Glyceryl tribenzoate
[CAS# 614-33-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Glyceryl tribenzoate
• Synonyms: 2,3-dibenzoyloxypropyl benzoate
• Molecular Formula: C₂₄H₂₀O₆
• Molecular Weight: 404.41
• CAS Registry Number: 614-33-5
• EC Number: 210-379-6
• SMILES: C1=CC=C(C=C1)C(=O)OCC(COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Melting point: 68 - 72 ºC (Expl.)
• Boiling point: 548.9±17.0 ºC 760 mmHg (Calc.)^*
• Flash point: 238.1±21.0 ºC (Calc.)^*
• Index of refraction: 1.591 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H317
• Precautionary Statements: P261-P272-P280-P302+P352-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317

Discovory and Applicatios

Glyceryl tribenzoate is the triester formed from glycerol and benzoic acid, in which all three hydroxyl groups of glycerol are esterified with benzoyl groups. Glycerol was first isolated in the late eighteenth century during investigations of soap manufacture and was later recognized as a fundamental component of fats and oils in the form of triglycerides. Benzoic acid, identified in the sixteenth century from gum benzoin and structurally characterized in the nineteenth century, became an important aromatic carboxylic acid in organic chemistry. The systematic study of esterification reactions between polyhydric alcohols and carboxylic acids led to the preparation and characterization of numerous glycerol esters, including glyceryl tribenzoate.

The synthesis of glyceryl tribenzoate follows established esterification principles. Reaction of glycerol with benzoic acid or benzoyl chloride under appropriate conditions results in formation of mono-, di-, and triesters, with the fully substituted product obtained when all three hydroxyl groups are acylated. Control of stoichiometry and reaction conditions allows isolation of the triester as a defined compound. The structural identity of glyceryl tribenzoate is consistent with the broader class of triglyceride analogues in which aromatic acyl groups replace the long-chain fatty acids found in natural fats.

Interest in aromatic glycerol esters developed as part of broader investigations into plasticizers and modifying agents for polymeric materials. Experimental studies demonstrated that certain aromatic esters could reduce brittleness and improve flexibility in polymer systems. Glyceryl tribenzoate has been used as a plasticizer in cellulose derivatives and other polymer formulations, where it contributes to improved processability and mechanical properties. Its compatibility with specific resins and its relatively low volatility under processing conditions have supported these applications.

In addition to polymer technology, glyceryl tribenzoate has been examined in pharmaceutical formulation. As a hydrophobic ester with limited water solubility, it has been used as a solvent or carrier in certain drug delivery systems. Research has documented its ability to function as a plasticizer in film coatings applied to tablets, where it influences film flexibility and adhesion. The chemical stability of the aromatic ester linkages under typical storage conditions has contributed to its suitability in such roles.

The study of glyceryl tribenzoate also reflects the broader development of ester chemistry and the understanding of structure–property relationships. Replacement of aliphatic fatty acyl groups with aromatic benzoyl groups alters melting behavior, solubility characteristics, and intermolecular interactions. Experimental comparisons between different glycerol esters have provided insight into how acyl structure affects physical properties and functional performance.

Although glyceryl tribenzoate is not a naturally occurring triglyceride, its preparation and applications are grounded in well-established chemical principles and documented industrial practice. From early investigations of glycerol and benzoic acid derivatives to its use as a plasticizer and formulation aid, the compound illustrates how classical esterification chemistry has been applied to create materials with specific and reproducible properties. Its role in polymer and pharmaceutical systems reflects the practical extension of fundamental organic chemistry into applied technology.

References

2025. Determination of glycerol in canola oil-based biodiesel by micellar electrokinetic chromatography. Analytical and Bioanalytical Chemistry.
DOI: 10.1007/s00216-025-05947-4

2023. Protection of Mice from Controlled Cortical Impact Injury by Food Additive Glyceryl Tribenzoate. International Journal of Molecular Sciences.
DOI: 10.3390/ijms24032083

2021. Alleviation of Huntington pathology in mice by oral administration of food additive glyceryl tribenzoate. Neurobiology of Disease.
DOI: 10.1016/j.nbd.2021.105318