| Size | Price | Stock | Qty |
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| 250mg |
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| 500mg |
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| 1g |
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| Targets |
Methyl 3,4-dihydroxybenzoate targets oxidative stress regulatory pathways, inflammatory response-related molecules, and apoptosis signaling proteins [1,2]
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| ln Vitro |
In A549 cells, methyl 3,4-dihydroxybenzoate (also known as methyl protocatechuate; protocatechuic acid methyl ester) reduces the toxicity of F- by modifying its bioavailability, intracellular calcium concentration, mitochondrial membrane integrity, and redox signaling[1].
Methyl 3,4-dihydroxybenzoate (10 μM–40 μM) dose-dependently protected A549 cells from fluoride-induced toxicity: 40 μM increased cell viability from 52% (fluoride alone) to 85% after 48 hours, as assessed by MTT assay [1] The compound (10 μM–40 μM) reduced fluoride-induced oxidative stress in A549 cells: 40 μM decreased intracellular reactive oxygen species (ROS) levels by 62%, malondialdehyde (MDA) content by 58%, and increased superoxide dismutase (SOD) activity by 45% and glutathione peroxidase (GSH-Px) activity by 53% [1] Methyl 3,4-dihydroxybenzoate (40 μM) inhibited fluoride-induced apoptosis in A549 cells: apoptotic rate decreased from 38% to 12% (Annexin V+/PI+), accompanied by a 2.3-fold increase in Bcl-2 protein expression, 65% reduction in Bax protein, and 70% decrease in cleaved caspase-3 levels (Western blot detection) [1] |
| ln Vivo |
Methyl 3,4-dihydroxybenzoate, also known as methyl protocatechuate (25 or 50 mg/kg bw/day), reduces oxidative stress and cellular F- accumulation. By reactivating RAGE and Nrf2 expression, methyl 3,4-dihydroxybenzoate slows the progression of inflammation and the fibrosis it causes[2].
In Wistar rats with fluoride-induced pulmonary toxicity (100 ppm NaF in drinking water for 8 weeks), oral administration of Methyl 3,4-dihydroxybenzoate (50 mg/kg, 100 mg/kg, q.d.) for 8 weeks dose-dependently alleviated lung injury [2] The 100 mg/kg dose reduced lung tissue MDA content by 63%, increased SOD activity by 58% and GSH-Px activity by 61%, and decreased myeloperoxidase (MPO) activity (inflammatory marker) by 65% [2] Methyl 3,4-dihydroxybenzoate (100 mg/kg) downregulated serum pro-inflammatory cytokines: TNFα levels decreased by 68% and IL-6 levels by 72%, and improved lung histopathology (reduced alveolar damage and inflammatory cell infiltration) [2] |
| Enzyme Assay |
Antioxidant enzyme activity assay: A549 cell lysates or rat lung tissue homogenates were incubated with assay buffers specific for SOD, GSH-Px, or catalase (CAT). For SOD, xanthine oxidase method was used to measure inhibition of superoxide anion; for GSH-Px, dithionitrobenzoic acid method was used to detect GSH oxidation; absorbance was measured at specific wavelengths to quantify enzyme activity [1,2]
Myeloperoxidase (MPO) activity assay: Rat lung tissue homogenates were mixed with assay buffer containing o-phenylenediamine and hydrogen peroxide. The reaction was conducted at 37°C for 30 minutes, and absorbance at 460 nm was measured to reflect MPO activity (inflammatory index) [2] |
| Cell Assay |
Cell viability assay: A549 cells were seeded in 96-well plates (5 × 10³ cells/well) and pre-treated with Methyl 3,4-dihydroxybenzoate (10 μM–40 μM) for 2 hours, then exposed to fluoride (200 μM) for 48 hours. MTT reagent was added, and absorbance at 570 nm was measured to calculate cell viability [1]
ROS detection assay: A549 cells were loaded with DCFH-DA fluorescent probe (20 μM) for 30 minutes, pre-treated with Methyl 3,4-dihydroxybenzoate (10 μM–40 μM) for 2 hours, then exposed to fluoride. ROS levels were quantified by flow cytometry and fluorescence microscopy [1] Apoptosis and Western blot assay: A549 cells were treated with Methyl 3,4-dihydroxybenzoate (40 μM) and fluoride for 48 hours. Apoptosis was detected by Annexin V-FITC/PI staining and flow cytometry; cell lysates were prepared for Western blot to detect Bcl-2, Bax, and cleaved caspase-3 protein levels [1] |
| Animal Protocol |
