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油酰单乙醇胺 |
| CAS No.: |
111-58-0 |
| 分子式： |
C20H39NO2 |
| 分子量： |
325.53 |
| 备注： |
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OleoylEthanolamide英文同义词N-(2-hydroxyethyl)-,(Z)-9-Octadecenamide;ODA;OLEICACID-2,6-DIISOPROPYLANILIDE;N-[2,6-BIS(1-METHYLETHYL)PHENYL]-9Z-OCTADECENAMIDE;N-Oleoylethanolamine,~98%;9Z-OCTADECENOYLETHANOLAMIDE;C18:1ANANDAMIDE;C18:1anandamide;Oleoylethanolamide(OEA)CAS号111-58-0分子式C20H39NO2分子量325.53EINECS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;原料;产品;食品添加剂;对照品;Intracellularreceptor;FluorobenzeneMol文件111-58-0.mol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±0.06g/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）形态白色固体酸度系数(pKa)14.49±0.10(Predicted)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-NSMILESC(NCCO)(=O)CCCCCCC/C=CCCCCCCCCLogP6.406(est)CAS数据库111-58-0(CASDataBaseReference)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用途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。生物活性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。靶点HumanEndogenousMetabolitePPAR-α体外研究Oleoylethanolamide(OEA),anendogenousPPAR-αligand,attenuatesliverfibrosistargetinghepaticstellatecells.OleoylethanolamidesuppressesTGF-β1induceChemicalbookdhepaticstellatecells(HSCs)activationinvitroviaPPAR-α.ToassesstheimpactofOleoylethanolamideonHSCsactivation,theexpressionlevelsofα-SMAandCol1ainTGF-β1-stimulatedHSCsareexaminedbyqPCR.ThemRNAlevelsofα-SMAandCol1aaremarkedlyinducedinthegroupofCFSCcellswithTGF-β1(5ng/mL)stimulationfor48h,whilethemRNAlevelsaresuppressedwhentreatedwithOleoylethanolamideinadose-dependentmanner.ImmunofluorescenceandwesternblotresultsshowthatOleoylethanolamidetreatmentdose-dependentlyinhibitstheproteinexpressionofα-SMA,themarkerofHSCactivation.TheinhibitoryeffectsofOleoylethanolamideonHSCsactivationarecompletelyblockedbyPPAR-αantagonistMK886(10μM).Moreover,themRNAandproteinexpressionlevelsofPPAR-αaredown-regulatedwithTGF-β1stimulation,whileOleoylethanolamidetreatmentrestoresthesechangesindose-dependentmanner.Inaddition,thephosphorylationofSmad2/3isupregulatedinthepresenceofTGF-β1stimulation,consistentwiththeobservedeffectsonHSCactivation,whileOleoylethanolamide(10μM)reducesthephosphorylationofSmad2/3inCFSCsimulatedwithTGF-β1.体内研究Oleoylethanolamide(OEA)cansignificantlysuppressthepro-fibroticcytokineTGF-β1negativelyregulategenesintheTGF-β1signalingpathway(α-SMA,collagen1a,andcollagen3a)inmicemodelsofhepaticfibrosis.TreatmentwithOleoylethanolamide(5mg/kg/day,intraperitonealinjection,i.p.)significantlyattenuatestheprogressofliverfibrosisinbothtwoexperimentalanimalmodelsbyblockingtheactivationofhepaticstellatecells(HSCs). |
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