Monolinolenin, also known as 1-monolinolenin or glyceryl monolinolenate, is a polyunsaturated monoglyceride esterified from glycerol and α-linolenic acid (ALA, 18:3 n-3). This lipid exhibits potent membrane-disrupting and antimicrobial properties due to its highly unsaturated acyl chain.
Chemical Structure
Monolinolenin has the molecular formula C21H36O4 and a molecular weight of 352.5 g/mol. It features a glycerol backbone with ALA attached at the sn-1 position, containing three cis double bonds at positions 9Z, 12Z, and 15Z. This configuration confers a conical molecular shape that favors negative curvature during lipid self-assembly and membrane interaction.
Physical Properties
Monolinolenin appears as a light-sensitive liquid or a low-melting solid with a melting range of 14–15 °C. It has a predicted density of 0.981 g/cm³, an estimated boiling point of approximately 485 °C, and a logP value of 6.27, indicating high lipophilicity. It is soluble in organic solvents such as chloroform and ethyl acetate but poorly soluble in water. Storage at −20 °C is recommended to limit oxidative degradation of its polyunsaturated fatty acid chain.
Biological Role
As a natural plant-derived metabolite, monolinolenin disrupts microbial membranes more efficiently than saturated monoglycerides, exhibiting broad-spectrum antimicrobial activity against both bacteria and fungi through lytic mechanisms. In addition, it contributes to essential fatty acid metabolism by serving as a reservoir of α-linolenic acid and may participate in lipid-mediated signaling pathways involved in inflammation modulation.
