Digitoxigenin

Base Information

• Chemical Name: Digitoxigenin
• CAS No.: 143-62-4
• Molecular Formula: C23H34 O4
• Molecular Weight: 374.521
• European Community (EC) Number: 205-603-4
• NSC Number: 407806
• UNII: S63WOD4VOL
• DSSTox Substance ID: DTXSID80162276
• Nikkaji Number: J5.822J
• Wikipedia: Digitoxigenin
• Wikidata: Q411469
• Pharos Ligand ID: QP1AQPQHXGGF
• Metabolomics Workbench ID: 35215
• ChEMBL ID: CHEMBL1453
• Mol file: 143-62-4.mol

Synonyms:Digitoxigenin;Uzarigenin

Chemical Property of Digitoxigenin

Chemical Property:

• Vapor Pressure: 2.36E-14mmHg at 25°C
• Melting Point: 253-255oC (dec.)(lit.)
• Refractive Index: 1.4433 (estimate)
• Boiling Point: 549.3°C at 760 mmHg
• PKA: 14.93±0.70(Predicted)
• Flash Point: 188.1°C
• PSA: 66.76000
• Density: 1.231g/cm³
• LogP: 3.60430
• Water Solubility.: 11.24mg/L(30 oC)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 374.24570956
• Heavy Atom Count: 27
• Complexity: 686

Purity/Quality:

≥85% ^*data from raw suppliers

Digitoxigenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=CC(=O)OC5)O)C)O
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@@]3(CC[C@@H]4C5=CC(=O)OC5)O)C)O
• Recent ClinicalTrials: A Feasibility Trial of Nivolumab With Neoadjuvant CF or DCF Therapy for Locally Advanced Esophageal Carcinoma
• Uses: Cardiotonic;Na+ K+ ATPase inhibitor

Technology Process of Digitoxigenin

There total 85 articles about Digitoxigenin 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: 97.0%

4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one (182573-64-4) → (+)-digitoxigenin (143-62-4)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 24h; Ambient temperature;

DOI:10.1021/ja962163m

Reference yield: 95.0%

digitoxin (71-63-6) → (+)-digitoxigenin (143-62-4)

Guidance literature:

With sulfuric acid; In methanol; at 0 ℃; for 5h;

DOI:10.1021/jo201850z

Reference yield: 85.0%

14-hydroxy-3β-tetrahydropyranyloxy-5β-card-20(22)-enolide (809-98-3) → (+)-digitoxigenin (143-62-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; at 60 ℃; for 1h;

upstream raw materials:

3β-O-(β-D-diginosyl)-14-hydroxy-5β,14β-card-20(22)-enolide

digitoxin

3β-O-(β-D-digitalosyl)-14-hydroxy-5β,14β-card-20(22)-enolide

digitoxin

Downstream raw materials:

3-epidigitoxigenin

digitoxigenin myristate

digitoxigenin palmitate

digitoxigenin stearate

Refernces

• 1、 Dinu, Cerasela Zoica,Dong, Chenbo,Eldawud, Reem,Gupta, Neha,O'Doherty, George,Rojanasakul, Yon,Stueckle, Todd A.,Wagner, Alixandra. "Potential antitumor activity of digitoxin and user-designed analog administered to human lung cancer cells". . . Retrieved 2020.
• 2、 Makarevich. "Cardiac glycosides of Cheiranthus allioni VIII". . p. 671 - 672. Retrieved 1972.
• 3、 Tamm,Rosselet. "-". . p. 1309,1313. Retrieved 1953.
• 4、 Almirante,Cerri. "Synthesis of digitoxigenin from 3β-[(tert-butyldimethylsilyl)oxy]-17α-iodo-5β-androstan-14β-ol via 17β stereoselective free-radical introduction of γ-butyrolactone moiety". . p. 3402 - 3404. Retrieved 1997.
• 5、 Stuhlemmer,Kreis. "Does the malonyl-coenzyme A:21-hydroxypregnane 21-hydroxy-malonyltransferase catalyze the first step in the formation of the butenolide ring of cardenolides?". . p. 2221 - 2224. Retrieved 1996.
• 6、 Meister et al.. "". . p. 1659,1665. Retrieved 1970.
• 7、 -. "GLYCOSYLATED CARDIOTONIC STEROIDS". Paragraph 0188. . Retrieved 2014/12/12.
• 8、 Bose, Chandana. "Digitoxigenin-3-O-β-D-glucopyranoside from the roots of Sapium sebiferum". experimental part. p. 1252 - 1254. Retrieved 2012/01/13.