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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:
1714433
Número MDL:
Código UNSPSC:
85151701
ID de la sustancia en PubChem:
NACRES:
NA.24

origen biológico

fish oil

Nivel de calidad

grado

analytical standard

Ensayo

≥98.5% (GC)

caducidad

limited shelf life, expiry date on the label

técnicas

HPLC: suitable
gas chromatography (GC): suitable

índice de refracción

n20/D 1.4977 (lit.)

mp

−54-−53 °C (lit.)

densidad

0.943 g/mL at 25 °C (lit.)

Formato

neat

grupo funcional

carboxylic acid

temp. de almacenamiento

−20°C

cadena SMILES

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-

Clave InChI

JAZBEHYOTPTENJ-JLNKQSITSA-N

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Descripción general

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.

Aplicación

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)

Acciones bioquímicas o fisiológicas

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

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

Otras notas

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

Código de clase de almacenamiento

10 - Combustible liquids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

200.1 °F - closed cup

Punto de inflamabilidad (°C)

93.4 °C - closed cup

Equipo de protección personal

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Certificados de análisis (COA)

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Visite la Librería de documentos

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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