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Key Documents

E6627

Sigma-Aldrich

cis-5,8,11,14,17-Eicosapentaenoic acid sodium salt

≥99% (capillary GC)

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About This Item

Linear Formula:
CH3(CH2CH=CH)5(CH2)3CO2Na
CAS Number:
Molecular Weight:
324.43
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

assay

≥99% (capillary GC)

form

film or powder

color

white to off-white

solubility

methanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

shipped in

dry ice

storage temp.

−20°C

SMILES string

[Na].CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI

1S/C20H30O2.Na.H/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

TVEGTERCKGGVCJ-LIJGWLRISA-N

Gene Information

human ... ALOX5(240)
mouse ... ALOX5(11689)
rat ... ALOX5(25290)

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General description

Eicosapentaenoic acid (EPA)/timnodonic acid is an omega-3 polyunsaturated fatty acid (PUFA). This long-chain fatty acid is mainly found in fish oil.

Application

cis-5,8,11,14,17-Eicosapentaenoic acid sodium salt has been used:
  • to study its effect on the pathology of lupus in drug-induced and spontaneous mouse models
  • to pretreat mouse alveolar macrophages to study the effect/relationship between amiodarone and eicosapentaenoic acid (EPA) concerning the cytokine release
  • to examine if pharmacological correction with EPA supplementation might restore autophagic flux and reduce renal lipotoxicity in mice

Biochem/physiol Actions

Eicosapentaenoic acid (EPA) possesses anti-hyperglycemic, anti-oxidant, anti-hyperlipidemic, and anti-inflammatory properties. It aids in improving vasoreactivity. EPA is capable of suppressing vascular smooth muscle proliferation. It ameliorates pulmonary hypertension by preventing Fyn kinase activity. EPA exhibits a beneficial effect on lipid metabolism. It is used to treat hypercholesterolemia and atherosclerosis.
5-Lipoxygenase inhibitor; reduces thromboxane A2 production.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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