3-Monoacetylgitoxigenin

Base Information

• Chemical Name: 3-Monoacetylgitoxigenin
• CAS No.: 1059-21-8
• Molecular Formula: C₂₅H₃₆O₆
• Molecular Weight: 432.557
• European Community (EC) Number: 631-280-8
• DSSTox Substance ID: DTXSID90909816
• Mol file: 1059-21-8.mol

Synonyms:BRN 0061015;3-Monoacetylgitoxigenin;1059-21-8;gitoxigenin 3-acetate;5-beta-CARD-20(22)-ENOLIDE, 3-beta,14,16-beta-TRIHYDROXY-, 3-ACETATE;[(3S,5R,10S,13R,14S,16S,17R)-14,16-dihydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate;3-beta,14,16-beta-Trihydroxy-5-beta-card-20(22)-enolide 3-acetate;3-beta,14,16-beta-Trihyroxy-5-beta-card-20(22)-enolide 3-acetate;DTXSID90909816;LS-52509;3-(Acetyloxy)-14,16-dihydroxycard-20(22)-enolide

Chemical Property of 3-Monoacetylgitoxigenin

Chemical Property:

• Vapor Pressure: 1.83E-16mmHg at 25°C
• Boiling Point: 591.7°Cat760mmHg
• Flash Point: 197.7°C
• PSA: 93.06000
• Density: 1.26g/cm³
• LogP: 3.14590
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 432.25118886
• Heavy Atom Count: 31
• Complexity: 821

Purity/Quality:

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

Safty Information:

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC2(C(C1)CCC3C2CCC4(C3(CC(C4C5=CC(=O)OC5)O)O)C)C
• Isomeric SMILES: CC(=O)O[C@H]1CC[C@]2([C@@H](C1)CCC3C2CC[C@]4([C@@]3(C[C@@H]([C@@H]4C5=CC(=O)OC5)O)O)C)C

Technology Process of 3-Monoacetylgitoxigenin

There total 12 articles about 3-Monoacetylgitoxigenin 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: 65.0%

gitoxigenin 3,16-diacetate (5996-03-2) → 3-Acetylgitoxigenin (1059-21-8)

Guidance literature:

With potassium hydrogencarbonate; In methanol; water; for 96h; Ambient temperature;

DOI:10.1021/jm00156a017

Reference yield: 17.0%

acetic anhydride (108-24-7) + gitoxigenin (545-26-6) → 3-Acetylgitoxigenin (1059-21-8) + gitoxigenin 3,16-diacetate (5996-03-2)

Guidance literature:

In chloroform; acetic acid; at 60 - 70 ℃; for 2h;

DOI:10.1021/jm00156a017

Reference yield:

gitoxin (4562-36-1) → 3-Acetylgitoxigenin (1059-21-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / 0.08 N aq. H₂SO₄ / methanol / 2.5 h / Heating

2: 56 percent / CHCl₃; acetic acid / 2 h / 60 - 70 °C

With sulfuric acid; In methanol; chloroform; acetic acid;

DOI:10.1021/jm00156a017

upstream raw materials:

methanol

2-methoxy-ethanol

potassium hydrogencarbonate

gitoxigenin 3,16-diacetate

Downstream raw materials:

3β-acetoxy-14-hydroxy-16β-(toluene-4-sulfonyloxy)-5β,14β-card-20(22)-enolide

Refernces

• 1、 Hashimoto, Toshihiro,Rathore, Hargovind,Satoh, Daisuke,Hong, George,Griffin, Jane F.,et al.. "Cardiac Glycosides. 6. Gitoxigenin C16 Acetates, Formates, Methoxycarbonates, and Digitoxosides. Synthesis and Na+, K+ -ATPase Inhibitory Activities". . p. 997 - 1003. Retrieved 2007/10/02.