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SML0384

Sigma-Aldrich

Eicosapentaenoyl ethanolamide

5 mg/mL in absolute ethanol, ≥98% (HPLC)

Sinónimos:

(5Z,8Z,11Z,14Z,17Z)-N-(2-Hydroxyethyl)-5,8,11,14,17-eicosapentaenamide, EPEA

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About This Item

Fórmula empírica (notación de Hill):
C22H35NO2
Número de CAS:
109001-03-8
Peso molecular:
345.52
Número MDL:
MFCD22416528
Código UNSPSC:
51111800
ID de la sustancia en PubChem:
329825384
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

solution

control farmacológico

regulated under CDSA - not available from Sigma-Aldrich Canada

condiciones de almacenamiento

protect from light
under inert gas

concentración

5 mg/mL in absolute ethanol

color

light yellow

temp. de almacenamiento

−20°C

cadena SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO

InChI

1S/C22H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h3-4,6-7,9-10,12-13,15-16,24H,2,5,8,11,14,17-21H2,1H3,(H,23,25)/b4-3-,7-6-,10-9-,13-12-,16-15-

Clave InChI

OVKKNJPJQKTXIT-JLNKQSITSA-N

Acciones bioquímicas o fisiológicas

Eicosapentaenoyl ethanolamide (EPEA) is a lipid mediator that has been found to suppress lifespan extension resulting from dietary restriction in C. elegans and also to have antiproliferative and anti-inflammatory actions. In C. elegans, it is believed to act as a metabolic signal that couples nutrient availability with growth and lifespan. EPEA is a member of the N-acylethanolamines (NAEs), lipid-derived signaling molecules that include the mammalian endocannabinoid arachidonoyl ethanolamide (AEA). In mammals, NAEs are believed to act primarily through cannabinoid receptors, although they can also interact with a variety of other targets, and EPEA has been shown to act as a CB1 and CB2 receptor agonist. However, C. elegans does not possess clear orthologues of the mammalian cannabinoid receptors which suggests that there are unidentified NAE receptors in nematodes that are possibly conserved mediators of NAE signaling.

Otras notas

Light and air sensitive; store in a freezer.

Código de clase de almacenamiento

10 - Combustible liquids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
062M4610V

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Mark Lucanic et al.
Nature, 473(7346), 226-229 (2011-05-13)
Dietary restriction is a robust means of extending adult lifespan and postponing age-related disease in many species, including yeast, nematode worms, flies and rodents. Studies of the genetic requirements for lifespan extension by dietary restriction in the nematode Caenorhabditis elegans
Strahil Iv Pastuhov et al.
Nature communications, 3, 1136-1136 (2012-10-18)
The ability of neurons to regenerate their axons after injury is determined by a balance between cellular pathways that promote and those that inhibit regeneration. In Caenorhabditis elegans, axon regeneration is positively regulated by the c-Jun N-terminal kinase mitogen activated
Celina Galles et al.
Scientific reports, 8(1), 6398-6398 (2018-04-25)
Proper cholesterol transport is crucial for the functionality of cells. In C. elegans, certain cholesterol derivatives called dafachronic acids (DAs) govern the entry into diapause. In their absence, worms form a developmentally arrested dauer larva. Thus, cholesterol transport to appropriate
Sylvie Callegari et al.
Journal of molecular biology, 431(15), 2835-2851 (2019-05-20)
Mitochondrial membrane proteins with internal targeting signals are inserted into the inner membrane by the carrier translocase (TIM22 complex). For this, precursors have to be initially directed from the TOM complex in the outer mitochondrial membrane across the intermembrane space
Michiel G J Balvers et al.
Metabolomics : Official journal of the Metabolomic Society, 8(6), 1130-1147 (2012-11-09)
It is well established that dietary intake of n-3 fatty acids is associated with anti-inflammatory effects, and this has been linked to modulation of the oxylipin and endocannabinoid metabolomes. However, the amount of data on specific tissue effects is limited
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