6322-83-4

Basic information

• Product Name: (4-BENZOYL-PHENOXY)-ACETIC ACID
• Synonyms: Acetic acid, (4-benzoylphenoxy)-;2-(4-benzoylphenoxy)acetic acid
• CAS NO: 6322-83-4
• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.26
• Mol File: 6322-83-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 450.1°C at 760 mmHg
• Flash Point: 171.8°C
• Appearance: /
• Density: 1.264g/cm³
• Vapor Pressure: 6.89E-09mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (4-BENZOYL-PHENOXY)-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (4-BENZOYL-PHENOXY)-ACETIC ACID(6322-83-4)
• EPA Substance Registry System: (4-BENZOYL-PHENOXY)-ACETIC ACID(6322-83-4)

Safety Data

• Hazardous Substances Data: 6322-83-4(Hazardous Substances Data)

Usage

General Description

(4-BENZOYL-PHENOXY)-ACETIC ACID, also known as fenbufen, is a nonsteroidal anti-inflammatory drug (NSAID) that is used for the treatment of inflammatory conditions such as rheumatoid arthritis, osteoarthritis, and other musculoskeletal disorders. It works by inhibiting the production of inflammatory prostaglandins, which are hormones that cause pain and swelling in the body. Fenbufen is a derivative of phenylacetic acid and has been found to have analgesic, anti-inflammatory, and antipyretic properties. It is available in various forms, including tablets and topical preparations, and is generally well-tolerated with few side effects when used as directed. However, it may cause gastrointestinal irritation and should be used with caution in individuals with a history of ulcers or gastrointestinal bleeding.

InChI:InChI=1/C15H12O4/c16-14(17)10-19-13-8-6-12(7-9-13)15(18)11-4-2-1-3-5-11/h1-9H,10H2,(H,16,17)

Upstream product

• 116413-49-1 (3-bromo-4-methoxyphenyl)-phenylmethanone 
• 98-88-4 benzoyl chloride 
• 578-57-4 2-bromoanisole 
• 57682-09-4 methyl 2-(4-benzoylphenoxy)acetate 
• 122-59-8 2-phenoxyacetic acid 
• 2555-49-9 phenoxyacetic acid ethyl ester 
• 1137-42-4 4-Hydroxybenzophenone 
• 51848-56-7 (4-benzoylphenoxy)acetic acid ethyl ester 

Downstream Products

• 117175-03-8 4-(α-hydroxybenzyl)phenoxyacetic acid 
• 924416-43-3 2-(4-benzoylphenoxy)-N-[1-(phenylmethyl)-4-piperidinyl]-acetamide 
• 791127-70-3 2-(4-benzoylphenoxy)-N-(pyridin-3-yl)acetamide 
• 117175-05-0 <4-(α-chlorobenzyl)phenoxy>acetic acid 
• 57682-09-4 methyl 2-(4-benzoylphenoxy)acetate 

Relevant articles and documents

Fibrate-based N-acylsulphonamides targeting carbonic anhydrases: synthesis, biochemical evaluation, and docking studies

A large library of fibrate-based N-acylsulphonamides was designed, synthesised, and fully characterised in order to propose them as zinc binders for the inhibition of human carbonic anhydrase (hCA) enzymatic activity. Synthesised compounds were tested aga

Studies on the collision-induced dissociation of adipoR agonists after electrospray ionization and their implementation in sports drug testing

AdipoR agonists are small, orally active molecules capable of mimicking the protein adiponectin, which represents an adipokine with antidiabetic and antiatherogenic effects. Two adiponectin receptors were reported in the literature referred to as adipoR1 and adipoR2. Activation of these receptors stimulates mitochondrial biogenesis and results in an improved oxidative metabolism (via adipoR1) and increased insulin sensitivity (via adipoR2). Hence, adipoR agonists are potentially performance enhancing substances and targets of proactive and preventive anti-doping measures. In this study, two adipoR agonists termed AdipoRon and 112254 as well as two isotopically labeled internal standards (ISTDs) were synthesized in three-step reactions. The products were fully characterized by nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MS) and density functional theory (DFT) computation. Collision-induced dissociation pathways following electrospray ionization were suggested based on the determined elemental compositions of product ions, comparison to product ions derived from labeled analogs (ISTDs), H/D-exchange experiments and the results of DFT calculations. The most abundant product ions were found at m/z 174, tentatively assigned to protonated 1-benzyl-1,2,3,4-tetrahydropyridine for AdipoRon, and m/z 207, suggested as protonated 1-(4-methoxybenzyl)piperazine, for 112254. Notably, the loss of the heterocyclic ring (i.e. piperazine and piperidine, respectively) in a supposedly intramolecular elimination reaction was observed in both cases. A qualitative determination of both AdipoR agonists in human plasma was established and fully validated for doping control purposes. Validation items such as recovery (86-89%), specificity, linearity, lower limit of detection (1ng/ml), intraday (3-18%) and interday (5-16%) precision as well as ion suppression or enhancement were determined. Based on these findings adipoR agonists can be implemented in sports drug testing procedures.

Effect of stilbene and chalcone scaffolds incorporation in clofibric acid on PPARα agonistic activity

In an effort to develop safe and efficacious compounds for the treatment of metabolic disorders, new compounds based on a combination of clofibric acid, the active metabolite of clofibrate, and trans-stilbene, chalcone, and other lipophilic groups were synthesized. They were evaluated for PPARα transactivation activity; all branched derivatives showed an increase of the transcriptional activity of receptor compared to the linear ones. Noteworthy, stilbene and benzophenone branched derivatives activated the PPARα better than clofibric acid.