Digallic acid

Base Information

• Chemical Name: Digallic acid
• CAS No.: 536-08-3
• Molecular Formula: C14H10 O9
• Molecular Weight: 322.228
• Hs Code.: 2918990090
• European Community (EC) Number: 208-624-7
• NSC Number: 59263
• UNII: 404KO0584X
• DSSTox Substance ID: DTXSID50871747
• Nikkaji Number: J6.349E
• Wikipedia: Digallic_acid
• Wikidata: Q4140499
• Pharos Ligand ID: R6KYSLNBRCLR
• Metabolomics Workbench ID: 52021
• ChEMBL ID: CHEMBL366356
• Mol file: 536-08-3.mol

Synonyms:digallic acid;gallic acid 5,6-dihydroxy-3-carboxyphenyl ester

Chemical Property of Digallic acid

Chemical Property:

• Vapor Pressure: 3.09E-22mmHg at 25°C
• Melting Point: 267-269°C
• Refractive Index: 1.7770 (estimate)
• Boiling Point: 727.8°C at 760 mmHg
• PKA: 4.11±0.10(Predicted)
• Flash Point: 278°C
• PSA: 164.75000
• Density: 1.815g/cm³
• LogP: 1.13200
• Storage Temp.: -20°C Freezer
• Water Solubility.: 0.5g/L(25 oC)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 322.03248189
• Heavy Atom Count: 23
• Complexity: 442

Purity/Quality:

99%, ^*data from raw suppliers

DigallicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)O
• Description: Digallic acid is a natural polyphenolic that can be produced by hydrolysis of gallotannins. Like other polyphenolic compounds, digallic acid has antioxidant activity that can be cytoprotective. Digallic acid inhibits reverse transcriptases from human immunodeficiency virus (Ki = 0.58 μM) and murine leukemia virus. It also inhibits calcium-activated chloride channels, blocking the initial agonist-stimulated chloride current.

Technology Process of Digallic acid

There total 17 articles about Digallic 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:

tannic acid (14937-32-7,15743-68-7,70470-10-9,50678-27-8) → 3,4,5-trihydroxybenzoic acid (149-91-7) + digallic acid (536-08-3) + para digallic acid (47307-06-2) + 2-hydroxyresorcinol (87-66-1)

Guidance literature:

at 200 ℃; for 0.5h;

DOI:10.1016/j.phytochem.2011.02.020

Reference yield:

chloroformic acid ethyl ester (541-41-3) → digallic acid (536-08-3)

Guidance literature:

With stannabenzene; Verseifen mit Pyridin;

DOI:10.2165/00019053-200119110-00003

Reference yield:

3,4-diacetoxy-5-(3,4,5-triacetoxy-benzoyloxy)-benzoic acid → digallic acid (536-08-3) + para digallic acid (47307-06-2)

Guidance literature:

With ammonium hydroxide;

upstream raw materials:

tetrachloromethane

diethyl ether

4-hydroxy-3,5-bis-methoxycarbonyloxy-benzoic acid

3,4,5-Trimethoxycarbonyloxybenzoylchlorid

Downstream raw materials:

methyl penta-O-methyl-m-digallate

ellagic acid

3,4,5-trihydroxybenzoic acid

para digallic acid

Refernces

• 1、 Maeda, Hajime,Kakoki, Narumi,Ayabe, Mami,Koga, Yuki,Oribe, Tomoko,Matsuo, Yosuke,Tanaka, Takashi,Kouno, Isao. "Ent-Eudesmane sesquiterpenoids, galloyl esters of the oak lactone precursor, and a 3-O-methylellagic acid glycoside from the wood of Platycarya strobilacea". experimental part. p. 796 - 803. Retrieved 2011/11/06.