Methyl behenate
[CAS# 929-77-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Methyl ester compound
• Name: Methyl behenate
• Synonyms: Methyl docosanoate; Methyl n-docosanoate; NSC 158426
• Molecular Formula: C₂₃H₄₆O₂
• Molecular Weight: 354.61
• CAS Registry Number: 929-77-1
• EC Number: 213-207-8
• SMILES: CCCCCCCCCCCCCCCCCCCCCC(=O)OC

Properties

• Solubility: Insoluble (3.9E^-5 g/L) (25 ºC), Calc.^*
• Density: 0.861±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 230-234 ºC (methanol )^** (Expl.)
• Refractive index: 1.4339 (589.3 nm 60 ºC)^*** (Expl.)
• Flash point: 113 ºC (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Alam, Perwez; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry 2009, V48B(3), P443-446.

^*** "Hazardous Substances Data Bank" data were obtained from the National Library of Medicine (US)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335-H412
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Methyl behenate is an ester of behenic acid, which is a saturated fatty acid with a long carbon chain (C22H44O2). It is formed through the esterification of behenic acid with methanol, resulting in a compound with the chemical formula C23H46O2. This colorless to white solid is widely used in various industries, including cosmetics, pharmaceuticals, and food production, due to its unique physical properties and chemical structure.

The synthesis of methyl behenate involves the esterification reaction between behenic acid and methanol in the presence of an acid catalyst. This process results in the formation of the ester bond between the carboxyl group of behenic acid and the hydroxyl group of methanol. The reaction is typically carried out under controlled temperatures to ensure high yield and purity of the product. Methyl behenate is also available through the transesterification of vegetable oils containing behenic acid, such as rapeseed oil or peanut oil, providing a more sustainable route to its production.

Methyl behenate is primarily used in the cosmetic and personal care industries due to its emollient properties. As a non-polar compound, it functions as a skin-conditioning agent that helps to moisturize and soften the skin. It is commonly found in lotions, creams, lip balms, and other skin care products where it imparts a smooth texture and enhances the feel of the product on the skin. Additionally, its high melting point makes it useful in formulations where solidification at room temperature is desirable, providing stability to the product. Methyl behenate is also used as a thickener in emulsions, where it helps to improve the consistency and stability of creams and lotions.

In the pharmaceutical industry, methyl behenate serves as an excipient in drug formulations. Its use as a stabilizing agent and a lubricant in the manufacturing of tablets and capsules is well-documented. Methyl behenate’s ability to improve the flow properties of powders and to provide controlled release of active ingredients makes it a valuable component in the development of sustained-release drug formulations. Additionally, methyl behenate is sometimes used in the preparation of topical pharmaceutical products, such as ointments and creams, due to its moisturizing and skin-softening effects.

Methyl behenate also has applications in the food industry, where it is used as a food additive and emulsifier. It is often employed in food formulations to enhance texture, mouthfeel, and stability. Methyl behenate can be found in various food products, including margarine, chocolate, and other confectionery items, where it helps to improve consistency and prevent separation of ingredients. Due to its non-toxic nature and high stability, methyl behenate is considered safe for use in food products and is often included in the formulation of low-fat or reduced-calorie foods.

Moreover, methyl behenate finds use in the production of lubricants, where it acts as an effective base oil for high-performance industrial lubricants and greases. Its low volatility and ability to resist oxidation make it particularly useful in applications requiring high thermal stability. It is also employed in the production of biodiesel, where it serves as a fuel additive to enhance the performance and combustion properties of the fuel.

In conclusion, methyl behenate is a versatile compound with a wide range of applications across several industries. Its ability to function as an emollient, excipient, stabilizer, and lubricant makes it a valuable ingredient in cosmetics, pharmaceuticals, food products, and industrial applications. As demand for sustainable and bio-based alternatives continues to grow, methyl behenate is likely to play an increasingly important role in the development of greener, more efficient formulations across various sectors.

References

2023. Effect of fatty acid profiles of waste cooking oil biodiesels on their thermal and physical properties. Journal of Thermal Analysis and Calorimetry, 148(15).
DOI: 10.1007/s10973-023-12279-x

2024. Determination of Free Fatty Acids in Foodstuff by Solid Phase Extraction and Gas Chromatography-Flame Ionization Detection Using H2SO4-MeOH Derivatization. Food Analytical Methods, 17(8).
DOI: 10.1007/s12161-024-02652-3

2024. High performance of a base catalyst from Moringa leaves ash for biodiesel conversion of low-grade Bali Malapari oil. Reaction Kinetics, Mechanisms and Catalysis, 137(3).
DOI: 10.1007/s11144-024-02637-7