3-Glucogallic acid

Base Information

• Chemical Name: 3-Glucogallic acid
• CAS No.: 91984-84-8
• Molecular Formula: C₁₃H₁₆O₁₀
• Molecular Weight: 332.264
• Metabolomics Workbench ID: 48489
• Wikidata: Q105340376
• Mol file: 91984-84-8.mol

Synonyms:3-Glucogallic acid;91984-84-8;3,4-dihydroxy-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid;CHEBI:185330;3,4-Dihydroxy-5-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzoic acid;3-(Beta-d-glucopyranosyloxy)-4,5-dihydroxy-benzoic acid;3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

Chemical Property of 3-Glucogallic acid

Chemical Property:

• XLogP3: -1.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 332.07434670
• Heavy Atom Count: 23
• Complexity: 418

Purity/Quality:

98% ^*data from raw suppliers

Gallicacid3-O-beta-D-glucopyranoside 95%min ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1O)O)OC2C(C(C(C(O2)CO)O)O)O)C(=O)O

Technology Process of 3-Glucogallic acid

There total 6 articles about 3-Glucogallic acid 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: 94.0%

3,4-(diphenylmethylendioxy)-5-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)benzoic acid (270061-97-7) → gallic acid-3-O-β-D-glucopyranoside (91984-84-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; acetone; for 4h;

DOI:10.1016/S0008-6215(99)00311-0

Reference yield:

3,4,5-trihydroxybenzoic acid (149-91-7) → gallic acid-3-O-β-D-glucopyranoside (91984-84-8) + β-glucogallin (13405-60-2,58511-73-2)

Guidance literature:

In water; for 96h;

DOI:10.1016/0031-9422(95)00456-H

Reference yield:

Ethyl gallate (831-61-8) → gallic acid-3-O-β-D-glucopyranoside (91984-84-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / pyridine / acetone / 16 h

2: 60 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h / 20 °C

3: 89 percent / KOH / 1,2-dimethoxy-ethane / 20 h

4: 94 percent / H₂ / Pd/C / acetone; H₂O / 4 h

With pyridine; potassium hydroxide; boron trifluoride diethyl etherate; hydrogen; palladium on activated charcoal; In 1,2-dimethoxyethane; dichloromethane; water; acetone; 1: Etherification / 2: Etherification / 3: Hydrolysis / 4: Hydrogenolysis;

DOI:10.1016/S0008-6215(99)00311-0

upstream raw materials:

gallic acid 3-O-β-D-(6′-O-galloyl)glucopyranoside

3,4-(diphenylmethylendioxy)-5-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)benzoic acid

3,4,5-trihydroxybenzoic acid

Ethyl gallate