E5641

Sigma-Aldrich

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

~100 μg/mL in ethanol, ≥95%

Synonym(s):
(±)11,12-EpETrE, 11,12-EET
Empirical Formula (Hill Notation):
C20H32O3
CAS Number:
Molecular Weight:
320.47
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥95%

concentration

~100 μg/mL in ethanol

storage temp.

−20°C

SMILES string

CCCCC\C=C\CC1OC1C\C=C\C\C=C\CCCC(O)=O

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+

InChI key

DXOYQVHGIODESM-ATELOPIESA-N

Packaging

Packaged under argon

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Precautionary Statements

RIDADR

UN1170 - class 3 - PG 2 - Ethanol, solution

WGK Germany

WGK 1

Flash Point(F)

48.2 °F - closed cup

Flash Point(C)

9 °C - closed cup

Yindi Ding et al.
The Journal of pharmacology and experimental therapeutics, 350(1), 14-21 (2014-04-26)
Cytochrome P450-derived epoxides of arachidonic acid [i.e., the epoxyeicosatrienoic acids (EETs)] are important lipid signaling molecules involved in the regulation of vascular tone and angiogenesis. Because many actions of 11,12-cis-epoxyeicosatrienoic acid (EET) are dependent on the activation of protein kinase...
Yong Zhou et al.
Shock (Augusta, Ga.), 47(5), 638-645 (2016-10-19)
Acute lung injury (ALI) is characterized by rapid alveolar injury, vascular leakage, lung inflammation, neutrophil accumulation, and induced cytokines production leading to lung edema. The mortality rate of patients suffering from ALI remains high. Epoxyeicosatrienoic acids (EETs) are cytochrome P450-dependent...
L Yang et al.
British journal of clinical pharmacology, 80(1), 28-44 (2015-02-07)
There is increasing evidence suggesting that epoxyeicosatrienoic acids (EETs) play an important role in cardioprotective mechanisms. These include regulating vascular tone, modulating inflammatory responses, improving cardiomyocyte function and reducing ischaemic damage, resulting in attenuation of animal models of cardiovascular risk...
Xiaojing Wang et al.
Scandinavian journal of immunology, 90(3), e12791-e12791 (2019-05-28)
The epoxyeicosatrienoic acids (EETs) are products of cytochrome P450 epoxygenases and have recently been found to have an anti-inflammatory activity. However, the role of EETs in non-alcoholic steatohepatitis has not been fully understood. In this study, we investigated the protective...
Annemarieke E Loot et al.
PloS one, 7(9), e46065-e46065 (2012-10-03)
In the systemic circulation, 11,12-epoxyeicosatrienoic acid (11,12-EET) elicits nitric oxide (NO)- and prostacyclin-independent vascular relaxation, partially through the activation of large conductance Ca(2+)-activated potassium (BK) channels. However, in the lung 11,12-EET contributes to hypoxia-induced pulmonary vasoconstriction. Since pulmonary artery smooth...

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