99-24-1

Basic information

• Product Name: Methyl gallate
• Synonyms: 3,4,5-trihydroxy-benzoicacimethylester;3,4,5-trihydroxybenzoic acid methyl ester (intermediate of bifendate);METHYL GALLATE(METHYL 3,4,5-TRIHYDROXYBENZOATE );METHYLGALLATE(RG);2-diazo-1-naphthol-5-sulfonic acid, ester with novolac;METHYGALLATE;3,4,5-trihydroxy-benzoic acidd methyl ester;METHYL 3,4,5-TRIHYDROXYBENZOATE / METHYL GALLATE
• CAS NO: 99-24-1
• Molecular Formula: C₈H₈O₅
• Molecular Weight: 184.15
• EINECS: 202-741-7
• Product Categories: Photo Active Compounds;Aromatic Esters;Organic acids;(intermediate of bifendate);Food additive ,Antioxidant anticorrosive
• Mol File: 99-24-1.mol
• Article Data: 97

Chemical Properties

• Melting Point: 201-204 °C
• Boiling Point: 278.08°C (rough estimate)
• Flash Point: 190.8 °C
• Appearance: White to slightly beige/Crystalline Powder
• Density: 1.3840 (rough estimate)
• Vapor Pressure: 1.02E-08mmHg at 25°C
• Refractive Index: 1.5690 (estimate)
• Storage Temp.: 2-8°C
• Solubility: ethanol: 50 mg/mL, clear
• PKA: 8.04±0.23(Predicted)
• Water Solubility: SOLUBLE IN HOT WATER
• Merck: 14,4345
• BRN: 2113180
• CAS DataBase Reference: Methyl gallate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl gallate(99-24-1)
• EPA Substance Registry System: Methyl gallate(99-24-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36/37-24/25
• WGK Germany: 3
• RTECS: LW8000000
• TSCA: Yes
• Hazardous Substances Data: 99-24-1(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 99-24-1 differently. You can refer to the following data:
1. 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.
2. 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

Different sources of media describe the Uses of 99-24-1 differently. You can refer to the following data:
1. Methyl gallate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells.
2. The gallate ester methyl gallate is used as an antioxidant. A ease was reported using a reprography paper.
3. Methyl 3,4,5-trihydroxybenzoate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells.

Contact allergens

This ester of gallic acid is used as an antioxidant agent. A case was reported by using a reprography paper.

Purification Methods

Methyl gallate [99-24-1] M 184.2, m 202o. Crystallise the gallate ester from MeOH. [Beilstein 10 IV 1998.]

InChI:InChI=1/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3

Upstream product

• 67-56-1 methanol 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 75-36-5 acetyl chloride 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 7778-39-4 orthoarsenic acid 
• 7783-06-4 hydrogen sulfide 
• 60-29-7 diethyl ether 
• 20189-90-6 3,4,5-triacetoxy-benzoic acid methyl ester 
• 7726-95-6 bromine 
• 7664-93-9 sulfuric acid 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 24093-81-0 methyl 3,5-dihydroxy-4-methoxybenzoate 
• 102310-68-9 methyl 3,4,5-tris(n-butan-1-yloxy)benzoate 
• 18603-13-9 3,4,5-tris-trimethylsilanyloxy-benzoic acid methyl ester 
• 69829-46-5 methyl 7-hydroxy-2,2-diphenylbenzo[d]-1,3-dioxole-5-carboxylate 
• 477-94-1 brevifolin 
• 67011-59-0 Diphenyl-(3,4,5-trihydroxy-phenyl)-methanol 
• 618-73-5 3,4,5-trihydroxybenzamide 
• 476-66-4 ellagic acid 
• 70424-94-1 methyl 3,4,5-tris(benzyloxy)benzoate 
• 91925-82-5 3,5-dihydroxy-4-(phenylmethoxy)benzoic acid methyl ester 
• 101448-64-0 3,4,5-tripropyloxybenzoic acid 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 83011-43-2 3-hydroxy-4,5-dimethoxybenzoate 
• 116119-01-8 methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate 

Relevant articles and documents

Anti-tyrosinase, antioxidant and antibacterial activities of gallic acid-benzylidenehydrazine hybrids and their application in preservation of fresh-cut apples and shrimps

A series of gallic acid-benzylidenehydrazine hybrids were synthesized and evaluated for their tyrosinase inhibitory activity. Thereinto, compounds 5d and 5f potently inhibited tyrosinase with IC50 of 15.3 and 3.3 μM, compared to kojic acid (44.4 μM). The inhibition mechanism suggested that 5d and 5f not only chelated with Cu2+, but also reduced Cu2+ to Cu1+ in the tyrosinase active site. Additionally, 5d and 5f exhibited strong DPPH scavenging and antibacterial activities against Vibrio parahaemolyticu and Staphylococcus aureus, which can be attributed to the function of gallic acid and hydrazone moiety. These compounds also exhibited capacity to preserve fresh-cut apples and shrimps. Finally, 5d and 5f exhibited low cytotoxic activity in a human cell line (HEK293). Therefore, these compounds possess anti-tyrosinase, antioxidant, and antibacterial activities, and can be used in the development of novel food preservatives.

One-Component Multifunctional Sequence-Defined Ionizable Amphiphilic Janus Dendrimer Delivery Systems for mRNA

Efficient viral or nonviral delivery of nucleic acids is the key step of genetic nanomedicine. Both viral and synthetic vectors have been successfully employed for genetic delivery with recent examples being DNA, adenoviral, and mRNA-based Covid-19 vaccines. Viral vectors can be target specific and very efficient but can also mediate severe immune response, cell toxicity, and mutations. Four-component lipid nanoparticles (LNPs) containing ionizable lipids, phospholipids, cholesterol for mechanical properties, and PEG-conjugated lipid for stability represent the current leading nonviral vectors for mRNA. However, the segregation of the neutral ionizable lipid as droplets in the core of the LNP, the "PEG dilemma", and the stability at only very low temperatures limit their efficiency. Here, we report the development of a one-component multifunctional ionizable amphiphilic Janus dendrimer (IAJD) delivery system for mRNA that exhibits high activity at a low concentration of ionizable amines organized in a sequence-defined arrangement. Six libraries containing 54 sequence-defined IAJDs were synthesized by an accelerated modular-orthogonal methodology and coassembled with mRNA into dendrimersome nanoparticles (DNPs) by a simple injection method rather than by the complex microfluidic technology often used for LNPs. Forty four (81%) showed activity in vitro and 31 (57%) in vivo. Some, exhibiting organ specificity, are stable at 5 °C and demonstrated higher transfection efficiency than positive control experiments in vitro and in vivo. Aside from practical applications, this proof of concept will help elucidate the mechanisms of packaging and release of mRNA from DNPs as a function of ionizable amine concentration, their sequence, and constitutional isomerism of IAJDs.

A novel colorimetric and ratiometric fluoride ion sensor derived from gallic acid

A novel colorimetric and ratiometric probe (SH-GA) for the fluoride ion detection was designed and synthesized from gallic acid. SH-GA exhibited a selective color change from colorless to yellow in the presence of F- among the eight anions (F-, Cl-, Br-, I-, H2PO4-, HSO4-, CH3COO-, and ClO4-), either in THF or DMF solutions. The binding stoichiometry between SH-GA and fluoride ions was determined to be 1?:?1, and the complexation constant was 1.5 × 103 M-1 in THF. The detection limit of the SH-GA probe reached as low as around 1 μM in THF. 1H NMR titration results and DFT calculations suggested a deprotonation process via hydrogen bonding interactions between the fluoride ion and amino group of SH-GA.