4-Dehydrowithaferin A

Base Information

• Chemical Name: 4-Dehydrowithaferin A
• CAS No.: 6850-30-2
• Molecular Formula: C28H36 O6
• Molecular Weight: 468.58
• DSSTox Substance ID: DTXSID00988157
• Wikidata: Q82976615
• Metabolomics Workbench ID: 126488
• ChEMBL ID: CHEMBL2047415
• Mol file: 6850-30-2.mol

Synonyms:4-dehydrowithaferin A;4-DWA

Chemical Property of 4-Dehydrowithaferin A

Chemical Property:

• Vapor Pressure: 2.94E-20mmHg at 25°C
• Boiling Point: 660.5°C at 760 mmHg
• Flash Point: 219.9°C
• PSA: 93.20000
• Density: 1.28g/cm³
• LogP: 3.56110
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 468.25118886
• Heavy Atom Count: 34
• Complexity: 1040

Purity/Quality:

99%min ^*data from raw suppliers

4-oxo Withaferin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6=O)C)O5)C)CO
• Isomeric SMILES: CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=CC6=O)C)O5)C)CO

Technology Process of 4-Dehydrowithaferin A

There total 4 articles about 4-Dehydrowithaferin A 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: 99.0%

27-O-(tert-butyldimethylsilyl)-4-dehydroxy-4-oxo-withaferin A (1214886-31-3) → 4-dehydroxy-4-oxowithaferin A (6850-30-2)

Guidance literature:

With Dowex 50WX₈-200; In acetone; at 20 ℃; for 24h;

DOI:10.1016/j.ejmech.2012.05.032

Reference yield: 62.0%

withaferin-A (5119-48-2) → 4-dehydroxy-4-oxowithaferin A (6850-30-2)

Guidance literature:

With manganese(IV) oxide; In chloroform; ethyl acetate; at 25 ℃; for 16h;

Reference yield:

withaferin A 27-tert-butyldimethylsilyl ether (1392820-18-6) → 4-dehydroxy-4-oxowithaferin A (6850-30-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; chromium(VI) oxide / dichloromethane / 6 h / 20 °C

2: Dowex 50WX₈-200 / acetone / 24 h / 20 °C

With pyridine; chromium(VI) oxide; In dichloromethane; acetone;

DOI:10.1016/j.ejmech.2012.05.032

upstream raw materials:

withaferin-A

withaferin A 27-tert-butyldimethylsilyl ether

27-O-(tert-butyldimethylsilyl)-4-dehydroxy-4-oxo-withaferin A

Refernces

• 1、 Perestelo, Nayra R.,Llanos, Gabriel G.,Reyes, Carolina P.,Amesty, Angel,Sooda, Kartheek,Afshinjavid, Saeed,Jiménez, Ignacio A.,Javid, Farideh,Bazzocchi, Isabel L.. "Expanding the Chemical Space of Withaferin A by Incorporating Silicon to Improve Its Clinical Potential on Human Ovarian Carcinoma Cells". . p. 4571 - 4585. Retrieved 2019.
• 2、 -. "WITHAFERIN A ANALOGS AND USES THEREOF". Page/Page column 71. . Retrieved 2010/04/06.