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Merck

44864

Supelco

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

analytical standard

Sinónimos:

EPA, Timnodonic acid

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About This Item

Fórmula lineal:
CH3(CH2CH=CH)5(CH2)3CO2H
Número de CAS:
Peso molecular:
302.45
Beilstein/REAXYS Number:
1714433
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

biological source

fish oil

Quality Level

grade

analytical standard

assay

≥98.5% (GC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

refractive index

n20/D 1.4977 (lit.)

mp

−54-−53 °C (lit.)

density

0.943 g/mL at 25 °C (lit.)

format

neat

functional group

carboxylic acid

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

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General description

cis-5,8,11,14,17-Eicosapentaenoic acid belongs to the class of long-chain omega-3 polyunsaturated fatty acids. It is synthesized in the human body from the essential fatty acid alpha-linolenic acid.

Application

This analyticalstandard can also be used as follows:

  • Optimization of capillary zone electrophoresis procedurecoupled with direct absorption UV detection (CZE-UV) to determine eicosapentaenoicacid and docosahexaenoic acids after their methylation in 10 different samplesof commercial omega-3 supplements
  • Simultaneous determination of eicosapentaenoic acid,docosahexaenoic acid, and arachidonic acid in human plasma samples by high-performanceliquid chromatography-electrochemical detection (HPLC-ECD)
  • Separation, identification, and quantification of eicosapentaenoicacid, docosahexaenoic acid, and arachidonic acid in human plasma samples by high-performanceliquid chromatography combined with tandem mass spectrometry (HPLC-MS/MS)

Biochem/physiol Actions

Inhibidor de 5-lipoxigenasa; reduce la producción de tromboxano A2.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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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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
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
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
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
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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