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99-24-1

99-24-1 Structure

99-24-1 Structure
IdentificationMore
[Name]

Methyl gallate
[CAS]

99-24-1
[Synonyms]

3,4,5-TRIHYDROXYBENZOIC ACID METHYL ESTER
AKOS 217-13
GALLIC ACID METHYL ESTER
GALLICIN
METHYL 3,4,5-TRIHYDROXYBENZOATE
METHYL GALLATE
RARECHEM AL BF 0070
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
Gallic acid methyl ester, Methyl 3,4,5-trihydroxybenzoate
Benzoic acid, 3,4,5-trihydroxy, methyl ester
Methyl 3,4,5-trihydroxybenzoate, 99 %
(3aS,10E)-3aβ,4,5,6,7,8,9,11aα-Octahydro-7α-hydroxy-6-methylene-3β,10-dimethylcyclodeca[b]furan-2(3H)-one
[EINECS(EC#)]

202-741-7
[Molecular Formula]

C8H8O5
[MDL Number]

MFCD00002194
[Molecular Weight]

184.15
[MOL File]

99-24-1.mol
Chemical PropertiesBack Directory
[Appearance]

white to slightly beige crystalline powder
[Melting point ]

201-204 °C
[Boiling point ]

278.08°C (rough estimate)
[density ]

1.3840 (rough estimate)
[refractive index ]

1.5690 (estimate)
[storage temp. ]

2-8°C
[solubility ]

ethanol: 50 mg/mL, clear
[form ]

Crystalline Powder
[pka]

8.04±0.23(Predicted)
[color ]

White to slightly beige
[Water Solubility ]

SOLUBLE IN HOT WATER
[Merck ]

14,4345
[BRN ]

2113180
[InChI]

1S/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3
[Contact allergens]

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

FBSFWRHWHYMIOG-UHFFFAOYSA-N
[SMILES]

COC(=O)c1cc(O)c(O)c(O)c1
[LogP]

0.860
[CAS DataBase Reference]

99-24-1(CAS DataBase Reference)
[EPA Substance Registry System]

99-24-1(EPA Substance)
Hazard InformationBack Directory
[Chemical Properties]

white to slightly beige crystalline powder
[Uses]

Methyl gallate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells.
[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.
[Definition]

ChEBI: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.
[Biological Activity]

A large number of cell and animal experiments have shown that MG has good therapeutic effects, such as anti-tumor, anti-inflammatory, anti-oxidation, anti-microbial, anti-malarial and so on[5].
[Source]

Methyl gallate is widely found in natural plants, such as Juglans mandshurica, Galla chinensis, Paeonia anomala, Phyllanthus emblica, Mangifera indica, Plicosepalus acacia, Carica papaya Linn, and Maple (Genus Acer)[5].
[storage]

Store at -20°C
[Purification Methods]

Methyl 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
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P301+P312+P330-P302+P352-P305+P351+P338
[Hazard Codes ]

Xn,Xi
[Risk Statements ]

R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact.
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
[WGK Germany ]

3
[RTECS ]

LW8000000
[TSCA ]

Yes
[HS Code ]

29182900
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Gallic acid
[Preparation Products]

4-BROMO-7-METHOXY-BENZO[1,3]DIOXOLE-5-CARBOXYLIC ACID METHYL ESTER-->3,4-DIHYDROXY-5-METHOXYBENZOIC ACID METHYL ESTER-->1,3-Benzenediol, 2,5-dimethoxy--->(4'-O-methyl)methyl gallate-->Octyl gallate-->5-METHYLPYROGALLOL-->Methyl 4,5-dimethoxy-3-hydroxybenzoate-->Methyl 3,4,5-trimethoxybenzoate-->7-(dimethylamino)-3,4-dihydroxy-1-(methoxycarbonyl)phenoxazin-5-ium chloride
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Methyl gallate(99-24-1).msds
Spectrum DetailBack Directory
[Spectrum Detail]

Methyl gallate(99-24-1)MS
Methyl gallate(99-24-1)1HNMR
Methyl gallate(99-24-1)13CNMR
Methyl gallate(99-24-1)IR1
Methyl gallate(99-24-1)IR2
Methyl gallate(99-24-1)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Methyl 3,4,5-trihydroxybenzoate, 99%(99-24-1)
[Alfa Aesar]

Methyl 3,4,5-trihydroxybenzoate, 98%(99-24-1)
[Sigma Aldrich]

99-24-1(sigmaaldrich)
[TCI AMERICA]

Methyl Gallate,>98.0%(GC)(T)(99-24-1)
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