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Acide cis-5,8,11,14,17-eicosapentaénoïque

analytical standard

Synonyme(s) :

Acide timnodonique, EPA

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About This Item

Formule linéaire :
CH3(CH2CH=CH)5(CH2)3CO2H
Numéro CAS:
Poids moléculaire :
302.45
Numéro Beilstein :
1714433
Numéro MDL:
Code UNSPSC :
85151701
ID de substance PubChem :
Nomenclature NACRES :
NA.24

Source biologique

fish oil

Niveau de qualité

Qualité

analytical standard

Pureté

≥98.5% (GC)

Durée de conservation

limited shelf life, expiry date on the label

Technique(s)

HPLC: suitable
gas chromatography (GC): suitable

Indice de réfraction

n20/D 1.4977 (lit.)

Pf

−54-−53 °C (lit.)

Densité

0.943 g/mL at 25 °C (lit.)

Format

neat

Groupe fonctionnel

carboxylic acid

Température de stockage

−20°C

Chaîne 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-

Clé InChI

JAZBEHYOTPTENJ-JLNKQSITSA-N

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Catégories apparentées

Description générale

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)

Actions biochimiques/physiologiques

Inhibiteur de la 5-lipoxygénase; réduit la production de thromboxane A2

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Autres remarques

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

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

200.1 °F - closed cup

Point d'éclair (°C)

93.4 °C - closed cup

Équipement de protection individuelle

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


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Certificats d'analyse (COA)

Lot/Batch Number

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Consulter la Bibliothèque de documents

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
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
Cindy A Francois et al.
The American journal of clinical nutrition, 77(1), 226-233 (2002-12-25)
Flaxseed oil is a rich source of 18:3n-3 (alpha-linolenic acid, or ALA), which is ultimately converted to 22:6n-3 (docosahexaenoic acid, or DHA), a fatty acid important for the development of the infant brain and retina. The objective of this study

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