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.

Physicochemical Properties

Molecular Formula	C8H8O5
Molecular Weight	184.1461
Exact Mass	184.037
CAS #	99-24-1
PubChem CID	7428
Appearance	White to off-white solid powder
Density	1.5±0.1 g/cm3
Boiling Point	450.1±40.0 °C at 760 mmHg
Melting Point	201-204 °C
Flash Point	190.8±20.8 °C
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.631
LogP	1.54
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Heavy Atom Count	13
Complexity	181
Defined Atom Stereocenter Count	0
InChi Key	FBSFWRHWHYMIOG-UHFFFAOYSA-N
InChi Code	InChI=1S/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3
Chemical Name	InChI=1S/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3
Synonyms	Gallincin; NSC 363001; NSC-363001; NSC363001;
HS Tariff Code	2934.99.9001
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)

Biological Activity

Targets	HIV-1
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].
References	[1]. Inhibitory effect of methyl gallate and gallic acid on oral bacteria. J Microbiol. 2008 Dec;46(6):744-50. [2]. Protective effect of methyl gallate from Toona sinensis (Meliaceae) against hydrogen peroxide-induced oxidative stress and DNA damage in MDCK cells. Food Chem Toxicol. 2004 May;42(5):843-50. [3]. Methyl gallate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells. J Immunol. 2010 Dec 1;185(11):6698-705. [4]. First report on isolation of methyl gallate with antioxidant, anti-HIV-1 and HIV-1 enzyme inhibitory activities from a mushroom (Pholiota adiposa). Environ Toxicol Pharmacol. 2014 Mar;37(2):626-37.
Additional Infomation	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. Methyl gallate has been reported in Camellia sinensis, Paeonia emodi, and other organisms with data available. See also: Paeonia lactiflora root (part of).

Solubility Data

Solubility (In Vitro)

DMSO : 36~100 mg/mL ( 195.49~543.04 mM )

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. 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. 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 corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

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.