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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

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About This Item

Empirical Formula (Hill Notation):
C20H32O3
CAS Number:
123931-40-8
Molecular Weight:
320.47
EC Number:
200-578-6
MDL number:
MFCD00132914
UNSPSC Code:
12352211
PubChem Substance ID:
24894343
NACRES:
NA.25

Quality Level

200

Assay

≥95%

concentration

~100 μg/mL in ethanol

lipid type

omega FAs

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
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

48.2 °F - closed cup

Flash Point(C)

9 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Andrea E Vasconez et al.
Acta physiologica (Oxford, England), 225(1), e13168-e13168 (2018-08-05)
The histone demethylase Jarid1b limits gene expression by removing the active methyl mark from histone3 lysine4 at gene promoter regions. A vascular function of Jarid1b is unknown, but a vasoprotective function to inflammatory and hypertrophic stimuli, like angiotensin II (AngII)
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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