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(±)17,18-DiHETE Exclusive

Cayman Chemical Item Number 10006999

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

(±)17,18-DiHETE

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Description

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., and 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., and 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. J Chromatogr 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., and 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., and 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).

Synonyms
  • (±)17,18-dihydroxy-eicosa-5,8,11,14-Tetraenoic Acid
Formal Name 17,​18-​dihydroxy-​5Z,​8Z,​11Z,​14Z-​eicosatetraenoic acid
Molecular Formula C20H32O4
Formula Weight 336.5
Formulation A solution in ethanol
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CC[C@@H]​(O)​[C@@H]​(O)​C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)​O

Background Reading

Yamane, M., Abe, A., and 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. J Chromatogr B 652 123-136 (1994).

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).

Oliw, E.H., and 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).

Brodowsky, I.D., and 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).

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

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(±)17,18-DiHETE is available in the following screening library:

Size Price Quantity Subtotal
25 µg $69.00 $0.00
50 µg $131.00 $0.00
100 µg $248.00 $0.00
250 µg $552.00 $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 2012-05-25. 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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