CAS: 94421-68-8; Anandamide
- 英文名称Anandamide
- 中文名称大麻素
- IUPAC名称N-Arachidonoyl-2-hydroxyethylamide
- 其它别名5,8,11,14-Eicosatetraenamide,N-(2-hydroxyethyl)-, (all-Z)-; Anandamide; Arachidonylethanolamide; N-(2-Hydroxyethyl)arachidonamide; N-(2-Hydroxyethyl)arachidonylamide; N-Arachidonoylethanolamide; N-Arachidonylethanolamide; N-Arachidonylethanolamine
- CAS编号94421-68-8
- MFCD编号:MFCD00153766
- FDA UNII编号:UR5G69TJKH
- 分子式:C22H37NO2
- 分子量:347.53
- 产品CID: 1994628
- 产品分类分析化学 → 食品安全 → 脂肪酸、脂肪酸甲酯
物理性质
MSDS等安全信息
上下游产品
CAS号506-32-1 花生四烯酸 | CAS号141-43-5 2-氨基乙醇 | CAS号2566-89-4 花生四烯酸甲酯 | CAS号543-27-1 氯甲酸异丁酯 | CAS号57303-04-5 Arachidonoyl Ch... | CAS号69205-93-2 arachidonic aci... | CAS号2002-24-6 盐酸乙醇胺合成工艺路线路线简述
- 合成目标产物 Anandamide 主要起始原料 Arachidonic Acid And Monoethanolamine
- 1808-26-0 = 94421-68-8
反应条件:1.1 5 °C; 18 °C; Rt -> 55 °C; 55 °C; 55 °C -> Rt; Rt
标题:Method Of Producing Ethanolamides Of Polyunsaturated Fatty Acids
参考文献:Russian Federation]
506-32-1 = 94421-68-8
反应条件:1.1 Reagents: 1,1′-Carbonyldiimidazole Solvents: Dichloromethane; 30 Min,Rt1.2 12 H,Rt1.3 Reagents: Ammonium Chloride Solvents: Dichloromethane,Water; Rt1.4 Reagents: Hydrochloric Acid; Ph 2,Rt
标题:A Convenient Protocol For The Synthesis Of Fatty Acid Amides
作者:Johansson,Silje J. R.; Johannessen,Tonje; Ellefsen,Christiane F.; Ristun,Mali S.; Antonsen,Simen; Et Al
参考文献:Synlett 日期:2019 卷标:30(2) 页码:213-217]
506-32-1 = 94421-68-8
反应条件:1.1 Reagents: Triethylamine,Butyl Chloroformate Solvents: Acetonitrile,Tetrahydrofuran1.2 Solvents: Methanol
标题:Synthesis Of Micelle-Forming Phosphoethanolamides Of Unsaturated Fatty Acids
作者:Aksenov,D. V.; Babitskaya,S. V.; Kisel,M. A.; Strel'Chenok,O. A.
