Glycerol trilaurate
[CAS 538-24-9]

Identification

• Classification: Surfactant >> Nonionic surfactant >> Polyol ester type
• Name: Glycerol trilaurate
• Synonyms: Lauric acid triglycerin ester; Lauric triglyceride; NSC 4061; Tridodecanoin; Tridodecanoyl glycerol; Triglyceride LaLaLa; Trilaurin; Trilauroylglycerol
• Molecular Formula: C₃₉H₇₄O₆
• Molecular Weight: 639.00
• CAS Registry Number: 538-24-9
• EC Number: 208-687-0
• SMILES: CCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*, 0.9 g/mL (Expl.)
• Melting point: 46.5 °C (Expl.)
• Boiling point: 643.3±22.0 °C 760 mmHg (Calc.)^*
• Flash point: 253.5±22.4 °C (Calc.)^*
• Index of refraction: 1.463 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

chemBlink Chemical Story

Glycerol trilaurate, more commonly known as **trilaurin**, is a triglyceride formed by the esterification of glycerol with three molecules of lauric acid. With the molecular formula C₃₉H₇₄O₆, it belongs to the family of triacylglycerols that constitute the principal storage lipids of plants and animals. Although trilaurin occurs naturally in oils rich in lauric acid, such as coconut and palm kernel oils, it is also prepared in highly purified form for scientific, pharmaceutical, cosmetic, and food applications.

The study of trilaurin is closely linked to the development of modern lipid chemistry. During the late nineteenth and early twentieth centuries, chemists sought to understand the composition of natural fats, which were known to be mixtures of numerous triglycerides rather than single compounds. The isolation and synthesis of chemically pure triglycerides, including trilaurin, provided an essential foundation for investigating the relationship between molecular structure and the physical properties of fats. These studies helped establish many of the concepts that underpin modern food chemistry and lipid science.

Because trilaurin contains three identical saturated fatty acid residues, it became one of the classical model compounds for investigating triglyceride crystal structures, melting behavior, polymorphism, and phase transitions. Unlike natural edible fats, which contain dozens or even hundreds of different triglycerides, pure trilaurin offers a well-defined molecular system that allows researchers to examine how molecular packing influences texture, stability, and thermal properties. As a result, it has been widely used in studies of fat crystallization and the manufacture of confectionery products.

Research on trilaurin has also contributed to understanding the relationship between molecular structure and nutritional behavior. Lauric acid, the fatty acid component of trilaurin, is classified as a medium-chain saturated fatty acid. Although the metabolism of pure trilaurin differs from that of free lauric acid or medium-chain triglycerides containing shorter fatty acids, studies of trilaurin have helped clarify digestion, lipase activity, and lipid absorption. These investigations have provided valuable information for nutritional science and lipid metabolism.

In pharmaceutical science, trilaurin has attracted attention as a biocompatible lipid excipient. Because it is chemically well defined, relatively stable, and biodegradable, it has been investigated as a component of lipid-based drug delivery systems, sustained-release formulations, and lipid nanoparticles. While more complex lipid mixtures are often employed commercially, pure trilaurin continues to serve as a useful reference material during formulation development.

The cosmetic industry also utilizes trilaurin because of its emollient properties and compatibility with a wide variety of ingredients. It contributes to smooth texture, improves skin feel, and enhances formulation stability in creams, lotions, and personal care products. In food technology, purified trilaurin is frequently employed as a reference lipid for analytical calibration, crystallization studies, and quality control rather than as a major edible fat itself.

Advances in analytical techniques, including X-ray diffraction, differential scanning calorimetry, nuclear magnetic resonance spectroscopy, and modern lipidomics, have made trilaurin one of the most thoroughly characterized triglycerides. Its crystal polymorphism has become a classical subject in physical chemistry because different crystal forms exhibit distinct melting points and stability, phenomena that are directly relevant to chocolate manufacture, specialty fats, and structured lipids.

Today, trilaurin remains an important reference compound linking chemistry, food science, pharmaceutical formulation, and materials research. Although consumers rarely encounter it by name, its contribution to understanding the physical chemistry of fats has been far greater than would be expected from such a structurally simple molecule. It exemplifies how a chemically pure lipid can serve as a model system for investigating the behavior of complex natural oils and for developing new lipid-based technologies.

**References**

1. Bailey, A.E. (1950) *Industrial Oil and Fat Products*. Interscience Publishers.

2. Small, D.M. (1986) *The Physical Chemistry of Lipids: From Alkanes to Phospholipids*. Plenum Press.

3. Sato, K. (2001) 'Crystallization behaviour of fats and lipids – a review', *Chemical Engineering Science*, 56, pp. 2255–2265.