Introduction to N-Oleoyl Sarcosine
N-Oleoyl sarcosine (CAS: 110-25-8) is an amphiphilic compound that belongs to the class of fatty acid derivatives of sarcosine, a naturally occurring amino acid. With its unique chemical structure and properties, N-Oleoyl sarcosine has found applications in diverse industries, including cosmetics, pharmaceuticals, and industrial formulations. The synthesis and production processes of N-Oleoyl sarcosine are critical to its functional characteristics, and its chemical behavior makes it a versatile compound in various formulations.
This article delves into the chemical properties, production process, and industrial uses of N-Oleoyl sarcosine, providing a comprehensive overview of its role in modern chemical engineering and its significance across different sectors.
1. Chemical Properties
1.1 Molecular Structure
N-Oleoyl sarcosine is a fatty acid amide derivative of sarcosine, where the amide group is bound to oleic acid through an amide bond. The molecular structure can be represented as:
- Molecular Formula: C22H43NO2
- Molecular Weight: 353.57 g/mol
- IUPAC Name: N-(9Z-octadecenoyl)-N-methylglycine
The structure consists of two main components:
- Oleoyl Group: The oleoyl group is a long-chain unsaturated fatty acid (C18:1), featuring a cis double bond between the 9th and 10th carbon atoms. This structure imparts hydrophobicity and amphiphilic properties to the compound.
- Sarcosine Backbone: Sarcosine is an amino acid derivative, where the amino group is substituted with a methyl group instead of the typical hydrogen atom in glycine. This change in the side chain makes sarcosine more hydrophilic, contributing to the amphiphilic nature of N-oleoyl sarcosine.
1.2 Physical and Chemical Properties
- Appearance: N-Oleoyl sarcosine is a waxy solid at room temperature. It may appear as a pale yellow to off-white solid or paste, depending on the purity and storage conditions.
- Solubility: It is soluble in organic solvents such as ethanol, methanol, chloroform, and acetone but poorly soluble in water due to the hydrophobic nature of the oleoyl group. The amphiphilic character allows it to form micelles or vesicles when incorporated into aqueous solutions in the presence of surfactants.
- Melting Point: The melting point of N-Oleoyl sarcosine is typically between 70°C and 80°C, depending on purity and the presence of crystalline forms.
- pH Stability: The amide bond is stable under neutral and mildly acidic conditions. However, extreme pH conditions (especially in highly basic environments) may lead to hydrolysis, breaking the amide bond and releasing oleic acid and sarcosine.
1.3 Chemical Reactivity
N-Oleoyl sarcosine’s chemical reactivity is influenced by the oleoyl group and the amide bond. The oleoyl group can undergo typical reactions of unsaturated fatty acids, such as oxidation, hydrogenation, or esterification. The amide bond may undergo hydrolysis, especially under acidic or basic conditions, resulting in the formation of oleic acid and sarcosine.
- Oxidation: The presence of a double bond in the oleoyl group makes N-Oleoyl sarcosine susceptible to oxidation, especially in the presence of heat and oxygen. This can lead to the formation of aldehydes, ketones, or hydroperoxides.
- Hydrolysis: Under basic conditions, the amide bond may undergo hydrolysis, splitting the molecule into its constituent parts—oleic acid and sarcosine. This process is more likely in highly alkaline environments.
- Esterification: The amide group can react with alcohols or other nucleophiles under appropriate conditions, potentially forming ester derivatives.
2. Production Process
The production of N-Oleoyl sarcosine typically involves a two-step synthetic pathway: the preparation of sarcosine and its subsequent acylation with oleic acid or oleic acid derivatives. The process requires the use of high-quality reactants and controlled conditions to ensure efficient conversion and high yields.
2.1 Synthesis of Sarcosine
Sarcosine (N-methylglycine) is typically prepared through the methylation of glycine using methyl iodide or dimethyl sulfate as a methylating agent. The synthesis involves the following steps:
- Preparation of Glycine Solution: Glycine is dissolved in water or an aqueous solution to facilitate the reaction.
- Methylation: Methyl iodide or dimethyl sulfate is added to the glycine solution under basic conditions (usually using sodium hydroxide). The methylating agent reacts with the amino group of glycine, replacing the hydrogen atom with a methyl group.
- Purification: The reaction mixture is neutralized and then purified through recrystallization or column chromatography to obtain pure sarcosine.