参考文献:Doklady Natsional'Noi Akademii Nauk Belarusi 日期:2001 卷标:45(2) 页码:63-66]
506-32-1 = 94421-68-8
反应条件:1.1 Reagents: Triethylamine,Butyl Chloroformate Solvents: Acetonitrile; 30 Min,-15 °C1.2 Solvents: Methanol; 15 Min,-15 °C; -15 °C -> Rt; 2 H,Rt1.3 Reagents: Hydrochloric Acid Solvents: Water
标题:Composition For The Treatment Of Immune Deficiencies And Methods For Its Preparation And Use
参考文献:World Intellectual Property Organization]
57303-04-5 = 94421-68-8
反应条件:1.1 Solvents: Dichloromethane; 0 °C; 1 H,Rt
标题:Synthesis And Evaluation Of Fatty Acid Amides On The N-Oleoylethanolamide-Like Activation Of Peroxisome Proliferator Activated Receptor α
作者:Takao,Koichi; Noguchi,Kaori; Hashimoto,Yosuke; Shirahata,Akira; Sugita,Yoshiaki
参考文献:Chemical & Pharmaceutical Bulletin 日期:2015 卷标:63(4) 页码:278-285]
57303-04-5 = 94421-68-8
反应条件:1.1 Reagents: Triethylamine Solvents: Dichloromethane; Rt; Rt -> Reflux; 1 H
标题:Organic Compounds With Flavor-Modifying Properties
参考文献:World Intellectual Property Organization]
506-32-1 = 94421-68-8
反应条件:1.1 Reagents: 1,1′-Carbonyldiimidazole Solvents: Dichloromethane; 1 H,Rt1.2 Rt; 2 H,Rt
标题:Synthesis,In Vitro And In Vivo Evaluation,And Radiolabeling Of Aryl Anandamide Analogues As Candidate Radioligands For In Vivo Imaging Of Fatty Acid Amide Hydrolase In The Brain
作者:Wyffels,Leonie; Muccioli,Giulio G.; De Bruyne,Sylvie; Moerman,Lieselotte; Sambre,Johan; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2009 卷标:52(15) 页码:4613-4622]
506-32-1 = 94421-68-8
反应条件:1.1 Catalysts: Lipase Calb (Candida Antarctica) Solvents: Ethanol; 5 H,25 °C1.2 Solvents: Water; 6 H,35 °C
标题:Two-Step Method For Preparing Cannabinoid With High Content And Application Thereof In The Field Of Oil Processing
参考文献:China]
506-32-1 = 94421-68-8
反应条件:1.1 Reagents: Triethylamine,Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 25 °C; 24 H,25 °C
标题:Involvement Of Reactive Oxygen Species In The Oleoylethanolamide Effects And Its Pyrazonilic Analogue In Melanoma Cells
作者:Antiqueira-Santos,Priscila; Dos Santos,Daiane S.; Hack,Carolina R. L.; Flores,Alex Fabiani C.; Montes D'Oca,Marcelo G.; Et Al
参考文献:Medicinal Chemistry Research 日期:2017 卷标:26(11) 页码:2727-2736]
506-32-1 = 94421-68-8
反应条件:1.1 Reagents: 4-(Dimethylamino)Pyridine,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Solvents: Acetonitrile; 0 °C -> Rt; 2 - 8 H,Rt
标题:Quantitative Method For The Profiling Of The Endocannabinoid Metabolome By Lc-Atmospheric Pressure Chemical Ionization-Ms
作者:Williams,John; Wood,Jodianne; Pandarinathan,Lakshmipathi; Karanian,David; Bahr,Benjamin; Et Al
参考文献:Analytical Chemistry (Washington 日期:2007 卷标:79(15) 页码:5582-5593]
2566-89-4 = 94421-68-8
反应条件:1.1 Catalysts: Lipase Calb (Candida Antarctica) Solvents: Diisopropyl Ether,Hexane; Rt; Rt -> 45 °C; 2 H,45 °C
标题:Enzymatic Synthesis Of N-Acylethanolamines: Direct Method For The Aminolysis Of Esters
作者:Whitten,Kyle M.; Makriyannis,Alexandros; Vadivel,Subramanian K.
