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| Targets |
Hydroxytoluic acid acts primarily as a modulator of lipid metabolism and the fibrinolytic system. As a salicylate derivative, it is believed to exert its effects through the inhibition of prostaglandin synthesis, similar to other salicylates, which have analgesic, antipyretic, and anti-inflammatory activities. Its antilipidemic properties are evidenced by its ability to lower plasma free fatty acids and cholesterol levels. The compound also activates the fibrinolytic system in human plasma, contributing to its antithrombotic potential. It may also target cyclooxygenase (COX) enzymes, given its structural similarity to salicylic acid.
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| ln Vitro |
Hydroxytoluic acid demonstrates significant fibrinolytic activity in human plasma by activating the fibrinolytic system. As a salicylate derivative, it may also inhibit prostaglandin synthesis through COX inhibition, which would contribute to its anti-inflammatory and analgesic effects. Its antilipidemic activity has been demonstrated by its ability to lower plasma free fatty acid and cholesterol levels. These in vitro activities support its potential use in cardiovascular and metabolic research.
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| ln Vivo |
Hydroxytoluic acid has been shown to lower plasma free fatty acid and cholesterol levels in vivo. Its long-acting salicylate properties suggest sustained biological activity. The compound's ability to activate the fibrinolytic system in human plasma indicates potential antithrombotic effects in vivo. As a salicylate derivative, it may also exhibit analgesic and antipyretic activities similar to other compounds in this class. However, detailed in vivo pharmacokinetic and pharmacodynamic data are limited.
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| Enzyme Assay |
The in vitro enzyme activity of Hydroxytoluic acid can be assessed by measuring its effects on the fibrinolytic system. Human plasma is incubated with the compound, and fibrinolytic activity is measured by monitoring the lysis of fibrin clots or by assaying for plasminogen activator activity. For COX inhibition studies, enzyme assays using purified COX-1 and COX-2 can be performed, where the production of prostaglandins from arachidonic acid is measured in the presence of the compound.
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| Cell Assay |
In vitro cellular experiments for Hydroxytoluic acid involve treating relevant cell lines, such as hepatocytes or endothelial cells, with the compound. The effects on lipid metabolism can be assessed by measuring the uptake and oxidation of fatty acids, as well as the expression of genes involved in cholesterol synthesis and metabolism. Its effects on the fibrinolytic system can be studied in endothelial cell cultures by measuring the production of tissue plasminogen activator (tPA) and plasminogen activator inhibitor-1 (PAI-1).
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| Animal Protocol |
In vivo animal experiments for Hydroxytoluic acid would involve administering the compound to animal models of hyperlipidemia or thrombosis. Blood samples would be collected to measure plasma free fatty acid, cholesterol, and triglyceride levels. Fibrinolytic activity could be assessed by measuring clot lysis time or by assaying for plasminogen activator activity in plasma. The compound's effects on platelet aggregation and thrombus formation could also be evaluated.
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| ADME/Pharmacokinetics |
Hydroxytoluic acid (3-Methylsalicylic acid) has a molecular weight of 152.15 g/mol and a molecular formula of C8H8O3. It is a small molecule that is soluble in organic solvents. As a salicylate derivative, it is expected to be absorbed from the gastrointestinal tract and metabolized in the liver. However, detailed pharmacokinetic parameters such as bioavailability, half-life, and volume of distribution are not extensively characterized in the available literature.
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| Toxicity/Toxicokinetics |
The toxicological profile of Hydroxytoluic acid is characteristic of salicylate derivatives. At therapeutic doses, salicylates are generally well-tolerated, but high doses can cause gastrointestinal irritation, bleeding, and tinnitus. The compound is for research use only and is not intended for human therapeutic use. Standard safety precautions should be followed when handling this compound.
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| References |
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| Additional Infomation |
3-Methylsalicylic acid is a monohydroxybenzoic acid composed of salicylic acid with a methyl group attached at the 3-position. It is a bacterial xenobiotic metabolite functionally related to salicylic acid. It has been reported to be found in Osmanthus fragrans, Stocksia brahuica, and other organisms with relevant data. Hydroxybenzoic acid is a long-acting salicylic acid derivative with lipid-lowering effects. Studies have shown that hydroxybenzoic acid can reduce plasma free fatty acid and cholesterol levels.
Hydroxytoluic acid (3-Methylsalicylic acid) is a long-acting salicylate derivative with antilipidemic properties. It has been shown to lower plasma free fatty acid and cholesterol levels and exhibits significant fibrinolytic activity in human plasma. The compound is used as an analytical reference standard in various research applications. It is also known as o-Cresotic acid and is available from various chemical suppliers for research purposes. |
| Molecular Formula |
C8H8O3
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|---|---|
| Molecular Weight |
152.15
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| Exact Mass |
152.047
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| CAS # |
83-40-9
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| PubChem CID |
6738
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| Appearance |
Off-white to pink solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
293.2±28.0 °C at 760 mmHg
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| Melting Point |
98-100 °C(lit.)
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| Flash Point |
145.4±20.5 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.600
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| Source |
Endogenously produced metabolite
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| LogP |
2.52
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
155
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(O)C1=CC=CC(C)=C1O
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| InChi Key |
WHSXTWFYRGOBGO-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8O3/c1-5-3-2-4-6(7(5)9)8(10)11/h2-4,9H,1H3,(H,10,11)
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| Chemical Name |
2-hydroxy-3-methylbenzoic acid
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| Synonyms |
NSC17561; NSC 17561; Hydroxytoluic acid
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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 Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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 : ≥ 1.6 mg/mL (~10.52 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (32.86 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (50.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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: ≥ 5 mg/mL (32.86 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 DMSO stock solution (50.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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: ≥ 5 mg/mL (32.86 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 DMSO stock solution (50.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.5725 mL | 32.8623 mL | 65.7246 mL | |
| 5 mM | 1.3145 mL | 6.5725 mL | 13.1449 mL | |
| 10 mM | 0.6572 mL | 3.2862 mL | 6.5725 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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