2monoglycerides

2-monoglycerides are a class of glycerol esters in which a single fatty acid is attached to the glycerol backbone at the sn-2 position. They are a specific type of monoacylglycerol, contrasted with 1- or 3-monoacylglycerides, which are positional isomers on the glycerol backbone.

These compounds are produced in biology primarily by the partial hydrolysis of triglycerides, a reaction catalyzed by lipases such as pancreatic lipase during fat digestion. They can also be prepared synthetically by esterifying glycerol with fatty acids or by glycerolysis of fats. In digestion, 2-monoglycerides can be absorbed and further processed for energy or saved as metabolic intermediates.

In fatty-acid signaling, certain 2-monoglycerides, notably 2-arachidonoylglycerol (2-AG), serve as bioactive lipids with roles in endocannabinoid signaling. More generally, 2-monoglycerides act as intermediates in lipid metabolism and can influence the properties of lipid digestion products.

In industry, 2-monoglycerides are used as emulsifiers and stabilizers in foods, cosmetics, and pharmaceutical formulations. They are amphiphilic, featuring a hydrophilic glycerol head and a hydrophobic fatty-acid tail, which helps them stabilize oil–water interfaces. Regulatory agencies often provide guidelines for their use, and certain grades are considered safe for use in foods under established limits.