2-[4-(2-carboxy-2-methylethyl)phenyl](3,3,3-2H3)propanoic acid

• ChemBase ID: 171494
• Molecular Formular: C13H16O4
• Molecular Mass: 236.26374
• Monoisotopic Mass: 236.10485899
• SMILES: c1c(ccc(c1)CC(C)C(=O)O)C(C)C(=O)O
• Canonical SMILES: OC(=O)C(Cc1ccc(cc1)C(C(=O)O)C)C
• InChI: InChI=1S/C13H16O4/c1-8(12(14)15)7-10-3-5-11(6-4-10)9(2)13(16)17/h3-6,8-9H,7H2,1-2H3,(H,14,15)(H,16,17)
• InChIKey: DIVLBIVDYADZPL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[4-(2-carboxy-2-methylethyl)phenyl](3,3,3-^2H₃)propanoic acid
• IUPAC Traditional name: 2-[4-(2-carboxy-2-methylethyl)phenyl](3,3,3-^2H₃)propanoic acid
• Synonyms: 4-(1-Carboxyethyl)-α-methylbenzenepropanoic Acid-d3; 2,4’-(2-Carboxypropyl)phenylpropionic Acid-d3; 2-[4-(2-Carboxypropyl)phenyl]propionic Acid-d3; Carboxyibuprofen-d3; Ibuprofen Carboxylic Acid-d3(Mixture of Diastereomers)

Database IDs

• CAS Number: 1216505-29-1
• PubChem SID: 164227404
• PubChem CID: 57347581

CALCULATED PROPERTIES

• Acid pKa: 3.972794
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.45117104
• LogD (pH = 7.4): -3.0014312
• Log P: 2.7792835
• Molar Refractivity: 62.4232 cm^3
• Polarizability: 24.263525 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 117-120°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I140017

The major labelled metabolite of Ibuprofen; may reduce the risk of cataract by protecting lenticular enzymes.

REFERENCES

• Bhuyan, K., et al.: Life Sci., 38, 1463 (1986)
• Blakytny, R., et al.: Biochem. J., 288, 303 (1986)
• Ganea, E., et al.: Eur. J. Biochem., 231, 181 (1986)
• Mitchell, J., et al.: Br. J. Pharmacol., 128, 1121 (1986)