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S8439

Sigma-Aldrich

Stearoyl ethanolamide

≥98%, crystalline

Sinónimos:

N-Stearoylethanolamine, NSE

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About This Item

Fórmula empírica (notación de Hill):
C20H41NO2
Número de CAS:
111-57-9
Peso molecular:
327.55
EC Number:
203-883-2
MDL number:
MFCD00045971
UNSPSC Code:
12352204
PubChem Substance ID:
24899792
NACRES:
NA.83

Quality Level

200

assay

≥98%

form

crystalline

storage temp.

−20°C

SMILES string

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)

InChI key

OTGQIQQTPXJQRG-UHFFFAOYSA-N

Gene Information

rat ... Cnr1(25248)

General description

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.

Biochem/physiol Actions

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Palmitoylethanolamide

Sigma-Aldrich

5.04359

Palmitoylethanolamide

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

Sigma-Aldrich

A8973

2-Arachidonyl glycerol

Structure and phase behavior of O-stearoylethanolamine: A combined calorimetric, spectroscopic and X-ray diffraction study
Tarafdar PK and Swamy MJ
Biochimica et Biophysica Acta - Biomembranes, 1798(5), 872-881 (2010)
Effects of N-stearoylethanolamine on anxiety-like behavioral reactions of rats after chronic alcoholization
Bondarenko OV, et al.
Biologija, 60(1) (2014)
Nazdar Ghafouri et al.
PloS one, 6(11), e27257-e27257 (2011-11-30)
N-acylethanolamines (NAEs) are endogenous compounds that regulate inflammation and pain. These include the cannabinoid ligand anandamide (AEA) and the peroxisome proliferator-activated receptor-α ligand palmitoylethanolamide (PEA). Little is known as to the levels of NAEs in pain states in human, particularly
n-stearoylethanolamine protects the brain and improves memory of mice treated with lipopolysaccharide or immunized with the extracellular domain of alpha7 nicotinic acetylcholine receptor
Lykhmus O, et al.
International Immunopharmacology, 52, 290-296 (2017)
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;
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