropregnenolone acetate;3.beta.-Acetoxypregna-5,16-dien-20-one;20-Oxopregna-5,16-dien-3-beta-yl acetate;(3-beta)-3-(Acetyloxy)pregna-5,16-dien-20-one;Pregna-5,16-dien-20-one, 3.beta.-hydroxy-, acetate;

Chemical Property of 16-Dehydropregnenolone acetate

Chemical Property:

• Appearance/Colour: White to almost white crystalline powder
• Vapor Pressure: 8.38E-09mmHg at 25°C
• Melting Point: 170-178 °C
• Refractive Index: 1.546
• Boiling Point: 464.4 °C at 760mmHg
• Flash Point: 200.1 °C
• PSA: 43.37000
• Density: 1.11g/cm³
• LogP: 5.00620
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 356.23514488
• Heavy Atom Count: 26
• Complexity: 702

Purity/Quality:

99.00% ^*data from raw suppliers

16-Dehydropregnenolone acetate ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)C)C)C
• Isomeric SMILES: CC(=O)C1=CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OC(=O)C)C)C
• General Description: 16-Dehydropregnenolone acetate (16-DPA) is a steroidal compound synthesized from diosgenin, characterized by a pregnane skeleton with a 5,16-diene structure and a 3β-acetoxy group. Its crystal structure reveals orthorhombic symmetry with distinct ring conformations: rings A and C in chair, ring B in half-chair, and ring D in envelope, with trans-fused B/C and C/D junctions. The synthesis has been optimized through greener methods, avoiding hazardous reagents like chromium or MnO₂, and employing catalytic KMnO₄ with NaIO₄ for oxidation, reducing waste and improving efficiency. 16-Dehydropregnenolone acetate serves as a key intermediate in steroid drug production.

Technology Process of 16-Dehydropregnenolone acetate

There total 69 articles about 16-Dehydropregnenolone acetate 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: 98.0%

3β-Hydroxy-Δ5.16-pregnadienon-(20) (1162-53-4,104010-41-5) + acetic acid (64-19-7,77671-22-8) → 3β-acetoxy-pregna-5,16-dien-20-one (979-02-2,38521-84-5,95720-31-3,122405-61-2)

Guidance literature:

With chloro-trimethyl-silane; at 20 ℃;

Reference yield: 95.0%

3β-acetoxy-20-hydroxyiminopregna-5,16-diene (23549-24-8,23549-26-0,2174-13-2) → 16-dehydropregnenolone acetate (979-02-2)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; water; for 0.333333h;

DOI:10.1016/S0040-4039(98)00392-X

Reference yield: 80.0%

3β,17α-diacetoxypregn-5-en-20-one (3517-38-2) → 16-dehydropregnenolone acetate (979-02-2)

Guidance literature:

upstream raw materials:

3β-Hydroxy-Δ^5.16-pregnadienon-(20)

acetic acid

3β-acetoxy-17-bromo-pregn-5-en-20-one

Pregna-5,16-diene-20-yne-3β-ol 3-Acetate

Downstream raw materials:

3β-Hydroxy-Δ^5.16-pregnadienon-(20)

Acetic acid 17-acetyl-10,13-dimethyl-16-phenylsulfanyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Δ¹⁶-5-α-Pregnenolon

3β-acetoxy-pregn-5-en-20-one

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