(+/-)17,18-DIHETE Chemical Properties

Boiling point:

515.8±50.0 °C(Predicted)

Density 

1.040±0.06 g/cm3(Predicted)

solubility 

DMF: 30 mg/ml
DMSO: 30 mg/ml
Ethanol: 30 mg/mlPBS (pH 7.2): .5 mg/ml

pka

4.78±0.10(Predicted)

(+/-)17,18-DIHETE Usage And Synthesis

Description

(±)17(18)-DiHETE is one of the major metabolites produced when eicosapentaenoic acid (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.5WARNING This product is not for human or veterinary use.

References

[1] MIKE VANROLLINS  Oscar A C  Peter D Frade. Oxidation of 5,8,11,14,17-eicosapentaenoic acid by hepatic and renal microsomes[J]. Biochimica et biophysica acta. General subjects, 1988, 966 1: Pages 133-149. DOI: 10.1016/0304-4165(88)90137-7
[2] MOTOTERU YAMANE  Sayoko Y  Akihisa Abe. 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]. Journal of Chromatography B: Biomedical Sciences and Applications, 1994, 652 2: Pages 123-136. DOI: 10.1016/0378-4347(93)e0394-6
[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 omega 3-hydroxylase and omega 3-epoxygenase.[J]. The Journal of Biological Chemistry, 1989, 264 30: 17845-17853.
[4] ERNST H. OLIW  Howard W S. Metabolism of polyunsaturated (n − 3) fatty acids by monkey seminal vesicles: isolation and biosynthesis of omega-3 epoxides[J]. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1991, 1086 3: Pages 287-294. DOI: 10.1016/0005-2760(91)90172-e
[5] IRENE D. BRODOWSKY  Ernst H O. Metabolism of 18:2(n − 6), 18:3(n − 3), 20:4(n − 6) and 20:5(n − 3) by the fungus Gaeumannomyces graminis: Identification of metabolites formed by 8-hydroxylation and by w2 and w3 oxygenation[J]. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1992, 1124 1: Pages 59-65. DOI: 10.1016/0005-2760(92)90126-g