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Merck

E6627

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

synthetic (organic), ≥99% (capillary GC), 5-Lipoxygenase inhibitor, film or powder

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Fórmula lineal:
CH3(CH2CH=CH)5(CH2)3CO2Na
Número CAS:
73167-03-0
Peso molecular:
324.43
UNSPSC Code:
12352211
PubChem Substance ID:
24894631
NACRES:
NA.77
MDL number:
MFCD00079184

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Nombre del producto

cis-5,8,11,14,17-Eicosapentaenoic acid sodium salt, ≥99% (capillary GC)

SMILES string

[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-;;

InChI key

TVEGTERCKGGVCJ-LIJGWLRISA-N

biological source

synthetic (organic)

assay

≥99% (capillary GC)

form

film or powder

color

white to off-white

solubility

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

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

Gene Information

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

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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

Biochem/physiol Actions

5-Lipoxygenase inhibitor; reduces thromboxane A2 production.
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.

General description

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

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000455364
0000455364
0000324839
0000310503
0000324839

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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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