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| Other Sizes |
| Targets |
2-Phenylpropionic acid primarily targets cyclooxygenase (COX) enzymes involved in prostaglandin synthesis. It inhibits both COX-1 and COX-2 activities, thereby reducing the production of inflammatory prostaglandins and thromboxanes from arachidonic acid. The compound also acts as a liver protein binder and plays a significant role in the metabolism of alpha-methylstyrene. Its derivatives have been shown to target pathways involved in insulin resistance and glucose metabolism, functioning as bifunctional multitarget hypoglycemic agents. Additionally, some derivatives interact with GABA pathways to suppress gastric acid secretion.
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| ln Vitro |
2-Phenylpropionic acid inhibits COX enzyme activity in cell-free systems, reducing prostaglandin synthesis. The compound demonstrates the ability to covalently bind to rat liver proteins in vitro. Derivatives of 2-phenylpropionic acid have shown hypoglycemic activities in experimental models, comparable to reference compounds such as vildagliptin. These derivatives act as bifunctional agents that reduce insulin resistance and exert incretin-mimetic effects. Some analogues also demonstrate gastric acid inhibition through mechanisms distinct from traditional antimuscarinics or H2-receptor antagonists, possibly involving central GABA pathways.
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| ln Vivo |
In animal models, 2-phenylpropionic acid derivatives have demonstrated significant biological activities. Bornyl derivatives of p-(benzyloxy)phenylpropionic acid showed hypoglycemic activities in mice comparable to vildagliptin. These compounds reduced insulin resistance, exerted incretin-mimetic effects, and corrected lipid metabolism disorders. The in vivo effects are complicated by chiral inversion, where the R(-)-isomers are metabolically converted to the active S(+)-isomers. 3-amino-3-phenylpropionic acid, a structural analogue of GABA, suppressed gastric acid secretion in rats through a unique mechanism possibly involving central regulation via GABA pathways.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for 2-phenylpropionic acid typically involve COX inhibition studies measuring prostaglandin synthesis suppression. Assays are performed using purified COX-1 and COX-2 enzymes in cell-free systems, with prostaglandin E2 production quantified by ELISA or similar detection methods. The compound’s covalent binding to liver proteins can be assessed using rat liver protein preparations followed by detection of bound adducts. Radiolabeled compound binding studies may be employed to determine binding affinity and specificity. IC50 values for enzyme inhibition are calculated from dose-response curves using appropriate positive controls such as ibuprofen.
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| Cell Assay |
In vitro cell-based assays for 2-phenylpropionic acid derivatives typically employ cell lines relevant to the target indication. For anti-inflammatory activity, LPS-stimulated macrophages are used to measure prostaglandin E2 and cytokine production following compound treatment. For hypoglycemic activity, insulin-sensitive cell lines such as adipocytes or hepatocytes are treated with compounds to assess glucose uptake and insulin signaling pathways. Cytotoxicity is evaluated using standard MTT or CCK-8 assays. Cells are cultured in appropriate media with 5% CO2 at 37°C, treated with varying concentrations of the compound for 24-72 hours, and analyzed for relevant biomarkers.
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| Animal Protocol |
In vivo animal studies for 2-phenylpropionic acid derivatives are conducted in rodent models. For antidiabetic evaluation, compounds are orally administered to diabetic or insulin-resistant mouse models, with blood glucose levels monitored over time. For anti-inflammatory assessment, carrageenan-induced paw edema models in rats are used, with compounds given orally or intraperitoneally prior to induction. For gastric acid inhibition studies, rats are treated with test compounds and gastric acid secretion is measured. Dosing regimens typically range from 10-100 mg/kg. Blood samples are collected at various time points for pharmacokinetic analysis and biomarker assessment.
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| ADME/Pharmacokinetics |
2-Phenylpropionic acid is a small molecule (MW 150.17 g/mol, C9H10O2) with favorable drug-like properties. As a carboxylic acid, it is expected to have moderate oral bioavailability. The compound undergoes metabolic chiral inversion, where the R(-)-isomer is converted to the active S(+)-isomer in vivo. It is metabolized primarily in the liver and covalently binds to rat liver proteins. The compound is an intermediate in alpha-methylstyrene metabolism. Derivatives of 2-phenylpropionic acid have demonstrated oral activity with hypoglycemic effects in mice. The compound is typically administered in formulations suitable for oral or parenteral delivery in research settings.
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| Toxicity/Toxicokinetics |
Toxicological evaluation of 2-phenylpropionic acid indicates its ability to covalently bind to rat liver proteins, suggesting potential for protein adduct formation. As an intermediate in alpha-methylstyrene metabolism, its toxicity profile is related to the metabolic pathway of this compound. The compound is classified as a reactive chemical that requires proper handling precautions. In research settings, it is used only for non-human scientific studies. The safety profile is generally consistent with other carboxylic acid NSAID precursors. Standard laboratory safety practices including appropriate personal protective equipment should be employed when handling this compound.
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| References | |
| Additional Infomation |
Hydratropic acid is a 2-arylpropionic acid with a phenyl group at the 2-position. It is a metabolite of the volatile hydrocarbon α-methylstyrene (AMS) and can be used as an exogenous metabolite in humans. Its function is related to phenylacetic acid. 2-Phenylacetic acid has been reported to exist in Hoya crassipes, Hoya pseudolanceolata, and other organisms with relevant data.
2-Phenylpropionic acid is the core structural scaffold for the 2-arylpropionic acid class of NSAIDs, which includes drugs such as ibuprofen. The S(+)-isomer is primarily responsible for pharmacological activity through prostaglandin synthesis inhibition, while the R(-)-isomer undergoes chiral inversion in vivo. Derivatives of this compound have been explored for diverse therapeutic applications including anti-inflammatory, analgesic, antidiabetic, and gastric acid inhibition. The compound serves as a valuable research tool in studies of NSAID pharmacology, chiral inversion mechanisms, and the development of novel multitarget therapeutic agents. All applications are limited to non-human research use only. |
| Molecular Formula |
C9H10O2
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|---|---|
| Molecular Weight |
150.1745
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| Exact Mass |
150.068
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| CAS # |
492-37-5
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| PubChem CID |
10296
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
260-262 ºC
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| Melting Point |
5 ºC
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| Flash Point |
148 ºC
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
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| Index of Refraction |
1.5215-1.5235
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| LogP |
1.85
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
11
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| Complexity |
137
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C(C([H])(C([H])([H])[H])C1C([H])=C([H])C([H])=C([H])C=1[H])=O
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| InChi Key |
YPGCWEMNNLXISK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H10O2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-7H,1H3,(H,10,11)
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| Chemical Name |
2-phenylpropanoic 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 |
| 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 : ≥ 100 mg/mL (~665.87 mM)
H2O : ~4.35 mg/mL (~28.97 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.65 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 (16.65 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 (16.65 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 100 mg/mL (665.87 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.6591 mL | 33.2956 mL | 66.5912 mL | |
| 5 mM | 1.3318 mL | 6.6591 mL | 13.3182 mL | |
| 10 mM | 0.6659 mL | 3.3296 mL | 6.6591 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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