参考文献:Tetrahedron Letters 日期:2012 卷标:53(43) 页码:5753-5755]
506-32-1 = 94421-68-8
反应条件:1.1 Reagents: Diisopropylethylamine,N-[1-(Cyano-2-Ethoxy-2-Oxoethylideneaminooxy)Dimethylamino(Morpholino)Uronium He... Solvents: Acetonitrile,Dichloromethane; 10 Min,Rt1.2 Solvents: Acetonitrile; 3 - 6 H,Rt
标题:Optimized Synthesis And Characterization Of N-Acylethanolamines And O-Acylethanolamines,Important Family Of Lipid-Signalling Molecules
作者:Ottria,Roberta; Casati,Silvana; Ciuffreda,Pierangela
参考文献:Chemistry And Physics Of Lipids 日期:2012 卷标:165(7) 页码:705-711]
506-32-1 = 94421-68-8
反应条件:1.1 Reagents: Ethanol Catalysts: Lipase Calb (Candida Antarctica) Solvents: Hexane; 55 °C1.2 55 °C
标题:Improved Enzymatic Procedure For The Synthesis Of Anandamide And N-Fatty Acylalkanolamine Analogues: A Combination Strategy To Antitumor Activity
作者:Quintana,Paula G.; Garcia Linares,Guadalupe; Chanquia,Santiago N.; Gorojod,Roxana M.; Kotler,Monica L.; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2016 卷标:2016(3) 页码:518-528]
287937-12-6 = 94421-68-8
反应条件:1.1 Reagents: 2-Mercaptoethanol Solvents: Isopropanol; 150 Min,25 °C1.2 Solvents: Isopropanol; 150 Min,25 °C1.3 Catalysts: Potassium Cyanide Solvents: Methanol; Overnight,50 °C
标题:Synthesis Of All-Trans Anandamide: A Substrate For Fatty Acid Amide Hydrolase With Dual Effects On Rabbit Platelet Activation
作者:Ferreri,Carla; Anagnostopoulos,Dimitris; Lykakis,Ioannis N.; Chatgilialoglu,Chryssostomos; Siafaka-Kapadai,Athanassia
参考文献:Bioorganic & Medicinal Chemistry 日期:2008 卷标:16(18) 页码:8359-8365]
506-32-1 = 94421-68-8
反应条件:1.1 Reagents: 1,1′-Carbonyldiimidazole Solvents: Dichloromethane; 1 H,Rt1.2 Rt; 3 H,Rt
标题:Radiosynthesis,In Vitro And In Vivo Evaluation Of 123I-Labeled Anandamide Analogues For Mapping Brain Faah
作者:Wyffels,Leonie; De Bruyne,Sylvie; Blanckaert,Peter; Lambert,Didier M.; De Vos,Filip
参考文献:Bioorganic & Medicinal Chemistry 日期:2009 卷标:17(1) 页码:49-56]
2566-89-4 = 94421-68-8
反应条件:1.1 24 H,80 °C
标题:Effects Of Fatty Acid-Ethanol Amine ( Fa-Ea ) Derivatives On Lipid Accumulation And Inflammation
作者:Li,Mengyu; Huang,Xiaoqing; Huang,Mengxian; Jin,Wenhui; Hong,Zhuan; Et Al
参考文献:Lipids 日期:2023 卷标:58(3) 页码:117-127]
506-32-1 = 94421-68-8
反应条件:1.1 Reagents: Triethylamine,Butyl Chloroformate Solvents: Acetonitrile; 30 Min,-15 °C1.2 Solvents: Methanol; 15 Min,-15 °C; -15 °C -> Rt; 2 H,Rt
标题:Preparation Of Amides Of Polyunsaturated Fatty Acids Having Aminoethanol And Amino Acids For Use As Pharmaceuticals
参考文献:United States]
120373-11-7 = 94421-68-8
反应条件:1.1 Reagents: Ethylenediamine,Nickel Acetate,Hydrogen,Sodium Borohydride Solvents: Ethanol; 3 - 4 H,Rt
标题:Solid-Phase Synthesis Of Anandamide Analogues
作者:Qi,Longwu; Meijler,Michael M.; Lee,Sang-Hyeup; Sun,Chengzao; Janda,Kim D.
