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

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

Uses

Used in Pharmaceutical Synthesis:
4-(4-Phenylbutoxy)benzoic acid is used as a key intermediate in the synthesis of various pharmaceuticals for its potential therapeutic applications. Its unique structure allows for the development of new drugs with improved efficacy and selectivity.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 4-(4-Phenylbutoxy)benzoic acid is utilized as a starting material for the design and synthesis of novel compounds with potential therapeutic properties. Its ability to bind with specific receptors makes it a valuable tool for studying the structure-activity relationships of bioactive molecules.
Used in Drug Development:
4-(4-Phenylbutoxy)benzoic acid is employed as a lead compound in drug discovery and development. Its strong receptor binding affinity and potential biological effects make it a promising candidate for the treatment of various diseases and conditions.
Used in Materials Science:
In the realm of materials science, 4-(4-Phenylbutoxy)benzoic acid has potential applications in the development of new materials and chemical compounds. Its unique structure and properties can be harnessed to create innovative materials with specific characteristics and functions.
Used in Chemical Research:
4-(4-Phenylbutoxy)benzoic acid serves as a valuable subject of study in chemical research. Its synthesis, properties, and potential applications are of interest to chemists working to advance the understanding of organic compounds and their role in various fields.

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

• 120-47-8 Ethyl 4-hydroxybenzoate 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 4830-93-7 1-Chloro-4-phenylbutane 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 10229-11-5 4-phenyl-but-3-yn-1-ol 
• 108-86-1 bromobenzene 
• 108-90-7 chlorobenzene 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 99-96-7 4-hydroxy-benzoic acid 
• 1589-82-8 phenylmagnesium bromide 
• 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

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

Relevant articles and documents

Preparation method of p-phenylbutoxybenzoic acid

The invention provides a preparation method of p-phenylbutoxybenzoic acid. 3-alkynyl-1-butanol is used as a raw material, a catalyst is added, and p-phenylbutoxybenzoic acid is synthesized through four-step reaction. The preparation method comprises the f

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 4-(4-phenylbutoxy) benzoic acid

The invention relates to a preparation method of 4-(4-phenylbutoxy) benzoic acid, which specifically comprises the following steps: a, performing a reaction on gamma-chlorobutanone with p-hydroxybenzoate under the catalysis of alkali to generate a compoun

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.

Synthesis method of 4-(4-phenylbutoxy) benzoic acid

The invention discloses a synthesis method of 4-(4-phenylbutoxy) benzoic acid. The synthesis method uses 1-bromo-4-phenylbutane, methylparaben, K2CO3, NaOH, H3PW12O40.6H20, dicyandiamide, P-W2C@NC andtoluene as main raw materials. According to the synthes

To a synthesis process of benzene butoxy benzoic acid (by machine translation)

The invention discloses a synthesis process of benzene butoxy benzoic acid, comprises the following synthetic steps: chlorobenzene with magnesium format obtained by reaction of Grignard reagent, Grignard reagent with 1 - bromo - 4 - chlorobutane coupling reaction to obtain the 1 - chloro - 4 - phenyl butane, 1 - chloro - 4 - phenyl butane with the hydroxy benzoic acid condensation reaction to get the butoxy benzoic acid, its reaction equation as follows: This synthetic route step is simple, easy to operate, in the course of synthesizing highly toxic intermediate [...] and avoids the generation of a large amount of waste water, thus not only environment friendly, thereby saving the production cost, the process is obtained by the synthesis of high-purity para-butoxy benzoic acid, suitable for large-scale industrial production. (by machine translation)

Selective Optimization of Pranlukast to Farnesoid X Receptor Modulators

Selective optimization of side activities (SOSA) offers an alternative entry to early drug discovery and may provide rapid access to bioactive new chemical entities with desirable properties. SOSA aims to reverse a drug's side activities through structural modification and to design out the drug's original main action. We identified a moderate side activity for the cysteinyl leukotriene receptor 1 (CysLT1R) antagonist pranlukast on the farnesoid X receptor (FXR). Systematic structural modification of the drug allowed remarkable optimization of its partial FXR agonism to sub-nanonmolar potency. The resulting FXR modulators lack any activity on CysLT1R and are characterized by high selectivity, high metabolic stability, and low toxicity. With their favorable in vitro profile, these SOSA-derived FXR modulators constitute a new FXR ligand chemotype that appears suitable for further preclinical evaluation.

Bent-core mesogens with an aromatic unit at the terminal position

Bent-core liquid crystals with a naphthalene central unit and an aromatic ring at the terminal position of molecular tails were synthesised with the aim of enhancing nanosegregation. It was found that the length of the spacer between the rigid core and the terminal aromatic moiety had a profound influence on the liquid crystal polymorphism. The homologues with short spacers exhibited nematic and columnar phases, whereas the homologue with long spacers exhibited a tilted lamellar phase with a liquid-like in-plane order, indicating an unusual morphology of the densely packed toroidal objects. The morphology can be changed to twisted ribbons by small additives adsorbed on the membrane surface. This is the first example of twisted ribbons constructed by a lamellar system with no long-range in-plane order.

A 4-( benzene butoxy) benzoic acid synthesis method

The invention relates to a method for chemically synthetizing 4-(benzene butoxy) benzoic acid. The method comprises the following steps: causing benzene butanol as shown in a formula (II) to carry out thermal reaction in the presence of alkali, and then i