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Merck
CN

E5641

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
NACRES:
NA.25
PubChem Substance ID:
24894343
UNSPSC Code:
12352211
EC Number:
200-578-6
MDL number:
MFCD00132914

Key Documents

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Product Name

11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoic acid, ~100 μg/mL in ethanol, ≥95%

InChI key

DXOYQVHGIODESM-ATELOPIESA-N

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+

SMILES string

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

assay

≥95%

concentration

~100 μg/mL in ethanol

lipid type

omega FAs

storage temp.

−20°C

Quality Level

200

Related Categories

Packaging

Packaged under argon

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

48.2 °F - closed cup

flash_point_c

9 °C - closed cup

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SLCP4467
SLCH2994
SLCG3097
SLCF9395
SLBZ2025

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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
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
Ahmad H Alammari et al.
Journal of pharmaceutical sciences, 109(7), 2321-2335 (2020-04-03)
Cytochrome P450 1B1 (CYP1B1) has been reported to have a major role in metabolizing arachidonic acid (AA) into cardiotoxic metabolites, mid-chain hydroxyeicosatetraenoic acids (HETEs). Recently, we have shown that fluconazole decreases the level of mid-chain HETEs in human liver microsomes.
Jun-xia Jiang et al.
PloS one, 10(6), e0128278-e0128278 (2015-06-04)
Cytochrome P-450 epoxygenase (EPOX)-derived epoxyeicosatrienoic acids (EETs), 5-lipoxygenase (5-LO), and leukotriene B4 (LTB4), the product of 5-LO, all play a pivotal role in the vascular inflammatory process. We have previously shown that EETs can alleviate oxidized low-density lipoprotein (ox-LDL)-induced endothelial
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