Trilaurin, also known as glyceryl trilaurate, is a saturated medium-chain triacylglycerol (TAG) formed by the esterification of glycerol with three lauric acid (dodecanoic acid, C12:0) chains. This waxy lipid, naturally present in coconut and palm kernel oils, occupies an intermediate position between short/medium-chain TAGs such as tricaprylin and longer-chain triglycerides. Trilaurin is valued for its emulsifying and thickening properties, as well as for its ability to provide sustained metabolic energy.
Chemical Structure
Trilaurin has the molecular formula C39H74O6 and a molecular weight of 639.0 g/mol. Its structure consists of a symmetric glycerol backbone esterified at the sn-1, sn-2, and sn-3 positions with straight-chain lauroyl groups. This configuration confers extreme lipophilicity (LogP ~15.4–15.5). The compound is identifiable in lipidomic analyses by its InChIKey (VMPHSYLJUKZBJJ), supporting reliable detection by LC–MS.
Physical Properties
Trilaurin appears as a white to light yellow crystalline powder with a melting point of approximately 44–49 °C, a density of about 0.9 g/cm³, and a boiling point near 592 °C. It is insoluble in water but readily soluble in organic solvents such as chloroform, ether, ethyl acetate, and hot ethanol, with solubility exceeding 20 mg/mL in DMF. The compound is stable when stored at −20 °C, and its solid state at room temperature makes it suitable for controlled-release and formulation applications.
Biological Functions
Upon digestion, trilaurin is hydrolyzed by pancreatic lipases to release lauric acid, a fatty acid known for its antimicrobial activity against Gram-positive bacteria and certain fungi. Metabolically, trilaurin serves as a sustained energy source through β-oxidation, providing a slower energy release than C8/C10 medium-chain triglycerides while retaining the biological benefits associated with coconut oil–derived laurates, including potential modulation of gut microbiota.
