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E6627

Sigma-Aldrich

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

≥99% (capillary GC)

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About This Item

Formule linéaire :
CH3(CH2CH=CH)5(CH2)3CO2Na
Numéro CAS:
Poids moléculaire :
324.43
Numéro MDL:
Code UNSPSC :
12352211
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Niveau de qualité

Pureté

≥99% (capillary GC)

Forme

film or powder

Couleur

white to off-white

Solubilité

methanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

[Na].CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI

1S/C20H30O2.Na.H/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

TVEGTERCKGGVCJ-LIJGWLRISA-N

Informations sur le gène

human ... ALOX5(240)
mouse ... ALOX5(11689)
rat ... ALOX5(25290)

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Description générale

Eicosapentaenoic acid (EPA)/timnodonic acid is an omega-3 polyunsaturated fatty acid (PUFA). This long-chain fatty acid is mainly found in fish oil.

Application

cis-5,8,11,14,17-Eicosapentaenoic acid sodium salt has been used:
  • to study its effect on the pathology of lupus in drug-induced and spontaneous mouse models
  • to pretreat mouse alveolar macrophages to study the effect/relationship between amiodarone and eicosapentaenoic acid (EPA) concerning the cytokine release
  • to examine if pharmacological correction with EPA supplementation might restore autophagic flux and reduce renal lipotoxicity in mice

Actions biochimiques/physiologiques

Eicosapentaenoic acid (EPA) possesses anti-hyperglycemic, anti-oxidant, anti-hyperlipidemic, and anti-inflammatory properties. It aids in improving vasoreactivity. EPA is capable of suppressing vascular smooth muscle proliferation. It ameliorates pulmonary hypertension by preventing Fyn kinase activity. EPA exhibits a beneficial effect on lipid metabolism. It is used to treat hypercholesterolemia and atherosclerosis.
5-Lipoxygenase inhibitor; reduces thromboxane A2 production.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Y Futamura
Japanese journal of pharmacology, 69(4), 335-341 (1995-12-01)
I studied the effect of amiodarone, a cationic amphiphilic drug, on the cytokine release and protein kinase C (PKC) activity of mouse alveolar macrophages. In addition, I examined the relationship between amiodarone and eicosapentaenoic acid (EPA) with respect to the
Lin Hai Kurahara et al.
Journal of molecular and cellular cardiology, 148, 50-62 (2020-09-06)
Pulmonary arterial hypertension (PAH) is a multifactorial disease characterized by pulmonary arterial vasoconstriction and remodeling. Src family tyrosine kinases, including Fyn, play critical roles in vascular remodeling via the inhibition of STAT3 signaling. EPA is known to inhibit Fyn kinase
Azusa Kobayashi et al.
Frontiers in immunology, 12, 650856-650856 (2021-07-03)
Accumulating evidence suggests that cholesterol accumulation in leukocytes is causally associated with the development of autoimmune diseases. However, the mechanism by which fatty acid composition influences autoimmune responses remains unclear. To determine whether the fatty acid composition of diet modulates
Yong-Ping Zhang et al.
Prostaglandins, leukotrienes, and essential fatty acids, 136, 85-94 (2017-08-06)
Omega-3 polyunsaturated fatty acids (n-3 PUFAs), docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA), have been reported to prevent neurodegenerative diseases such as Alzheimer's disease (AD) in both experimental and clinical/epidemiological studies. However, whether DHA and EPA from natural products exert
Takeshi Yamamoto et al.
Autophagy, 17(7), 1700-1713 (2020-06-18)
Recently, we identified a novel mechanism of lipotoxicity in the kidney proximal tubular cells (PTECs); lipid overload stimulates macroautophagy/autophagy for the renovation of plasma and organelle membranes to maintain the integrity of the PTECs. However, this autophagic activation places a

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