66622-47-7

Basic information

• Product Name: 2-(3-ISOBUTYLPHENYL)PROPANOIC ACID
• Synonyms: IBUPROFEN IMPURITY A;2-(3-ISOBUTYLPHENYL)PROPANOIC ACID;M-Isobutyl Ibuprofen;(2RS)-2-[3-(2-Methylpropyl)phenyl] propanoic acid;2-(3-Isobutylphenyl)propionic Acid;α-Methyl-3-(2-Methylpropyl)benzeneacetic Acid, α-(3-Isobutylphenyl)propionic Acid;α-Methyl-3-(2-Methylpropyl)phenylacetic Acid;Ibuprofen IMpurity-A (EP)
• CAS NO: 66622-47-7
• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.28
• Product Categories: Aromatics;Inhibitors;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 66622-47-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 314.8±11.0 °C(Predicted)
• Appearance: /
• Density: 1.029±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.35±0.10(Predicted)
• CAS DataBase Reference: 2-(3-ISOBUTYLPHENYL)PROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-ISOBUTYLPHENYL)PROPANOIC ACID(66622-47-7)
• EPA Substance Registry System: 2-(3-ISOBUTYLPHENYL)PROPANOIC ACID(66622-47-7)

Safety Data

• Hazardous Substances Data: 66622-47-7(Hazardous Substances Data)

Usage

Description

2-(3-Isobutylphenyl)propanoic acid, also known as m-Isobutyl Ibuprofen, is an impurity of Ibuprofen (I140000) with the molecular formula C15H22O2. It is a derivative of the widely used nonsteroidal anti-inflammatory drug (NSAID) Ibuprofen, featuring an additional isobutyl group attached to the phenyl ring. This modification results in altered chemical and biological properties compared to the parent compound.

Uses

Used in Pharmaceutical Research:
2-(3-Isobutylphenyl)propanoic acid is used as a research compound for studying its potential as a potent noncompetitive interleukin-8 inhibitor. Interleukin-8 is a chemokine involved in various inflammatory processes, and its inhibition can be beneficial in treating conditions with excessive inflammation.
Used in Drug Development:
As an impurity of Ibuprofen, 2-(3-Isobutylphenyl)propanoic acid plays a role in drug development by helping researchers understand the effects of structural modifications on the pharmacological properties of NSAIDs. This knowledge can contribute to the design of more effective and safer anti-inflammatory medications.
Used in Quality Control:
In the pharmaceutical industry, 2-(3-Isobutylphenyl)propanoic acid serves as a reference standard for quality control purposes. It helps ensure the purity and potency of Ibuprofen-containing products by providing a benchmark for comparison during testing and analysis.
Used in Toxicological Studies:
Understanding the toxicological profile of 2-(3-Isobutylphenyl)propanoic acid is essential for assessing the safety of Ibuprofen and its derivatives. This information can guide the development of safer medications and inform regulatory decisions regarding the use of these compounds in human therapy.

Synthesis Reference(s)

Synthesis, p. 444, 1983 DOI: 10.1055/s-1983-30369

Upstream product

• 124-38-9 carbon dioxide 
• 96921-44-7 1-(1-Chloro-ethyl)-3-isobutyl-benzene 
• 1551102-45-4 C₁₃H₁₇NO 
• 147283-87-2 methyl [3-[[(trifluoromethyl)sulfonyl]oxy]phenyl]-acetate 
• 42058-59-3 3-hydroxy-benzeneacetic acid, methyl ester 
• 621-37-4 m-hydroxyphenylacetic acid 
• 859828-49-2 methyl 2-{3-(trifluoromethanesulfonyloxy)phenyl}propanoate 
• 859828-57-2 methyl 2-(3-isobutylphenyl)propanoate 

Downstream Products

• 1425473-17-1 C₁₆H₂₆O₂Si 
• 1425473-71-7 C₁₉H₃₂O₂Si 
• 1425474-23-2 C₁₉H₃₂O₂Si 

Relevant articles and documents

Preparation method of ibuprofen impurity A

The invention discloses a preparation method of an ibuprofen impurity A (shown as a formula I). According to the preparation method, 3-methyl bromophenylacetate is used as a raw material and methyl onhydrogen is removed through alkali; then Suzuki reaction is carried out and the raw material is coupled with isobutaneboronic acid to generate 2-(3-isobutyl phenyl)methyl propionate; finally, the 2-(3-isobutyl phenyl)methyl propionate is hydrolyzed and neutralized to obtain the ibuprofen impurity A. The preparation method disclosed by the invention has the advantages that the raw material is cheap and easy to obtain, synthesis steps are simple, reaction conditions are moderate and the post-treatment is simple; a technology is stable and has good repeatability, so that the production cost isgreatly reduced, and commercial production and batch supply are facilitated.

2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors

The CXC chemokine CXCL8/IL-8 plays a major role in the activation and recruitment of polymorphonuclear (PMN) cells at inflammatory sites. CXCL8 activates PMNs by binding the seven-transmembrane (7-TM) G-protein-coupled receptors CXC chemokine receptor 1 (CXCR1) and CXC chemokine receptor 2 (CXCR2). (R)-Ketoprofen (1) was previously reported to be a potent and specific noncompetitive inhibitor of CXCLS-induced human PMNs chemotaxis. We report here molecular modeling studies showing a putative interaction site of 1 in the TM region of CXCR1. The binding model was confirmed by alanine scanning mutagenesis and photoaffinity labeling experiments. The molecular model driven medicinal chemistry optimization of 1 led to a new class of potent and specific inhibitors of CXCL8 biological activity. Among these, repertaxin (13) was selected as a clinical candidate drug for prevention of post-ischemia reperfusion injury.