| Size | Price | Stock | Qty |
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| 25g |
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| Other Sizes |
| Targets |
Type II 17beta-hydroxysteroid dehydrogenase (potential target). Phenylpropiolic acid has been tested as an inhibitor of type II 17beta-hydroxysteroid dehydrogenase for the treatment of osteoporosis. It is also an enzyme extinguishing agent used in palladium-catalyzed decarboxylation coupling reactions. As a click chemistry reagent, it targets azide-containing molecules in chemical reactions (CuAAc). Its endogenous role and specific molecular targets in vivo are not well-defined.
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| ln Vitro |
Phenylpropiolic acid is a click chemistry reagent that contains an alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing azide groups. It is also an enzyme extinguishing agent used in palladium-catalyzed decarboxylation coupling reactions. In enzyme inhibition studies, it has been tested as an inhibitor of type II 17beta-hydroxysteroid dehydrogenase. It may also have antibacterial activity. The compound is an endogenous metabolite and a phenylpropanoid natural product. However, detailed IC₅0 and potency values are not widely reported in the search results.
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| ln Vivo |
Phenylpropiolic acid is an endogenous metabolite present in plants, where it is involved in plant resistance pathways, synthesizing antibiotic compounds, and producing signals implicated in the mounting of plant resistance. It has also been tested as an inhibitor of type II 17beta-hydroxysteroid dehydrogenase for the treatment of osteoporosis, suggesting potential in vivo effects on steroid metabolism and bone health. Phenylpropiolic acid derivatives have shown promising applications in antimicrobials, with antibacterial activity against foodborne pathogens like Listeria monocytogenes. However, detailed in vivo studies in mammalian systems are limited. It is also used as a key intermediate in the synthesis of anti-cancer drugs.
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| Enzyme Assay |
For click chemistry (CuAAc) applications, dissolve Phenylpropiolic acid in DMSO or DMF at 10-100 mM. Prepare an azide-containing compound in the same solvent. Add copper(II) sulfate (CuSO4, 0.5-1 mM) and a reducing agent such as sodium ascorbate (2-10 mM). Incubate the reaction mixture at room temperature or 37degC for 1-24 hours. Monitor the reaction by TLC, HPLC, or LC-MS. The product is the 1,4-disubstituted 1,2,3-triazole. For enzyme assays, pre-incubate the compound with type II 17beta-hydroxysteroid dehydrogenase enzyme and measure activity using a spectrophotometric or fluorogenic substrate. However, detailed assay protocols for enzyme inhibition are not provided in the search results.
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| Cell Assay |
For cell-based studies, Phenylpropiolic acid can be used to study alkyne-azide cycloaddition in live cells (bioorthogonal chemistry) after azide labeling of biomolecules. For antibacterial testing, culture bacteria (e.g., Listeria monocytogenes) in appropriate medium. Treat with Phenylpropiolic acid at concentrations ranging from 10-1000 uM for 24 hours. Measure bacterial growth by OD₆00 or by colony-forming unit (CFU) counting. For cytotoxicity studies, culture mammalian cells (e.g., cancer cells) and treat with Phenylpropiolic acid (1-100 uM) for 24-72 hours, then measure cell viability by MTT or CCK-8 assay. The compound is used as a key intermediate in the synthesis of anticancer drugs, suggesting potential antiproliferative activity.
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| Animal Protocol |
For in vivo antimicrobial studies, infect mice with Listeria monocytogenes or other susceptible pathogens. Administer Phenylpropiolic acid by oral gavage or intraperitoneal injection at appropriate doses (to be determined, likely 10-100 mg/kg). Monitor survival, bacterial load in tissues (spleen, liver), and inflammatory markers. For osteoporosis studies, administer the compound to ovariectomized rats (a model of postmenopausal osteoporosis) to assess its effects on bone mineral density and bone turnover markers. The compound has been tested as an inhibitor of type II 17beta-hydroxysteroid dehydrogenase for the treatment of osteoporosis. However, detailed in vivo dosing and efficacy data are not provided in the search results.
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| ADME/Pharmacokinetics |
Phenylpropiolic acid: Molecular formula C₉H₆O2 (or C₆H₅C≡CCOOH). Molecular weight: 146.14 g/mol. Appearance: Solid. Melting point: 136-138degC. Boiling point: 302.6+/-15.0 degC at 760 mmHg. Solubility: Soluble in DMSO, ethanol, and organic solvents. Storage: Store powder at -20degC, sealed, protected from light and moisture. It is also known as 3-Phenylpropiolic acid, 3-Phenylprop-2-ynoic acid, and Phenylpropynoic acid. The compound is an endogenous metabolite and is also used as a click chemistry reagent.
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| Toxicity/Toxicokinetics |
Phenylpropiolic acid is an endogenous metabolite with low to moderate toxicity. It is a carboxylic acid and may cause skin and eye irritation. Standard laboratory safety precautions should be followed when handling the pure compound: wear appropriate personal protective equipment (lab coat, gloves, safety glasses), avoid inhalation of powder and contact with skin/eyes, wash hands thoroughly after handling. It is a combustible solid (storage class code 11). Not for human therapeutic use without further validation. Always consult the Safety Data Sheet (SDS) for detailed safety information. For research use only.
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| Additional Infomation |
Phenylpropiolic acid is an alkyne compound, formed by replacing the alkyne hydrogen with a phenyl group in propynic acid. It is an α,β-unsaturated monocarboxylic acid, belonging to the alkyne family and the benzene group. Functionally, it is related to propynic acid.
Phenylpropiolic acid is an endogenous metabolite and a click chemistry reagent containing an alkyne group, enabling it to undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with azide-containing molecules. It is also an enzyme extinguishing agent used in palladium-catalyzed decarboxylation coupling reactions. As a phenylpropanoid natural product, it occurs in plants and is involved in plant resistance pathways. It has been tested as an inhibitor of type II 17beta-hydroxysteroid dehydrogenase for the treatment of osteoporosis. The compound is also a key intermediate in the synthesis of pharmaceutical agents, particularly anti-cancer drugs, and is used in creating fluorescent probes for biological imaging. For research use only; not for human therapeutic use. |
| Molecular Formula |
C9H6O2
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|---|---|
| Molecular Weight |
146.14
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| Exact Mass |
146.036
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| CAS # |
637-44-5
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| PubChem CID |
69475
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
302.6±15.0 °C at 760 mmHg
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| Melting Point |
136 - 139 °C
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| Flash Point |
151.0±16.9 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.603
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| LogP |
2.61
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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 |
1
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| Heavy Atom Count |
11
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| Complexity |
200
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C(C=C1)C#CC(=O)O
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| InChi Key |
XNERWVPQCYSMLC-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)
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| Chemical Name |
3-phenylprop-2-ynoic 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 (684.28 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (17.11 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 (17.11 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 (17.11 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 | 6.8428 mL | 34.2138 mL | 68.4275 mL | |
| 5 mM | 1.3686 mL | 6.8428 mL | 13.6855 mL | |
| 10 mM | 0.6843 mL | 3.4214 mL | 6.8428 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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