2-Linoleoylglycerol

Base Information

• Chemical Name: 2-Linoleoylglycerol
• CAS No.: 3443-82-1
• Molecular Formula: C₂₁H₃₈O₄
• Molecular Weight: 354.53
• UNII: 7OVH75512R
• DSSTox Substance ID: DTXSID301016998
• Nikkaji Number: J116.897E
• Wikidata: Q27145325
• Metabolomics Workbench ID: 119505
• Mol file: 3443-82-1.mol

Synonyms:2-lino-Gl;2-linoleoyl-glycerol;2-linoleoylglycerol

Chemical Property of 2-Linoleoylglycerol

Chemical Property:

• Vapor Pressure: 1.91E-11mmHg at 25°C
• Melting Point: 9°C
• Refractive Index: 1.488
• Boiling Point: 485 °C at 760 mmHg
• PKA: 13.54±0.10(Predicted)
• Flash Point: 157 °C
• PSA: 66.76000
• Density: 0.981 g/cm³
• LogP: 4.69630
• Storage Temp.: ?20°C
• Solubility.: Chloroform (Slightly), DMF (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 18
• Exact Mass: 354.27700969
• Heavy Atom Count: 25
• Complexity: 346

Purity/Quality:

98%Min ^*data from raw suppliers

2-Linoleoyl-rac-glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCCCCCCCC(=O)OC(CO)CO
• Isomeric SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC(CO)CO
• Uses: 2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB1 receptor. The congener of 2-AG in which a linoleoyl group replaces the arachidonoyl group is 2-linoleoyl glycerol (2-LG), and this compound also appears in vivo in conjunction with 2-AG. Although the intrinsic activity of 2-LG is low, it potentiates the activity of other endocannabinoids, including 2-AG. This “entourage” effect has been attributed to blockade of the breakdown and reuptake pathways that normally function to reduce endocannabinoid levels rapidly upon release. A fatty acid monoglycerides in vegetable oils with medium unsaturation.

Technology Process of 2-Linoleoylglycerol

There total 6 articles about 2-Linoleoylglycerol 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: 77.0%

2-((9Z,12Z)-octadeca-9,12-dienoyloxy)propane-1,3-diyl dibutyrate (402562-28-1) → 2-linoleoyl glycerol (126392-16-3,3443-82-1)

Guidance literature:

With Rhizomucor miehei lipase; ethanol; at 20 ℃; for 24h; regiospecific reaction; Enzymatic reaction;

DOI:10.1016/j.tet.2012.04.101

Reference yield: 65.7%

1,2,3-tri(cis,cis-9,12-octadecadienoyloxy)propane (537-40-6) → 2-linoleoyl glycerol (126392-16-3,3443-82-1)

Guidance literature:

With Novozym 435; ethanol; at 25 ℃; for 4h; Enzymatic reaction;

DOI:10.1007/s11746-012-2113-z

Reference yield:

linoleyl chloride (7459-33-8) → 2-linoleoyl glycerol (126392-16-3,3443-82-1)

Guidance literature:

With pyridine; chloroform; Erhitzen des Reaktionsprodukts mit Triaethylborat und Borsaeure und Behandeln einer Loesung des danach isolierten Reaktionsprodukts in Aether mit Wasser;

DOI:10.1021/ja01118a004

upstream raw materials:

2-O-(9,10,12,13-Tetrabromstearoyl)-glycerin

linoleyl chloride

5-<9,10,12,13-Tetrabrom-stearoyloxy>-2-phenyl-<1,3>dioxan

2-((9Z,12Z)-octadeca-9,12-dienoyloxy)propane-1,3-diyl dibutyrate

Downstream raw materials:

1-monolinoleoyl-rac-glycerol

1-olein-2-linolein

Refernces

• 1、 Compton, David L.,Laszlo, Joseph A.,Appell, Michael,Vermillion, Karl E.,Evans, Kervin O.. "Influence of fatty acid desaturation on spontaneous acyl migration in 2-monoacylglycerols". . p. 2259 - 2267. Retrieved 2013/01/15.