(R)-(-)-Ibuprofen

Base Information

• Chemical Name: (R)-(-)-Ibuprofen
• CAS No.: 51146-57-7
• Molecular Formula: C13H18 O2
• Molecular Weight: 206.285
• Hs Code.: 2916399090
• European Community (EC) Number: 610-621-4
• UNII: 99W8H60N62
• Nikkaji Number: J384.812D
• Wikidata: Q27120818
• Pharos Ligand ID: JSN8X494Y19Z,JSNCQPWTHATF
• Metabolomics Workbench ID: 56807
• ChEMBL ID: CHEMBL427526
• Mol file: 51146-57-7.mol

Synonyms:(R)-(-)-Ibuprofen;51146-57-7;(R)-Ibuprofen;(-)-Ibuprofen;levibuprofen;l-Ibuprofen;(R)-2-(4-Isobutylphenyl)propanoic acid;r-ibuprofen;(2R)-2-[4-(2-methylpropyl)phenyl]propanoic acid;(2R)-2-(4-isobutylphenyl)propanoic acid;(-)-Ibuprophen;Ibuprofen, (-)-;CHEMBL427526;UNII-99W8H60N62;CHEBI:47835;(r,s)-ibuprofen;R-(-)-p-Isobutylhydratropic acid;alphaR-Sethyl-4-(2-methylpropyl)benzeneacetic acid;(R)-alpha-methyl-4-(2-methylpropyl)benzeneacetic acid;99W8H60N62;Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-, (R)-;(alphaR)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid;(R,S)-2-(4-(2-methylpropyl)phenyl)propanoic acid;IZP;(r)(-) ibuprofen;(r)(-)-ibuprofen;(R)-IBUPROPHEN;IBUPROFEN, (R)-;SCHEMBL29057;EX-A1358;BDBM50169044;HY-78131B;MFCD00069290;s5899;AKOS027320481;CS-1394;AC-32024;DS-11337;EN300-6505221;Q27120818;(-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid;(-)-.ALPHA.-METHYL-4-(2-METHYLPROPYL)BENZENEACETIC ACID;benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-, (alphaR)-;(.ALPHA.R)-.ALPHA.-METHYL-4-(2-METHYLPROPYL)BENZENEACETIC ACID;BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, (R)-;Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-, (alphaR)- (9CI);BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, (.ALPHA.R)-

Chemical Property of (R)-(-)-Ibuprofen

Chemical Property:

• Vapor Pressure: 0.000139mmHg at 25°C
• Melting Point: 41-42°C
• Refractive Index: 1.5290 (estimate)
• Boiling Point: 319.6°Cat760mmHg
• PKA: 4.41±0.10(Predicted)
• Flash Point: 216.7°C
• PSA: 37.30000
• Density: 1.029g/cm³
• LogP: 3.07320
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• Water Solubility.: 369.3mg/L(25 oC)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 206.130679813
• Heavy Atom Count: 15
• Complexity: 203

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-(-)-Ibuprofen ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1=CC=C(C=C1)C(C)C(=O)O
• Isomeric SMILES: C[C@H](C1=CC=C(C=C1)CC(C)C)C(=O)O
• Description: Ibuprofen is a non-steroidal anti-inflammatory drug with diverse biochemical actions, most notably inhibiting COX-1 and COX-2 (IC50s = 2.6 and 1.53 μM, respectively). It is commonly synthesized as a racemic mixture of (S) and (R) isomers (Item No. item 70280). (R)-Ibuprofen is an enantiomer that is generally not considered a COX inhibitor and is instead thought to be involved in pathways of lipid metabolism as it is incorporated into triglycerides along with fatty acids. The (R) enantiomer can, however, inhibit NF-κB activation (IC50 = 121.8 μM) in response to T-cell stimulation as well as block superoxide formation, β-glucuronidase release, and LTB4 generation by stimulated neutrophils (IC50 values range from 40-100 μM). 50-60% of (R)-ibuprofen is inverted to (S)-ibuprofen in humans after oral administration.
• Uses: A nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer.

Technology Process of (R)-(-)-Ibuprofen

There total 112 articles about (R)-(-)-Ibuprofen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

ibuprofen (15687-27-1,58560-75-1) → (S)-ibuprofen (51146-56-6,58560-75-1) + (R)-ibuprofene (51146-57-7,58560-75-1)

Guidance literature:

With 2C₈H₈N₅O₂^(1-)*Cu⁽²⁺⁾; In acetonitrile; at 25 ℃; Resolution of racemate;

DOI:10.1021/jacs.9b06500

Reference yield: 75.0%

carbon monoxide (201230-82-2) + p-isobutylstyrene (63444-56-4) → (S)-ibuprofen (51146-56-6,58560-75-1) + (R)-ibuprofene (51146-57-7,58560-75-1)

Guidance literature:

carbon monoxide; p-isobutylstyrene; With methoxy(cyclooctadiene)rhodium(I) dimer; 1,2-bis((3aS,8aS)-2,2-dimethyl-4,4,8,8-tetraphenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-yl)benzene; hydrogen; In tetrahydrofuran; at 45 ℃; for 24h; under 15001.5 Torr;

With sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 0 - 20 ℃;

DOI:10.1002/adsc.201400657

Reference yield: 39.0%

ibuprofen (15687-27-1,58560-75-1) + bis(1-naphthyl)methanol (62784-66-1) → (R)-ibuprofen di(1-naphthyl)methyl ester (1116086-46-4) + (S)-ibuprofen (51146-56-6,58560-75-1) + (R)-ibuprofene (51146-57-7,58560-75-1)

Guidance literature:

With (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; p-Methoxybenzoic anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 12h; optical yield given as %ee; Resolution of racemate;

DOI:10.1002/ejoc.200800942

upstream raw materials:

Vinyl bromide

1-(4-isobutylphenyl)ethylzinc bromide

carbon monoxide

p-isobutylstyrene

Downstream raw materials:

(S)-(+)-methyl 2-(4-isobutylphenyl)propionate

(R)-ibuprofen methyl ester

3-hydroxy-2-(4-isobutyl-phenyl)-2-methyl-propionic acid

2-(4-isobutyl-phenyl)-N-pyridin-3-yl-propionamide

Refernces

• 1、 Fan, Xinjiong,Fu, Yao,Liu, Xiaolong,Zhao, Meng. "Reshaping the active pocket of esterase Est816 for resolution of economically important racemates". . p. 6126 - 6133. Retrieved 2021/09/28.
• 2、 Corella-Ochoa, M. Nieves,Tapia, Jesús B.,Rubin, Heather N.,Lillo, Vanesa,González-Cobos, Jesús,Nú?ez-Rico, José Luis,Balestra, Salvador R.G.,Almora-Barrios, Neyvis,Lledós, Marina,Gu?ll-Bara, Arnau,Cabezas-Giménez, Juanjo,Escudero-Adán, Eduardo C.,Vidal-Ferran, Anton,Calero, Sofiá,Reynolds, Melissa,Martí-Gastaldo, Carlos,Galán-Mascarós, José Ramón. "Homochiral Metal-Organic Frameworks for Enantioselective Separations in Liquid Chromatography". . p. 14306 - 14316. Retrieved 2019/10/11.