Monoeicosapentaenoin, also known as 1-monoeicosapentaenoin or 1-eicosapentaenoyl glycerol, is a polyunsaturated monoglyceride formed by esterification of glycerol with eicosapentaenoic acid (EPA, 20:5 n-3). This omega-3–derived lipid is actively investigated for its involvement in anti-inflammatory signaling pathways, membrane structure modulation, and advanced drug delivery systems. Its functional behavior follows trends observed in related mono- and polyunsaturated monoglycerides such as monoolein and monolinolenin.
Chemical Structure
Monoeicosapentaenoin has the molecular formula C23H36O4 and a molecular weight of approximately 388.5 g/mol. The molecule consists of a glycerol backbone esterified at the sn-1 position with eicosapentaenoic acid (all-cis-5,8,11,14,17-eicosapentaenoic acid). The presence of five cis double bonds confers a highly unsaturated character, a pronounced conical molecular geometry, and increased susceptibility to oxidative degradation.
Physical Properties
This highly unsaturated monoglyceride is typically observed as a pale yellow, light-sensitive oil with a melting point below 0 °C. It exhibits a density of approximately 0.98 g/cm³ and high lipophilicity (logP ≈ 6.5). Monoeicosapentaenoin is soluble in organic solvents such as chloroform and ethanol but displays negligible solubility in water. Similar to monolinolein, it can form inverse lyotropic liquid-crystalline phases. For long-term stability, storage at −80 °C under an inert nitrogen atmosphere is recommended to minimize oxidative degradation.
