| Size | Price | Stock | Qty |
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| 100mg |
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| 500mg |
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| Other Sizes |
| Targets |
COX-2 Human Endogenous Metabolite; Leukotriene B4 12-hydroxydehydrogenase (LTB4DH) – Induces LTB4DH expression (synergistically with calycosin or formononetin) [3]
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| ln Vitro |
- In HepG2 cells, gallic acid (8 μg/mL) alone did not induce LTB4DH mRNA expression; but in combination with Radix Astragali extracts or calycosin (10 μg/mL) or formononetin (10 μg/mL), it synergistically induced LTB4DH expression after 24 h treatment [3]
- In human neutrophils, gallic acid (8 μg/mL) combined with calycosin (10 μg/mL) induced LTB4DH mRNA expression in a time-dependent manner (detectable after 6 h) [3] - In human neutrophils, gallic acid (8 μg/mL) alone showed weak LTB4DH induction; combination with calycosin (10 μg/mL) or formononetin (10 μg/mL) significantly increased LTB4DH mRNA expression (p < 0.001) [3] - Gallic acid (8 μg/mL) combined with calycosin (10 μg/mL) diminished LTB4 (100 nM)-induced neutrophil survival: after 18 h treatment, viable neutrophils decreased from 40.3% (LTB4 alone) to 27.7% (combination), comparable to untreated control (26.4%) [3] - Gallic acid (8 μg/mL) combined with calycosin (10 μg/mL) inhibited LTB4-induced neutrophil chemotaxis in a TransWell assay (pore size 8 μm) after 24 h pre-treatment; combination showed strongest inhibition against 10 nM and 100 nM LTB4 [3] Gallic acid is an antioxidant that has the ability to block COX-2[1]. The number of viable neutrophils after an 18-hour treatment with gallic acid drops sharply from 40.3% to 27.7%, which is quite similar to the 26.4% of neutrophils that were not treated. The myocytolysis caused by isoproterenol cannot be inhibited by gallic acid[3]. |
| ln Vivo |
- In isoproterenol-induced mouse model of myocardial infarction (male C57BL/6 mice, 6-8 weeks, 20-22 g), gallic acid (8 mg/kg/day, i.p. for 3 days) alone failed to attenuate isoproterenol-induced myocytolysis (H&E staining). However, combination with calycosin (40 mg/kg/day, i.p.) synergistically preserved cardiac morphology [3]
- Gallic acid alone (8 mg/kg/day, i.p.) showed inhibitory effect on isoproterenol-induced neutrophil infiltration (Ly6G immunohistochemistry), but combination with calycosin (40 mg/kg/day) synergistically reduced infiltration (p < 0.05) [3] - Gallic acid alone did not significantly reduce isoproterenol-induced increase in myeloperoxidase (MPO) activity; combination with calycosin significantly reduced MPO activity (p < 0.05) [3] - Gallic acid alone (8 mg/kg/day) effectively reduced isoproterenol-induced increase in malondialdehyde (MDA) levels (p < 0.05); combination with calycosin also showed significant reduction (p < 0.01) [3] There is no significant difference seen between the food consumption (2.6±0.08 g/day, p=0.69) and body weight (2.5±0.69 g, p=0.76) of the Gallic acid group and the control group (food intake: 2.41± 0.14 g/day and body weight: 2.83±0.84 g/day). After two weeks of treatment, there is a considerable improvement in the blood glucose tolerance of the gallic acid group. Following a two-week treatment period, the blood glucose tolerance of the Gallic acid group is likewise considerably better at 90 and 120 minutes (p<0.05) than that of the control group. Compared to the control group (1.08±0.20 mM), the serum triglyceride concentration in the gallic acid group (0.67±0.03 mM, p<0.05) is much lower. The control group's total cholesterol concentration (3.19±0.27 mM) and the gallic acid group's (3.01±0.18 mM) concentrations are comparable[2]. |
| Cell Assay |
- HepG2 cells were seeded in 6-well plates overnight and treated with gallic acid (8 μg/mL) alone or in combination with herbal fractions, calycosin (10 μg/mL), or formononetin (10 μg/mL) for 24 h. Total RNA was extracted and RT-PCR was performed for LTB4DH mRNA detection [3]
- Human neutrophils were freshly isolated and treated with gallic acid (8 μg/mL) and calycosin (10 μg/mL) in combination for 0, 3, 6, 9, and 18 h. RT-PCR was used to detect LTB4DH mRNA expression [3] - Human neutrophils were treated with LTB4 (100 nM) alone or combined with gallic acid (8 μg/mL) and calycosin (10 μg/mL) for 3, 6, 9, and 18 h. Apoptosis was analyzed by Annexin V-FITC/PI staining and flow cytometry [3] - Human neutrophils were pre-treated with gallic acid (8 μg/mL) and calycosin (10 μg/mL) individually or in combination for 24 h. Cells were labeled with Calcein AM (5 μM) and chemotaxis was assayed using TransWell plates (8 μm pore) toward LTB4 (0, 10, 100 nM) for 3 h. Migrated cells were quantified by fluorescence (ex/em 485/530 nm) [3] |
| Animal Protocol |
