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

Description

2-Linoleoyl-rac-glycerol, also known as 2-Linoleoyl glycerol (2-LG), is a 2-monoglyceride derived from linoleoyl, a polyunsaturated fatty acid. It is a colorless oil and has been identified as a natural endocannabinoid ligand for the CB1 receptor. 2-LINOLEOYL-RAC-GLYCEROL is characterized by its ability to potentiate the activity of other endocannabinoids, such as 2-Arachidonoyl glycerol (2-AG), through the "entourage" effect, which involves blocking the breakdown and reuptake pathways that normally reduce endocannabinoid levels rapidly upon release.

Uses

Used in Pharmaceutical Applications:
2-Linoleoyl-rac-glycerol is used as a pharmaceutical agent for its endocannabinoid activity. It plays a role in modulating the endocannabinoid system, which is involved in various physiological processes, including pain, mood, appetite, and memory. 2-LINOLEOYL-RAC-GLYCEROL's ability to potentiate the activity of other endocannabinoids, such as 2-AG, makes it a valuable candidate for research and potential therapeutic applications in various medical conditions.
Used in the Food Industry:
2-Linoleoyl-rac-glycerol is used as a fatty acid monoglyceride in vegetable oils with medium unsaturation. It contributes to the overall quality and stability of the oils, enhancing their nutritional value and improving their shelf life. 2-LINOLEOYL-RAC-GLYCEROL's presence in vegetable oils also provides health benefits due to its role in the endocannabinoid system.
Used in Cosmetic Applications:
2-Linoleoyl-rac-glycerol can be used in the cosmetic industry as an ingredient in skincare and hair care products. Its endocannabinoid activity may provide potential benefits for skin health and hair growth, making it a valuable addition to cosmetic formulations.
Used in Research:
2-Linoleoyl-rac-glycerol is used as a research compound for studying the endocannabinoid system and its role in various physiological processes. 2-LINOLEOYL-RAC-GLYCEROL's ability to potentiate the activity of other endocannabinoids makes it an important tool for understanding the complex interactions within the system and for developing new therapeutic strategies.

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

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

Downstream Products

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

Relevant articles and documents

Application of chemoenzymatic hydrolysis in the synthesis of 2-monoacylglycerols

The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2 h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24 h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved.

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.