(2S)-2-(3-benzoylphenyl)propanoic acid

• ChemBase ID: 148572
• Molecular Formular: C16H14O3
• Molecular Mass: 254.28056
• Monoisotopic Mass: 254.09429431
• SMILES: C[C@@H](c1cccc(c1)C(=O)c1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)[C@H](c1cccc(c1)C(=O)c1ccccc1)C
• InChI: InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)/t11-/m0/s1
• InChIKey: DKYWVDODHFEZIM-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(3-benzoylphenyl)propanoic acid
• IUPAC Traditional name: (+)-ketoprofen
• Synonyms: (S)-(+)-3-Benzoyl-α-methylbenzeneacetic acid; (S)-2-(3-Benzoylphenyl)propionic acid; (S)-(+)-Ketoprofen; (+)-Ketoprofen; (S)-Ketoprofen; Dexketoprofen; Keral; (S)-(+)-Ketoprofen; (S)-(+)-3-苯甲酰基-α-甲基苯乙酸; (S)-2-(3-苯甲酰基苯基)丙酸; (S)-(+)-酮洛芬

Database IDs

• CAS Number: 22161-81-5
• MDL Number: MFCD00673316
• PubChem SID: 24896218; 24870770; 162242747
• PubChem CID: 667550

CALCULATED PROPERTIES

• Acid pKa: 3.882609
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.9908713
• LogD (pH = 7.4): 0.39084414
• Log P: 3.6133335
• Molar Refractivity: 72.5156 cm^3
• Polarizability: 28.005615 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 61-64°C; 75-78 °C(lit.)
• Optical Rotation: [α]22/D +49°, c = 1 in methanol

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: CY1572790
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36/37/38-50/53
• Safety Statements: 26-60-61
• GHS Pictograms: GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335-H400
• GHS Precautionary statements: P261-P273-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... IL8RA(3577), PTGS1(5742), PTGS2(5743)mouse ... Ptgs2(19225)

Product Information

• Purity: 99%
• Linear Formula: C6H5COC6H4CH(CH3)CO2H

DETAILS

Sigma Aldrich - K2135

Biochem/physiol Actions
Non-steroidal anti-inflammatory agent; non-selective inhibitor of COX-1 and COX-2.

Sigma Aldrich - 471909

Packaging
1 g in glass bottle

Toronto Research Chemicals - K200805

Anti-inflammatory; analgesic.

REFERENCES

• Ueno, K., et al.: J. Med. Chem., 19, 941 (1976)
• Liversidge, G.G., Anal. Profiles Drug Subs., 10, 443 (1976)
• Jamali, F., et al.: Clin. Pharmacokinet., 19, 197 (1976)