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S8439

Sigma-Aldrich

Stearoyl ethanolamide

≥98%, crystalline

Synonyme(s) :

N-Stearoylethanolamine, NSE

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About This Item

Formule empirique (notation de Hill):
C20H41NO2
Numéro CAS:
111-57-9
Poids moléculaire :
327.55
Numéro CE :
203-883-2
Numéro MDL:
MFCD00045971
Code UNSPSC :
12352204
ID de substance PubChem :
24899792
Nomenclature NACRES :
NA.83

Niveau de qualité

200

Pureté

≥98%

Forme

crystalline

Température de stockage

−20°C

Chaîne SMILES 

CCCCCCCCCCCCCCCCCC(=O)NCCO

InChI

1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23)

Clé InChI

OTGQIQQTPXJQRG-UHFFFAOYSA-N

Informations sur le gène

rat ... Cnr1(25248)

Description générale

Stearoyl ethanolamide, also called N-stearoylethanolamine (NSE) is present ubiquitously in all mammals. It exists in three isoforms when synthesized. It has therapeutic potential to modulate immune and inflammatory responses. It also possess antioxidative and membranoprotective functionality. NSE molecules pack in tail-to-tail fashion in lipid bilayer.

Application

Stearoyl ethanolamide (NSE) has been used as standard for quantifying in house synthesized NSE using thin layer chromatography.

Actions biochimiques/physiologiques

Most abundant fatty acid ethanolamide produced by PLD hydrolysis of cell membrane phospholipids.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Palmitoylethanolamide

Sigma-Aldrich

5.04359

Palmitoylethanolamide

2-Arachidonyl glycerol ~10 mg/mL, ≥98% (HPLC)

Sigma-Aldrich

A8973

2-Arachidonyl glycerol

Murat Oz et al.
Archives of biochemistry and biophysics, 434(2), 344-351 (2005-01-11)
The effects of saturated long-chain (C: 16-22) N-acylethanolamines and a series of saturated fatty acids with the same length of carbon chains were investigated on depolarization-induced (45)Ca(2+) fluxes mediated by voltage-dependent Ca(2+) channels in transverse tubule membrane vesicles from rabbit
Salvatore Terrazzino et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 18(13), 1580-1582 (2004-08-04)
Given the recent demonstration that oleoylethanolamide (OEA), a cannabinoid receptor-inactive N-acylethanolamine, decreases food intake by activating the nuclear receptor PPARalpha (peroxisome proliferator-activated receptor alpha) in the periphery, we here evaluated the effects of both saturated and unsaturated C18 N-acylethanolamides (C18:0;
M Dalle Carbonare et al.
Journal of neuroendocrinology, 20 Suppl 1, 26-34 (2008-05-09)
N-acylethanolamines, which include the endocannabinoid anandamide and the cannabinoid receptor-inactive saturated compounds N-palmitoyl ethanolamine and N-stearoyl ethanolamine, are ethanolamines of long-chain fatty acids degraded by fatty acid amide hydrolase (FAAH) known to accumulate in degenerating tissues and cells. Whilst much
Mauro Maccarrone et al.
The Biochemical journal, 366(Pt 1), 137-144 (2002-05-16)
Stearoylethanolamide (SEA) is present in human, rat and mouse brain in amounts comparable with those of the endocannabinoid anandamide (arachidonoylethanolamide; AEA). Yet, the biological activity of SEA has never been investigated. We synthesized unlabelled and radiolabelled SEA to investigate its
Polymorphism of N-stearoylethanolamine: differential scanning calorimetric, vibrational spectroscopic (FTIR), and crystallographic studies
Wouters J, et al.
Chemistry and Physics of Lipids, 119(1), 13-21 (2002)
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