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 
• 66656-94-8 methyl 6-O-galloyl-α-D-glucopyranoside 
• 60-29-7 diethyl ether 
• 20189-90-6 3,4,5-triacetoxy-benzoic acid methyl ester 
• 7726-95-6 bromine 
• 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 
• 7664-93-9 sulfuric acid 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 18603-13-9 3,4,5-tris-trimethylsilanyloxy-benzoic acid methyl ester 
• 24093-81-0 methyl 3,5-dihydroxy-4-methoxybenzoate 
• 102898-72-6 methyl 3,4,5-tris(pentyloxy)benzoate 
• 342886-36-6 3,4,5-tris(octyloxy)benzoic acid methyl ester 
• 158921-39-2 methyl 3,4,5-tris(n-decan-1-yloxy)benzoate 
• 219993-13-2 methyl [3,4,5-tris(n-tetradecan-1-yloxy)]benzoate 
• 123126-39-6 methyl [3,4,5-tris(n-dodecan-1-yloxy)]benzoate 
• 154492-27-0 4-Methoxy-3,5-bis-(4-methoxycarbonyl-2-nitro-phenoxy)-benzoic acid methyl ester 
• 188685-33-8 methyl [3,4,5-tris(n-octadecan-1-yloxy)]benzoate 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 244020-49-3 3,4,5-Tris-((R)-3,7-dimethyl-oct-6-enyloxy)-benzoic acid methyl ester 
• 146300-69-8 3,4-(diphenylmethylenedioxy)-5-hydroxybenzoic acid 
• 476-66-4 ellagic acid 
• 32773-02-7 hexahydroxydiphenic acid 

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.

Design, Synthesis, and Antifungal Activity of Alkyl Gallates Against Plant Pathogenic Fungi In Vitro and In Vivo

A series of alkyl gallates was synthesized by reacting gallic acid with the corresponding alcohols. Their structures were determined on the basis of spectroscopic data, including NMR and MS. The antifungal activities of these compounds against plant pathogenic fungi in vitro and in vivo were assessed.

Polyhydroxybenzoic acid derivatives as potential new antimalarial agents

With more than 200 million cases and 400,000 related deaths, malaria remains one of the deadliest infectious diseases of 2021. Unfortunately, despite the availability of efficient treatments, we have observed an increase in people infected with malaria since 2015 (from 211 million in 2015 to 229 million in 2019). This trend could partially be due to the development of resistance to all the current drugs. Therefore, there is an urgent need for new alternatives. We have, thus, selected common natural scaffolds, polyhydroxybenzoic acids, and synthesized a library of derivatives to better understand the structure–activity relationships explaining their antiplasmodial effect. Only gallic acid derivatives showed a noticeable potential for further developments. Indeed, they showed a selective inhibitory effect on Plasmodium (IC50 ~20 μM, SI > 5) often associated with interesting water solubility. Moreover, this has confirmed the critical importance of free phenolic functions (pyrogallol moiety) for the antimalarial effect. Methyl 4-benzoxy-3,5-dihydroxybenzoate (39) has, for the first time, been recognized as a potential lead for future research because of its marked inhibitory activity against Plasmodium falciparum and its significant hydrosolubility (3.72 mM).