(9Z)-N-(2-hydroxyethyl)octadec-9-enamide
N-oleoyl ethanolamine
CAS: 111-58-0
Molecular Formula: C20H39NO2
(9Z)-N-(2-hydroxyethyl)octadec-9-enamide - Names and Identifiers
| Name | N-oleoyl ethanolamine |
| Synonyms | ODA Oleamide MEA UNII-1HI5J9N8E6 N-Oleoylethanolamine N-oleoyl ethanolamine Oleoyl monoethanolamide Oleoylethanolamide(OEA) N-(2-Hydroxyethyl)oleamide 9Z-OCTADECENOYLETHANOLAMIDE Monoethanolamine oleic acid amide OLEIC ACID-2,6-DIISOPROPYL ANILIDE N-(2-Hydroxyethyl)-9-octadecenamide 9-Octadecenamide, N-(2-hydroxyethyl)- (9Z)-N-(2-hydroxyethyl)octadec-9-enamide N-(2-hydroxyethyl)-,(Z)-9-Octadecenamide 9-Octadecenamide, N-(2-hydroxyethyl)-, (Z)- 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- N-[2,6-BIS(1-METHYLETHYL)PHENYL]-9Z-OCTADECENAMIDE |
| CAS | 111-58-0 |
| EINECS | 203-884-8 |
| InChI | InChI=1/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9- |
| InChIKey | BOWVQLFMWHZBEF-KTKRTIGZSA-N |
(9Z)-N-(2-hydroxyethyl)octadec-9-enamide - Physico-chemical Properties
| Molecular Formula | C20H39NO2 |
| Molar Mass | 325.53 |
| Density | 0.915±0.06 g/cm3(Predicted) |
| Melting Point | 63-64 °C |
| Boling Point | 496.4±38.0 °C(Predicted) |
| Flash Point | 254°C |
| Solubility | Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 35 mg/ml) |
| Vapor Presure | 6.22E-12mmHg at 25°C |
| Appearance | White powder |
| Color | White |
| pKa | 14.49±0.10(Predicted) |
| Storage Condition | -20°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. |
| Refractive Index | 1.473 |
| MDL | MFCD00045972 |
| In vitro study | Oleoylethanolamide (OEA), an endogenous PPAR-α ligand, attenuates liver fibrosis targeting hepatic stellate cells. Oleoylethanolamide suppresses TGF-β1 induced hepatic stellate cells (HSCs) activation in vitro via PPAR-α. To assess the impact of Oleoylethanolamide on HSCs activation, the expression levels of α-SMA and Col1a in TGF-β1-stimulated HSCs are examined by qPCR. The mRNA levels of α-SMA and Col1a are markedly induced in the group of CFSC cells with TGF-β1 (5 ng/mL) stimulation for 48h, while the mRNA levels are suppressed when treated with Oleoylethanolamide in a dose-dependent manner. Immunofluorescence and western blot results show that Oleoylethanolamide treatment dose-dependently inhibits the protein expression of α-SMA, the marker of HSC activation. The inhibitory effects of Oleoylethanolamide on HSCs activation are completely blocked by PPAR-α antagonist MK886 (10 μM). Moreover, the mRNA and protein expression levels of PPAR-α are down-regulated with TGF-β1 stimulation, while Oleoylethanolamide treatment restores these changes in dose-dependent manner. In addition, the phosphorylation of Smad 2/3 is upregulated in the presence of TGF-β1 stimulation, consistent with the observed effects on HSC activation, while Oleoylethanolamide (10 μM) reduces the phosphorylation of Smad2/3 in CFSC simulated with TGF-β1. |
| In vivo study | Oleoylethanolamide (OEA) can significantly suppress the pro-fibrotic cytokine TGF-β1 negatively regulate genes in the TGF-β1 signaling pathway (α-SMA, collagen 1a, and collagen 3a) in mice models of hepatic fibrosis. Treatment with Oleoylethanolamide (5 mg/kg/day, intraperitoneal injection, i.p.) significantly attenuates the progress of liver fibrosis in both two experimental animal models by blocking the activation of hepatic stellate cells (HSCs). |
(9Z)-N-(2-hydroxyethyl)octadec-9-enamide - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 2 |
| Hazard Class | IRRITANT |
(9Z)-N-(2-hydroxyethyl)octadec-9-enamide - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Use | Oleoyl monoethanolamine is an agonist of peroxisome proliferator-activated receptor α (PPAR- α). N-oleoyl ethanolamide produces intestinal signals that stimulate central dopamine activity, establishing a link between caloric-self-balance and happy-self-balance. Oleoyl ethanolamide is considered to be the molecular mechanism for the success of gastric bypass surgery. N-oleoyl ethanolamide is a selective GPR55 agonist. |
| biological activity | Oleoylethanolamide is a high affinity endogenous PPAR-α agonist, which can be used for related research on obesity and arteriosclerosis. |
Last Update：2024-04-09 20:45:29
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View History
(9Z)-N-(2-hydroxyethyl)octadec-9-enamide
1-(戊-4-烯-1-基)哌啶-3-羧酸乙酯
4-((2-甲氧基乙氧基)甲氧基)苯甲醛
6-Oxa-2-azabicyclo[3.1.0]hexane-2-carboxylic acid, 1,1-dimethylethyl ester
α,α-二甲基-4-(3-苯基-2-喹喔啉基)苯甲胺盐酸盐
RZDMCGPZDGKURQ-UHFFFAOYSA-N
胞苷 2':3'-环一磷酸 单钠盐
Nazartinib (EGF816)
Valproate Sodium Impurity 19
2-乙炔基-4-(三氟甲基)苯胺
1-(戊-4-烯-1-基)哌啶-3-羧酸乙酯
4-((2-甲氧基乙氧基)甲氧基)苯甲醛
6-Oxa-2-azabicyclo[3.1.0]hexane-2-carboxylic acid, 1,1-dimethylethyl ester
α,α-二甲基-4-(3-苯基-2-喹喔啉基)苯甲胺盐酸盐
RZDMCGPZDGKURQ-UHFFFAOYSA-N
胞苷 2':3'-环一磷酸 单钠盐
Nazartinib (EGF816)
Valproate Sodium Impurity 19
2-乙炔基-4-(三氟甲基)苯胺