Methyl 3,5-dihydroxy-4-methoxybenzoate

Base Information

• Chemical Name: Methyl 3,5-dihydroxy-4-methoxybenzoate
• CAS No.: 24093-81-0
• Molecular Formula: C9H10O5
• Molecular Weight: 198.175
• Hs Code.: 2918999090
• European Community (EC) Number: 811-111-6
• DSSTox Substance ID: DTXSID20415758
• Nikkaji Number: J728.796H
• Metabolomics Workbench ID: 138952
• ChEMBL ID: CHEMBL491990
• Mol file: 24093-81-0.mol

Synonyms:methyl 3,5-dihydroxy-4-methoxybenzoate;24093-81-0;3,5-Dihydroxy-4-methoxybenzoic acid methyl ester;Methyl-4-O-methylgallate;(4'-O-methyl)methyl gallate;CHEMBL491990;SCHEMBL2728130;DTXSID20415758;MFCD00017195;AKOS006283782;methyl3,5-dihydroxy-4-methoxybenzoate;AS-59139;CS-0181788;FT-0699716;M2794;T72134;Benzoic acid,3,5-dihydroxy-4-methoxy,methyl ester;Benzoic acid, 3,5-dihydroxy-4-methoxy, methyl ester

Chemical Property of Methyl 3,5-dihydroxy-4-methoxybenzoate

Chemical Property:

• Vapor Pressure: 5.51E-07mmHg at 25°C
• Melting Point: 147.0 to 151.0 °C
• Boiling Point: 400.4oC at 760 mmHg
• PKA: 8?+-.0.15(Predicted)
• Flash Point: 164.4oC
• PSA: 75.99000
• Density: 1.337g/cm3
• LogP: 0.89300
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 198.05282342
• Heavy Atom Count: 14
• Complexity: 193

Purity/Quality:

98%,99%, ^*data from raw suppliers

methyl 3,5-dihydroxy-4-methoxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1O)C(=O)OC)O

Technology Process of Methyl 3,5-dihydroxy-4-methoxybenzoate

There total 20 articles about Methyl 3,5-dihydroxy-4-methoxybenzoate 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: 99.0%

methyl 3,5-diacetoxy-4-methoxy benzoate (13089-97-9) → methyl 3,5-dihydroxy-4-methoxybenzoate (24093-81-0)

Guidance literature:

With potassium carbonate; In methanol; water; for 0.333333h; Ambient temperature;

DOI:10.1080/00397919608004560

Reference yield: 76.0%

methyl galloate (99-24-1) + methyl iodide (74-88-4) → methyl 3,5-dihydroxy-4-methoxybenzoate (24093-81-0)

Guidance literature:

methyl galloate; With potassium carbonate; In N,N-dimethyl-formamide; at 85 ℃; for 1h;

methyl iodide; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1248/cpb.54.1662

Reference yield: 64.0%

methyl galloate (99-24-1) + methyl iodide (74-88-4) → methyl 3,5-dihydroxy-4-methoxybenzoate (24093-81-0) + 3-hydroxy-4,5-dimethoxybenzoate (83011-43-2)

Guidance literature:

methyl galloate; With potassium carbonate; In N,N-dimethyl-formamide; at 85 ℃; for 1h;

methyl iodide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16.5h;

DOI:10.1002/anie.201803887

upstream raw materials:

diazomethane

diethyl ether

methyl galloate

1-methyl-4-nitrosobenzene

Downstream raw materials:

3,4,5-trimethoxybenzoic acid methyl ester

3-hydroxy-4,5-dimethoxybenzoate

methyl 3,5-di(methoxymethyloxy)-4-methoxybenzoate

2-(3,5-bis(benzyloxy)-4-methoxyphenyl)acetonitrile

Refernces

• 1、 Lipp, Alexander,Ferenc, Dorota,Gütz, Christoph,Geffe, Mario,Vierengel, Nina,Schollmeyer, Dieter,Sch?fer, Hans J.,Waldvogel, Siegfried R.,Opatz, Till. "A Regio- and Diastereoselective Anodic Aryl–Aryl Coupling in the Biomimetic Total Synthesis of (?)-Thebaine". supporting information. p. 11055 - 11059. Retrieved 2018/08/21.
• 2、 Paramita, Rafika Indah,Arsianti, Ade,Radji, Maksum. "Synthesis and cytotoxic activities of hexyl-esters derivatives of gallic acid against MCF-7 cell line". . p. 295 - 300. Retrieved 2018/03/21.