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17(18)-EpETE

Cayman Chemical Item Number 50861

17,18-epoxy Eicosatetraenoic Acid; 17,18 EEQ

17(18)-EpETE

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Description

The epoxygenase pathway is one of the three major branches of eicosanoid biosynthesis.1,2 However, the cytochrome P450 metabolites of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) have been little studied relative to arachidonate epoxygenase metabolites. 17(18)-EpETE is biosynthesized by the stereospecific epoxidation of the ω-3 bond of EPA. 17(18)-EpETE at 100 nM was found to be a potent and selective activator of BK-type calcium activated potassium ion channels in vascular smooth muscle cells.3 It is possible that some of the physiologic effects of fish oil-enhanced diets could be due to this epoxygenase metabolite.

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

2 Oliw, E.H., Bylund, J., and Herman, C. Bisallylic hydroxylation and epoxidation of polyunsaturated fatty acids by cytochrome P450. Lipids 31 1003-1996 (1996).

3 Lauterbach, B., Barbosa-Sicard, E., Wang, M., et al. Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activators. Hypertension 39 609-613 (2002).

Synonyms
  • 17,18-epoxy Eicosatetraenoic Acid
  • 17,18 EEQ
Formal Name (±)17(18)-​epoxy-​5Z,​8Z,​11Z,​14Z-​eicosatetraenoic acid
Molecular Formula C20H30O3
Formula Weight 318.5
Formulation A solution in ethanol
Purity ≥90%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CC[C@H]​1O[C@H]​1C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)​O

Background Reading

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

Oliw, E.H., Bylund, J., and Herman, C. Bisallylic hydroxylation and epoxidation of polyunsaturated fatty acids by cytochrome P450. Lipids 31 1003-1996 (1996).

Lauterbach, B., Barbosa-Sicard, E., Wang, M., et al. Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activators. Hypertension 39 609-613 (2002).

17(18)-EpETE is available in the following screening library:

Size Price Quantity Subtotal
25 µg $38.00 $0.00
50 µg $72.00 $0.00
100 µg $137.00 $0.00
500 µg $608.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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