参考文献:Organic Letters 日期:2004 卷标:6(10) 页码:1673-1675]
57303-04-5 = 94421-68-8
反应条件:1.1 Solvents: Ethyl Acetate; 0.5 H,32 °C
标题:Preparation And Purification Of Arachidonylethanolamide
参考文献:China]
506-32-1 = 94421-68-8
反应条件:1.1 Reagents: 4-(Dimethylamino)Pyridine,1-Hydroxybenzotriazole Solvents: Dichloromethane; Rt; 30 Min,Rt -> 0 °C1.2 Reagents: Hydrochloric Acid,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride; 0 °C; 3 H,0 °C -> Rt1.3 16 H,Rt1.4 Reagents: Water; Rt
标题:Preparation Of Anandamide And 2-Arachidonyl Glycerol Compounds
参考文献:World Intellectual Property Organization
N-(2-Hydroxyethyl)-5,8,11,14-Eicosatetraynamide置于nickel Diacetate Sodium Tetrahydroborate,氢气,乙二胺体系中,用 乙醇 作为反应溶剂,以5%的收率获得产物大麻素
参考文献:Solid-Phase Synthesis Of Anandamide Analogues
标题:Solid-Phase Synthesis Of Anandamide Analogues
摘要:The Endocannabinoids Are Amides And Esters Of Arachidonic Acid That Can Mimic The Pharmacological Properties Of Delta(9)-Tetrahydrocannabinol (Delta(9)-Thc). Anandamide,The Most Prominent Of The Endocannabinoids,Has Been Implicated In Both Metabolic/physiological Roles Of The Central Nervous System,Making It An Attractive Medicinal Target. As Such,We Report The First Solid-Phase Methodology That Expedites Access To Various Anandamide Analogues. Our Synthesis Features A Repetitive Cu-Mediated Coupling Reaction Between Terminal Alkynes And Propargyl Halides Or Allylic Halides.
DOI:10.1021/ol049474J
海关参考信息
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专利信息
专利号:US-2020079715-A1
优先权日:2018-09-06
标题 :2-position modification for synthesis of resorcinol scaffolding
发明人：DAVIS ROBERT; BLACK JACOB; SMELTZER THOMAS; COLVIN SEAN
权利人:CANOPY HOLDINGS LLC
摘要:A resorcinol with modifications at the 2-position is provided. The reactant resorcinol may have a variety of functional groups at each of the 1, 3, and 5 position such as a hydroxide, a lower alkyl group, a phenyl, a substituted phenyl, a lower alkenyl, or a lower alkynyl sp 2 carbon group (e.g., substituted phenyl, vinyl), sp (e.g., alkyne), hydrogen. The resorcinol is modified at the 2-position with a nucleophile or an electrophile. The resulting resorcinol may serve as a stable intermediate for the synthesis of cannabinoid or cannabinoid derivatives.
专利号:US-2013302247-A1
优先权日:2012-05-09
标 题:Synthesis of fluoroarachidonic acid and methods of use thereof
发明人：PICHIKA RAMAIAH; ECKELMAN WILLIAM C; RAPOPORT STANLEY I; TAHA AMEER; KOTTA KISHORE
权利人:US HEALTH; UNIV CALIFORNIA
摘要:There are provided, inter alia, methods for diagnosis of the extent of neuroinflammation in a subject. The methods include administering an 18 F-labeled arachidonic acid to a subject in need thereof, obtaining a positron emission tomography (PET) scan of the subject, and determine the extent of neuroinflammation from the PET scan. There are provided, inter alia, methods of synthesis of reagents useful for the production of an 18 F-labeled arachidonic acid.
专利号:WO-2022192582-A1
优先权日:2021-03-10
标 题 :Methods of synthesizing halogenated cannabinoids and derivatives of cannabinoids
发明人：DAVIS ROBERT; BLACK JACOB; SMELTZER THOMAS; COLVIN SEAN
权利人:TREEHOUSE BIOSCIENCES INC
摘要:The technology described herein provides for the synthesis of various cannabinoids, cannabinoid derivatives, and intermediate molecules useful in the synthesis of cannabinoids. For example, the technology described herein provides methods for synthesis of cannabinoids halogenated at the 4-position.
