51146-57-7

Basic information

• Product Name: (R)-(-)-IBUPROFEN
• Synonyms: (R)-(-)-2-(4-ISOBUTYLPHENYL)-PROPIONIC ACID;(R)-(-)-IBUPROFEN;(R)-IBUPROFEN;(-)-Ibuprophen;(R)-2-(4-Isobutylphenyl)propanoic acid;Benzeneacetic acid, α-methyl-4-(2-methylpropyl)-, (R)-;Benzeneacetic acid, α-methyl-4-(2-methylpropyl)-, (αR)-;l-Ibuprofen
• CAS NO: 51146-57-7
• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.28
• Product Categories: Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 51146-57-7.mol
• Article Data: 98

Chemical Properties

• Melting Point: 41-42°C
• Boiling Point: 305.14°C (rough estimate)
• Flash Point: 216.7°C
• Appearance: /
• Density: 1.0176 (rough estimate)
• Vapor Pressure: 0.000139mmHg at 25°C
• Refractive Index: 1.5290 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 4.41±0.10(Predicted)
• Water Solubility: 369.3mg/L(25 oC)
• CAS DataBase Reference: (R)-(-)-IBUPROFEN(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-IBUPROFEN(51146-57-7)
• EPA Substance Registry System: (R)-(-)-IBUPROFEN(51146-57-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 51146-57-7(Hazardous Substances Data)

Usage

Description

(R)-(-)-Ibuprofen, also known as (R)-Ibuprofen, is an enantiomer of the non-steroidal anti-inflammatory drug (NSAID) Ibuprofen. It is synthesized as a racemic mixture of (S) and (R) isomers, with the (R) enantiomer not being a COX inhibitor like its (S) counterpart. Instead, it is involved in lipid metabolism and can inhibit NF-κB activation and block superoxide formation, β-glucuronidase release, and LTB4 generation by stimulated neutrophils. Approximately 50-60% of (R)-ibuprofen is converted to (S)-ibuprofen in humans after oral administration.

Uses

Used in Pharmaceutical Industry:
(R)-(-)-Ibuprofen is used as a precursor in the synthesis of the active (S)-isomer of Ibuprofen, which is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic, antipyretic, and anti-inflammatory properties. The (S)-isomer is responsible for the majority of the drug's therapeutic effects.
Used in Research Applications:
(R)-(-)-Ibuprofen is used as a research tool to study the differences in biological activity and metabolism between the (R) and (S) enantiomers of Ibuprofen. This helps in understanding the stereoselectivity of drug action and the potential for developing enantiomer-specific drugs with improved safety and efficacy profiles.
Used in Lipid Metabolism Studies:
(R)-(-)-Ibuprofen is used in research to investigate its role in lipid metabolism, as it is incorporated into triglycerides along with fatty acids. This can provide insights into the potential use of (R)-Ibuprofen or its derivatives in the development of therapies targeting lipid-related disorders.
Used in Inflammation and Immune Response Research:
(R)-(-)-Ibuprofen is used in studies to explore its potential effects on NF-κB activation, superoxide formation, β-glucuronidase release, and LTB4 generation by stimulated neutrophils. This can contribute to the understanding of its role in modulating inflammation and immune responses, which may lead to the development of new therapeutic strategies for inflammatory and immune-related diseases.

InChI:InChI=1/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m1/s1

Upstream product

• 593-60-2 Vinyl bromide 
• 125231-12-1 1-(4-isobutylphenyl)ethylzinc bromide 
• 201230-82-2 carbon monoxide 
• 63444-56-4 p-isobutylstyrene 
• 15687-27-1 ibuprofen 
• 61566-34-5 (+/-)-ibuprofen methyl ester 
• 58609-73-7 2-(4-isobutylphenyl)propanenitrile 
• 121839-78-9 (2R)-2-[4-(2-methylpropyl)phenyl]propanamide 
• 85711-18-8 1-isobutyl-4-[(R)-1-methylallyl]benzene 
• 85711-17-7 1-isobutyl-4-[(S)-1-methylallyl]benzene 
• 113544-36-8 (R)-2-(4-Isobutyl-phenyl)-propionic acid (3aR,5R,6S,6aR)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 113544-28-8 (R)-3-O-(2-(4-isobutylphenyl)propionyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 123054-56-8 2-(4-Isobutyl-phenyl)-propionic acid (S)-1,2-dimethyl-propyl ester 
• 123054-49-9 2-(4-Isobutyl-phenyl)-propionic acid (R)-methoxycarbonyl-phenyl-methyl ester 

