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Methyl gallate

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-M1004

  • Specification : 98%

  • CAS number : 99-24-1

  • Formula : C8H8O5

  • Molecular Weight : 184.15

  • PUBCHEM ID : 7428

  • Volume : 20mg

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Catalogue Number

BF-M1004

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

184.15

Appearance

Off-white crystalline powder

Botanical Source

Paeonia lactiflora

Structure Type

Phenolics

Category

Standards;Natural Pytochemical;API

SMILES

COC(=O)C1=CC(=C(C(=C1)O)O)O

Synonyms

Methyl gallate/3,4,5-Trihydroxybenzoic acid methyl ester/Benzoic acid, 3,4,5-trihydroxy-, methyl ester/Methyl 3,4,5-trihydroxybenzoate

IUPAC Name

methyl 3,4,5-trihydroxybenzoate

Density

1.5±0.1 g/cm3

Solubility

Methanol; DMSO

Flash Point

190.8±20.8 °C

Boiling Point

450.1±40.0 °C at 760 mmHg

Melting Point

201-204 °C

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2918290000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:99-24-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30314293

Abstract

In the present paper, methyl gallate (MeG), a simple polyphenol and also the monomer of hydrolysable tannins, was selected to study the deprotonation process for the hydroxyls of the galloyl group by the combined use of spectroscopic measurements and quantum chemical calculations. The results of quantum chemical calculations show that the deprotonated form of methyl gallate undergoes the para-quinoid localization in the benzene ring, compared with free methyl gallate. The predicted spectra obtained from the free and deprotonated methyl gallate models are in agreement with the experimental UV-visible (UV-vis) absorption spectra. In the same way, the vibrational spectra of the para-quinoid MeG models validate the proposed mechanism of the deprotonation of MeG molecule. The pH influence on the deprotonation reaction and oxidization of phenolic groups has been also investigated. The pKa values of MeG were evaluated using the chemometric modeling method. The first acid dissociation constant (pKa1) for MeG was evaluated to be 4.20 ± 0.01, and the second one (pKa2) was 10.78 ± 0.06.

KEYWORDS

methyl gallate; pH titration; polyphenol; spectroscopic method; tannins

Title

Deprotonation Mechanism of Methyl Gallate: UV Spectroscopic and Computational Studies.

Author

Zhang L1, Liu Y2, Wang Y3.

Publish date

2018 Oct 11

PMID

28272351

Abstract

In the field of bone research, various natural derivatives have emerged as candidates for osteoporosis treatment by targeting abnormally elevated osteoclastic activity. Methyl gallate, a plant-derived phenolic compound, is known to have numerous pharmacological effects against inflammation, oxidation, and cancer. Our purpose was to explore the relation between methyl gallate and bone metabolism. Herein, we performed screening using methyl gallate by tartrate resistant acid phosphatase (TRAP) staining and revealed intracellular mechanisms responsible for methyl gallate-mediated regulation of osteoclastogenesis by Western blotting and quantitative reverse transcription polymerase chain reaction (RT-PCR). Furthermore, we assessed the effects of methyl gallate on the characteristics of mature osteoclasts. We found that methyl gallate significantly suppressed osteoclast formation through Akt and Btk-PLCγ2-Ca2+ signaling. The blockade of these pathways was confirmed through transduction of cells with a CA-Akt retrovirus and evaluation of Ca2+ influx intensity (staining with Fluo-3/AM). Indeed, methyl gallate downregulated the formation of actin ring-positive osteoclasts and resorption pit areas. In agreement with in vitro results, we found that administration of methyl gallate restored osteoporotic phenotype stimulated by acute systemic injection of lipopolysaccharide in vivo according to micro-computed tomography and histological analysis. Our data strongly indicate that methyl gallate may be useful for the development of a plant-based antiosteoporotic agent.

KEYWORDS

Akt; Ca2+ signaling; bone resorption; methyl gallate; osteoclast; osteoporosis

Title

Methyl Gallate Inhibits Osteoclast Formation and Function by Suppressing Akt and Btk-PLCγ2-Ca2+ Signaling and Prevents Lipopolysaccharide-Induced Bone Loss.

Author

Baek JM1, Kim JY2, Lee CH3,4, Yoon KH5,6, Lee MS7,8.

Publish date

2017 Mar 7

PMID

29116460

Abstract

Methyl gallate is a gallotannin widely distributed in nature. Previous studies have demonstrated its antioxidant, anti-inflammatory, antimicrobial and anti-tumor activities. In the present study, the activity of methyl gallate on experimental models of inflammatory bowel disease has been investigated. Experimental colitis was induced in Sprague-Dawley rats through the intracolonic instillation of an acetic acid solution (2 mL, 4% v/v). Methyl gallate (100 and 300 mg/kg, p.o.) and the reference drug mesalazine (100 mg/kg, p.o.) were tested. Methyl gallate induced a significant reduction in the colon weight/length ratio and macroscopic lesion score. Besides, the malondialdehyde content and the GSSG/GSH ratio were remarkably decreased. Furthermore, the administration of methyl gallate reduced the expression of COX2, IL-6, TNFα and the severity of microscopic tissue damage induced by acetic acid, while the mean goblet cell density was significantly higher in both the group treated with methyl gallate and the one treated with mesalazine, in comparison with untreated animals. The Na+K+ATPase pump activity was recovered in treated groups (control: 827.2 ± 59.6, colitis: 311.6 ± 54.8, methyl gallate 100 mg/kg: 642.2 ± 175.0, methyl gallate 300 mg/kg: 809.7 ± 100.6, mesalazine: 525.3 ± 81.7). Methyl gallate was also found to induce a significant reduction in the castor oil-induced intestinal motility in Swiss mice, decreasing the peristalsis by 74.5 and 58.82% at 100 and 300 mg/kg p.o., respectively. This compound also antagonized the jejunum contractions induced by Ach and CaCl2. This study demonstrates that methyl gallate exerts beneficial effects in a preclinical model of intestinal disorders.

KEYWORDS

Antispasmodic effect; Experimental colitis; Intestinal motility; Methyl gallate

Title

Potential usefulness of methyl gallate in the treatment of experimental colitis.

Author

Anzoise ML1, Basso AR1, Del Mauro JS1, Carranza A2, Ordieres GL1, Gorzalczany S3.

Publish date

2018 Jun


Description :

Methyl gallate is a plant phenolic with antioxidant, anticancer, and anti-inflammatory activities. Methyl gallate also shows bacterial inhibition activity.