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SML0384

Sigma-Aldrich

Eicosapentaenoyl ethanolamide

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

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Synonym(s):
(5Z,8Z,11Z,14Z,17Z)-N-(2-Hydroxyethyl)-5,8,11,14,17-eicosapentaenamide, EPEA
Empirical Formula (Hill Notation):
C22H35NO2
CAS Number:
Molecular Weight:
345.52
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

solution

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage condition

protect from light
under inert gas

concentration

5 mg/mL in absolute ethanol

color

light yellow

storage temp.

−20°C

SMILES string

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-

InChI key

OVKKNJPJQKTXIT-JLNKQSITSA-N

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This Item
M2939SML0563840887C
vibrant-m

SML0384

Eicosapentaenoyl ethanolamide

vibrant-m

SML0563

Docosahexaenoyl ethanolamide

vibrant-m

840887C

22:6 PA

form

solution

form

methyl acetate solution (10 mg/mL)

form

ethanol solution (5 mg/ml)

form

liquid

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

drug control

-

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

drug control

-

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

-

storage temp.

−20°C

storage temp.

−70°C

storage temp.

−20°C

storage temp.

−20°C

storage condition

protect from light, under inert gas

storage condition

-

storage condition

-

storage condition

-

Biochem/physiol Actions

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.

Other Notes

Light and air sensitive; store in a freezer.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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
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
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
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
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

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