Epiafzelechin 3-O-gallate

Base Information

• Chemical Name: Epiafzelechin 3-O-gallate
• CAS No.: 108907-43-3
• Molecular Formula: C₂₂H₁₈O₉
• Molecular Weight: 426.38
• DSSTox Substance ID: DTXSID701308092
• Nikkaji Number: J895.717G
• Wikidata: Q105250941
• Metabolomics Workbench ID: 21868
• ChEMBL ID: CHEMBL159706
• Mol file: 108907-43-3.mol

Synonyms:Epiafzelechin 3-O-gallate;108907-43-3;(-)-epiafzelechin 3-O-gallate;(-)-Epiafzelechin Gallate;(-)-Epiafzelechin 3-gallate;[(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate;(2R,3R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate;Benzoic acid, 3,4,5-trihydroxy-, (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-2H-1-benzopyran-3-yl ester;epiafzelechin 3-gallate;3-Galloyl-(-)-epiafzelechin;CHEMBL159706;SCHEMBL9100860;CHEBI:136552;DTXSID701308092;LMPK12020038;AKOS040761680;5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate;[(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-3-yl] 3,4,5-trihydroxybenzoate;(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

Chemical Property of Epiafzelechin 3-O-gallate

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 426.09508215
• Heavy Atom Count: 31
• Complexity: 610

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

(-)-Epiafzelechin3-O-gallate ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
• Isomeric SMILES: C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

Technology Process of Epiafzelechin 3-O-gallate

There total 24 articles about Epiafzelechin 3-O-gallate 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: 82.0%

(+)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate (773859-55-5) → Afzelechin gallate (108907-43-3)

Guidance literature:

With hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 6h;

DOI:10.1016/j.tet.2004.06.113

Reference yield: 82.0%

(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate (773859-60-2) → epi-Afzelechin gallate (108907-43-3)

Guidance literature:

With 5% Pd(OH)₂/C; hydrogen; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.5h;

DOI:10.1039/c003464a

Reference yield:

3,4,5-tribenzyloxybenzoic acid (1486-48-2) → epi-Afzelechin gallate (108907-43-3)

Guidance literature:

Multi-step reaction with 3 steps

1: (COCl)2 / CH₂Cl₂; tetrahydrofuran / 3 h / Heating

2: 82 percent / DMAP / CH₂Cl₂ / 0 - 20 °C

3: 80 percent / H₂ / Pd(OH)2/C / tetrahydrofuran; methanol / 6 h / 20 °C

With dmap; oxalyl dichloride; hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tet.2004.06.113

upstream raw materials:

(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

1,3-dibenzylphloroglucinol

3,4,5-tribenzyloxybenzoic acid

3,4,5-tris(benzyloxy)benzoyl chloride

Downstream raw materials:

(-)-epiafzelechin

Refernces

• 1、 Wan, Sheng Biao,Chan, Tak Hang. "Enantioselective synthesis of afzelechin and epiafzelechin". . p. 8207 - 8211. Retrieved 2007/10/03.