(+/-)8,9-EET Chemical Properties

Boiling point:

456.2±20.0 °C(Predicted)

Density 

0.983±0.06 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

DMF: 50 mg/ml
DMSO: 50 mg/ml
Ethanol: 50 mg/mlPBS pH 7.2: 1 mg/ml

pka

4.77±0.10(Predicted)

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

16-26-36

RIDADR 

UN 1170 3/PG 2

(+/-)8,9-EET Usage And Synthesis

Uses

(+/-)8,9-Epoxyeicosa-5Z,11Z,14Z-trienoic acid is a glucagon inducer in pancreatic islets.

References

[1] N. CHACOS . Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid[J]. Biochemical and biophysical research communications, 1982, 104 3: Pages 916-922. DOI: 10.1016/0006-291x(82)91336-5
[2] E. OLIW J O F Guengerich. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates.[J]. The Journal of Biological Chemistry, 1982, 109 1: 3771-3781. DOI: 10.1016/s0021-9258(18)34848-8
[3] JI Y. ZHANG . Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase[J]. Biochemical and biophysical research communications, 1992, 183 1: Pages 138-143. DOI: 10.1016/0006-291x(92)91619-2
[4] JONAS BYSTROM. Endogenous epoxygenases are modulators of monocyte/macrophage activity.[J]. PLoS ONE, 2011: e26591. DOI: 10.1371/journal.pone.0026591
[5] AMY A RAND. Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2017, 114 17: 4370-4375. DOI: 10.1073/pnas.1616893114
[6] T KATOH. Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney.[J]. American Journal of Physiology, 1991, 261 4 Pt 2: F578-86. DOI: 10.1152/ajprenal.1991.261.4.f578
[7] FADUMO A. ISSE . Quantification of Epoxyeicosatrienoic acids Enantiomers: The development of reliable and practical liquid chromatography mass Spectrometry assay[J]. Journal of Chromatography B, 2024, 1247: Article 124346. DOI: 10.1016/j.jchromb.2024.124346
[8] ZONGYUAN WU, FANG WEI*   Analytical Strategy for Oxylipin Annotation by Combining Chemical Derivatization-Based Retention Index Algorithm and Feature Tandem Mass Spectrometric Fragmentation as a Biomarker Discovery Tool[J]. Analytical Chemistry, 2023, 95 43: 15933-15942. DOI: 10.1021/acs.analchem.3c02789
[9] ANDREI KORNILOV. Revising the structure of a new eicosanoid from human platelets to 8,9-11,12-diepoxy-13-hydroxyeicosadienoic acid.[J]. The Journal of Biological Chemistry, 2019, 294 23: 9225-9238. DOI: 10.1074/jbc.ra119.008915
[10] REUT LEVI-ROSENZVIG . 5,6-δ-DHTL, a stable metabolite of arachidonic acid, is a potential EDHF that mediates microvascular dilation[J]. Free Radical Biology and Medicine, 2017, 103: Pages 87-94. DOI: 10.1016/j.freeradbiomed.2016.12.022

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