Noladin ether

Base Information

• Chemical Name: Noladin ether
• CAS No.: 222723-55-9
• Molecular Formula: C23H40O3
• Molecular Weight: 364.5619
• UNII: 0D295FLV8W
• DSSTox Substance ID: DTXSID901018178
• Nikkaji Number: J778.939D
• Wikipedia: 2-Arachidonyl_glyceryl_ether
• Wikidata: Q3877880
• Pharos Ligand ID: FPUHP84T84YA
• Metabolomics Workbench ID: 5779
• ChEMBL ID: CHEMBL146346
• Mol file: 222723-55-9.mol

Synonyms:2-arachidonyl glyceryl ether;noladin ether

Chemical Property of Noladin ether

Chemical Property:

• Vapor Pressure: 1.31E-11mmHg at 25°C
• Refractive Index: 1.502
• Boiling Point: 488.9 °C at 760 mmHg
• Flash Point: 249.5 °C
• PSA: 49.69000
• Density: 0.948 g/cm³
• LogP: 5.50190
• Storage Temp.: Desiccate at -20°C
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 18
• Exact Mass: 364.29774513
• Heavy Atom Count: 26
• Complexity: 379

Purity/Quality:

99% ^*data from raw suppliers

HU310 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCCOC(CO)CO
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCOC(CO)CO
• Description: 2-Arachidonyl glycerol ether (2-AG ether) selectively binds to cannabinoid (CB) receptor 1 (Kis = 21.2 and >3,000 nM for CB1 and CB2, respectively, in a radioligand binding assay). It is a potent and selective agonist of CB1 and GPR55 with EC50 values of 10, 37, and >30,000 nM for CB1, GPR55, and CB2, respectively. 2-AG ether displays the typical tetrad of CB activities in mice. It is more chemically stable than 2-AG , with an endogenous half-life of hours rather than minutes. However, it is at least 10-fold less potent than 2-AG in eliciting typical CB1-mediated responses. 2-AG ether elicits modest reductions in intraocular pressure in rabbits when administered at doses exceeding 50 μg per eye. It increases aqueous humor outflow via the CB1 receptor in the trabecular meshwork. Administration of 2-AG ether to the nucleus accumbens (0.0625-1 μg) increases dietary intake and enhances fat consumption in rats given access to both high-carbohydrate and high-fat diets.
• Uses: HU 310 is an endogenous GPR55 and CB1 receptors agonist. HU 310 has been shown to induce hyperglycia in rats. HU 310 can be used to investigate the biological roles of GPR55 and CB1 receptors.

Technology Process of Noladin ether

There total 6 articles about Noladin ether 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: 87.0%

2-(5,8,11,14-eiosatetraenyl)-1,3-benzylideneglycerol (500910-43-0) → noladin ether (222723-55-9)

Guidance literature:

In hydrogenchloride; methanol;

Reference yield: 59.0%

methane sulfonyl chloride + arachidonyl alcohol (13487-46-2) → eicosa-5,8,11,14-tetraenylmethanesulfonate (57302-96-2) + noladin ether (222723-55-9)

Guidance literature:

With potassium carbonate; In pyridine; water;

Reference yield:

arachidonyl alcohol (13487-46-2) → noladin ether (222723-55-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 0.33 h / 20 °C

2: 44 percent / Ag₂O; NBu₄NI / dimethylformamide / 6 h / 90 °C

3: 62 percent / boric acid; trimethyl borate / 0.33 h / 100 °C

With Trimethyl borate; methyltriphenoxyphosphonium iodide; boric acid; tetra-(n-butyl)ammonium iodide; silver(l) oxide; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.48.903

upstream raw materials:

2-(5,8,11,14-eiosatetraenyl)-1,3-benzylideneglycerol

arachidonyl alcohol

all cis 5,8,11,14-eicosatetraenoic acid

5,8,11,14-eicosatetraenyl iodide

Refernces

• 1、 -. "Synthetic endogenous cannabinoids analogues and uses thereof". . . Retrieved 2008/06/13.