(±)11(12)-EET

Product Name(±)11(12)-EET
CAS123931-40-8
MFC20H32O3
MW320.47
EINECS200-578-6
MOL File123931-40-8.mol

Chemical Properties

Boiling point	461.8±33.0 °C(Predicted)
Density	0.983±0.06 g/cm3(Predicted)
Flash point	9℃
storage temp.	-20°C
solubility	DMF: 50 mg/ml; DMSO: 50 mg/ml; Ethanol: 50 mg/ml; PBS pH 7.2: 1 mg/ml
pka	4.75±0.10(Predicted)
form	Liquid
color	Colorless to light yellow
InChI	1S/C20H32O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h6,8-10,12-13,18-19H,2-5,7,11,14-17H2,1H3,(H,21,22)/b8-6+,12-9+,13-10+
InChIKey	DXOYQVHGIODESM-ATELOPIESA-N
SMILES	CCCCC\C=C\CC1OC1C\C=C\C\C=C\CCCC(O)=O

Safety Information

Hazard Codes	F
Risk Statements	11
Safety Statements	7-16
RIDADR	UN1170 - class 3 - PG 2 - Ethanol, solution
WGK Germany	1
Storage Class	3 - Flammable liquids
Hazard Classifications	Eye Irrit. 2 Flam. Liq. 2

Usage And Synthesis

Description

(±)11(12)-EET is a fully racemic version of the R/S enantiomeric forms biosynthesized from arachidonic acid by cytochrome P450 enzymes. A higher proportion of 11(R),12(S)-EET is produced by the CYP450 isoforms CYP2C23 and CYP2C24 while CYP2B2 produces a higher proportion of 11(S),12(R)-EET. 11(12)-EET has been shown, along with 8(9)-EET , to play a role in the recovery of depleted calcium pools in cultured smooth muscle cells. It also inhibits basolateral 18-pS potassium channels in the renal cortical collecting duct when used at a concentration of 100 nM. 11(12)-EET (50 μg/kg per day) increases adhesion of isolated peripheral blood leukocytes in a chamber coated with P-selectin and ICAM-1 but does not affect choroidal neovascularization size following laser photocoagulation. It also has anti-inflammatory, angiogenic, and cardioprotective properties.

Uses

14(15)-Epoxy-5Z,8Z,11Z-eicosatrienoic Acid-D11 is a deuterium labelled 14(15)-Epoxy-5Z,8Z,11Z-eicosatrienoic Acid (E350670), which is a useful research chemical that acts as an endothelium-derived hyperpolarizing factor in bovine coronary arteries to mediate vascular effects of vasoactive hormones.

References

[1] 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.
[2] 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.
[3] 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
[4] 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
[5] 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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