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SML0384

Eicosapentaenoyl ethanolamide

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C22H35NO2
CAS Number:
109001-03-8
Molecular Weight:
345.52
NACRES:
NA.77
PubChem Substance ID:
329825384
UNSPSC Code:
51111800
MDL number:
MFCD22416528

Key Documents

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Product Name

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

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-

SMILES string

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

InChI key

OVKKNJPJQKTXIT-JLNKQSITSA-N

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

Quality Level

100

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.
Eicosapentaenoyl ethanolamide (EPEA) is a lipid mediator; suppresses lifespan extension; anti proliferative and anti-inflammatory.

Other Notes

Light and air sensitive; store in a freezer.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000071605
062M4610V

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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
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
Gil Bar-Sela et al.
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Cannabis or its derivatives are widely used by patients with cancer to help with cancer symptoms and treatment side effects. However, cannabis has potent immunomodulatory properties. To determine if cannabis consumption during immunotherapy affects therapy outcomes, we conducted a prospective
Tobias Dietsche et al.
PLoS pathogens, 12(12), e1006071-e1006071 (2016-12-16)
Bacterial type III protein secretion systems inject effector proteins into eukaryotic host cells in order to promote survival and colonization of Gram-negative pathogens and symbionts. Secretion across the bacterial cell envelope and injection into host cells is facilitated by a
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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