2.2 Oleoylation Reaction
Once pure sarcosine is available, the oleoylation step involves the acylation of sarcosine with oleic acid or its derivatives. The process typically requires an amide formation catalyst, such as carbodiimide or activating agents like EDC (1-ethyl-3-(3-dimethylaminopropyl) carbodiimide). The oleoylation reaction proceeds as follows:
- Activation of Oleic Acid: Oleic acid or oleyl derivatives are mixed with the activation reagent (e.g., EDC) to form an activated intermediate, such as an acyl ester.
- Reaction with Sarcosine: The activated oleic acid reacts with the amino group of sarcosine, forming the amide bond and releasing the byproduct (e.g., urea or carbodiimide).
- Purification: The crude product is purified through methods like recrystallization, solvent extraction, or chromatography to yield pure N-Oleoyl sarcosine.
The purity of the final product is critical in determining its performance in industrial applications, and it is typically determined using techniques such as HPLC, NMR spectroscopy, and mass spectrometry.
3. Applications of N-Oleoyl Sarcosine
N-Oleoyl sarcosine has a wide range of applications, primarily owing to its amphiphilic nature and its ability to act as a surfactant, emulsifier, and stabilizer. Below are some of the key industrial and commercial applications of this compound:
3.1 Cosmetics and Personal Care
In the cosmetic industry, N-Oleoyl sarcosine is used as a surfactant, emulsifier, and conditioner in a variety of skincare and haircare products. Its amphiphilic properties allow it to improve the stability and texture of formulations, such as creams, lotions, shampoos, and body washes.
- Emulsifying Agent: Due to its ability to lower the surface tension between oil and water, N-Oleoyl sarcosine is often used in formulations that contain both hydrophilic and hydrophobic ingredients, ensuring uniform dispersion of ingredients.
- Conditioning Agent: The compound can also act as a hair conditioner, improving the manageability and smoothness of hair by forming a thin, protective layer around the hair shaft.
- Skin Softening: N-Oleoyl sarcosine is known for its ability to retain moisture in the skin, acting as a humectant in formulations like moisturizers and body lotions.
3.2 Pharmaceutical Industry
In the pharmaceutical industry, N-Oleoyl sarcosine is primarily used as a solubilizing agent in drug formulations, particularly for poorly soluble drugs. It can be employed to enhance the bioavailability of hydrophobic drugs by forming micelles or lipid-based formulations.
- Drug Delivery Systems: The amphiphilic nature of N-Oleoyl sarcosine makes it a potential candidate for drug delivery systems, such as liposomes, nanoemulsions, or micelles. These systems can improve the solubility and absorption of hydrophobic drugs in the gastrointestinal tract.
- Topical Formulations: Due to its gentle surfactant properties, N-Oleoyl sarcosine is also used in the formulation of topical drug delivery systems, including creams and ointments, for the sustained release of active pharmaceutical ingredients.
3.3 Industrial Applications
N-Oleoyl sarcosine is also used in various industrial applications, including detergents, lubricants, and textile processing. Its surfactant properties make it effective in cleaning formulations, while its emulsifying and dispersing properties are useful in industrial lubrication.
- Industrial Detergents: N-Oleoyl sarcosine can be used in heavy-duty industrial cleaners, where its ability to emulsify oils and grease proves beneficial in removing tough stains from machinery and equipment.
- Lubricants: As an emulsifier, N-Oleoyl sarcosine is used in the formulation of lubricants, where it helps to stabilize oil-water mixtures and reduce friction between moving parts.
- Textile Industry: The compound is used in textile processing for its ability to act as a dispersing agent, improving the uniformity of dyeing and finishing processes.
3.4 Food Industry
In some cases, N-Oleoyl sarcosine can be used as a food additive, particularly as an emulsifier in processed food
products. Its amphiphilic nature allows it to stabilize oil-water mixtures, which is essential for improving the texture and consistency of various food products.
- Emulsifier in Processed Foods: N-Oleoyl sarcosine is used in products like margarine, dressings, sauces, and mayonnaise. It helps prevent separation of oil and water, ensuring that the product maintains a uniform texture and appearance throughout its shelf life.
- Stabilizer in Dairy Products: The compound is also utilized in dairy products like ice cream, where it helps to create smooth textures and prevent the formation of ice crystals by stabilizing fat droplets in the mixture.
