30131-16-9

Basic information

• Product Name: 4-(4-Phenylbutoxy)benzoic acid
• Synonyms: Benzoic acid,4-(4-phenylbutoxy)-;4-(4-phenyl-1-butoxy)benzoic acid;4-(4-Phenylbutoxy)benzoic acid (Pranlukast);4-(4-PHENYLBUTOXY)BENZOIC ACID;4-(4-phenylbutoxy)benzoic acid (intermediate of pranlukast);P-Phenylbutoxybenzoic acid;4-(4-Phenylbutoxy)be
• CAS NO: 30131-16-9
• Molecular Formula: C₁₇H₁₈O₃
• Molecular Weight: 270.32
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;(intermediate of pranlukast)
• Mol File: 30131-16-9.mol
• Article Data: 15

Chemical Properties

• Melting Point: 129.0 to 133.0 °C
• Boiling Point: 454.264 °C at 760 mmHg
• Flash Point: 166.704 °C
• Appearance: White crystalline powder
• Density: 1.145 g/cm³
• Vapor Pressure: 1.91E-08mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 4.47±0.10(Predicted)
• CAS DataBase Reference: 4-(4-Phenylbutoxy)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Phenylbutoxy)benzoic acid(30131-16-9)
• EPA Substance Registry System: 4-(4-Phenylbutoxy)benzoic acid(30131-16-9)

Safety Data

• Hazardous Substances Data: 30131-16-9(Hazardous Substances Data)

Usage

General Description

4-(4-Phenylbutoxy)benzoic acid is a chemical compound with the molecular formula C21H20O3. It is a derivative of benzoic acid with a phenylbutoxy group attached to the fourth position of the benzene ring. 4-(4-Phenylbutoxy)benzoic acid is commonly used in the synthesis of pharmaceuticals and has been studied for its potential therapeutic applications. It may also have potential uses in the development of new materials and chemical compounds. Additionally, 4-(4-Phenylbutoxy)benzoic acid is known for its strong affinity towards binding with certain receptors in the body, leading to potential effects on biological systems. Overall, this compound has a range of potential applications in the fields of medicine, materials science, and chemical research.

InChI:InChI=1/C17H18O3/c1-2-3-12-20-16-10-8-14(9-11-16)13-4-6-15(7-5-13)17(18)19/h4-11H,2-3,12H2,1H3,(H,18,19)

Upstream product

• 99-76-3 methyl 4-hydroxylbenzoate 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 1589-82-8 phenylmagnesium bromide 
• 108-90-7 chlorobenzene 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 4830-93-7 1-Chloro-4-phenylbutane 
• 10229-11-5 4-phenyl-but-3-yn-1-ol 
• 108-86-1 bromobenzene 
• 99-96-7 4-hydroxy-benzoic acid 
• 138631-41-1 4-(4-phenylbutoxy)benzonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 3360-41-6 4-phenyl-butan-1-ol 
• 136450-05-0 methyl 4-(4-Phenylbutoxy)benzoate 

Downstream Products

• 108807-05-2 4-(4-phenyl-1-butoxy)benzoyl chloride 
• 136450-06-1 3-[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone 
• 136450-08-3 ethyl 4-oxo-8-(4-(4-phenylbutoxy)benzamido)chromene-2-carboxylate 
• 103176-67-6 ONO-RS-347 
• 103177-37-3 pranlukast 

Relevant articles and documents

Development and application of a high-throughput screening assay for identification of small molecule inhibitors of the P. falciparum reticulocyte binding-like homologue 5 protein

The P. falciparum parasite, responsible for the disease in humans known as malaria, must invade erythrocytes to provide an environment for self-replication and survival. For invasion to occur, the parasite must engage several ligands on the host erythrocyte surface to enable adhesion, tight junction formation and entry. Critical interactions include binding of erythrocyte binding-like ligands and reticulocyte binding-like homologues (Rhs) to the surface of the host erythrocyte. The reticulocyte binding-like homologue 5 (Rh5) is the only member of this family that is essential for invasion and it binds to the basigin host receptor. The essential nature of Rh5 makes it an important vaccine target, however to date, Rh5 has not been targeted by small molecule intervention. Here, we describe the development of a high-throughput screening assay to identify small molecules which interfere with the Rh5-basigin interaction. To validate the utility of this assay we screened a known drug library and the Medicines for Malaria Box and demonstrated the reproducibility and robustness of the assay for high-throughput screening purposes. The screen of the known drug library identified the known leukotriene antagonist, pranlukast. We used pranlukast as a model inhibitor in a post screening evaluation cascade. We procured and synthesised analogues of pranlukast to assist in the hit confirmation process and show which structural moieties of pranlukast attenuate the Rh5 – basigin interaction. Evaluation of pranlukast analogues against P. falciparum in a viability assay and a schizont rupture assay show the parasite activity was not consistent with the biochemical inhibition of Rh5, questioning the developability of pranlukast as an antimalarial. The high-throughput assay developed from this work has the capacity to screen large collections of small molecules to discover inhibitors of P. falciparum Rh5 for future development of invasion inhibitory antimalarials.

Preparation method of p-phenylbutoxybenzoic acid

The invention discloses a preparation method of p-phenylbutoxybenzoic acid. The preparation method comprises the following steps: using tetrahydrofuran as an initial raw material; carrying out a catalytic reaction with benzoyl chloride to prepare 4-chlorobutanol benzoate; carrying out a Friedel-Crafts alkylation reaction and hydrolysis on 4-chlorobutanol benzoate and benzene to obtain 4-phenylbutanol, carrying out a reaction on the 4-phenylbutanol and thionyl chloride to obtain 4-phenylchlorobutane, carrying out an alkylation reaction on the 4-phenylchlorobutane and methyl p-hydroxybenzoate under the action of potassium carbonate to obtain methyl p-phenylbutoxybenzoate. The raw materials used in the invention are cheap and easily available, the process is easy to realize industrialization,and the obtained final product has the advantages of high purity, novel route, short synthesis route, no dangerous process and simple equipment.

Preparation method for p-phenylbutoxybenzoic acid

The invention provides a preparation method for p-phenylbutoxybenzoic acid, belonging to the field of organic synthesis. According to the invention, palladium-based catalytic coupling is adopted, andthe Grignard reaction and the Friedel-Craft reaction are avoided, thereby avoiding the production of blue-green copper ion wastewater and generation of a large amount of acidic wastewater due to usageof aluminum trichloride; the preparation method of the invention is friendly to environment, simple in synthesis route and high in the yield of each step; and halogeno-benzene is used for replacing more expensive phenylmagnesium bromide and used as a starting material, so the preparation cost of p-phenylbutoxybenzoic acid is lowered. The p-phenylbutoxybenzoic acid obtained in the invention has good crystal form, high purity and good solubility. The data of embodiments of the invention show that the total yield of p-phenylbutoxybenzoic acid prepared in the invention is 60% or above, and the HPLC purity of p-phenylbutoxybenzoic acid is 99.9% or above.