Ethyl oleate
[CAS# 111-62-6]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Carboxylic acid and ester perfume >> Aliphatic carboxylate
• Name: Ethyl oleate
• Synonyms: ethyl (Z)-octadec-9-enoate
• Molecular Formula: C₂₀H₃₈O₂
• Molecular Weight: 310.51
• CAS Registry Number: 111-62-6
• EC Number: 203-889-5
• FEMA: 2450
• SMILES: CCCCCCCC/C=CCCCCCCCC(=O)OCC

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*, 0.87 g/mL (Expl.)
• Melting point: -32 °C (Expl.)
• Index of Refraction: 1.455, Calc.^*, 1.451 (Expl.)
• Boiling Point: 385.9±21.0 °C (760 mmHg), Calc.^*, 392.1-394.8 °C (Expl.)
• Flash Point: 91.8±20.4 °C, Calc.^*, 79.4 °C (Expl.)

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

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

Ethyl oleate is an organic compound classified as a fatty acid ester, specifically the ethyl ester of oleic acid. It has the molecular formula C₂₀H₃₈O₂ and is a colorless to pale yellow liquid with a mild odor. It is slightly soluble in water but highly soluble in organic solvents such as ethanol, chloroform, and ether. Ethyl oleate is naturally present in trace amounts in some animal fats and vegetable oils, and it can be synthesized through the esterification of oleic acid with ethanol under acid-catalyzed conditions. This reaction is a typical example of Fischer esterification, where an alcohol reacts with a carboxylic acid in the presence of an acid catalyst to form an ester and water.

Ethyl oleate has widespread applications in the pharmaceutical industry, primarily as a vehicle for drug delivery in injectable formulations. It is commonly used as a carrier oil in intramuscular and subcutaneous injections because of its ability to dissolve lipophilic drugs, ensuring their efficient absorption and controlled release. Some pharmaceutical formulations containing steroid hormones, such as testosterone and progesterone, utilize ethyl oleate as a solvent to facilitate drug delivery. Its favorable properties, such as its biocompatibility and non-toxic nature at appropriate dosages, have made it a preferred excipient in parenteral formulations.

In the food industry, ethyl oleate serves as a food additive, primarily as a flavoring agent and solvent for lipid-soluble compounds. It is used in small amounts to enhance the sensory characteristics of certain processed food products. Regulatory bodies in some countries have approved ethyl oleate for limited use in food applications, considering its low toxicity and biodegradability. Its presence in naturally occurring fats and oils also supports its use in the food sector.

Ethyl oleate is widely utilized in the cosmetics and personal care industry as an emollient and skin-conditioning agent. It is a common ingredient in creams, lotions, and hair care products, where it contributes to the smooth texture, spreadability, and moisturizing properties of formulations. Due to its ability to improve the absorption of active ingredients, ethyl oleate is sometimes included in transdermal and topical drug formulations to enhance skin penetration.

Beyond pharmaceuticals, food, and cosmetics, ethyl oleate has been investigated for industrial applications. It has been used as a biodegradable solvent and lubricant in formulations requiring low-toxicity, environmentally friendly components. Its chemical stability and compatibility with various organic compounds make it suitable for specialized industrial uses, including its role as a processing aid in certain chemical reactions. Additionally, it has been explored as a potential biofuel component due to its favorable combustion characteristics and renewability as a derivative of plant oils.

Ethyl oleate has been the subject of various studies focusing on its physicochemical properties, stability, and compatibility with active pharmaceutical ingredients. Research has demonstrated that it is generally safe for human use when applied within established regulatory limits. However, in high concentrations or with prolonged exposure, some individuals may experience mild irritation or sensitivity reactions.

Due to its versatility, ethyl oleate has established itself as a valuable compound across multiple industries. Its role as a pharmaceutical excipient, food additive, cosmetic ingredient, and industrial solvent underscores its importance in commercial and scientific applications. The ability to derive it from renewable sources such as plant oils further enhances its appeal as a sustainable chemical component in various formulations.

References

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DOI: 10.1007/s13346-024-01732-5

2024. Design and Development of Gastro-retentive Gel Forming System Comprising Curcumin Loaded Nanostructured Lipid Carrier for Stomach Specific Delivery. Journal of Cluster Science, 35(8).
DOI: 10.1007/s10876-024-02702-0

2024. Unlocking relief: formulation, characterization, and in vivo assessment of salicylic acid-loaded microemulgel for psoriasis management. Naunyn-Schmiedeberg's Archives of Pharmacology, 397(12).
DOI: 10.1007/s00210-024-03447-3