Ouabagenin

Base Information

• Chemical Name: Ouabagenin
• CAS No.: 508-52-1
• Molecular Formula: C23H34 O8
• Molecular Weight: 438.51
• European Community (EC) Number: 637-151-2
• UNII: R2692W2T67
• ChEMBL ID: CHEMBL2068926
• DSSTox Substance ID: DTXSID901026559
• Metabolomics Workbench ID: 65400
• Nikkaji Number: J6.238C
• Wikidata: Q1724241
• Mol file: 508-52-1.mol

Synonyms:1 beta,3 beta,5,11 alpha,14,19- hexahydroxy-5 beta-card-20(22)-enolide;g-strophanthidin;ouabagenin

Chemical Property of Ouabagenin

Chemical Property:

• Vapor Pressure: 1.51E-23mmHg at 25°C
• Melting Point: 250-256℃
• Boiling Point: 714°Cat760mmHg
• Flash Point: 246.9°C
• PSA: 147.68000
• Density: 1.52g/cm³
• LogP: -0.36680
• Storage Temp.: 2-8°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 438.22536804
• Heavy Atom Count: 31
• Complexity: 813

Purity/Quality:

95%-98% ^*data from raw suppliers

OUABAGENIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 23-28-33
• Safety Statements: 45

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CC(C3C(C1(CCC2C4=CC(=O)OC4)O)CCC5(C3(C(CC(C5)O)O)CO)O)O
• Isomeric SMILES: C[C@]12C[C@H]([C@H]3[C@H]([C@]1(CC[C@@H]2C4=CC(=O)OC4)O)CC[C@]5([C@@]3([C@@H](C[C@@H](C5)O)O)CO)O)O

Technology Process of Ouabagenin

There total 61 articles about Ouabagenin 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: 92.0%

C50H98O8Si5 → ouabagenin (508-52-1)

Guidance literature:

With hydrogenchloride; methanol; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jacs.8b12870

Reference yield: 90.0%

C28H41BO8 (1418284-06-6) → ouabagenin (508-52-1)

Guidance literature:

With hydrogenchloride; In methanol; at 23 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ja512022r

Reference yield: 88.0%

4-((3R,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-5,11,12a,14b-tetrahydroxy-3a,8,8-trimethylhexadecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-3-yl)furan-2(5H)-one (1178-61-6) → ouabagenin (508-52-1)

Guidance literature:

With hydrogenchloride; In methanol; at 50 ℃; for 4h;

DOI:10.1002/anie.200704959

upstream raw materials:

1,19-acetonide-3-(tert-butyldimethylsiloxy)ouabagenin

ouabain

4-((3R,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-5,11,12a,14b-tetrahydroxy-3a,8,8-trimethylhexadecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-3-yl)furan-2(5H)-one

C₃₇H₄₆O₁₃

Downstream raw materials:

C₅₅H₆₂O₁₆

Refernces

• 1、 Overman, Larry E.,Rucker, Paul V.. "Investigations directed at the total synthesis of ouabain. Lessons learned from degradation studies". . p. 1297 - 1314. Retrieved 2000.
• 2、 Khatri, Hem Raj,Bhattarai, Bijay,Kaplan, Will,Li, Zhongzheng,Curtis Long, Marcus John,Aye, Yimon,Nagorny, Pavel. "Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation". . p. 4849 - 4860. Retrieved 2019/03/26.
• 3、 Renata, Hans,Zhou, Qianghui,Dünstl, Georg,Felding, Jakob,Merchant, Rohan R.,Yeh, Chien-Hung,Baran, Phil S.. "Development of a concise synthesis of ouabagenin and hydroxylated corticosteroid analogues". . p. 1330 - 1340. Retrieved 2015/02/19.