4-(beta-D-Glucopyranosyloxy)-3-methoxybenzoic acid

Base Information

• Chemical Name: 4-(beta-D-Glucopyranosyloxy)-3-methoxybenzoic acid
• CAS No.: 32142-31-7
• Molecular Formula: C14H18O9
• Molecular Weight: 330.292
• DSSTox Substance ID: DTXSID80556358
• Nikkaji Number: J752.921J
• Wikidata: Q27137300
• Mol file: 32142-31-7.mol

Synonyms:32142-31-7;Vanillic acid glucoside;VANILLIC ACID 4-BETA-D-GLUCOSIDE;4-(beta-D-Glucopyranosyloxy)-3-methoxybenzoic acid;3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid;Vanillic acid 4-beta-D-glucopyranoside;Vanillic acid 4--D-glucoside;SCHEMBL19798068;CHEBI:68950;DTXSID80556358;AKOS040763520;FS-8350;PD044524;HY-114760;CS-0064269;E88980;4-(beta-D-glucopyranosyloxy)-3-methoxy-benzoic acid;Q27137300;Vanillic acid 4-beta-D-glucoside, analytical standard;4-HYDROXY-3-METHOXYBENZOIC ACID 4-BETA-D-GLUCOSIDE

Chemical Property of 4-(beta-D-Glucopyranosyloxy)-3-methoxybenzoic acid

Chemical Property:

• Boiling Point: 597.3±50.0 °C(Predicted)
• PKA: 4.23±0.10(Predicted)
• PSA: 145.91000
• Density: 1.550±0.06 g/cm3(Predicted)
• LogP: -1.42790
• Storage Temp.: 2-8°C
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 330.09508215
• Heavy Atom Count: 23
• Complexity: 404

Purity/Quality:

≥98% ^*data from raw suppliers

Vanillic acid 4-β-D-glucoside analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C(=O)O)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)C(=O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of 4-(beta-D-Glucopyranosyloxy)-3-methoxybenzoic acid

There total 8 articles about 4-(beta-D-Glucopyranosyloxy)-3-methoxybenzoic 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:

methyl 3-methoxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetoxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoate (72500-10-8) → 4-(β-D-glucopyranosyloxy)-3-methoxybenzoic acid (32142-31-7)

Guidance literature:

With sodium methylate; In methanol; at 40 ℃;

DOI:10.1248/cpb.40.851

Reference yield:

3-methoxy-4-[(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)oxy]benzoic acid (110664-71-6) → 4-(β-D-glucopyranosyloxy)-3-methoxybenzoic acid (32142-31-7)

Guidance literature:

With potassium hydroxide; In methanol; at 25 ℃;

DOI:10.1080/14786419.2020.1827399

Reference yield:

4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6) → 4-(β-D-glucopyranosyloxy)-3-methoxybenzoic acid (32142-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Ag₂O, pyridine / 3 h / Ambient temperature

2: MeONa / methanol / 40 °C

With pyridine; sodium methylate; silver(l) oxide; In methanol;

DOI:10.1248/cpb.40.851

upstream raw materials:

methyl 3-methoxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetoxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoate

4-hydroxy-3-methoxybenzoic acid methyl ester

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

α-D-glucopyranose peracetylate

Downstream raw materials:

3-methoxy-4-hydroxybenzoic acid