N-Oleoylethanolamine

CATALOG # 1751
Amount 100 mg
Price $230.00
Qty
 
N-Oleoylethanolamine
  • Catalog #:1751
  • Scientific Name:N-Oleoylethanolamine
  • Common Name:NOE; Activity: acid ceramidase inhibitor
  • Empirical Formula:C20H39NO2
  • CAS#111-58-0
  • SDSView Material Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:326
  • Unit:100 mg
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, GC, identity confirmed by MS
  • Melting Point:63-66°C
  • Solubility:chloroform, ethanol, methanol, ethyl ether, DMSO
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    N-Oleoylethanolamine is a naturally occurring acylethanolamide that has been shown to have many biological functions. N-Oleoylethanolamine has been shown to be an efficacious inhibitor of acid ceramidase as well as an inhibitor of glucosylation of natural ceramides.1 It is specifically an inhibitor of the acid ceramidase found in human kidney and cerebellum with an IC50 of approximately 500μM. Farber’s disease is characterized by a lack of acid ceramidase activity and N-oleoylethanolamine can be used to study aspects of this disease. Whereas the inhibitor D-MAPP potently inhibits alkaline ceramidase (IC50 approximately 5μM) N-oleoylethanolamine shows only slight inhibitory characteristics towards this ceramidase.2 N-Oleoylethanolamine is chemically related to the endocannabinoid anandamide, although it is not a cannabinoid itself. It is produced, during feeding, in the small-intestinal enterocytes from oleic acid and phosphatidylethanolamine and acts as a satiety signal (by engaging peroxisome proliferator-activated receptors) and alters gastrointestinal motility. The levels of N-oleoylethanolamine are low during food deprivation (which activates a hunger signal) and normalize with food intake (which activates a satiety, but not a satiation, signal through sensory afferent neurons). It has been shown to reduce weight gain in rats and mice and has been suggested as a tool to combat obesity, diabetes, and eating disorders.3 N-Oleoylethanolamine is also released during sleep deprivation and it is thought that it may act as an endogenous neuroprotective signal.4 Other functions of N-oleoylethanolamine include altering peripheral lipid metabolism, inhibiting gastric emptying, inhibiting insulin metabolic and mitogenic signaling, enhancing memory consolidation, and altering stress responses.

    References:
    1. A. Spinedi et al. “N-Oleoylethanolamine inhibits glucosylation of natural ceramides in CHP-100 neuroepithelioma cells: possible implications for apoptosis” Biochem Biophys Res Commun, vol. 255 pp. 456-459, 1999
    2. A. Bielawska et al. “(1S,2R)-D-erythro-2-(N-Myristoylamino)-1-phenyl-1-propanol as an Inhibitor of Ceramidase” Journal of Biological Chemistry, vol. 271 pp. 12646-12654, 1996
    3. R. Capasso and A. Izzo “Gastrointestinal Regulation of Food Intake: General Aspects and Focus on Anandamide and Oleoylethanolamide” Journal of Neuroendocrinology, vol. 20 pp. 39-46, 2008
    4. D. Koethe et al. “Sleep deprivation increases oleoylethanolamide in human cerebrospinal fluid” J Neural Transm, vol. 116 pp. 301-305, 2009