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
• Uses: 16-Dehydropregnenolone Acetate is the dehydration product of Pregnenolone Acetate (). 16-Dehydropregnenolone Acetate is used in the preparation of pregnane derivatives and its glycosides as potential anticancer agents.

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-acetoxy-pregn-5-en-20-one

16-dehydropregnenolone

3β,9α-dihydroxypregna-5,16-dien-20-one

3β,7α,9α-trihydroxypregna-5,16-dien-20-one

Refernces

• 1、 Malanina,G.G. et al.. "". . . Retrieved 1974.
• 2、 Micovic,Ivanovic,Piatak. "Simplified preparation of 16-dehydropregnenolone acetate". . p. 591 - 592. Retrieved 1990.
• 3、 Baruah, Diganta,Das, Ram Nath,Konwar, Dilip. "Facile green synthesis of 16-dehydropregnenolone acetate (16-DPA) from diosgenin". . p. 79 - 84. Retrieved 2016.
• 4、 Mancino, Valentina,Cerra, Bruno,Piccinno, Alessandro,Gioiello, Antimo. "Continuous Flow Synthesis of 16-Dehydropregnenolone Acetate, a Key Synthon for Natural Steroids and Drugs". supporting information. p. 600 - 607. Retrieved 2018/05/14.
• 5、 Jastrzebska, Izabella,Morzycki, Jacek W.. "Some observations on solasodine reactivity". . p. 13 - 17. Retrieved 2017/09/15.