2-(pentanoyloxy)benzoic acid

• ChemBase ID: 154189
• Molecular Formular: C12H14O4
• Molecular Mass: 222.23716
• Monoisotopic Mass: 222.08920893
• SMILES: CCCCC(=O)Oc1ccccc1C(=O)O
• Canonical SMILES: CCCCC(=O)Oc1ccccc1C(=O)O
• InChI: InChI=1S/C12H14O4/c1-2-3-8-11(13)16-10-7-5-4-6-9(10)12(14)15/h4-7H,2-3,8H2,1H3,(H,14,15)
• InChIKey: WJHZBTMHUNVIKC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(pentanoyloxy)benzoic acid
• IUPAC Traditional name: 2-(pentanoyloxy)benzoic acid
• Synonyms: 2-Valeryloxybenzoic acid; Valerylsalicylic acid; vsa; Valeryl Salicylate

Database IDs

• CAS Number: 64206-54-8
• MDL Number: MFCD00041466
• PubChem SID: 24724662; 162248328
• PubChem CID: 135269

CALCULATED PROPERTIES

• Acid pKa: 3.414088
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.7536666
• LogD (pH = 7.4): -0.57154864
• Log P: 2.8277628
• Molar Refractivity: 58.2755 cm^3
• Polarizability: 22.63444 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble24 mL/mL; H2O: insoluble
• Apperance: white
• Melting Point: 86-87 °C(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H14O4

DETAILS

Sigma Aldrich - V2889

Biochem/physiol Actions
Selective, irreversible COX-1 inhibitor. The selectivity for COX-1 vs COX-2 shows the IC50 values for ovine COX-1 vs COX-2 of 0.8 μM vs. 15 mM respectively.