S8439
Stearoyl ethanolamide
≥98%, crystalline
Synonym(s):
N-Stearoylethanolamine, NSE
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About This Item
Empirical Formula (Hill Notation):
C20H41NO2
CAS Number:
Molecular Weight:
327.55
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.83
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Quality Level
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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)
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
Effects of N-stearoylethanolamine on anxiety-like behavioral reactions of rats after chronic alcoholization
Bondarenko OV, et al.
Biologija, 60(1) (2014)
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)
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
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