专利号:WO-2022226312-A1
优先权日:2021-04-22
标 题:Combination nucleotide pool depletion for treatment of viral infections and cancers
发明人：KUMAR VIKRAM; HESSON DAVID; DEMAREST JAMES
权利人:CLEAR CREEK BIO INC
摘要:The invention provides methods of treating cancers and viral infections by providing a combination of agents that inhibit both nucleotide synthesis and nucleotide salvage in the cells of a subject to prevent cancer proliferation and viral replication. The invention provides methods of depleting nucleotide pools by using both inhibitors of dihydroorotate dehydrogenase (DHODH), such as brequinar, which block synthesis of pyrimidine-based nucleotides, in combination of one or more nucleotide salvage inhibitors, for example deoxycytidine kinase (dCK) inhibitors, Equilibrative nucleoside transporter (ENT) inhibitors, and Uridine-cytidine kinase (UCK) inhibitors, which inhibit salvage of purine and/or pyrimidine-based nucleotides or nucleosides
专利号:US-7955816-B2
优先权日:2006-05-02
标 题 :Design and synthesis of biotinylated probes for N-acyl-ethanolamines
发明人：MACCARRONE MAURO; ODDI SERGIO; FEZZA FILOMENA; FINAZZI AGRO′ ALESSANDRO
权利人:UNI DEGLI STUDI DI ROMA & LDQUO TOR VERGATA & RDQUO; UNI DEGLI STUDI DI TERAMO
摘要:The present invention relates to the synthesis and characterization of biotinylated analogue of N-arachidonoylethanolamine (AEA) and its use as a tool to study AEA transport and trafficking through biochemical and morphological techniques. In particular biotinylated AEA (b-AEA, for which we propose the common name MM22) is suitable to design highly sensitive and simple methods for the non-radioactive detection and quantitation of AEA from complex samples, which would offer a useful alternative approach to the routinely used radiometric assays. The invention also relates to the use of b-AEA as a potential therapeutic and diagnostic agent.
专利号:US-11512097-B2
优先权日:2019-11-25
标题 :Heterocyclic compounds as Delta-5 desaturase inhibitors and methods of use
发明人：ALLEN JENNIFER R; BELTRANI MICHELA; BOURBEAU MATTHEW P; DAMYANOVA TEODORA P; LINGARD IAIN; MINATTI ANA E; VINCETTI PAOLO
权利人:AMGEN INC
摘要:The present disclosure provides compounds useful for the inhibition of Delta-5 Desaturase (“D5Dâ€?). The compounds have a general Formula I n nwherein the variables of Formula I are defined herein. This disclosure also provides pharmaceutical compositions comprising the compounds, uses of the compounds, and compositions for treatment of, for example, a metabolic or cardiovascular disorder. Further, the disclosure provides intermediates useful in the synthesis of compounds of Formula I.
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主要参考文献
1: de Ceballos ML. The endocannabinoid system offers a target for Alzheimer's disease treatment through inhibition of fatty acid amide hydrolase (FAAH). FEBS J. 2025 Apr 2. doi: 10.1111/febs.70082. Epub ahead of print.
13:e19125. doi: 10.7717/peerj.19125.
3: Bononi G, Granchi C, Tuccinardi T, Minutolo F. Identification of a Possible Endocannabinoid-Mediated Mechanism of Action of Cetylated Fatty Acids. Biomolecules. 2025 Mar 2;15(3):363. doi: 10.3390/biom15030363.
合成参考文献
参考文献:10.1186/1743-7075-8-51
摘要:Piscitelli F, Carta G, Bisogno T, Murru E, Cordeddu L, Berge K, Tandy S, Cohn JS, Griinari M, Banni S, Di Marzo V. Effect of dietary krill oil supplementation on the endocannabinoidome of metabolically relevant tissues from high-fat-fed mice. Nutr Metab (Lond). 2011 Jul 13;8(1):51.
参考文献:10.1186/1471-2210-11-6
摘要:Hayase T. Differential effects of TRPV1 receptor ligands against nicotine-induced depression-like behaviors. BMC Pharmacol. 2011 Jul 18;11():6.
参考文献:10.1007/s00213-011-2412-3
摘要:Dasilva MA, Grieve KL, Cudeiro J, Rivadulla C. Endocannabinoid CB1 receptors modulate visual output from the thalamus. Psychopharmacology (Berl). 2012 Feb;219(3):835–45. doi: 10.1007/s00213-011-2412-3.
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