Downstream Products

• 81576-55-8 (S)-(+)-methyl 2-(4-isobutylphenyl)propionate 
• 81576-57-0 (R)-ibuprofen methyl ester 
• 121734-80-3 (R)-2-(4-Isobutyl-phenyl)-N-((S)-1-phenyl-ethyl)-propionamide 
• 93469-76-2 3-hydroxy-2-(4-isobutyl-phenyl)-2-methyl-propionic acid 
• 593279-84-6 2-(4-isobutyl-phenyl)-N-pyridin-3-yl-propionamide 
• 593279-83-5 2-(4-isobutyl-phenyl)-N-pyridin-2-yl-propionamide 
• 266359-83-5 repertaxin 
• 354899-91-5 (S)-2-[(R)-2-(4-isobutylphenyl)propionylamino]propionic acid methyl ester 
• 114978-05-1 (R)-2-(4-isobutylphenyl)propionyl chloride 
• 59512-29-7 2-(4-isobutyl-phenyl)-N-phenyl-propionamide 

Relevant articles and documents

O 2-(N -Hydroxy(methoxy)-2-ethanesulfonamido) protected diazen-1-ium-1,2-diolates: Nitric oxide release via a base-induced β-elimination cleavage

O2-(Ethanesulfohydroxamic acid) and O2-(N-methoxy-2- ethanesulfonylamido) diazen-1-ium-1,2-diolates (4-7), a novel type of O 2-(protected) diazeniumdiolate, were synthesized using a key thioacetate oxidation reaction. Nitr

Bidentate phosphine-phosphine oxide ligand and intermediate, preparation method and application thereof

The invention discloses a bidentate phosphine-phosphine oxide ligand and an intermediate, a preparation method and application thereof. The phosphine oxide compound is shown as a formula I and/or ent-I. The phosphine oxide compound is used as a metal ligand and is applied to Suzuki-Miyaura coupling reaction so that generation of self-coupled by-products is avoided, and an alpha-aryl carbonyl compound is obtained; and the dosages of the ligand and the metal catalyst are less.

Preparation and characterization of a new open-tubular capillary column for enantioseparation by capillary electrochromatography

In order to use the enantioseparation capability of cationic cyclodextrin and to combine the advantages of capillary electrochromatography (CEC) with open-tubular (OT) column, in this study, a new OT-CEC, coated with cationic cyclodextrin (1-allylimidazolium-β-cyclodextrin [AI-β-CD]) as chiral stationary phase (CSP), was prepared and applied for enantioseparation. Synthesized AI-β-CD was characterized by infrared (IR) spectrometry and mass spectrometry (MS). The preparation conditions for the AI-β-CD-coated column were optimized with the orthogonal experiment design L9(34). The column prepared was characterized by scanning electron microscopy (SEM) and elemental analysis (EA). The results showed that the thickness of stationary phase in the inner surface of the AI-β-CD-coated columns was about 0.2 to 0.5?μm. The AI-β-CD content in stationary phase based on the EA was approximately 2.77?mmol·m?2. The AI-β-CD-coated columns could separate all 14 chiral compounds (histidine, lysine, arginine, glutamate, aspartic acid, cysteine, serine, valine, isoleucine, phenylalanine, salbutamol, atenolol, ibuprofen, and napropamide) successfully in the study and exhibit excellent reproducibility and stability. We propose that the column, coated with AI-β-CD, has a great potential for enantioseparation in OT-CEC.