Ethyl oleate (English name Ethyl Oleate), also known as cis-9-octadecenoic acid ethyl ester (cis-9-Octadecenoic acid, ethyl ester), 9-octadecenoic acid ethyl ester ester), colorless oily liquid, flammable, insoluble in water, soluble in organic solvents. It is mainly used in the preparation of lubricants, water repellants, resin toughening agents, surfactants, pharmaceutical excipients, plasticizers and ointment bases and other organic chemicals, and also used as fragrances.

Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. Ethyl oleate is a liquid lipid component in nanostructured lipid carriers (NLC). NLC is an orally available delivery vehicle for trans-ferulic acid (TFA).

The main function of ethyl oleate:

1. Used as lubricant, water repellant and resin toughening agent.

2. It is used in the preparation of surfactants and other organic chemicals, and also used as fragrances, pharmaceutical excipients, plasticizers and ointment bases, etc. Use lubricants.

3. Water repellent. Resin toughening agent. Gas chromatography stationary solution (maximum operating temperature is 120°C, solvent is methanol and diethyl ether). Uses Used as a gas chromatography stationary liquid, solvent, lubricant and toughening agent for resins

Special talk about the application in medicine

1. Ethyl oleate is mainly used as a vehicle for some intramuscular injections, as well as for subdermally implanted biodegradable microcapsules and cyclosporine microemulsions.

2. Ethyl oleate is a suitable solvent for steroids and other lipophilic drugs, and its properties are similar to almond oil and peanut oil. However, compared to fatty oils, ethyl oleate is less viscous and readily absorbed by body tissues. Therefore, it is often used in the manufacture of injections, liniments, ointments and pharmaceutical intermediates.

3. Ethyl oleate can also be used as a solvent for subcutaneous injection drugs.

Nowadays, ethyl oleate raw materials are abundant, but ordinary raw material manufacturers usually do not have the production and packaging conditions for medicinal products, and dust, particles and other impurities are easily mixed in the preparation process, resulting in raw materials that cannot meet the requirements of the Pharmacopoeia. Raw material manufacturers are scarce and products are scarce, which makes it difficult to meet the pharmaceutical industry’s demand for pharmaceutical-grade ethyl oleate.

Common reactions of ethyl oleate

(1) Hydrolysis reaction: ethyl oleate undergoes hydrolysis reaction in the presence of an acid catalyst to generate a reaction equilibrium mixture of oleic acid, ethanol, water ethyl oleate, and the like. When a base is used as a catalyst, the product is oleate, and the reaction is irreversible, also known as saponification. In addition, high-pressure steam hydrolysis can also be performed at high temperature of 185~300 °C to generate oleic acid and methanol.

(2) Ammonolysis, alcoholysis and transesterification: ethyl oleate reacts with ammonia to generate oleic acid amide and ethanol, and reacts with other fatty alcohols other than ethanol to generate new oleate and ethanol. Ethyl oleate reacts with another ester and the ester groups are exchanged to form a new oleate and carboxylate. The above reaction has catalysts such as acid and alkali, which can speed up the reaction.

The production method of ethyl oleate:

It is obtained by esterification of ethanol and oleic acid. Mix oleic acid and ethanol, add catalyst concentrated sulfuric acid or p-toluenesulfonic acid, and heat to reflux. Cooled, neutralized with alkali to pH 8-9, washed with water until neutral, dried over anhydrous calcium chloride, distilled under reduced pressure, and obtained by intercepting ethyl oleate fraction. Mesoporous molecular sieve SBA-15-SO3 can also be used as a catalyst, the molar ratio of methanol and oleic acid is excessive, heating, refluxing at a temperature of 130 ° C for 4 hours, cooling, filtration, distillation, and intercepting the ethyl oleate fraction to obtain ethyl oleate.

Ethyl oleate can also be obtained by transesterification of another oleate with ethanol

Storage conditions

Iron drum or glass bottle packaging. It should be stored in a cool, ventilated warehouse, away from fire and heat sources. Storage temperature -20ºC

Stability

1. Prohibit contact with air, light and oxidants. Avoid eye and skin contact.

2. Exist in flue-cured tobacco leaves.

3. Naturally present in cocoa, buckwheat, certain fruits and alcohol.