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E7006

Sigma-Aldrich

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

≥85%, liquid

Synonym(s):

EPA, Timnodonic acid

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About This Item

Linear Formula:
CH3(CH2CH=CH)5(CH2)3CO2H
CAS Number:
10417-94-4
Molecular Weight:
302.45
Beilstein:
1714433
MDL number:
MFCD00065716
UNSPSC Code:
12352211
PubChem Substance ID:
24894640
NACRES:
NA.25

biological source

fish oil

Assay

≥85%

form

liquid

refractive index

n20/D 1.4977 (lit.)

mp

−54-−53 °C (lit.)

density

0.943 g/mL at 25 °C (lit.)

functional group

carboxylic acid

lipid type

omega FAs

shipped in

ambient

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

mouse ... Pparg(19016)

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Biochem/physiol Actions

5-Lipoxygenase inhibitor; reduces thromboxane A2 production.

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

Certificates of Analysis (COA)

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Vigdis Aas et al.
Journal of lipid research, 47(2), 366-374 (2005-11-23)
This study was conducted to evaluate the chronic effects of eicosapentaenoic acid (EPA) on fatty acid and glucose metabolism in human skeletal muscle cells. Uptake of [14C]oleate was increased >2-fold after preincubation of myotubes with 0.6 mM EPA for 24
I Hafström et al.
Arthritis and rheumatism, 31(5), 585-592 (1988-05-01)
Fourteen patients with rheumatoid arthritis (RA) were studied before, during, and after a 1-week total fast. Disease activity decreased, as did the neutrophil release of lysozyme induced by the ionophore A23187. The ability of zymosan-activated RA patient serum to aggregate
J A Dunstan et al.
Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology, 34(8), 1237-1242 (2004-08-10)
Breast milk contains many immunomodulatory factors (soluble CD14 (sCD14), IgA and cytokines) with the potential to influence infant immune development. To determine if changes in breast milk omega-3 polyunsaturated fatty acid (n-3 PUFA) composition as a result of maternal dietary
C Calzada et al.
Biochimica et biophysica acta, 1127(2), 147-152 (1992-07-29)
The modulatory effects of eicosapentaenoic acid (EPA) on platelet arachidonic acid (AA) metabolism were applied to an in vitro model of oxidant stress. Unstimulated normal human blood platelets were first treated with a thiol-oxidizing agent, azodicarboxylic acid bis(dimethylamide) (diamide) (1
S Sipka et al.
Clinical immunology and immunopathology, 79(3), 224-228 (1996-06-01)
Free eicosapentaenoic acid (EPA) was found to inhibit dose dependently the chemiluminescence of human neutrophil granulocytes phagocytosing zymosan and their chemotaxis induced by C5a-containing zymosan-activated serum (ZAS) and platelet-activating factor. Rigidification of plasma membranes in the ZAS-treated cells could be
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