2-hydroxy-2-[4-(2-methylpropyl)phenyl]propanoic acid

• ChemBase ID: 170641
• Molecular Formular: C13H18O3
• Molecular Mass: 222.28022
• Monoisotopic Mass: 222.12559444
• SMILES: c1cc(ccc1CC(C)C)C(O)(C)C(=O)O
• Canonical SMILES: CC(Cc1ccc(cc1)C(C(=O)O)(O)C)C
• InChI: InChI=1S/C13H18O3/c1-9(2)8-10-4-6-11(7-5-10)13(3,16)12(14)15/h4-7,9,16H,8H2,1-3H3,(H,14,15)
• InChIKey: APEODKDQAWQDLW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-2-[4-(2-methylpropyl)phenyl]propanoic acid
• IUPAC Traditional name: 2-hydroxy-2-[4-(2-methylpropyl)phenyl]propanoic acid
• Synonyms: α-Ηydroxy-α-methyl-4-(2-methylpropyl)benzeneacetic Acid; 2-(4-Isobutylphenyl)-2-hydroxypropionic Acid; 2-(p-Isobutylphenyl)lactic Acid; 2-Hydroxy-2-(4-isobutylphenyl)propionic Acid; rac α-Hydroxy Ibuprofen

Database IDs

• CAS Number: 60057-62-7
• PubChem SID: 164226551
• PubChem CID: 5228577

CALCULATED PROPERTIES

• Acid pKa: 4.1397233
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.6422902
• LogD (pH = 7.4): -0.05537056
• Log P: 3.0181794
• Molar Refractivity: 62.2089 cm^3
• Polarizability: 24.263683 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid
• Melting Point: 95-97°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H942863

A potential precursor of Ibuprofen and Naproxen. Antiinflammatory agent.

REFERENCES

• Williams, K., et al.: Pharm. Ther., 46, 273 (1990)
• Evans, A., et al.: Eur. J. Clin. Pharmacol., 42, 237 (1990)
• Tucker, G., et al.: Lancet, 355, 1085 (1990)
• Tan, S., et al.: Xenobiotica, 32, 683 (1990)
• Fura, A., et al.: J. Pharm. Biomed. Anal., 32, 51