Description

(-)-Ibuprofen, also known as (R)-(-)-Ibuprofen or levibuprofen, is the enantiomer of the widely used nonsteroidal anti-inflammatory drug (NSAID) Ibuprofen. With a molecular formula of C₁₃H₁₈O₂ and CAS number 51146-57-7, this chiral compound is characterized by its (R)-configuration at the alpha carbon. As a selective inhibitor of cyclooxygenase (COX) enzymes, (-)-Ibuprofen exhibits potent anti-inflammatory, analgesic, and antipyretic properties. This high-purity pharmaceutical intermediate is particularly valuable for research into enantioselective drug metabolism and the development of single-enantiomer medications. The compound is supplied as a white to off-white crystalline powder with >98% enantiomeric excess, making it ideal for pharmacological studies, chiral separations, and as a reference standard in analytical chemistry.

Properties

• CAS Number: 51146-57-7
• Complexity: 203
• IUPAC Name: (2R)-2-(4-isobutylphenyl)propanoic acid
• InChI: InChI=1S/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
• InChI Key: HEFNNWSXXWATRW-SNVBAGLBSA-N
• Exact Mass: 206.130679813
• Molecular Formula: C13H18O2
• Molecular Weight: 206.28
• SMILES: C[C@H](C1=CC=C(C=C1)CC(C)C)C(=O)O
• Topological: 37.3
• Monoisotopic Mass: 206.130679813
• Dissociation Constants: 4.44
• Synonyms: (R)-(-)-Ibuprofen, 51146-57-7, (-)-Ibuprofen, l-Ibuprofen, (R)-2-(4-Isobutylphenyl)propanoic acid, (-)-Ibuprophen, Ibuprofen, (-)-, R-(-)-p-Isobutylhydratropic acid, IBUPROFEN, (R)-, 99W8H60N62, alphaR-Sethyl-4-(2-methylpropyl)benzeneacetic acid, Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-, (R)-, (alphaR)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid, (-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid, (-)-.ALPHA.-METHYL-4-(2-METHYLPROPYL)BENZENEACETIC ACID, benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-, (alphaR)-, BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, (R)-, (.ALPHA.R)-.ALPHA.-METHYL-4-(2-METHYLPROPYL)BENZENEACETIC ACID, BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, (.ALPHA.R)-, 610-621-4, (R)-Ibuprofen, levibuprofen, r-ibuprofen, (2R)-2-[4-(2-methylpropyl)phenyl]propanoic acid, (2R)-2-(4-isobutylphenyl)propanoic acid, CHEMBL427526, CHEBI:47835, (r,s)-ibuprofen, (R)-alpha-methyl-4-(2-methylpropyl)benzeneacetic acid, MFCD00069290, (R,S)-2-(4-(2-methylpropyl)phenyl)propanoic acid, UNII-99W8H60N62, IZP, (r)(-) ibuprofen, (r)(-)-ibuprofen, (R)-IBUPROPHEN, (R)-(-)-Ibuprofen?, SCHEMBL29057, EX-A1358, BDBM50169044, HY-78131B, s5899, AKOS027320481, CS-1394, FI24527, AC-32024, DS-11337, NS00116011, EN300-6505221, (a-R)-a-Methyl-4-(2-methylpropyl)benzeneacetic Acid, Q27120818, Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-, (alphaR)- (9CI)

(-)-Ibuprofen is primarily used in pharmacological research to study the stereoselective metabolism and pharmacokinetics of ibuprofen enantiomers. It serves as a valuable reference standard for chiral HPLC method development and validation in pharmaceutical analysis. Researchers utilize this compound to investigate the differential COX inhibition profiles between ibuprofen enantiomers and their distinct biological activities. The (R)-enantiomer is also employed in studies of chiral inversion processes in vivo.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
• H361 (50%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Precautionary Statements

• P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P304+P340, P305+P351+P338, P318, P319, P330, P337+P317, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Eye Irrit. 2 (50%)
• STOT SE 3 (50%)
• Repr. 2 (50%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.