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Methyl gallate

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CAS:99-24-1
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Methyl gallate manufacturers

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Methyl gallate Basic information
Product Name:Methyl gallate
Synonyms: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;Gallic acid methyl ester, Methyl 3,4,5-trihydroxybenzoate
CAS:99-24-1
MF:C8H8O5
MW:184.15
EINECS:202-741-7
Product Categories:Food additive ,Antioxidant anticorrosive;(intermediate of bifendate);Aromatic Esters;Organic acids;Photo Active Compounds
Mol File:99-24-1.mol
Methyl gallate Structure
Methyl gallate Chemical Properties
Melting point 201-204 °C
Boiling point 278.08°C (rough estimate)
density 1.3840 (rough estimate)
refractive index 1.5690 (estimate)
storage temp. Inert atmosphere,Room Temperature
solubility ethanol: 50 mg/mL, clear
pka8.04±0.23(Predicted)
form Crystalline Powder
color White to slightly beige
Water Solubility SOLUBLE IN HOT WATER
Merck 14,4345
BRN 2113180
InChI1S/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3
InChIKeyFBSFWRHWHYMIOG-UHFFFAOYSA-N
SMILESCOC(=O)c1cc(O)c(O)c(O)c1
LogP0.860
CAS DataBase Reference99-24-1(CAS DataBase Reference)
EPA Substance Registry SystemBenzoic acid, 3,4,5-trihydroxy-, methyl ester (99-24-1)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38-43
Safety Statements 26-36/37-24/25
WGK Germany 3
RTECS LW8000000
TSCA TSCA listed
HS Code 29182900
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
Methyl gallate English
ACROS English
SigmaAldrich English
ALFA English
Methyl gallate Usage And Synthesis
DescriptionMethyl 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.
DescriptionMethyl 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.
Chemical Propertieswhite to slightly beige crystalline powder
UsesMethyl gallate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells.
UsesThe gallate ester methyl gallate is used as an antioxidant. A ease was reported using a reprography paper.
UsesMethyl 3,4,5-trihydroxybenzoate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells.
DefinitionChEBI: Methyl 3,4,5-trihydroxybenzoate is a gallate ester obtained by the formal condensation of gallic acid with methanol. It exhibits anti-oxidant, anti-tumor, anti-microbial and anti-inflammatory properties. It has a role as a plant metabolite, an anti-inflammatory agent and an antioxidant.
Contact allergensThis ester of gallic acid is used as an antioxidant agent. A case was reported by using a reprography paper.
Purification MethodsMethyl gallate [99-24-1] M 184.2, m 202o. Crystallise the gallate ester from MeOH. [Beilstein 10 IV 1998.]
References[1] MISO JEON  Yong S K  Naimur Rahman. Wnt/β-catenin signaling plays a distinct role in methyl gallate–mediated inhibition of adipogenesis[J]. Biochemical and biophysical research communications, 2016, 479 1: Pages 22-27. DOI: 10.1016/j.bbrc.2016.08.178
[2] PRASANTA K. BAG . In vivo fluid accumulation-inhibitory, anticolonization and anti-inflammatory and in vitro biofilm-inhibitory activities of methyl gallate isolated from Terminalia chebula against fluoroquinolones resistant Vibrio cholerae[J]. Microbial pathogenesis, 2019, 128: Pages 41-46. DOI: 10.1016/j.micpath.2018.12.037
[3] HEEKYUNG LEE. Methyl gallate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells.[J]. Journal of immunology, 2010: 6698-6705. DOI: 10.4049/jimmunol.1001373
[4] LUANA BARBOSA CORREA. Anti-inflammatory Effect of Methyl Gallate on Experimental Arthritis: Inhibition of Neutrophil Recruitment, Production of Inflammatory Mediators, and Activation of Macrophages[J]. Journal of Natural Products , 2016, 79 6: 1554-1566. DOI: 10.1021/acs.jnatprod.5b01115
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