While N-Oleoyl sarcosine is not as commonly used as other food emulsifiers like lecithin or mono- and diglycerides, its potential applications in the food industry are expanding, particularly in more specialized or niche markets.
4. Environmental and Safety Considerations
Despite its widespread industrial use, the environmental impact and safety of N-Oleoyl sarcosine are important considerations. Due to its natural derivation from sarcosine and oleic acid, the compound is relatively biodegradable compared to many synthetic surfactants and emulsifiers. However, as with any chemical, proper handling, disposal, and use are essential to minimize environmental contamination and ensure worker safety.
4.1 Biodegradability
N-Oleoyl sarcosine is more biodegradable than many synthetic surfactants due to its natural fatty acid content. Oleic acid, the primary component, is readily biodegradable in both aerobic and anaerobic conditions. Additionally, the sarcosine backbone, being an amino acid derivative, is also biodegradable. However, the rate of biodegradation may depend on environmental factors such as temperature, oxygen levels, and microbial activity.
4.2 Toxicity and Safety
In terms of toxicity, N-Oleoyl sarcosine is considered to have low toxicity, especially when compared to traditional surfactants and chemical additives. It is generally regarded as safe for use in cosmetics and pharmaceuticals at appropriate concentrations. However, exposure to high concentrations can lead to irritation of the skin, eyes, or respiratory system. As with all chemicals, it is recommended to handle N-Oleoyl sarcosine with caution, using personal protective equipment (PPE) like gloves and goggles, especially in industrial or laboratory settings.
- Skin Irritation: While N-Oleoyl sarcosine is typically mild and non-irritating at low concentrations, it can cause skin irritation or sensitization in sensitive individuals or at high concentrations.
- Eye Irritation: Direct contact with the eyes should be avoided, as it may cause mild irritation.
- Inhalation: Inhalation of dust or vapors should be minimized to prevent respiratory irritation, especially in industrial settings.
Regulatory agencies like the FDA and European Medicines Agency (EMA) regulate its use in cosmetics and pharmaceutical formulations, ensuring that the compound is used within safe limits.
5. Conclusion
In conclusion, N-Oleoyl sarcosine (CAS: 110-25-8) is a chemical compound with a broad spectrum of industrial and commercial applications due to its unique amphiphilic properties. Derived from the combination of oleic acid and sarcosine, this fatty acid derivative plays a vital role in enhancing the performance and stability of various products, particularly in cosmetics, pharmaceuticals, food, and industrial applications.
Summary of Key Points:
- Chemical Properties: The amphiphilic nature of N-Oleoyl sarcosine is driven by the combination of the hydrophobic oleoyl group and the hydrophilic sarcosine backbone. This balance allows it to function as an effective surfactant, emulsifier, and stabilizer in various formulations.
- Production Process: The synthesis of N-Oleoyl sarcosine involves a two-step process: the preparation of sarcosine through methylation of glycine, followed by the acylation of sarcosine with oleic acid. The process requires careful control of reaction conditions to ensure high yield and purity of the final product.
- Applications: N-Oleoyl sarcosine’s most notable uses include its role in personal care products, where it serves as an emulsifier and conditioning agent, and in the pharmaceutical industry, where it acts as a solubilizer for hydrophobic drugs. The compound also finds utility in industrial formulations such as detergents, lubricants, and textile processing.
- Environmental and Safety Considerations: Given its natural origin and biodegradable nature, N-Oleoyl sarcosine poses minimal environmental risks. However, like any chemical compound, safety protocols must be followed during production and handling to minimize the potential for irritation or injury.
With increasing demand for sustainable and biodegradable ingredients across various industries, N-Oleoyl sarcosine holds significant promise for continued growth in application. As research into its potential expands, it is likely that new uses for this compound will emerge, particularly in more specialized markets such as advanced drug delivery systems, eco-friendly personal care products, and sustainable industrial formulations. Therefore, N-Oleoyl sarcosine represents an important chemical in modern chemical engineering, providing versatility and functionality in a wide range of industrial applications while contributing to the growing trend toward green chemistry.
As industries continue to focus on sustainability and consumer safety, N-Oleoyl sarcosine’s natural composition, mildness, and effectiveness position it as a key player in the future of both commercial and industrial formulations.