Cayman Chemical | (±)-17,18-DiHETE | Description • (±)17,18-dihydroxy-eicosa-5,8,11,14-Tetraenoic Acid

10006999 (±)-17,18-DiHETE

(±)17,18-dihydroxy-eicosa-5,8,11,14-Tetraenoic Acid

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• See more Fatty Acids; Oxylipins; Cytochrome P450; Nutrition/Diet; Oxidative Injury

Chemical structure definitions are available for many Cayman products. See Chemical Structure Database for details.

Eicosapentaenoic acid (EPA) is an ω-3 fatty acid abundantly available in marine organisms. 17,18-DiHETE is one of the major metabolites produced when EPA is incubated with various rat tissue homogenates or cynomolgus monkey seminal vesicles.^1,2,3,4 The route of production of 17,18-DiHETE likely proceeds through cytochrome P450-catalyzed epoxidation at the ω-3 double bond followed by conversion to the vicinal diols by epoxide hydrolase. EPA is also metabolized preferentially by Gaeumannomyces graminis to 17,18-DiHETE.⁵

1 VanRollins, M., Frade, P.D., Carretero, O.A. Oxidation of 5,8,11,14,17-eicosapentaenoic acid by hepatic and renal microsomes. Biochim Biophys Acta 996 133-149 (1988).

2 Yamane, M., Abe, A., Yamane, S. High-performance liquid chromatography-thermospray mass spectrometry of epoxy polyunsaturated fatty acids and epoxyhydroxy polyunsaturated fatty acids from an incubation mixture of rat tissue homogenate. Journal of Chromatography B 652 123-136 (1994).

3 Oliw, E.H. Biosynthesis of 18(RD)-hydroxyeicosatetraenoic acid from arachidonic acid by microsomes of monkey seminal vesicles. Some properties of a novel fatty acid w3-hydroxylase and w3-epoxygenase. J Biol Chem 264(30) 17845-17853 (1989).

4 Oliw, E.H., Sprecher, H.W. Metabolism of polyunsaturated (n-3) fatty acids by monkey seminal vesicles: Isolation and biosynthesis of omega-3 epoxides. Biochim Biophys Acta 1086 287-294 (1991).

5 Brodowsky, I.D., Oliw, E.H. Metabolism of 18:2(n-3), 20:4(n-6), and 2-:5(n-3) by the fungus Gaeumannomyces graminis: Identification of metabolites formed by 8-hydroxylation and by w2 and w3 oxygenation. Biochim Biophys Acta 1124 59-65 (1992).

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Purchase 10006999 (±)-17,18-DiHETE

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Warning This product is not for human or veterinary use.

Pricing updated 2010-03-19.
Prices are subject to change without notice.

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