Digitalinum verum

Base Information

• Chemical Name: Digitalinum verum
• CAS No.: 71-63-6
• Molecular Formula: C41H64O13
• Molecular Weight: 764.951
• Hs Code.: 2938900000
• NSC Number: 7529
• Wikidata: Q104391766
• Mol file: 71-63-6.mol

Synonyms:AWD, Digitoxin;Bürger, Digitoxin;Coramedan;Didier, Digitoxin;Digimed;Digimerck;Digitaline Nativelle;Digitoxin;Digitoxin AWD;Digitoxin Bürger;Digitoxin Didier;Digitoxin Philo;Digitoxin-Philo;Digophton;Nativelle, Digitaline

Chemical Property of Digitalinum verum

Chemical Property:

• Appearance/Colour: odorless white or pale buff microcrystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 240 °C
• Refractive Index: 17 ° (C=2, CHCl3)
• Boiling Point: 902.3 °C at 760 mmHg
• PKA: 13.50±0.70(Predicted)
• Flash Point: 269.5 °C
• PSA: 182.83000
• Density: 1.33 g/cm³
• LogP: 3.24730
• Storage Temp.: Dark Room
• Solubility.: chloroform: soluble
• Water Solubility.: 3.9mg/L(25 oC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 7
• Exact Mass: 764.43469209
• Heavy Atom Count: 54
• Complexity: 1410

Purity/Quality:

98%,99%, ^*data from raw suppliers

Digitoxin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,F
• Statements: 23/25-33-39/23/24/25-23/24/25-11
• Safety Statements: 45-36/37-16

MSDS Files:

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CCC7(C6(CCC7C8=CC(=O)OC8)O)C)C)C)C)O)O
• Description: Digitoxin is the most powerful and reliable of the glucosides which have been extracted from digitalis leave. It is a cardiac glycoside (CG). It is a cardiotonic drug, which exhibits cardiac and anti-cancer properties. Digitoxin inhibits nuclear factor kappa B (NF-κB) signaling. It is used to treat congestive heart failure and cardiac arrhythmia. Digitoxin prevents microtubule formation. Digitoxin is a cardiac glycoside that has been found in Digitalis and has diverse biological activities. It inhibits human recombinant α1β1, α2β2, and α3β1 subunit-containing Na+/K+-ATPases with Ki values of 250, 63, and 136 nM, respectively. Digitoxin inhibits the human-ether-a-go-go (hERG) potassium channel, also known as Kv11.1, in HEK293 cells expressing hERG (IC50 = 11.1 nM). It enhances developed tension and contractile force in electrically stimulated isolated guinea pig left atrial muscle when used at concentrations of 0.2 and 0.4 μM, respectively. Dietary administration of digitoxin (~1 mg/kg per day) attenuates congestive heart failure and reduces myocardial hypertrophy in a rat model of myocardial infarction induced by coronary artery ligation. Digitoxin is also cytotoxic to a panel of 10 human cancer cell lines, including myeloma, lymphoma, and leukemia cancer cells, with IC50 values ranging from 12 to 76 nM. Formulations containing digitoxin have previously been used in the treatment of congestive heart failure and cardiac arrhythmias.
• Uses: Digitoxin is used for chronic cardiac insufficiency, tachyarrhythmia form of atrial fibrillation, paroxysmal ciliary arrhythmia, and paroxysmal supraventricular tachycaria. Digitoxin has been used as a labeled drugs for binding sites on human serum albumin (HSA). It has also been used to test its anti-transmissible gastroenteritis virus (TGEV) activity.
• Indications: Digitoxin (Dig) is an FDA approved drug for the treatment of cardiac disease.Digitoxin is used for the treatment of heart failure, especially in people with impaired kidney function. It is also used to treat certain kinds of heart arrhythmia, such as atrial fibrillation.Digoxin is used to treat heart failure and abnormal heart rhythms (arrhythmias). It also helps the heart work better and control heart rate. Digoxin may be used after a heart attack. This medication comes in various forms: tablet, capsule, or pediatric elixir (liquid). It is available under the brand names Lanoxin, Cardoxin, Digitek, Digox, and Lanoxicaps.
• Therapeutic Function: Cardiotonic, Topical venotonic

Technology Process of Digitalinum verum

There total 49 articles about Digitalinum verum 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: 83.0%

digitoxigen O-[2'',6''-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-O-[3'-O-acetyl-2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside (57292-22-5) → digitoxin (71-63-6)

Guidance literature:

With lithium hydroxide; In methanol; water; at 20 ℃; for 2h;

DOI:10.1021/ol061683b DOI:10.1021/jo062534+

Reference yield: 68.0%

Lanatoside A → digitoxin (71-63-6)

Guidance literature:

With biocellulase; In water; at 37 ℃; for 48h;

DOI:10.1002/ardp.19873200818

Reference yield:

3,4-bis-(tert-butyldimethylsilyl)-1,5-anhydro-2,6-dideoxy-D-ribo-hex-1-enitol (279684-76-3) → digitoxin (71-63-6)

Guidance literature:

Multi-step reaction with 12 steps

1: PPh₃; HBr / toluene / 6 h

2: 99 percent / DIBAL / CH₂Cl₂ / -78 °C

3: 96 percent / DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation

4: Bu₄NF / tetrahydrofuran

5: Et₃N; DMAP / CH₂Cl₂

6: 71 percent / PPh₃; HBr / toluene / 6 h

7: 98 percent / DIBAL / CH₂Cl₂ / -78 °C

8: DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation

9: Et₃N; DMAP / CH₂Cl₂

10: PPh₃; HBr / CHCl₃

11: (NH₄)HF₂; N-methylpyrrolidine / dimethylformamide / 70 °C

12: NaOMe / methanol

With 1-Methylpyrrolidine; 1,4-diaza-bicyclo[2.2.2]octane; dmap; ammonium fluoride-hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen bromide; sodium methylate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; tungsten hexacarbonyl; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1002/1521-3773(20011001)40:19<3653::AID-ANIE3653>3.0.CO;2-W

upstream raw materials:

(21',23'-epoxy-14'-hydroxy-24'-nor-5'β,14'β-chola-10',22'-dien-3'β-yl) O-<2''',6'''-dideoxy-β-D-ribo-hexopyranosyl>-(1->4)-O-<2'',6''-dideoxy-β-D-ribo-hexopyranosyl>-(1->4)-<2,6-dideoxy-β-D-ribo-hexopyranoside>

acetyldigitoxin

Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A

3',4'-di-O-acetyl digitoxin

Downstream raw materials:

D-digitoxose

Digitoxigenin

digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(2,6-dideoxy-β-D-ribo-hexopyranoside)

evatromonoside

Refernces

• 1、 Ma, Yuyong,Li, Zhongzhen,Shi, Hefang,Zhang, Jian,Yu, Biao. "Assembly of digitoxin by gold(I)-catalyzed glycosidation of glycosyl o-alkynylbenzoates". experimental part. p. 9748 - 9756. Retrieved 2012/01/04.
• 2、 Hou, Dianjie,Lowary, Todd L.. "Recent advances in the synthesis of 2-deoxy-glycosides". scheme or table. p. 1911 - 1940. Retrieved 2010/03/01.