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E2011
cis-5,8,11,14,17-Eicosapentaenoic acid
from fish oil, ≥99% (GC), liquid, 5-Lipoxygenase inhibitor
cis-5,8,11,14,17-Eicosapentaenoic acid
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Synonym(s):
EPA, Timnodonic acid
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About This Item
Linear Formula:
CH3(CH2CH=CH)5(CH2)3CO2H
CAS Number:
Molecular Weight:
302.45
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
Beilstein/REAXYS Number:
1714433
Pricing and availability is not currently available.
Product Name
cis-5,8,11,14,17-Eicosapentaenoic acid, ≥99%
biological source
fish oil
Quality Level
assay
≥99%
form
liquid
refractive index
n20/D 1.4977 (lit.)
mp
−54-−53 °C (lit.)
solubility
methanol: 50 mg/mL, clear, colorless
density
0.943 g/mL at 25 °C (lit.)
storage temp.
−20°C
SMILES string
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O
InChI
1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChI key
JAZBEHYOTPTENJ-JLNKQSITSA-N
Gene Information
human ... ALOX5(240)
mouse ... ALOX5(11689), Pparg(19016)
rat ... ALOX5(25290)
General description
Eicosapentaenoic acid is a polyunsaturated fatty acid (PUFAs) and is synthesized from linolenic acid. It is distributed in phospholipid bilayers of the cell membrane, synaptic membranes of the brain and retina. It is obtained majorly from fish oil, seaweed, phytoplankton, and camelina. Being an Omega-3 fatty acid, it shows cis-trans conformations.
Application
cis-5,8,11,14,17-Eicosapentaenoic acid has been used:
- to test pharmacologic effect on steatosis in hepatocytes
- as an analytical standard in Raman spectra measurements to characterize human breast cancer samples
- in lipid peroxidation assay in mouse embryonic fibroblasts and in pre-treatment of cells for cell viability studies
Biochem/physiol Actions
5-Lipoxygenase inhibitor; reduces thromboxane A2 production.
Eicosapentaenoic acid (EPA) is essential for healthy living and alleviates obesity. It decreases the triglyceride levels by modulating very-low-density lipoprotein(VLDL) levels.
1 of 1
This Item | |||
|---|---|---|---|
| form liquid | form - | form film or powder | form - |
| assay ≥99% | assay ≥98.5% (GC) | assay ≥99% (capillary GC) | assay ≥99% |
| Quality Level 200 | Quality Level 100 | Quality Level 200 | Quality Level 200 |
| storage temp. −20°C | storage temp. −20°C | storage temp. −20°C | storage temp. −20°C |
| solubility methanol: 50 mg/mL, clear, colorless | solubility - | solubility methanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow | solubility - |
| density 0.943 g/mL at 25 °C (lit.) | density 0.943 g/mL at 25 °C (lit.) | density - | density 0.914 g/mL at 25 °C (lit.) |
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Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
200.1 °F - closed cup
flash_point_c
93.4 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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Nutrition and traumatic brain injury: improving acute and subacute health outcomes in military personnel (2011)
Docosahexaenoic acid enhances methylmercury-induced endoplasmic reticulum stress and cell death and eicosapentaenoic acid potentially attenuates these effects in mouse embryonic fibroblasts
Takanezawa Y, et al.
Toxicology Letters, 306(15), 35-42 (2019)
omega-3 Fatty acids reverse lipotoxity through induction of autophagy in nonalcoholic fatty liver disease
Chen Y, et al.
Nutrition, 31(11-12), 1423-1429 (2015)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| E2011-10MG | 04061833602386 |
| E2011-50MG | 04061833602409 |
| E2011-100MG | 04061838063663 |
| E2011-25MG | 04061833602393 |