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:
Molecular Weight:
345.52
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
51111800
MDL number:
Assay:
≥98% (HPLC)
Form:
solution
Quality level:
Storage condition:
protect from light, under inert gas
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
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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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
Gil Bar-Sela et al.
Cancers, 12(9) (2020-09-03)
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SML0384-5MG | 04061832559896 |
| SML0384-25MG | 04061832559889 |
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