Oleoylethanolamide (OEA) (111-58-0) Specifications
N-oleoyl ethanolamine;Oleamide MEA;Oleoyl monoethanolamide;
|Molecular Weight||325.5 g/mol|
|Monoisotopic Mass||325.537 g·mol−1|
|Melting Point||59–60 °C (138–140 °F; 332–333 K)|
|Boiling Point||496.4±38.0 °C(Predicted)|
|Solubility in ethanol and DMSO||Soluble|
|Application||Phamaceutical field; supplments;|
What is Oleoylethanolamide(OEA)?
Oleoylethanolamide(OEA) is an endogenous peroxisome proliferator-activated receptor alpha (PPAR-alpha) agonist. It is a naturally occurring glycolamide lipid with a variety of unique homeostasis properties such as appetite control, anti-inflammatory activity, stimulation of lipolysis and fatty acid oxidation. Oleoylethanolamide can be considered a hormone of the intestinal brain axis. Oatmeal, nuts, and cocoa powder are the major foods sources of Oleoylethanolamide in meals. However, the amount of Oleoylethanolamide found in these foods is low (fewer than 2 µg / g).
As a biologically active lipid medium, oleylethanolamide (OEA) is produced in the intestine and other tissues, and is involved in mammalian energy balance regulation, regulating food intake and lipid metabolism, such as it can regulate Vertebrate food and body weight. Oleoylethanolamide is a fatty acid ethanolamide (FAE), a monounsaturated analog of endocannabinoid arachidonic acid ethanolamide (anandamide), and a functional antagonist of anandamide. It is worth noting that Oleoylethanolamide is different from anandamide, it is independent of the cannabinoid receptor, and exerts its biological function through other pathways, regulating PPAR-α activity to stimulate lipolysis. Oleoylethanolamide is a potential and safer anti-obesity drug that replaces CB1 antagonism.
Preclinical studies have shown that Oleoylethanolamide is also an effective anti-inflammatory and antioxidant compound that exerts neuroprotective effects in alcoholism. Exogenous administration of Oleoylethanolamide can effectively prevent alcohol-induced TLR4-mediated proinflammatory cascades, thereby reducing the release of proinflammatory cytokines and chemokines, oxidative and nitrosative stress, and ultimately prevents nerve damage in the frontal cortex of rodents.
What does of Oleoylethanolamide(OEA) work?
In obese people, OEA can regulate the energy homeostasis and appetite mainly by activation of various receptors including proximal proliferator-activated receptor-α (PPAR-α), G-protein-coupled receptor 119 (GPR119) and transient receptor potential cation channel subfamily V (TRPV1). Indeed, OEA activates these receptors and delays meal initiation, reduces meal size, decreases intervals between meals and finally modulates body weight.
Moreover, some experimental studies shows that OEA also suppresses the expression of IL-6, interleukin-8 (IL-8), intercellular adhesion molecule-1 (ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1) in TNF-α induced inflammation in human umbilical vein endothelial cells through the activation of inflammatory receptors. OEA also inhibited the nuclear factor kappa-B (NF-kB) pathway in the body. In YT et al’s survey, OEA (50 µmol/L) inhibited the TNF-α induced VCAM-1 expression in HUVEC.
The benefits of Oleoylethanolamide(OEA)
As a ceramidase inhibitor, an endogenous agonist of the GPR119 receptor, Oleoylethanolamide is effective against neurodegenerative diseases, anti-atherosclerosis, apoptosis, pain relief, enhanced lipid metabolism, and cells on islet β cells. Protection and other metabolic diseases have a good protective effect. In addition, it can reduce body fat by controlling appetite, control weight, and achieve weight loss. Oleoylethanolamide also has the ability to reduce inflammation and lower cholesterol levels.
The uses of Oleoylethanolamide(OEA)
- Phamaceutical field Dietary supplments
- Gaetani S, Oveisi F, Piomelli D (2003). “Modulation of meal pattern in the rat by the anorexic lipid mediator oleoylethanolamine”. Neuropsychopharmacology. 28 (7): 1311–6. doi:10.1038/sj.npp.1300166. PMID 12700681.
- Lo Verme J, Gaetani S, Fu J, Oveisi F, Burton K, Piomelli D (2005). “Regulation of food intake by oleoylethanolamine”. Cell. Mol. Life Sci. 62 (6): 708–16. doi:10.1007/s00018-004-4494-0. PMID 15770421.
- Giuseppe Astarita; Bryan C. Rourke; Johnnie B. Andersen; Jin Fu; Janet H. Kim; Albert F. Bennett; James W. Hicks & Daniele Piomelli (2005-12-22). “Postprandial increase of oleoylethanolamine mobilization in small intestine of the Burmese python (Python molurus)”. Am J Physiol Regul Integr Comp Physiol. 290 (5): R1407–R1412. doi:10.1152/ajpregu.00664.2005. PMID 16373434.
- Gaetani S, Kaye WH, Cuomo V, Piomelli D (September 2008). “Role of endocannabinoids and their analogues in obesity and eating disorders”. Eat Weight Disord. 13 (3): e42–8. PMID 19011363.
- Serrano A, et al. Oleoylethanolamide: effects on hypothalamic transmitters and gut peptides regulating food intake. Neuropharmacology. (2011)
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