ChemicalBook Product Catalog Petrochemical Oils 11R(12S)-EET

11R(12S)-EET

Product Name11R(12S)-EET
CAS123931-38-4
MFC20H32O3
MW320.47
EINECS
MOL File123931-38-4.mol

Chemical Properties

Boiling point	461.840±33.00 °C(Press: 760.00 Torr)(predicted)
Density	0.983±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
solubility	Acetonitrile: Sparingly soluble: 1-10 mg/ml Ethanol: Slightly soluble: 0.1-1 mg/ml
pka	4.752±0.10(predicted)

Usage And Synthesis

Uses

11R(12S)-EET is a cis-epoxytrienoic acid (EETs) derivative that is metabolized by cytoplasmic cyclooxygenases. Studies have shown that 14(R), 15(S)-, 11(S),12(R)-, and 8(S),9(R)-EETs are metabolized at significantly higher rates than their enantiomers. Enzyme-catalyzed hydration revealed that water addition was non-regioselective for the 11,12-EET enantiomers, whereas water addition occurred primarily at the C9 position for both enantiomers of 8,9-EET. These results suggest that the metabolic properties of 11R(12S)-EET and other EET enantiomers in enzyme-catalyzed processes are significantly affected by their stereostructures[1].

References

[1] Zeldin DC, et al. Metabolism of epoxyeicosatrienoic acids by cytosolic epoxide hydrolase: substrate structural determinants of asymmetric catalysis. Arch Biochem Biophys. 1995 Jan 10;316(1):443-51. DOI:10.1006/abbi.1995.1059
[2] J H CAPDEVILA R C H J R Falck. Cytochrome P450 and arachidonic acid bioactivation. Molecular and functional properties of the arachidonate monooxygenase.[J]. Journal of Lipid Research, 2000, 41 2: 163-181.
[3] B E DAIKH. Regio- and stereoselective epoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C9.[J]. Journal of Pharmacology and Experimental Therapeutics, 1994, 271 3: 1427-1433.
[4] YONGDE ZHANG. EET homologs potently dilate coronary microvessels and activate BK(Ca) channels.[J]. American journal of physiology. Heart and circulatory physiology, 2001, 280 6 1: H2430-40. DOI: 10.1152/ajpheart.2001.280.6.h2430
[5] PATRICK Y.-K WONG J. R F Pi Shiang Lai. Mechanism and signal transduction of 14 (R), 15 (S)-epoxyeicosatrienoic acid (14,15-EET) binding in guinea pig monocytes[J]. Prostaglandins & other lipid mediators, 2000, 62 4: Pages 321-333. DOI: 10.1016/s0090-6980(00)00079-4
[6] PENG SUN. High potassium intake enhances the inhibitory effect of 11,12-EET on ENaC.[J]. Journal of The American Society of Nephrology, 2010, 21 10: 1667-1677. DOI: 10.1681/asn.2009111110
[7] YINDI DING. The biological actions of 11,12-epoxyeicosatrienoic acid in endothelial cells are specific to the R/S-enantiomer and require the G(s) protein.[J]. Journal of Pharmacology and Experimental Therapeutics, 2014, 350 1: 14-21. DOI: 10.1124/jpet.114.214254

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