9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-

Base Information

• Chemical Name: 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-
• CAS No.: 111-58-0
• Molecular Formula: C₂₀H₃₉NO₂
• Molecular Weight: 325.535
• DSSTox Substance ID: DTXSID00859196
• Mol file: 111-58-0.mol

Synonyms:N-(2-hydroxyethyl)octadec-9-enamide;9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-;D0Z2PV;N-Oleoylethanolamide;Oleamide MEA;Oleic acid monoethanolamide;N-(9-octadecenoyl)ethanolamine;DTXSID00859196;BOWVQLFMWHZBEF-UHFFFAOYSA-N;HMS3267N20;HMS3371C02;HMS3870J03;AKOS028108896;FT-0603311

Chemical Property of 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-

Chemical Property:

• Appearance/Colour: white to off-white solid
• Vapor Pressure: 6.22E-12mmHg at 25°C
• Melting Point: 50-60oC
• Refractive Index: 1.473
• Boiling Point: 496.35 °C at 760 mmHg
• PKA: 14.49±0.10(Predicted)
• Flash Point: 253.984 °C
• PSA: 49.33000
• Density: 0.915 g/cm³
• LogP: 5.52330
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 35 mg/ml)
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 17
• Exact Mass: 325.298079487
• Heavy Atom Count: 23
• Complexity: 277

Purity/Quality:

85%,98%, ^*data from raw suppliers

N-?Oleoylethanolamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)NCCO
• Description: Oleoyl ethanolamide (OEA) is an analog of the endocannabinoid AEA found in brain tissue and in chocolate. It is one of the long chain fatty acid ethanolamides that accumulates rapidly in infarcted tissue, but its biosynthesis is reduced in the intestine of rats following food deprivation. OEA is an endogenous, potent agonist for PPARα, exhibiting an EC50 value of 120 nM in a transactivation assay. Systemic administration of OEA suppresses food intake and reduces weight gain in rats (10 mg/kg intraperitoneally) and PPARα wild-type mice, but not in PPARα knockout mice. These data indicate that OEA regulates food intake by a PPARα-mediated mechanism.
• Uses: N-Oleoyl Ethanolamide is an agonist of peroxisome proliferator-activated receptor-α (PPAR-α). N-Oleoyl Ethanolamide generates an intestinal signal that stimulates central dopamine activity establishing a link between caloric-homeostatic and hedonic-homeostatic controllers. Oleoyl Ethanolamide has been implicated as the molecular mechanism associated with gastric bypass success. N-Oleoyl Ethanolamide is a selective GPR55 agonist.
• Biological Functions: N-Oleoyl Ethanolamide is also a predominant NAE species in the injured rat brain, and it has also been found to be the major NAE species in a human brain that has suffered a hemispheric stroke. As early as 1975, N-Oleoyl Ethanolamide was synthesized as an inhibitor of ceramidase, the enzyme that degrades ceramide. Ceramide is involved in the regulation of apoptosis and cell proliferation. Cannabinoid-induced apoptosis in glioma cells is mediated via formation of ceramide. On a tentative basis, it can be suggested that anandamide-induced apoptosis may be aggravated by the presence of N-Oleoyl Ethanolamide because this leads to increased formation of ceramide. There are numerous studies in which N-Oleoyl Ethanolamide has been shown to facilitate the apoptosis-inducing effect of different compounds mediated via increased ceramide levels. However, it has also been reported that N-Oleoyl Ethanolamide decreases ceramide levels in JB6 P+ cells by an unknown mechanism. Recently, N-Oleoyl Ethanolamide has been shown to have a CB1-receptor-independent anorexic effect by inhibiting some intestinal neuronal functions in the rat, and it also causes vasodilation in rat mesenteric arterial segments by an unknown receptor mechanism. Whether these recently discovered biological effects of N-Oleoyl Ethanolamide are of significance for neuroprotection is not known, but it indicates that nonendocannabinoid NAEs are also bioactive molecules with potential for cerebral actions.

Technology Process of 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-

There total 12 articles about 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(Z)-9-octadecenoyl chloride (112-77-6) + ethanolamine (141-43-5) → N-oleoylethanolamine (7545-20-2,111-58-0)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 4h;

Reference yield: 96.8%

cis-Octadecenoic acid (112-80-1,2027-47-6) + ethanolamine (141-43-5) → N-oleoylethanolamine (7545-20-2,111-58-0)

Guidance literature:

With Candida antarctica lipase; water; In hexane; at 65 ℃; for 3h; Time; Temperature; Concentration;

Reference yield: 95.1%

→ N-oleoylethanolamine (7545-20-2,111-58-0)

Guidance literature:

With triethylamine; diisopropyl-carbodiimide; In dichloromethane; at 20 ℃; for 4h;

In ethanol; at 20 ℃; for 0.5h; Inert atmosphere;

upstream raw materials:

cis-Octadecenoic acid

ethanolamine

(Z)-9-octadecenoyl chloride

O-oleoylethanolamide trifluoroacetate

Downstream raw materials:

N-[(9Z)-1-oxo-9-octadecenyl]glycine

2-(8-heptadecenyl)-2-oxazoline

Phosphoric acid dibenzyl ester 2-((Z)-octadec-9-enoylamino)-ethyl ester

NAEPA

Refernces

• 1、 Giuffrida, Andrea,Rodriguez De Fonseca, Fernando,Nava, Felice,Loubet-Lescoulie, Patrick,Piomelli, Daniele. "Elevated circulating levels of anandamide after administration of the transport inhibitor, AM404". . p. 161 - 168. Retrieved 2000.
• 2、 Klenova,Belousova. "Membrane-stabilizing properties of cis-9-octadecenoic acid N-(2-hydroxyethyl)amide". . p. 423 - 424. Retrieved 2002.
• 3、 Lin, Sonyuan,Khanolkar, Atmaram D.,Fan, Pusheng,Goutopoulos, Andreas,Qin, Ce,Papahadjis, Demetris,Makriyannis, Alexandras. "Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability". . p. 5353 - 5361. Retrieved 1998.
• 4、 Park, Yoon-Seok,Jang, Hyun-Jung,Lee, Kyung-Ho,Hahn, Tae-Ryong,Paik, Young-Sook. "Prolyl endopeptidase inhibitory activity of unsaturated fatty acids". . p. 1238 - 1242. Retrieved 2006.
• 5、 -. "Chemical synthesizing method of N-oleoyl ethanolamine". Paragraph 0022-0027; 0031-0035; 0040-0044. . Retrieved 2018/05/01.