See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

Join us! · SLAS2012 1st Annual Conference & Exhibition · San Diego, California · February 4-8, 2012 · Booth 445

(±)17,18-DiHETE Exclusive

Cayman Chemical Item Number 10006999

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

(±)17,18-DiHETE

See more

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
Copy SMILES to clipboard
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).

Show all 5 Hide all but first 3

(±)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 2012-02-04. 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.

Related Products

(±)11,12-DHET
(±)14,15-DHET
(±)14,15-DiHETE Exclusive
14(15)-EpETE
(±)5,6-DHET
5,6-DiHETE Exclusive
(±)8,9-DHET
Show all 7 Hide all but first 3

Downloads

Batch-specific Information

Login to access batch-specific information

Cayman Chemical is a manufacturer, supplier and vendor of biochemical reagents, assay kits, antibodies, and proteins.

Other Resources
Management Team Company Profile Company History ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2012 Cayman Chemical Company

Lost password?