3443-82-1

Basic information

• Product Name: 2-LINOLEOYL-RAC-GLYCEROL
• Synonyms: 9Z,12Z-OCTADECADIENOIC ACID, 2-GLYCERYL ESTER;2-LG;2-LINOLEOYL GLYCEROL;2-LINOLEOYL-RAC-GLYCEROL;(9Z,12Z)-9,12-Octadecadienoic acid 2-hydroxy-1-(hydroxymethyl)ethyl ester;2-Monolinolein;2-O-Linoleoylglycerol;2-O-Linoleoyl-L-glycerol
• CAS NO: 3443-82-1
• Molecular Formula: C₂₁H₃₈O₄
• Molecular Weight: 354.52
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols
• Mol File: 3443-82-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 9°C
• Boiling Point: 485 °C at 760 mmHg
• Flash Point: 2℃
• Appearance: /
• Density: 0.981 g/cm³
• Vapor Pressure: 1.91E-11mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: ?20°C
• Solubility: Chloroform (Slightly), DMF (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 13.54±0.10(Predicted)
• Stability: Temperature Sensitive
• BRN: 1715064
• CAS DataBase Reference: 2-LINOLEOYL-RAC-GLYCEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-LINOLEOYL-RAC-GLYCEROL(3443-82-1)
• EPA Substance Registry System: 2-LINOLEOYL-RAC-GLYCEROL(3443-82-1)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37
• RIDADR: UN 1648 3 / PGII
• WGK Germany: 3
• Hazardous Substances Data: 3443-82-1(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

Different sources of media describe the Uses of 3443-82-1 differently. You can refer to the following data:
1. 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.
2. A fatty acid monoglycerides in vegetable oils with medium unsaturation.

Definition

ChEBI: A 2-monoglyceride where linoleoyl forms the 2-acyl group.

InChI:InChI=1/C21H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-20(18-22)19-23/h6-7,9-10,20,22-23H,2-5,8,11-19H2,1H3/b7-6-,10-9-

Upstream product

• 537-40-6 1,2,3-tri(cis,cis-9,12-octadecadienoyloxy)propane 
• 402562-28-1 2-((9Z,12Z)-octadeca-9,12-dienoyloxy)propane-1,3-diyl dibutyrate 
• 107011-30-3 5-<9,10,12,13-Tetrabrom-stearoyloxy>-2-phenyl-<1,3>dioxan 
• 7459-33-8 linoleyl chloride 
• 10564-39-3 2-O-(9,10,12,13-Tetrabromstearoyl)-glycerin 

Downstream Products

• 106292-55-1 1-olein-2-linolein 
• 2258-92-6 1-monolinoleoyl-rac-glycerol 

Relevant articles and documents

Influence of fatty acid desaturation on spontaneous acyl migration in 2-monoacylglycerols

The effect of desaturation from the C9 to the C15 carbon of 2-monoacylglycerol (2-MAG) fatty acids on spontaneous acyl migration is described. Three 2-MAG species, 2-monooleoylglycerol (C18:1 cis-Δ9), 2-monolinoleoylglycerol (C18:2 cis-Δ9,12), and 2-monolinolenoylglycerol (C18:3 cis-Δ9,12,15) were synthesized by lipase-catalyzed ethanolysis of their respective triacylglycerols and isolated in >60 % yield and at 2-MAG purities of >95 % relative to 1-monoacylglycerol (1-MAG). 1H-NMR spectroscopy was used to monitor the spontaneous acyl migration of the 2-MAG species over a temperature range from 20 to 80 °C. The relative energies of activation calculated from the Arrhenius relationships of the 2-MAG acyl migration rate constants were 73.3, 68.0, and 72.9 kJ mol-1 for the three 2-MAG species, respectively. Density functional calculations performed using the B3LYP functional at the 6-31+G* basis set on the three ketal ring intermediate of the three 2-MAG species followed a similar trend with a lack of relative energetic preference associated with the degree of desaturation. The kinetically determined relative activation energies were approximately twofold higher than the theoretical relative Gibbs free energies of the intermediates, suggesting that other factors influence acyl migration. In general, increasing desaturation after the C9 carbon of 2-MAG fatty acids had no appreciable effect on acyl migration rates. AOCS (outside the USA) 2012.

Biologically active lipids binding membrane receptors

Neutral lipids are provided characterized by binding to phorboid and ingenoid receptors. These lipids are found in a wide variety of cellular sources as well as milk and may be isolated by specific extraction and chromatographic procedures. Depending upon the source, the glycerides may be mono- or di-glycerides, wherein the total number of carbon atoms of the fatty acids is in the range of 18 to 26, so that the monoglyceride has a fatty acid of at least 18 carbon atoms, while the di-glyceride has a fatty acid of at least 14 carbon atoms.