| Size | Price | Stock | Qty |
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| 10g |
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| 25g |
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| 50g |
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| 100g |
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| 200g |
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| Other Sizes |
Purity: ≥98%
Methyl gallate (Gallincin; NSC 363001), the methyl ester of gallic acid, is a plant phenolic with important biological activities such as antioxidant, anticancer, and anti-inflammatory propertes. Methyl gallate also shows antibacterial activity.
| Targets |
HIV-1
Methyl gallate exhibits antimicrobial activity against a range of oral bacteria, with minimal inhibitory concentration (MIC) values determined for various cariogenic and periodontopathic bacteria. |
|---|---|
| ln Vitro |
At a low dosage of methyl gallate (MIC=1 mg/mL), A. viscosus growth is totally inhibited. While Lactobacillus species are completely inhibited at a relatively high concentration (MIC=8 mg/mL), S. mutans and S. sobrinus exhibit intermediate sensitivity to methyl gallate (MIC=2-4 mg/mL)[1]. Cells exposed to a brief H2O2 treatment may experience less lipid peroxidation when methyl gallate is added at a concentration of 100 mM. Furthermore, cells treated with methyl gallate were able to stop intracellular glutathione (GSH) from being depleted after three hours of exposure to 8.0 mM H2O2[2]. Methyl gallate prevents effector CD4+ T cells from being suppressed by Treg cells and prevents Treg migration into the tumor environment. Furthermore, methyl gallate significantly reduces the expression of forkhead box P3 (Foxp3)[3].
Methyl gallate showed inhibitory effects on the growth of cariogenic bacteria: MIC for Actinomyces viscosus = 1 mg/ml; MIC for Streptococcus mutans and Streptococcus sobrinus = 2-4 mg/ml; MIC for Lactobacillus spp. = 8 mg/ml. - Methyl gallate also inhibited periodontopathic bacteria: MIC for Porphyromonas gingivalis, Fusobacterium nucleatum, Prevotella loescheii, and Tannerella forsythia = 1 mg/ml. - Methyl gallate significantly inhibited in vitro plaque accumulation (artificial biofilm formation) by S. mutans in a concentration-dependent manner. At 1 mg/ml, it reduced biofilm wet weight from 198.5 ± 51.8 mg (control) to 41.6 ± 11.8 mg; at 4 mg/ml, reduction was to 1.7 ± 0.6 mg. - Methyl gallate significantly inhibited in vitro adherence of S. mutans in a dose-dependent manner. At 1 mg/ml, inhibition was 87.2 ± 0.3% of control; at 2 mg/ml, 88.5 ± 0.5%; at 4 mg/ml, 94.4 ± 1.2%. - In cytotoxicity assays using human oral epithelial KB cells, Methyl gallate at concentrations up to 8 mg/ml for 24 hours did not show obvious cytotoxic effects. Cell viabilities were 100.0 ± 6.0%, 110.0 ± 10.9%, 95.0 ± 1.6%, and 90.0 ± 7.2% of control at 1, 2, 4, and 8 mg/ml, respectively. |
| ln Vivo |
In C57BL/6 mice bearing subcutaneous EL-4 lymphoma, intraperitoneal administration of Methyl gallate (200 µg per mouse, three times per week from day 5 post-tumor inoculation) significantly reduced tumor growth and prolonged survival (approximately 20% survival at 90 days vs. all controls dying between 38-70 days).
- The antitumor effect of Methyl gallate was dependent on the presence of T cells. In T cell-deficient nu/nu mice, Methyl gallate did not reduce tumor growth or prolong survival. - In Treg-depleted mice (achieved by anti-CD25 antibody administration prior to tumor inoculation), Methyl gallate did not provide additional benefit in tumor growth inhibition or survival, indicating that its antitumor activity is mediated through modulation of Treg cells. - In tumor-bearing Foxp3ᴱᴳFP mice, Methyl gallate treatment significantly reduced the proportion of splenic CD4⁺CD25⁺Foxp3ʰⁱᵍʰ Treg cells and decreased tumor-infiltrating CD25⁺Foxp3⁺ Treg cells by 42.9% compared to controls. - Confocal microscopy confirmed a significant decrease in Foxp3⁺ cell infiltration within tumors from Methyl gallate-treated mice. |
| Enzyme Assay |
HIV-1 reverse transcriptase inhibitory activity was assessed using an ELISA kit. The assay measured the ability of methyl gallate to inhibit the enzymatic activity of HIV-1 RT in a concentration-dependent manner. Azidothymidine was used as a positive control. [4]
HIV-1 integrase inhibitory activity was tested in vitro using a 3′-processing model. Recombinant HIV-1 integrase was incubated with substrate DNA, and the inhibition of DNA cleavage/integration was measured. Raltegravir was used as a positive control. [4] HIV-1 protease inhibitory activity was evaluated using an E. coli expressed recombinant HIV-1 PR. The assay detected inhibitory effects by observing bacterial growth curves in the presence of the enzyme inducer IPTG. Pepstatin A was used as a positive control. [4] |
| Cell Assay |
Antibacterial Activity Assay (Broth Microdilution Method): Bacterial strains (cariogenic and periodontopathic) in logarithmic growth phase were inoculated into culture medium containing serial dilutions of Methyl gallate in 96-well plates. The final inoculum concentrations were 5 × 10^5 CFU/ml for cariogenic bacteria and 1 × 10^6 CFU/ml for periodontopathic bacteria. Plates were incubated aerobically or anaerobically at 37°C for 24 hours. Bacterial growth was measured by optical density at 600 nm. The MIC was defined as the lowest concentration that restricted growth to an absorbance ≤ 0.1.
