| Size | Price | Stock | Qty |
|---|---|---|---|
| 10g |
|
||
| Other Sizes |
| Targets |
4-Ethynylbenzoic acid itself does not have a specific biological target. Its derivatives have shown biological activity, with ethyl-3,4-dihydroxybenzoate (a derivative) inhibiting prolyl 4-hydroxylase, an enzyme crucial for collagen synthesis during procollagen biosynthesis. This inhibition leads to reduced collagen production in human skin fibroblast cultures. In esophageal squamous cell carcinoma cells, the same derivative induces apoptosis and autophagy through upregulation of NDRG1 and BNIP3 genes. The compound serves as a building block for synthesizing target molecules rather than as a direct pharmacological agent.
|
|---|---|
| ln Vitro |
In vitro, derivatives of 4-ethynylbenzoic acid have demonstrated biological activities. Ethyl-3,4-dihydroxybenzoate inhibits collagen synthesis in human skin fibroblast cultures through post-translational inhibition of 4-hydroxyproline synthesis. In esophageal squamous cell carcinoma cells, it induces apoptosis and autophagy via upregulation of genes such as NDRG1 and BNIP3, which are involved in cell cycle regulation and cellular metabolism. The parent compound itself is primarily used as a chemical reagent for synthesizing these bioactive derivatives.
|
| ln Vivo |
In vivo studies on 4-ethynylbenzoic acid itself are limited as it is a chemical reagent rather than a drug candidate. Its derivatives may be evaluated in animal models for anticancer or antifibrotic activities, but detailed in vivo data for the parent compound are not available. The compound is primarily used in research settings for organic synthesis and bioconjugation applications.
|
| Enzyme Assay |
In a typical non-cellular enzyme assay involving 4-ethynylbenzoic acid derivatives, the test compound is incubated with purified prolyl 4-hydroxylase in a buffer system (e.g., Tris-HCl, pH 7.4, containing ascorbate, α-ketoglutarate, and Fe²⁺) at 37°C. Enzyme activity is measured by monitoring the hydroxylation of peptide substrates or by quantifying 4-hydroxyproline production. Inhibitory potency (IC50) is determined from dose-response curves. Controls include enzyme alone and vehicle controls. The compound's ethynyl group may also be used in Click chemistry-based binding studies.
|
| Cell Assay |
For cell-based studies using 4-ethynylbenzoic acid derivatives, cells (e.g., human skin fibroblasts or esophageal squamous cell carcinoma cells) are cultured in DMEM or RPMI-1640 supplemented with 10% FBS. Cells are treated with varying concentrations of the test compound for 24–72 hours. Cell viability is assessed by MTT or CCK-8 assays. Apoptosis is evaluated by flow cytometry (Annexin V/PI staining). Gene expression changes (NDRG1, BNIP3) are quantified by qRT-PCR, and protein levels are analyzed by western blotting. Collagen production is measured by ELISA or hydroxyproline assays. Vehicle controls (DMSO or ethanol) are included.
|
| Animal Protocol |
In vivo studies with 4-ethynylbenzoic acid derivatives may involve administration to rodents via oral gavage or intraperitoneal injection. For anticancer studies, tumor-bearing mice are treated with the test compound, and tumor growth is monitored. For fibrosis models, compounds are evaluated for their ability to reduce collagen deposition in tissues. Blood samples are collected for pharmacokinetic analysis, and tissues are harvested for histopathological examination. All procedures follow institutional animal care guidelines.
|
| ADME/Pharmacokinetics |
4-Ethynylbenzoic acid is a synthetic chemical reagent and is not subject to pharmacokinetic evaluation as a drug. Its physicochemical properties include poor aqueous solubility but good solubility in organic solvents. The ethynyl group provides a handle for Click chemistry bioconjugation, enabling the attachment of the compound to various biomolecules for drug delivery and imaging applications. The compound is stable under normal storage conditions and is available in high purity (≥98%).
|
| Toxicity/Toxicokinetics |
The toxicological profile of 4-ethynylbenzoic acid as a pure chemical reagent has not been extensively characterized. As with most organic compounds, standard laboratory safety precautions should be observed, including the use of personal protective equipment (gloves, goggles, lab coat) and adequate ventilation. It may cause skin and eye irritation upon contact. Ingestion or inhalation should be avoided. Appropriate first-aid measures should be in place, and spills should be cleaned up promptly.
|
| Additional Infomation |
4-Ethynylbenzoic acid is not a drug but a valuable chemical reagent and building block in drug discovery. It is classified as a PROTAC linker and is used in the synthesis of proteolysis-targeting chimeras for targeted protein degradation. The compound is also widely employed in Click chemistry for bioconjugation applications, enabling the attachment of drug molecules to targeting ligands or imaging agents. Its ethynyl functionality allows for copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, making it an essential tool in chemical biology and medicinal chemistry. It is not approved for clinical use.
|
| Molecular Formula |
C9H6O2
|
|---|---|
| Molecular Weight |
146.14
|
| Exact Mass |
146.036
|
| CAS # |
10602-00-3
|
| Related CAS # |
192705-28-5
|
| PubChem CID |
589706
|
| Appearance |
Orange to reddish brown solid powder
|
| Density |
1.2±0.1 g/cm3
|
| Boiling Point |
277.2±23.0 °C at 760 mmHg
|
| Melting Point |
192 °C(dec.)
|
| Flash Point |
126.4±17.3 °C
|
| Vapour Pressure |
0.0±0.6 mmHg at 25°C
|
| Index of Refraction |
1.592
|
| LogP |
2.08
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
11
|
| Complexity |
191
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C#CC1=CC=C(C=C1)C(=O)O
|
| InChi Key |
SJXHLZCPDZPBPW-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C9H6O2/c1-2-7-3-5-8(6-4-7)9(10)11/h1,3-6H,(H,10,11)
|
| Chemical Name |
4-ethynylbenzoic acid
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO: 100 mg/mL (684.28 mM)
|
|---|---|
| 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
