P9114

6-(2-Propargyloxyphenyl)hexanoic acid

≥98%, solid

• Synonym(s): PPOH
• Empirical Formula (Hill Notation): C₁₅H₁₈O₃
• CAS Number: 206052-01-9
• Molecular Weight: 246.30
• MDL number: MFCD03453622
• UNSPSC Code: 12352106
• PubChem Substance ID: 329820341
• NACRES: NA.77

Properties

• biological source: synthetic
• Quality Level: 200
• Assay: ≥98%
• form: solid
• shipped in: wet ice
• storage temp.: −20°C
• SMILES string: OC(=O)CCCCCc1ccccc1OCC#C
• InChI: 1S/C15H18O3/c1-2-12-18-14-10-7-6-9-13(14)8-4-3-5-11-15(16)17/h1,6-7,9-10H,3-5,8,11-12H2,(H,16,17)
• InChI key: CUNYTKVXYZYERK-UHFFFAOYSA-N

Description

General description

PPOH is a synthetic, acetylenic fatty acid and a selective inhibitor of arachidonate epoxygenation reactions catalyzed by certain microsomal cytochrome P450 (CYP) enzymes. PPOH inhibits the reaction of epoxide formation (IC₅₀ of 90 μM) at arachidonate positions 11 and 12 by CYP4A2 and CYP4A3 isozymes. PPOH does not inhibit the ω-hydroxylation reaction of CYP4A1 leading to the formation of 20-HETE.1 Arachidonate metabolism studies using inhibitors such as PPOH may be useful in elucidating the role of metabolites in regulating renal function and hypertension.

Biochem/physiol Actions

Selective inhibitor of epoxygenation catalyzed by CYP450 isozymes.

Preparation Note

PPOH is soluble in the following organic solvents:ethanol, DMSO, and N,N-dimethylformamide (DMF). It is at least soluble to 50 mg/ml in each solvent. The organic solvents should first be purged with an inert gas such as argon before preparation of the stock solutions to minimize any possible oxidation of the unsaturated PPOH. Stock solutions will be stable for at least one year as aliquots stored at –20 °C and under a layer of argon or dry nitrogen. The stock solution should be further diluted into aqueous buffers or isotonic saline (ensure that the residual amount of organic solvent is not causing physiological effects at low concentrations of the organic solvent) for biological experiments. Alternatively, if an organic solvent-free aqueous solution is desired, directly dissolve the crystalline PPOH in aqueous buffers. The solubility of PPOH is at least 0.5 mg/ml in PBS buffer, pH 7.2. Do not store aqueous solutions for more than one day.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves