Taxifolin 6-C-glucoside

Base Information

• Chemical Name: Taxifolin 6-C-glucoside
• CAS No.: 112494-39-0
• Molecular Formula: C21H22 O12
• Molecular Weight: 466.39
• DSSTox Substance ID: DTXSID10150065
• Nikkaji Number: J3.041.280J
• Wikidata: Q83015997
• Mol file: 112494-39-0.mol

Synonyms:taxifolin 6-C-glucoside

Chemical Property of Taxifolin 6-C-glucoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 914.7°Cat760mmHg
• Flash Point: 320.9°C
• PSA: 217.60000
• Density: 1.79g/cm³
• LogP: -1.29880
• XLogP3: -1
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 3
• Exact Mass: 466.11112613
• Heavy Atom Count: 33
• Complexity: 707

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C2C(C(=O)C3=C(O2)C=C(C(=C3O)C4C(C(C(C(O4)CO)O)O)O)O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1[C@@H]2[C@H](C(=O)C3=C(O2)C=C(C(=C3O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O)O

Technology Process of Taxifolin 6-C-glucoside

There total 20 articles about Taxifolin 6-C-glucoside 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:

(+/-)-taxifolin (480-18-2,24198-97-8,98006-93-0,111003-33-9,114761-89-6,17654-26-1,5117-01-1) → (2R,3R)-(+)-3',4',5,7-tetrahydroxydihydroflavonol-6-C-β-D-glucopyranoside (112494-39-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Resolution of racemate

2: scandium tris(trifluoromethanesulfonate) / water; acetonitrile / 48 h / Inert atmosphere; Reflux

With scandium tris(trifluoromethanesulfonate); In water; acetonitrile;

DOI:10.1055/s-0040-1707971

Reference yield:

(E)-3-(3,4-bis(methoxymethoxy)phenyl)-1-(2,4,6-tris(methoxymethoxy)phenyl)-prop-2-en-1-one (36804-12-3) → (2R,3R)-(+)-3',4',5,7-tetrahydroxydihydroflavonol-6-C-β-D-glucopyranoside (112494-39-0)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydroxide; dihydrogen peroxide / methanol / 5 h / 20 °C / Inert atmosphere

2: hydrogenchloride / methanol; water; tetrahydrofuran / 2 h / 55 °C / Inert atmosphere

3: Resolution of racemate

4: scandium tris(trifluoromethanesulfonate) / water; acetonitrile / 48 h / Inert atmosphere; Reflux

With hydrogenchloride; dihydrogen peroxide; sodium hydroxide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1055/s-0040-1707971

Reference yield:

3,5-dihydroxyphenol (108-73-6) → (2R,3R)-(+)-3',4',5,7-tetrahydroxydihydroflavonol-6-C-β-D-glucopyranoside (112494-39-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

1.2: 5 h / -5 °C / Inert atmosphere

2.1: trifluoromethylsulfonic anhydride / dichloromethane / 0.08 h / -5 °C / Inert atmosphere

2.2: -5 °C / Inert atmosphere

3.1: sodium hydroxide; dihydrogen peroxide / methanol / 5 h / 20 °C / Inert atmosphere

4.1: hydrogenchloride / methanol; water; tetrahydrofuran / 2 h / 55 °C / Inert atmosphere

5.1: Resolution of racemate

6.1: scandium tris(trifluoromethanesulfonate) / water; acetonitrile / 48 h / Inert atmosphere; Reflux

With hydrogenchloride; trifluoromethylsulfonic anhydride; dihydrogen peroxide; sodium hydride; sodium hydroxide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1055/s-0040-1707971

upstream raw materials:

(E)-3-(3,4-bis(methoxymethoxy)phenyl)-1-(2,4,6-tris(methoxymethoxy)phenyl)-prop-2-en-1-one

(+/-)-taxifolin

D-Glucose

catechin

Refernces