- Plaque Accumulation Assay (Beaker-Wire Test): Methyl gallate at various concentrations (0.0625, 0.25, 1, 4 mg/ml) was added to BHI medium containing 5% sucrose, 0.5% yeast extract, and 0.1 M MES buffer (pH 6.5). S. mutans (1 × 10^6 CFU/ml) was inoculated. Stainless steel wires were immersed in the beakers and incubated with slow agitation at 37°C for 24 hours. The wires were weighed, and plaque accumulation was determined by subtracting the initial wire weight. - Adherence Inhibition Assay: BHI broth containing 2% sucrose and various concentrations of Methyl gallate (0.0625 to 4 mg/ml) was inoculated with overnight cultures of S. mutans in microtiter plates. After incubation, non-adherent cells were removed by rinsing. Adherent bacteria were stained with 0.1% crystal violet, extracted with ethanol, and measured at 595 nm. - Cytotoxicity Assay (MTT Assay): Human oral epithelial KB cells were treated with Methyl gallate (1-8 mg/ml) for 24 hours. MTT solution (5 mg/ml) was added, and plates were incubated for 4 hours at 37°C under 5% CO2. Formazan crystals were dissolved with DMSO, and absorbance was measured at 540 nm. |
| Animal Protocol |
Tumor Model: C57BL/6, Foxp3ᴱᴳFP C57BL/6, or nu/nu mice were inoculated subcutaneously in the right flank with 1 × 10⁴ EL-4 lymphoma cells.
- Treg Depletion: For some experiments, anti-CD25 antibody (clone PC61, 500 µg) was administered intraperitoneally on days -3, -2, and -1 relative to tumor inoculation to deplete CD4⁺CD25⁺ Treg cells. - Drug Administration: Methyl gallate (200 µg per mouse) or saline (control) was administered intraperitoneally three times per week, starting from day 5 after tumor inoculation. - Tumor and Tissue Analysis: Tumor volume was measured approximately three times per week. Mice were sacrificed at day 21 post-inoculation. Splenocytes and single-cell suspensions from tumors (prepared by enzymatic digestion with collagenase A, hyaluronidase, and DNase I) were analyzed by flow cytometry for Treg cell populations. - Confocal Microscopy: Tumor tissues from Foxp3ᴱᴳFP mice were embedded, frozen, sectioned (20 µm thick), and analyzed by confocal microscopy to visualize and quantify Foxp3ᴱᴳFP-positive (Treg) cell infiltration. |
| Toxicity/Toxicokinetics |
MTT assay results showed that methyl gallate at a concentration as high as 8 mg/ml had no significant cytotoxic effect on KB cells within 24 hours.
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| References |
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| Additional Infomation |
Methyl gallate (3,4,5-trihydroxybenzoate) is a gallic acid ester obtained by the condensation of gallic acid and methanol. It possesses antioxidant, antitumor, antibacterial, and anti-inflammatory properties. It is a plant metabolite with anti-inflammatory and antioxidant effects. Methyl gallate has been reported to be found in tea trees (Camellia sinensis), peonies (Paeonia emodi), and several other organisms with relevant data. See also: Paeonia lactiflora root (part). Methyl gallate is a major component of gallnut (Galla rhois), a traditional herb. It exhibits antibacterial activity against both cariogenic and periodontal pathogens. It inhibits the formation and adhesion of Streptococcus mutans biofilms, which are key processes in plaque and dental caries formation. This study demonstrates that methyl gallate exhibits a stronger inhibitory effect on bacterial growth and biofilm formation compared to gallic acid. This research suggests that methyl gallate, due to its antibacterial and anti-biofilm properties and low cytotoxicity to oral cells, may be an effective candidate drug for controlling dental caries and periodontal disease. Epithelial cells.
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| Molecular Formula |
C8H8O5
|
|---|---|
| Molecular Weight |
184.1461
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| Exact Mass |
184.037
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| CAS # |
99-24-1
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| PubChem CID |
7428
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
450.1±40.0 °C at 760 mmHg
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| Melting Point |
201-204 °C
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| Flash Point |
190.8±20.8 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.631
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| LogP |
1.54
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
13
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| Complexity |
181
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
FBSFWRHWHYMIOG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3
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| Chemical Name |
InChI=1S/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3
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| Synonyms |
Gallincin; NSC 363001; NSC-363001; NSC363001;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : 36~100 mg/mL ( 195.49~543.04 mM )
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.58 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.58 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (13.58 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.4304 mL | 27.1518 mL | 54.3036 mL | |
| 5 mM | 1.0861 mL | 5.4304 mL | 10.8607 mL | |
| 10 mM | 0.5430 mL | 2.7152 mL | 5.4304 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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