2-[4-(1-hydroxy-2-methylpropyl)phenyl]propanoic acid

• ChemBase ID: 157640
• Molecular Formular: C13H18O3
• Molecular Mass: 222.28022
• Monoisotopic Mass: 222.12559444
• SMILES: CC(C)C(c1ccc(cc1)C(C)C(=O)O)O
• Canonical SMILES: CC(C(c1ccc(cc1)C(C(=O)O)C)O)C
• InChI: InChI=1S/C13H18O3/c1-8(2)12(14)11-6-4-10(5-7-11)9(3)13(15)16/h4-9,12,14H,1-3H3,(H,15,16)
• InChIKey: RMOQYHYFRKTDRI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[4-(1-hydroxy-2-methylpropyl)phenyl]propanoic acid
• IUPAC Traditional name: 2-[4-(1-hydroxy-2-methylpropyl)phenyl]propanoic acid
• Synonyms: 2-[4-(1-Hydroxy-2-methylpropyl)phenyl]propionic acid; 1-Hydroxyibuprofen; 4-(1-Hydroxy-2-methylpropyl)-α-methylbenzeneacetic Acid; 2-[4'-(1-Hydroxy-2-methylpropyl)phenyl]propionic Acid; Ibuprofen Impurity L; 1-Hydroxy Ibuprofen (Ibuprofen Impurity L)(Mixture of Diastereomers)

Database IDs

• CAS Number: 53949-53-4
• MDL Number: MFCD08275586
• PubChem SID: 162251777
• PubChem CID: 45117195

CALCULATED PROPERTIES

• Acid pKa: 4.5450687
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.6912364
• LogD (pH = 7.4): -0.08148625
• Log P: 2.6907008
• Molar Refractivity: 62.1704 cm^3
• Polarizability: 24.338736 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 80-85°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302

Product Information

• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C13H18O3

DETAILS

Sigma Aldrich - 32496

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - H942858

Degradation product of Ibuprofen. Ibuprofen impurity L.

REFERENCES

• Forrest, J., et al.: Clin. Pharmacokinet., 7(2)
• 93 (2)
• Shockcor, J., et al.: Xenobiotica, 26, 189 (2)
• Nicholls, A., et al.: Chem. Res. Toxicol., 14, 975 (2)
• Holmes, E., et al.: Toxicol. Sci., 87, 1 (2)