油酰单乙醇胺
中文名称 | 油酰单乙醇胺 |
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中文同义词 | N-(2-羟乙基)-(Z)-9-十八烯酰胺;油酰乙醇胺(OEA);油酰乙醇胺;油酰单乙醇胺;硝酸二十酯;油酰胺 MEA;油酰乙醇胺(CAS号:111-58-0);油酰乙醇胺(油酰单乙醇胺) |
英文名称 | Oleoyl Ethanolamide |
英文同义词 | N-(2-hydroxyethyl)-,(Z)-9-Octadecenamide;OLEIC ACID-2,6-DIISOPROPYL ANILIDE;N-[2,6-BIS(1-METHYLETHYL)PHENYL]-9Z-OCTADECENAMIDE;N-Oleoylethanolamine, ~98%;9Z-OCTADECENOYLETHANOLAMIDE;C18:1 ANANDAMIDE;C18:1 anandamide;Oleoylmonoethanolamide;Oleyl monoethanolamide |
CAS号 | 111-58-0 |
分子式 | C20H39NO2 |
分子量 | 325.53 |
EINECS号 | 203-884-8 |
相关类别 | 催化剂及助剂;橡胶助剂;脂类;氮化合物;医药原料;化工中间体;Fluorobenzene;Intracellular receptor;原料;产品;食品添加剂;对照品 |
Mol文件 | 111-58-0.mol |
结构式 | ![]() |
油酰单乙醇胺 性质
熔点 | 63-64 °C |
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沸点 | 496.4±38.0 °C(Predicted) |
密度 | 0.915±0.06 g/cm3(Predicted) |
储存条件 | -20°C |
溶解度 | 可溶于DMSO(高达25mg/ml)或乙醇(高达35mg/ml) |
酸度系数(pKa) | 14.49±0.10(Predicted) |
形态 | 白色固体 |
颜色 | 白色 |
稳定性 | 自购买之日起 2 年内保持稳定。 DMSO 或乙醇溶液可在 -20°C 下保存长达 1 个月。 |
InChI | InChI=1S/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 |
SMILES | C(NCCO)(=O)CCCCCCC/C=C\CCCCCCCC |
LogP | 6.406 (est) |
CAS 数据库 | 111-58-0(CAS DataBase Reference) |
EPA化学物质信息 | 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- (111-58-0) |
Human Endogenous Metabolite
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PPAR-α
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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.
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).