(8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide

Base Information

• Chemical Name: (8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide
• CAS No.: 150314-34-4
• Molecular Formula: C₂₂H₃₉NO₂
• Molecular Weight: 349.557
• ChEMBL ID: CHEMBL121229
• DSSTox Substance ID: DTXSID201199860
• Metabolomics Workbench ID: 4658
• Pharos Ligand ID: 64UM796U8LH7
• Wikidata: Q27087920
• Mol file: 150314-34-4.mol

Synonyms:anandamide (20.3,n-6);homo-gamma-linolenoyl ethanolamide;homo-gamma-linolenylethanolamide

Chemical Property of (8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide

Chemical Property:

• Vapor Pressure: 4.41E-13mmHg at 25°C
• Boiling Point: 522.1°Cat760mmHg
• PKA: 14.49±0.10(Predicted)
• Flash Point: 269.5°C
• PSA: 49.33000
• Density: 0.929g/cm³
• LogP: 5.85550
• XLogP3: 6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 17
• Exact Mass: 349.298079487
• Heavy Atom Count: 25
• Complexity: 372

Purity/Quality:

99% ^*data from raw suppliers

Anandamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCC=CCC=CCC=CCCCCCCC(=O)NCCO
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)NCCO
• Uses: (8Z,11Z,14Z)-N-(2-Hydroxyethyl)-8,11,14-eicosatrienamide is an endocannabinoid that binds to recombinant human CB1 and CB2 receptors. (8Z,11Z,14Z)-N-(2-Hydroxyethyl)-8,11,14-eicosatrienamide is a CB1 and CB2 agonist and an adenylyl cyclase inhibitor.

Technology Process of (8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide

There total 3 articles about (8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

cis-8,11,14-eicosatrienoic acid (7324-41-6,68820-40-6,133939-47-6,133939-49-8,1783-84-2) + ethanolamine (141-43-5) → N-dihomo-γlinolenoyl ethanolamide (150314-34-4)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.9b00994

Reference yield:

cis-8,11,14-eicosatrienoic acid (7324-41-6,68820-40-6,133939-47-6,133939-49-8,1783-84-2) → N-dihomo-γlinolenoyl ethanolamide (150314-34-4)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride

With oxalyl dichloride;

DOI:10.1021/jm00072a026

Reference yield:

ethanolamine (141-43-5) + di-homo-gamma-linolenyl chloride (126104-52-7) → N-dihomo-γlinolenoyl ethanolamide (150314-34-4)

Guidance literature:

DOI:10.1021/jm00072a026

upstream raw materials:

ethanolamine

di-homo-gamma-linolenyl chloride

cis-8,11,14-eicosatrienoic acid

Refernces

• 1、 Hanus, Lumir,Gopher, Asher,Almog, Shlomo,Mechoulam, Raphael. "Two New Unsaturated Fatty Acid Ethanolamides in Brain That Bind to the Cannabinoid Receptor". . p. 3032 - 3034. Retrieved 2007/10/02.