Glyceryl behenate
[CAS# 30233-64-8]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Carboxylic acid and ester perfume >> Aliphatic carboxylate
• Name: Glyceryl behenate
• Synonyms: 2,3-Dihydroxypropyl docosanoate
• Molecular Formula: C₂₅H₅₀O₄
• Molecular Weight: 414.66
• CAS Registry Number: 30233-64-8
• EC Number: 250-097-0
• SMILES: CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(CO)O

Properties

• Solubility: 0.0001167 mg/L (25 °C water)
• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.470, Calc.^*
• Melting point: 199.26 °C
• Boiling Point: 494.77 °C, 525.8±30.0 °C (760 mmHg), Calc.^*
• Flash Point: 161.3±18.1 °C, 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

Discovery and Applications

Glyceryl behenate is a well-characterized compound widely used in the pharmaceutical, cosmetic, and food industries. It is a waxy substance composed primarily of glyceryl esters of behenic acid, a long-chain saturated fatty acid with 22 carbon atoms. Chemically, glyceryl behenate is known as glycerol tribehenate, with the molecular formula C₆₉H₁₃₄O₆, although commercial preparations may contain mono-, di-, and tri-esters of behenic acid. It appears as a white to off-white powder or waxy solid, insoluble in water but soluble in oils and certain organic solvents.

The substance was introduced into industrial use as interest grew in lipophilic excipients and structuring agents for controlled drug delivery and cosmetic applications. It is derived through esterification of glycerol with behenic acid, a process that yields a mixture of esters depending on reaction conditions. The resulting product is a physiologically inert and biocompatible material, which has led to its acceptance in a wide range of formulations.

In pharmaceuticals, glyceryl behenate is commonly used as a lipid-based excipient for controlled-release and sustained-release drug delivery systems. It functions as a matrix-forming agent in oral solid dosage forms, particularly tablets and pellets. When incorporated into formulations, glyceryl behenate forms a lipid matrix that modulates the diffusion of the active pharmaceutical ingredient, enabling prolonged drug release profiles. This property has been utilized to improve the pharmacokinetics of various poorly water-soluble drugs and to reduce dosing frequency.

Glyceryl behenate is also employed in the development of solid lipid nanoparticles and lipid-based drug delivery systems. Its low melting point, good lipid compatibility, and physical stability contribute to its effectiveness in encapsulating and delivering lipophilic drugs. It is especially valued for its ability to create stable emulsions and solid lipid dispersions, aiding in the enhancement of bioavailability for drugs with limited aqueous solubility.

In cosmetics and personal care products, glyceryl behenate serves as a viscosity-increasing agent, opacifier, and emollient. It is found in formulations such as creams, lotions, lipsticks, and sunscreens, where it imparts a smooth, non-greasy texture and helps stabilize emulsions. Its film-forming properties contribute to improved product consistency and moisture retention. Due to its mildness and skin compatibility, it is often used in products for sensitive skin and in formulations that require long-term dermal application.

In the food industry, glyceryl behenate may be utilized as a food-grade additive or processing aid, although its primary uses remain in pharmaceutical and cosmetic contexts. It is included in various pharmacopeias, including the European Pharmacopoeia and the United States Pharmacopeia-National Formulary, which specify quality standards for its use as an excipient.

From a physicochemical standpoint, glyceryl behenate exhibits thermal and oxidative stability, making it suitable for manufacturing processes involving elevated temperatures. It maintains structural integrity under storage conditions and does not readily undergo hydrolysis or oxidation. These attributes, combined with its low toxicity and lack of irritancy, contribute to its widespread approval for human use.

Its applications are further supported by its non-hygroscopic nature and compatibility with a broad range of active pharmaceutical ingredients and cosmetic components. Glyceryl behenate can be processed by techniques such as direct compression, hot-melt extrusion, and spray congealing, enabling flexibility in product formulation and scale-up.

The performance of glyceryl behenate in various delivery systems has been extensively evaluated and documented in the literature. It continues to be a key component in modern formulation science, valued for its role in improving drug stability, modulating release profiles, and enhancing the sensory qualities of cosmetic products.

References

2001. Controlled release of tramadol hydrochloride from matrices prepared using glyceryl behenate. European Journal of Pharmaceutics and Biopharmaceutics, 52(2).
DOI: 10.1016/s0939-6411(01)00173-4

2023. Effect of Active Pharmaceutical Ingredient, Lipid Composition, and Thermal Processing on the Physical Stability of Local Anesthetic-loaded Lipid Microparticles. Journal of Pharmaceutical Innovation, 18(3).
DOI: 10.1007/s12247-023-09720-x

2024. Solid lipid nanocarriers for drug delivery: design innovations and characterization strategies—a comprehensive review. Discover Applied Sciences, 6(5).
DOI: 10.1007/s42452-024-05897-z