123931-40-8

123931-40-8 structure

Name: (11S,12R)-EET
Chemical Name: 11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoic acid
CAS Number: 123931-40-8
Molecular Formula: C₂₀H₃₂O₃
Molecular Weight: 320.466
Catalog: Signaling Pathways Immunology/Inflammation NOD-like Receptor (NLR)
Create Date: 2016-06-09 17:26:22
Modify Date: 2024-01-11 00:16:16
(±)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].

Name	11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoic acid
Synonyms	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

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.

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

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

90080-08-3

123931-40-8

Literature: Mosset, Paul; Yadagiri, Pendri; Lumin, Sun; Capdevila, Jorge; Falck, J. R. Tetrahedron Letters, 1986 , vol. 27, # 50 p. 6035 - 6038

109296-17-5

123931-40-8

Literature: Mosset, Paul; Yadagiri, Pendri; Lumin, Sun; Capdevila, Jorge; Falck, J. R. Tetrahedron Letters, 1986 , vol. 27, # 50 p. 6035 - 6038

73958-09-5

123931-40-8

Literature: Mosset, Paul; Yadagiri, Pendri; Lumin, Sun; Capdevila, Jorge; Falck, J. R. Tetrahedron Letters, 1986 , vol. 27, # 50 p. 6035 - 6038

506-32-1

123931-40-8

123931-38-4

129172-62-9

Detail

Literature: Mesaros, Clementina; Lee, Seon Hwa; Blair, Ian A. Rapid Communications in Mass Spectrometry, 2010 , vol. 24, # 22 p. 3237 - 3247

Precursor 3
109296-17-5 73958-09-5 506-32-1
DownStream 0

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