Fluoride-induced pulmonary toxicity rat model: Wistar rats (180–220 g) were randomized into 4 groups (n=6/group): control (normal drinking water), fluoride alone (100 ppm NaF in drinking water), low-dose drug (fluoride + 50 mg/kg Methyl 3,4-dihydroxybenzoate), high-dose drug (fluoride + 100 mg/kg Methyl 3,4-dihydroxybenzoate). The compound was dissolved in normal saline and administered by gavage once daily for 8 weeks. Rats were sacrificed, and serum and lung tissues were collected for biochemical analysis and histopathological examination [2]
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| Toxicity/Toxicokinetics |
In A549 cells, concentrations up to 40 μM of methyl 3,4-dihydroxybenzoate did not cause cytotoxicity (cell viability >95%) [1]. No significant changes in body weight, hematological parameters (white blood cells, red blood cells, platelets), or biochemical parameters (ALT, AST, BUN, creatinine) were observed in rats treated with methyl 3,4-dihydroxybenzoate (100 mg/kg, orally, once daily for 8 weeks). Histopathological examination of the liver, kidneys, and heart revealed no drug-related lesions [2].
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| References | |
| Additional Infomation |
Methyl 3,4-dihydroxybenzoate is a methyl ester formed by the condensation of the carboxyl group of 3,4-dihydroxybenzoic acid with methanol. It possesses dual functions of antioxidant, neuroprotective, and plant metabolism-enhancing properties. It is a methyl ester belonging to the catechol group. Functionally, it is related to 3,4-dihydroxybenzoic acid. Methyl 3,4-dihydroxybenzoate has been reported to be found in tea (Camellia sinensis), perilla (Perilla frutescens), and other organisms with relevant data. See also: Acai berry pulp (partial). Methyl 3,4-dihydroxybenzoate (protocatechuic acid methyl ester) is a widely distributed natural phenolic ester in plants [1,2]. Its mechanisms of mitigating fluoride toxicity include scavenging reactive oxygen species, enhancing antioxidant enzyme activity, inhibiting lipid peroxidation, downregulating pro-inflammatory cytokines, and inhibiting mitochondrial apoptosis pathway [1,2].
This compound has strong antioxidant and anti-inflammatory activities and has potential application value in reducing tissue damage caused by fluoride [1,2]. |
| Molecular Formula |
C8H8O4
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|---|---|
| Molecular Weight |
168.1467
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| Exact Mass |
168.042
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| CAS # |
2150-43-8
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| Related CAS # |
Methyl 3,4-dihydroxybenzoate-d3-1;2733147-54-9
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| PubChem CID |
287064
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| Appearance |
White to off-white solid
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
351.5±22.0 °C at 760 mmHg
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| Melting Point |
134-135°C
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| Flash Point |
148.5±15.8 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.588
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| LogP |
1.69
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
12
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| Complexity |
168
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O(C([H])([H])[H])C(C1C([H])=C([H])C(=C(C=1[H])O[H])O[H])=O
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| InChi Key |
CUFLZUDASVUNOE-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8O4/c1-12-8(11)5-2-3-6(9)7(10)4-5/h2-4,9-10H,1H3
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| Chemical Name |
methyl 3,4-dihydroxybenzoate
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| Synonyms |
Methyl 3,4-dihydroxybenzoate; Methyl protocatechuate; Protocatechuic acid methyl ester
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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 (~297.35 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.87 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 (14.87 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 (14.87 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 | 5.9471 mL | 29.7354 mL | 59.4707 mL | |
| 5 mM | 1.1894 mL | 5.9471 mL | 11.8941 mL | |
| 10 mM | 0.5947 mL | 2.9735 mL | 5.9471 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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