Selective inhibitor of epoxygenation reactions catalyzed by CYP4A2 and CYP4A3
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PPOH

Item No. 75760

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(2-propynyloxy)-benzenehexanoic acid
CAS Number
206052-01-9
Molecular Formula
C15H18O3
Formula Weight
246.3
Purity
≥99%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 50 mg/mlEthanol: 100 mg/mlEthanol:PBS (pH 7.2) (1:4): .05 mg/mlPBS (pH 7.2): 0.5 mg/ml
SMILES
C#CCOC1=CC=CC=C1CCCCCC(O)=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $21

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    5 mg

    $86

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    10 mg

    $152

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    50 mg

    $655

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    Product Description

    Arachidonic acid is converted by microsomal CYP450 enzymes to a variety of epoxides, ω-1 and ω-hydroxylated compounds via what is known as the epoxidase pathway.1,2,3 PPOH is a selective inhibitor of the epoxygenation reactions catalyzed by specific CYP450 isozymes.4 PPOH inhibits the formation of arachidonate 11,12 epoxides by CYP4A2 and CYP4A3 enzymes with an IC50 of 9 µM, but has effect on the formation of 20-HETE, the ω-hydroxylation product of CYP4A1.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Capdevila, J.H., Karara, A., Waxman, D.J., et al. Cytochrome P-450 enzyme-specific control of the regio- and enantiofacial selectivity of the microsomal arachidonic acid epoxygenase. The Journal of Biological Chemisty 265(19), 10865-10871 (1990).

    2. Sacerdoti, D., Abraham, N.G., McGiff, J.C., et al. Renal cytochrome P-450-dependent metabolism of arachidonic acid in spontaneously hypertensive rats. Biochem. Pharmacol. 37(3), 521-527 (1988).

    3. Fitzpatrick, F.A., and Murphy, R.C. Cytochrome P-450 metabolism of arachidonic acid: Formation and biological actions of “epoxygenase”-derived eicosanoids. Pharmacol. Rev. 40(4), 229-241 (1989).

    4. Imig, J.D., Falck, J.R., and Inscho, E.W. Contribution of cytochrome P450 epoxygenase and hydroxylase pathways to afferent arteriolar autoregulatory responsiveness. Br. J. Pharmacol. 127(6), 1399-1405 (1999).

    5. Wang, M.H., Brand-Schieber, E., Zand, B.A., et al. Cytochrome P450-derived arachidonic acid metabolism in the rat kidney: Characterization of selective inhibitors. J. Pharmacol. Exp. Ther. 284(3), 966-973 (1998).