油酰单乙醇胺

油酰单乙醇胺

中文名称油酰单乙醇胺
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 结构式

油酰单乙醇胺 性质

熔点63-64 °C
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。
InChIInChI=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-
InChIKeyBOWVQLFMWHZBEF-KTKRTIGZSA-N
SMILESC(NCCO)(=O)CCCCCCC/C=C\CCCCCCCC
LogP6.406 (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)

油酰单乙醇胺 用途与合成方法

油酰单乙醇胺是过氧化物酶体增殖物激活受体α (PPAR- α)的激动剂。N-油酰乙醇酰胺产生肠道信号,刺激中枢多巴胺活动,在热量-自我平衡和快乐-自我平衡之间建立联系。油酰乙醇酰胺被认为是胃旁路手术成功的分子机制。N-油酰乙醇酰胺是一种选择性GPR55激动剂。Oleoylethanolamide 是一种高亲和力的内源性 PPAR-α 激动剂,可用于肥胖和动脉硬化的相关研究。

Human Endogenous Metabolite

PPAR-α

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).

安全信息

危险品标志Xi
危险类别码36/37/38
安全说明26-36
WGK Germany2
危险等级IRRITANT

MSDS信息

更新日期产品编号产品名称CAS号包装价格
2024/01/25HY-107542Oleoylethanolamide1 mg363元
2024/01/25HY-107542Oleoylethanolamide5 mg800元

油酰单乙醇胺 上下游产品信息

"油酰单乙醇胺"相关产品信息
油酸铵 油酸酰胺 N-异丙基-(Z)-9-十八烯酰胺 (Z)-N,N-二(2-羟基乙基)-9-十八烯酸酰胺 油酰胺MEA磺基琥珀酸酯二钠 油酸乙酯 油酸钾 油酸甲酯 油酸酐 油酸钠 油酸 油酸丁酯 三乙醇胺油酸皂 油酰胺DIPA 油酰胺MIPA磺基琥珀酸酯二钠 油酰胺DEA (Z)-(R)-N-((2-羟基-1-甲基)乙基)-9-烯十八酰胺 (Z)-(S)-N-((2-羟基-1-甲基)乙基)-9-烯十八酰胺 油酰乙醇胺
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