Methyl gallate

Base Information

• Chemical Name: Methyl gallate
• CAS No.: 99-24-1
• Molecular Formula: C8H8O5
• Molecular Weight: 184.149
• Hs Code.: 2918.29
• European Community (EC) Number: 202-741-7
• NSC Number: 363001
• UNII: 623D3XG80C
• DSSTox Substance ID: DTXSID3059189
• Nikkaji Number: J4.967K
• Wikipedia: Methyl_gallate
• Wikidata: Q15425833
• Metabolomics Workbench ID: 143431
• ChEMBL ID: CHEMBL65675
• Mol file: 99-24-1.mol

Synonyms:gallic acid, methyl ester;methyl 3,4,5-trihydroxybenzoate;methyl gallate

Chemical Property of Methyl gallate

Chemical Property:

• Appearance/Colour: white to slightly beige crystalline powder
• Vapor Pressure: 1.02E-08mmHg at 25°C
• Melting Point: 201-204 °C
• Refractive Index: 1.63
• Boiling Point: 450.1 °C at 760 mmHg
• PKA: 8.04±0.23(Predicted)
• Flash Point: 190.8 °C
• PSA: 86.99000
• Density: 1.501 g/cm³
• LogP: 0.59000
• Storage Temp.: 2-8°C
• Solubility.: ethanol: 50 mg/mL, clear
• Water Solubility.: SOLUBLE IN HOT WATER
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 184.03717335
• Heavy Atom Count: 13
• Complexity: 181

Purity/Quality:

99.0%min ^*data from raw suppliers

Methyl gallate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: COC(=O)C1=CC(=C(C(=C1)O)O)O
• Description: Methyl gallate is a phenolic compound found in Terminalia myriocarpa and Geranium niveum. It is also found in wine. It is the methyl ester of gallic acid. Methyl gallate is a phenol that has been found in Meliaceae and has diverse biological activities. It reduces adipogenic hormonal stimulation-induced lipid accumulation in 3T3-L1 cells when used at a concentration of 50 μM. Methyl gallate is active against V. cholerae in vitro (MIC = 32 μg/ml) and reduces V. cholerae-induced intestinal fluid accumulation in suckling mice when administered at doses of 50, 100, and 200 mg/kg. It reduces tumor growth and decreases the number of intratumor CD25+Foxp3high regulatory T cells (Tregs) in an EL-4 model of murine lymphoma. Methyl gallate (0.7, 7, and 70 mg/kg) reduces knee joint edema and leukocyte, neutrophil, and mononuclear cell infiltration in a mouse model of zymosan-induced arthritis.
• Uses: Methyl gallate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells. The gallate ester methyl gallate is used as an antioxidant. A ease was reported using a reprography paper. Methyl 3,4,5-trihydroxybenzoate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells.

Technology Process of Methyl gallate

There total 29 articles about Methyl gallate 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: 85.0%

methyl 3,4,5-tris(methoxymethoxy)benzoate → methyl galloate (99-24-1)

Guidance literature:

With toluene-4-sulfonic acid; In neat (no solvent, solid phase); at 20 ℃; for 0.75h; Green chemistry;

DOI:10.2174/1570178614666170321103650

Reference yield: 84.0%

3,4,5-trihydroxybenzoic acid (149-91-7) + dimethyl sulfate (77-78-1) → methyl galloate (99-24-1)

Guidance literature:

With sodium hydrogencarbonate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; at 40 ℃; for 0.416667h;

DOI:10.1080/00397910701845480

Reference yield: 72.0%

methyl 3-(3β-acetoxyurs-12-en-28-oyloxy)-4,5-(methoxymethylenedioxy)benzoate → methyl galloate (99-24-1) + methyl-3-hydroxy-4,5-[(R,S)-methoxymethylenedioxy]benzoate + (3β-acetoxyurs-12-en)-28-oylhydrazide

Guidance literature:

With hydrazine hydrate; In isopropyl alcohol; at 22 - 26 ℃; for 8h;

DOI:10.1007/s10600-021-03546-0

upstream raw materials:

methanol

3,4,5-trihydroxybenzoic acid

methyl 6-O-galloyl-α-D-glucopyranoside

3,4,5-triacetoxy-benzoic acid methyl ester

Downstream raw materials:

methyl 3,4,5-tris(n-butan-1-yloxy)benzoate

brevifolin

Diphenyl-(3,4,5-trihydroxy-phenyl)-methanol

3,4,5-trihydroxybenzamide

Refernces

• 1、 Popov,Wang,Qi,Shul’ts,Turks. "Synthesis and Antioxidant Activity of New N-Containing Hybrid Derivatives of Gallic and Ursolic Acids". . p. 1042 - 1046. Retrieved 2021/11/26.
• 2、 Zhao, Xiao-Long,Li, Chun-Qing,Song, Xiao-Mei,Yan, Shuang-Mei,Luo, Du-Qiang. "Design, Synthesis, and Antifungal Activity of Alkyl Gallates Against Plant Pathogenic Fungi In Vitro and In Vivo". . p. 38 - 43. Retrieved 2021/02/01.