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E2011

Sigma-Aldrich

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

cis-5,8,11,14,17-Eicosapentaenoic acid
1 of 1 reviewers received a sample product or took part in a promotion

from fish oil, ≥99% (GC), liquid, 5-Lipoxygenase inhibitor

Synonym(s):

EPA, Timnodonic acid

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Estimated to ship onJuly 07, 2025Details


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10 MG
€277.00
25 MG
€550.00
50 MG
€989.00
100 MG
€1,760.00

About This Item

Linear Formula:
CH3(CH2CH=CH)5(CH2)3CO2H
CAS Number:
Molecular Weight:
302.45
Beilstein:
1714433
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77

€277.00


Estimated to ship onJuly 07, 2025Details


Request a Bulk Order

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)

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Show Differences

1 of 4

This Item
44864E6627L2376
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

-

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.[1] It is obtained majorly from fish oil, seaweed, phytoplankton, and camelina.[2] Being an Omega-3 fatty acid, it shows cis-trans conformations.[3]

Application

cis-5,8,11,14,17-Eicosapentaenoic acid has been used:
  • to test pharmacologic effect on steatosis in hepatocytes[4]
  • as an analytical standard in Raman spectra measurements to characterize human breast cancer samples[5]
  • in lipid peroxidation assay in mouse embryonic fibroblasts and in pre-treatment of cells for cell viability studies[6]

Biochem/physiol Actions

5-Lipoxygenase inhibitor; reduces thromboxane A2 production.
Eicosapentaenoic acid (EPA) is essential for healthy living and alleviates obesity.[2] It decreases the triglyceride levels by modulating very-low-density lipoprotein(VLDL) levels.[7]

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

200.1 °F - closed cup

Flash Point(C)

93.4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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  1. SETU, Kilkenny road , Carlow Ireland
    • Reviews 3
    • Votes 2
    5 out of 5 stars.

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    good service and product quality, arrived on time and the correct chemical.

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