Tricaprin, also known as glyceryl tridecanoate or tri(caprate), is a medium-chain triacylglycerol (TAG) composed of three capric acid (decanoic acid, C10:0) chains esterified to a glycerol backbone. This neutral lipid is part of the medium-chain triglyceride (MCT) series, alongside tricaprylin and tricaproin, and is valued for its rapid digestion, efficient energy metabolism, and formulation versatility in food and pharmaceutical applications.
Chemical Structure
Tricaprin has the molecular formula C33H62O6 and a molecular weight of 554.85 g/mol. Its symmetric sn-glycerol backbone is esterified with straight-chain decanoyl groups at the sn-1, sn-2, and sn-3 positions. This structure confers high lipophilicity and facilitates efficient hydrolysis by lipases, releasing capric acid for rapid absorption via the portal vein.
Physical Properties
Tricaprin appears as a white to off-white solid or a pale yellow liquid, with a melting point of approximately 31–32 °C. It has a density of ~0.98 g/cm³, a boiling point of about 254 °C at 5 mmHg, and a refractive index near 1.44. The compound is insoluble in water but shows limited solubility in chloroform and DMSO upon sonication. It is stable at −20 °C, and its low viscosity makes it suitable for emulsification-based formulations.
Biological Functions
As a key component of MCTs, tricaprin undergoes rapid intestinal hydrolysis, delivering decanoic acid directly to the liver where it is metabolized via β-oxidation and ketogenesis rather than being stored in adipose tissue. This metabolic profile supports rapid energy availability and has been associated with antiandrogenic, antihyperglycemic, and antimicrobial activities, as well as enhanced nutrient absorption.
