Catechin 7-glucoside

Base Information

• Chemical Name: Catechin 7-glucoside
• CAS No.: 65597-47-9
• Molecular Formula: C₂₁H₂₄O₁₁
• Molecular Weight: 452.415
• Metabolomics Workbench ID: 21890
• Wikidata: Q105288345
• Mol file: 65597-47-9.mol

Synonyms:Catechin 7-glucoside;Catechin 7-O-beta-D-glucopyranoside;Catechim 7-O-beta-D-xyloside;CHEBI:191435;2-[[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Chemical Property of Catechin 7-glucoside

Chemical Property:

• Vapor Pressure: 3.42E-25mmHg at 25°C
• Boiling Point: 773.8°C at 760 mmHg
• Flash Point: 421.8°C
• Density: 1.674g/cm³
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 452.13186158
• Heavy Atom Count: 32
• Complexity: 623

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC2=CC(=CC(=C21)O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC(=C(C=C4)O)O)O

Technology Process of Catechin 7-glucoside

There total 4 articles about Catechin 7-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:

UDP-glucose (133-89-1) + catechin (154-23-4) → (2R,3S)-catechin 7-O-β-D-glucopyranoside (88197-03-9,122564-90-3,65597-47-9) + (+)-catechin 4'-O-β-D-glucopyranoside (105330-52-7)

Guidance literature:

With glucosyltransferase UGT₇₁A₁₅; In aq. buffer; at 30 ℃; Enzymatic reaction;

DOI:10.1016/j.foodchem.2018.06.019

Reference yield:

(2S,3R,4S,5S,6R)-2-[(2R,3R)-4-Benzylsulfanyl-2-(3,4-dihydroxy-phenyl)-3,5-dihydroxy-chroman-7-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (105330-39-0,105452-68-4) → (2R,3S)-catechin 7-O-β-D-glucopyranoside (88197-03-9,122564-90-3,65597-47-9)

Guidance literature:

With hydrogen; acetic acid; Raney-nickel (W-4); In ethanol; for 0.5h; Ambient temperature;

DOI:10.1248/cpb.34.3208

Reference yield:

uridine 5'-diphosphoglucose disodium salt (6858-46-4,7333-33-7,14656-80-5,28053-08-9,53829-41-7,108320-88-3,137868-52-1) + catechin (154-23-4) → (2R,3S)-catechin 7-O-β-D-glucopyranoside (88197-03-9,122564-90-3,65597-47-9)

Guidance literature:

With magnesium(II) chloride hexahydrate; at 35 ℃; for 20h;

DOI:10.1021/jf9034095

upstream raw materials:

(2S,3R,4S,5S,6R)-2-[(2R,3R)-4-Benzylsulfanyl-2-(3,4-dihydroxy-phenyl)-3,5-dihydroxy-chroman-7-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

catechin

uridine 5'-diphosphoglucose disodium salt

UDP-glucose

Downstream raw materials:

5,3',4'-tri-O-methyl-(+)-catechin

catechin

(2S,3R,4S,5S,6R)-2-[(2R,3S)-2-(3,4-Dimethoxy-phenyl)-3-hydroxy-5-methoxy-chroman-7-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Refernces

• 1、 Raab, Thomas,Barron, Denis,Arce Vera, Francia,Crespy, Vanessa,Oliveira, Manuel,Williamson, Gary. "Catechin Glucosides: Occurrence, synthesis, and stability". experimental part. p. 2138 - 2149. Retrieved 2010/09/04.
• 2、 Kashiwada,Nonaka,Nishioka. "Tannins and related compounds. XLV. Rhubarb. (5). Isolation and characterization of flavan-3-ol and procyanidin glucosides". . p. 3208 - 3222. Retrieved 2007/10/02.