Digoxigenin

Base Information

• Chemical Name: Digoxigenin
• CAS No.: 1672-46-4
• Molecular Formula: C23H34 O5
• Molecular Weight: 390.52
• European Community (EC) Number: 216-806-2
• UNII: NQ1SX9LNAU
• DSSTox Substance ID: DTXSID6051778
• Nikkaji Number: J7.551E
• Wikipedia: Digoxigenin
• Wikidata: Q420728
• Pharos Ligand ID: 7XRPV22YMSLK
• Metabolomics Workbench ID: 35222
• ChEMBL ID: CHEMBL1153
• Mol file: 1672-46-4.mol

Synonyms:Digoxigenin;Lanadigenin

Chemical Property of Digoxigenin

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 2.4E-16mmHg at 25°C
• Melting Point: 222 °C(lit.)
• Refractive Index: 1.6120 (estimate)
• Boiling Point: 589.4 °C at 760 mmHg
• PKA: 14.44±0.70(Predicted)
• Flash Point: 203 °C
• PSA: 86.99000
• Density: 1.297 g/cm³
• LogP: 2.57510
• Storage Temp.: room temp
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 390.24062418
• Heavy Atom Count: 28
• Complexity: 718

Purity/Quality:

≥98% ^*data from raw suppliers

Digoxigenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CC(C4(C3(CCC4C5=CC(=O)OC5)O)C)O)O
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2C[C@H]([C@]4([C@@]3(CC[C@@H]4C5=CC(=O)OC5)O)C)O)O
• Uses: DIGOXIGENIN is a steroid used as a probe in the detection of different viruses,it is also used as a non-isotopic label for DNA. cardiotonic, positive inotropic activity 'Diagnosis;Mainly used as a non-isotopic label for DNA

Technology Process of Digoxigenin

There total 36 articles about Digoxigenin 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%

digoxin (20830-75-5) → digoxigenin (1672-46-4)

Guidance literature:

With sulfuric acid; In methanol; for 1h; Reflux;

Reference yield: 95.0%

3β-Acetoxy-12β,14-dihydroxy-5β,14β-card-20(22)-enolid (80680-86-0) → digoxigenin (1672-46-4)

Guidance literature:

With hydrogenchloride; for 16h; Ambient temperature;

DOI:10.1002/jlac.198219821203

Reference yield: 7.9%

digoxin (20830-75-5) → C23H32O4 + digoxigenin (1672-46-4)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; Sealed tube;

DOI:10.1021/acs.jnatprod.9b01060

upstream raw materials:

digoxin

beta-Acetyldigoxin

3'''-acetyldigoxin

lanatoside C

Downstream raw materials:

digoxigenin 3β-β-D-glucoside

Refernces

• 1、 Salphati, Laurent,Benet, Leslie Z.. "Metabolism of digoxin and digoxigenin digitoxosides in rat liver microsomes: Involvement of cytochrome P4503A". . p. 171 - 185. Retrieved 1999.
• 2、 Keshk, Sherif,Mostafa,Tawfik,Elshemy. "Biotransformation of extracted digitoxin from Digitalis lanata by Streptomyces". . p. 458 - 462. Retrieved 2011.
• 3、 Welzel,Stein,Milkova. "14beta-Hydroxysteroids. VII. Synthesis of digoxigenin and digitoxigenin from deoxycholic acid". . p. 2119 - 2134. Retrieved 1982.
• 4、 Burdette, Joanna E.,Chen, Xiaozhuo,Cheng, Xiaolin,Heath, Kimberly,Johnson, Michael E.,Kinghorn, A. Douglas,Ren, Jinhong,Ren, Yulin,Ribas, Hennrique T.,Shriwas, Pratik,Wu, Sijin. "Na+/K+-ATPase-Targeted Cytotoxicity of (+)-Digoxin and Several Semisynthetic Derivatives". . . Retrieved 2020/03/05.