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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/REAXYS Number:
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

10 - Combustible liquids

wgk_germany

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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Hyeon Ho Kim et al.
Journal of lipid research, 47(5), 921-930 (2006-02-10)
Skin aging can be attributed to photoaging (extrinsic) and chronological (intrinsic) aging. Photoaging and intrinsic aging are induced by damage to human skin attributable to repeated exposure to ultraviolet (UV) irradiation and to the passage of time, respectively. In our
Wendy L Hall et al.
The Journal of nutrition, 138(2), 287-291 (2008-01-22)
Diets rich in eicosapentaenoic acid [EPA; 20:5(n-3)] are associated with decreased arterial stiffness, but postprandial effects on vascular function are unknown. We investigated whether an EPA-enriched high-fat meal could improve postprandial vascular function. Seventeen healthy men ingested 2 test meals
Hyeon Ho Kim et al.
Journal of lipid research, 46(8), 1712-1720 (2005-06-03)
Ultraviolet (UV) irradiation regulates UV-responsive genes, including matrix metalloproteinases (MMPs). Moreover, UV-induced MMPs cause connective tissue damage and the skin to become wrinkled and aged. Here, we investigated the effect of eicosapentaenoic acid (EPA), a dietary omega-3 fatty acid, on
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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