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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

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Certificates of Analysis (COA)

Lot/Batch Number
SLCM8875
SLCD5176
SLCB0183
SLBW4198
SLBP1471V

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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
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
Richard J Woodman et al.
Atherosclerosis, 166(1), 85-93 (2002-12-17)
Type 2 diabetes and hypertension are both associated with an increased risk of atherothrombosis. We assessed whether purified eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) from fish oil have differential effects on platelet, fibrinolytic and vascular function in patients with
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
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