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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
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Product Name
cis-5,8,11,14,17-Eicosapentaenoic acid, ≥99%
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-
SMILES string
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O
InChI key
JAZBEHYOTPTENJ-JLNKQSITSA-N
biological source
fish oil
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
Quality Level
Gene Information
human ... ALOX5(240)
mouse ... ALOX5(11689), Pparg(19016)
rat ... ALOX5(25290)
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1 of 4
This Item | 44864 | E6627 | L2376 |
|---|---|---|---|
| assay ≥99% | assay ≥98.5% (GC) | assay ≥99% (capillary GC) | assay ≥99% |
| form liquid | form - | form film or powder | form - |
| 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 - |
| biological source fish oil | biological source fish oil | biological source synthetic (organic) | biological source - |
Application
cis-5,8,11,14,17-Eicosapentaenoic acid has been used:
- to test pharmacologic effect on steatosis in hepatocytes[1]
- as an analytical standard in Raman spectra measurements to characterize human breast cancer samples[2]
- in lipid peroxidation assay in mouse embryonic fibroblasts and in pre-treatment of cells for cell viability studies[3]
Biochem/physiol Actions
5-Lipoxygenase inhibitor; reduces thromboxane A2 production.
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.[6] It is obtained majorly from fish oil, seaweed, phytoplankton, and camelina.[4] Being an Omega-3 fatty acid, it shows cis-trans conformations.[7]
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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Che-Hsin Lee et al.
International journal of molecular sciences, 15(6), 10334-10349 (2014-06-12)
Recent studies have shown that free fatty acids are associated with chronic inflammation, which may be involved in vascular injury. The intake of eicosapentaenoic acid (EPA) can decrease cardiovascular disease risks, but the protective mechanisms of EPA on endothelial cells
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)
Effect of eicosapentaenoic acid and docosahexaenoic acid on myogenesis and mitochondrial biosynthesis during murine skeletal muscle cell differentiation
Hsueh TY, et al.
Frontiers in nutrition, 5, 15-15 (2018)
A Comprehensive Review of Chemistry, Sources and Bioavailability of Omega-3 Fatty Acids
Cholewski M, et al.
Nutrients, 10(11), 1662-1662 (2018)
Omega-3 fatty acids eicosapentaenoic acid and docosahexaenoic acid and their mechanisms of action on apolipoprotein B-containing lipoproteins in humans: a review
Oscarsson J and Hurt-Camejo E
Lipids in Health and Disease, 16(1), 149-149 (2017)
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