3,4-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide

Base Information

• Chemical Name: 3,4-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide
• CAS No.: 953037-17-7
• Molecular Formula: C13H14O10
• Molecular Weight: 330.248
• Mol file: 953037-17-7.mol

Synonyms:3,4-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide;5-Carboxy-2-hydroxyphenyl β-D-Glucopyranosiduronic Acid

Chemical Property of 3,4-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide

Chemical Property:

• PSA: 173.98000
• LogP: -1.63860
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)

Purity/Quality:

99.90% ^*data from raw suppliers

3,4-DihydroxybenzoicAcid3-O-β-D-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3,4-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide is a metabolite of Protocatechuic aldehyde, a major bioactive phenolic acid in the roots of Salvia miltiorrhiza.

Technology Process of 3,4-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide

There total 8 articles about 3,4-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide 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: 96.0%

5-carboxy-2-hydroxyphenyl-β-D-glucopyranosiduronic acid dipotassium salt → 5-carboxy-2-hydroxyphenyl-β-D-glucopyranosiduronic acid (953037-17-7)

Guidance literature:

With Dowex 50WX₄-400 acidic ion-exchange resin; In water; pH=2 - 3; Inert atmosphere;

DOI:10.1016/j.tet.2012.03.100

Reference yield:

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) + benzyl 3,4-dihydroxybenzoate (80003-86-7) → 5-carboxy-2-hydroxyphenyl-β-D-glucopyranosiduronic acid (953037-17-7) + 4-carboxy-2-hydroxyphenyl-β-D-glucopyranosiduronic acid (121379-64-4)

Guidance literature:

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate; benzyl 3,4-dihydroxybenzoate; With boron trifluoride diethyl etherate; In dichloromethane; at -20 - 20 ℃; for 4h; Inert atmosphere; Molecular sieve;

With sodium methylate; In methanol; at 20 ℃; for 0.25h; Inert atmosphere;

With lithium hydroxide; In water; at 20 ℃; for 0.0833333h; Overall yield = 34 mg;

DOI:10.1021/acs.jafc.6b05629

Reference yield:

Ethyl protocatechuate (3943-89-3) → 5-carboxy-2-hydroxyphenyl-β-D-glucopyranosiduronic acid (953037-17-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / 2 h / 0 °C / Inert atmosphere

2.1: potassium carbonate; potassium iodide / acetone / 24 h / Inert atmosphere; Reflux

3.1: water; sodium carbonate / tetrahydrofuran; methanol / 20 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / dichloromethane / 4 h / -20 - 15 °C / Inert atmosphere; Molecular sieve

5.1: water; potassium hydroxide / methanol / 72 h / 0 - 4 °C / Inert atmosphere

5.2: 20 °C / 760.05 Torr

6.1: Dowex 50WX₄-400 acidic ion-exchange resin / water / pH 2 - 3 / Inert atmosphere

With pyridine; boron trifluoride diethyl etherate; water; sodium carbonate; potassium carbonate; potassium iodide; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; 2.1: Williamson synthesis;

DOI:10.1016/j.tet.2012.03.100

upstream raw materials:

methyl 1-O-(5-ethoxycarbonyl-2-benzyloxyphenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate

ethyl 3-acetoxy-4-benzyloxybenzoate

Ethyl protocatechuate

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate

Refernces

• 1、 Zhang, Qingzhi,Raheem, K. Saki,Botting, Nigel P.,Slawin, Alexandra M.Z.,Kay, Colin D.,O'Hagan, David. "Flavonoid metabolism: The synthesis of phenolic glucuronides and sulfates as candidate metabolites for bioactivity studies of dietary flavonoids". . p. 4194 - 4201. Retrieved 2012/07/14.