(11S,12R)-EET

Names

[ Name ]:
(11S,12R)-EET

[Synonym ]:
5,8-Decadienoic acid, 10-[(2S,3R)-3-[(2Z)-2-octen-1-yl]oxiranyl]-, (5Z,8Z)-
(5Z,8Z)-10-{(2S,3R)-3-[(2Z)-2-Octen-1-yl]-2-oxiranyl}-5,8-decadienoic acid
(11S,12R)-EET
(5Z,8Z)-10-{(2S,3R)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
(5Z,8Z)-10-{(2S,3R)-3-[(2Z)-2-Octen-1-yl]-2-oxiranyl}-5,8-decadie noic acid

Biological Activity

[Description]:

(±)11(12)-EET is a NLRP3 inflammasome inhibitor. (±)11(12)-EET can be used for the research of anti-inflammatory, angiogenic and cardioprotective[1][2][3][4][6].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Immunology/Inflammation >> NOD-like Receptor (NLR)

Research Areas >> Inflammation/Immunology

[Target]

NLRP3 inflammasome

[In Vitro]

(±)11(12)-EET (5 μM; 10 mimutes; macrophages) depresses NLRP3 protein expression, dramatically decreases the expression of pro-IL-1β in cells and the supernatant and reduces the intracellular ROS[1]. Western Blot Analysis[1] Cell Line: Macrophages Concentration: 5 μM Incubation Time: 10 mimutes Result: Depresses NLRP3 protein expression. Immunofluorescence[1] Cell Line: Macrophages Concentration: 5 μM Incubation Time: 10 mimutes Result: Reduced the intracellular ROS.

[In Vivo]

(±)11(12)-EET increases adhesion of isolated peripheral blood leukocytes in a chamber coated with P-selectin and ICAM-1 in 50 µg/kg[5].

[References]

[1]. Luo XQ, et al. Epoxyeicosatrienoic acids inhibit the activation of NLRP3 inflammasome in murine macrophages. J Cell Physiol. 2020;235(12):9910-9921.

[2]. Chacos N, et al. Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. Biochem Biophys Res Commun. 1982;104(3):916-922.

[3]. Oliw EH, et al. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. J Biol Chem. 1982;257(7):3771-3781.

[4]. Capdevila JH, et al. Cytochrome P450 and arachidonic acid bioactivation. Molecular and functional properties of the arachidonate monooxygenase. J Lipid Res. 2000;41(2):163-181.

[5]. Wang Z, et al. Arachidonic acid inhibits basolateral K channels in the cortical collecting duct via cytochrome P-450 epoxygenase-dependent metabolic pathways. Am J Physiol Renal Physiol. 2008;294(6):F1441-F1447.

[6]. Spector AA. Arachidonic acid cytochrome P450 epoxygenase pathway. J Lipid Res. 2009;50 Suppl(Suppl):S52-S56.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
461.8±33.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₀H₃₂O₃

[ Molecular Weight ]:
320.466

[ Flash Point ]:
154.6±18.9 °C

[ Exact Mass ]:
320.235138

[ PSA ]:
49.83000

[ LogP ]:
6.30

[ Vapour Pressure ]:
0.0±2.4 mmHg at 25°C

[ Index of Refraction ]:
1.501

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H319

[ Precautionary Statements ]:
P210-P280-P305 + P351 + P338-P337 + P313-P403 + P235

[ RIDADR ]:
UN1170 - class 3 - PG 2 - Ethanol, solution

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Protective effects of n-6 fatty acids-enriched diet on intestinal ischaemia/reperfusion injury involve lipoxin A4 and its receptor.

Br. J. Pharmacol. 172(3) , 910-23, (2015)

Long-term intake of dietary fatty acids is known to predispose to chronic inflammation, but their effects on acute intestinal ischaemia/reperfusion (I/R) injury is unknown. The aim of this study was t...

Cyp2c44 epoxygenase in the collecting duct is essential for the high K+ intake-induced antihypertensive effect.

Am. J. Physiol. Renal Physiol. 307(4) , F453-60, (2014)

Cytochrome P-450, family 2, subfamily c, polypeptide 44 (Cyp2c44) epoxygenase metabolizes arachidonic acid (AA) to epoxyeicosatrienoic acids (EETs) in kidney and vascular tissues. In the present study...

UHPLC-MS/MS analysis of arachidonic acid and 10 of its major cytochrome P450 metabolites as free acids in rat livers: effects of hepatic ischemia.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 964 , 153-63, (2014)

The cytochrome P450 metabolites of arachidonic acid (AA) are mostly present in tissues, such as the liver, as bound to phospholipids, with only a small fraction available as free acids. The purpose of...

Related Compounds

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