(+)-Catechin 8-C-glucoside

Base Information

• Chemical Name: (+)-Catechin 8-C-glucoside
• CAS No.: 105371-26-4
• Molecular Formula: C₂₁H₂₄O₁₁
• Molecular Weight: 452.415
• Wikidata: Q105343321
• Mol file: 105371-26-4.mol

Synonyms:(+)-Catechin 8-C-glucoside;8-Glucosyl-(+)-catechin;8-Glucopyranosyl-(+)-catechin;SCHEMBL12392360;CHEBI:191703;2-(3,4-dihydroxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-chromene-3,5,7-triol

Chemical Property of (+)-Catechin 8-C-glucoside

Chemical Property:

• XLogP3: -1
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 3
• Exact Mass: 452.13186158
• Heavy Atom Count: 32
• Complexity: 637

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(OC2=C1C(=CC(=C2C3C(C(C(C(O3)CO)O)O)O)O)O)C4=CC(=C(C=C4)O)O)O

Technology Process of (+)-Catechin 8-C-glucoside

There total 10 articles about (+)-Catechin 8-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:

D-glucose (50-99-7) + catechin (154-23-4) → (+)-catechin 6-C-β-D-glucopyranoside (105371-27-5) + (+)-catechin 8-C-β-D-glucopyranoside (105371-26-4)

Guidance literature:

With toluene-4-sulfonic acid; In 1,4-dioxane; at 80 ℃; for 10h;

DOI:10.1248/cpb.34.3208

Reference yield:

D-Glucose (2280-44-6) + catechin (154-23-4) → (+)-catechin-6-C,8-C-β-D-diglucopyranoside + (+)-epicatechin-6-C-β-D-glucopyranoside + (+)-catechin 6-C-β-D-glucopyranoside (105371-27-5) + (+)-catechin 8-C-β-D-glucopyranoside (105371-26-4)

Guidance literature:

With potassium carbonate; In water; at 80 ℃; for 0.166667h; Further byproducts.;

DOI:10.1021/jf0719508

Reference yield:

(2S,3R,4S,5S,6R)-2-[5-((2R,3S)-3-Hydroxy-5,7-dimethoxy-chroman-2-yl)-2-methoxy-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (105330-58-3) → (+)-catechin 8-C-β-D-glucopyranoside (105371-26-4)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylsulfoxide; H₂O / 37 °C / hesperidinase

2: 28 mg / p-toluenesulfonic acid / dioxane / 10 h / 80 °C

With toluene-4-sulfonic acid; In 1,4-dioxane; water; dimethyl sulfoxide;

DOI:10.1248/cpb.34.3208

upstream raw materials:

D-glucose

catechin

D-Glucose

(2S,3R,4S,5S,6R)-2-[5-((2R,3S)-3-Hydroxy-5,7-dimethoxy-chroman-2-yl)-2-methoxy-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

(+)-catechin 8-C-β-D-glucopyranoside