- Male C57BL/6 mice (6-8 weeks, 20-22 g) were randomly divided into 5 groups (n=6): Control (saline + vehicle, i.p., 0.5 mL/day for 3 days); ISO group (saline i.p. day1, then isoproterenol 100 mg/kg/day s.c. day2-3); ISO+GA (gallic acid 8 mg/kg/day i.p. for 3 days + isoproterenol 100 mg/kg/day s.c. day2-3); ISO+CA (calycosin 40 mg/kg/day i.p. for 3 days + isoproterenol day2-3); ISO+CA+GA (calycosin 40 mg/kg/day + gallic acid 8 mg/kg/day i.p. for 3 days + isoproterenol day2-3). Isoproterenol dissolved in 0.9% saline; gallic acid dissolved in 5% ethanol in 0.9% saline. Isoproterenol injected 10 min after drug injection [3]
- Half of animals from each group were euthanized by pentobarbital (200 mg/kg, i.p.) and fixed with 4% paraformaldehyde. Heart tissues were paraffin-embedded, sectioned (5 μm), and stained with H&E for histopathology [3] - For immunohistochemistry, cardiac sections were boiled in citrate buffer (pH=6) for 15 min, blocked in 5% goat serum for 1 h, probed with anti-Ly6G primary antibody (1:50) at 4°C overnight, then incubated with FITC-conjugated secondary antibody (1:200) for 1.5 h at room temperature. Images acquired by laser scanning microscope [3] - Frozen hearts were homogenized in PBS (pH 6.0) with 0.5% hexadecyltrimethylammonium hydroxide, centrifuged at 12,000 rpm for 20 min at 4°C. Supernatants were used for MPO activity and MDA level assays. Protein concentration determined by Bio-Rad protein assay [3] |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Easily absorbed from the gastrointestinal tract. After administration to rabbits, most of it is excreted unchanged in the urine, but small amounts are also excreted as pyrogallic acid and 4-methoxy-3,5-dihydroxybenzoic acid. Metabolism/Metabolites Gallic acid…is methylated to 3,5-dihydroxy-4-methoxybenzoic acid by catechol-O-methyltransferase. This enzyme is located in the sol component and is present in the liver, kidneys, skin, blood cells, glandular tissue, and nerve fibers. It requires S-adenosylmethionine as a methyl donor, as well as Mg++ or other divalent ions. After administration to rabbits, most of it is excreted unchanged in the urine, but small amounts are also excreted as pyrogallic acid and 4-methoxy-3,5-dihydroxybenzoic acid. After metabolism by intestinal flora, gallic acid is decarboxylated to pyrogallic acid. Gallic acid is converted into gallic acid-β-D-glucuronide in rabbits. /Excerpt from table/ |
| References |
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| Additional Infomation |
- Gallic acid was previously isolated from Radix Paeoniae Rubra through a bioactivity-guided fractionation procedure [3]
- Gallic acid alone does not induce LTB4DH expression; it requires combination with calycosin or formononetin for synergistic induction [3] - The combination of gallic acid and calycosin represents a novel “multidrugs on one target” strategy for treating neutrophil-mediated myocardial injury [3] |
| Molecular Formula |
C7H8O6
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|---|---|
| Molecular Weight |
188.13
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| Exact Mass |
188.032
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| CAS # |
5995-86-8
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| Related CAS # |
Gallic acid;149-91-7
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| PubChem CID |
24721416
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| Appearance |
White to off-white solid powder
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| Density |
1.694
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| Boiling Point |
596.6ºC at 760 mmHg
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| Melting Point |
252 °C (dec.)(lit.)
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| Flash Point |
250 °C
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| LogP |
0.437
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
13
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| Complexity |
169
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=C(C=C(C(=C1O)O)O)C(=O)O.O
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| InChi Key |
IUTKPPDDLYYMBE-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H6O5.H2O/c8-4-1-3(7(11)12)2-5(9)6(4)10;/h1-2,8-10H,(H,11,12);1H2
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| Chemical Name |
3,4,5-trihydroxybenzoic acid;hydrate
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| Synonyms |
Gallic acid monohydrate; 3,4,5-Trihydroxybenzoic acid monohydrate; Gallic acid, monohydrate; UNII-48339473OT; 5995-86-8;
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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 : 50 mg/mL (265.77 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.29 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 (13.29 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 (13.29 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 | 5.3155 mL | 26.5774 mL | 53.1547 mL | |
| 5 mM | 1.0631 mL | 5.3155 mL | 10.6309 mL | |
| 10 mM | 0.5315 mL | 2.6577 mL | 5.3155 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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