Ethyl Oleate

Category

Carrier Excipients

Molecular Formula

C20H38O2

Molecular Weight

310.51

Grade

Pharmceutical Excipients

Description

Ethyl oleate occurs as a pale yellow to almost colorless, mobile, oily liquid with a taste resembling that of olive oil and a slight, but not rancid odor. Ethyl oleate is described in the USP as consisting of esters of ethyl alcohol and high molecular weight fatty acids, principally oleic acid. A suitable antioxidant may be included.

UNII

Z2Z439864Y

Chemical Name

(Z)-9-Octadecenoic acid, ethyl ester

CAS Number

111-62-6

Synonyms

Crodamol EO; ethylis oleas; ethyl 9-octadecenoate; Kessco EO; oleic acid, ethyl ester.

Administration route

Intramuscular; transdermal

Dosage Form

Intramuscular injection and transdermal patches

Stability and Storage Conditions

Ethyl oleate should be stored in a cool, dry place in a small, well-filled, well-closed container, protected from light. When a partially filled container is used, the air should be replaced by nitrogen or another inert gas. Ethyl oleate oxidizes on exposure to air, resulting in an increase in the peroxide value. It remains clear at 5℃, but darkens in color on standing. Antioxidants are frequently used to extend the shelf life of ethyl oleate. Protection from oxidation for over 2 years has been achieved by storage in amber glass bottles with the addition of combinations of propyl gallate, butylated hydroxyanisole, butylated hydroxytoluene, and citric or ascorbic acid. A concentration of 0.03% w/v of a mixture of propyl gallate (37.5%), butylated hydroxytoluene (37.5%), and butylated hydroxyanisole (25%) was found to be the best antioxidant for ethyl oleate. Ethyl oleate may be sterilized by heating at 150℃ for 1 hour.

Source and Preparation

Ethyl oleate is prepared by the reaction of ethanol with oleoyl chloride in the presence of a suitable hydrogen chloride acceptor.

Applications

Ethyl oleate is primarily used as a vehicle in certain parenteral preparations intended for intramuscular administration. It has also been used as a solvent for drugs formulated as biodegradable capsules for subdermal implantation and in the preparation of microemulsions containing cyclosporin and norcantharidin. Microemulsion formulations containing ethyl oleate have also been proposed for topical and ocular delivery, and for liver targeting following parenteral administration. Ethyl oleate has been used in topical gel formulations, and in self-microemulsifying drug delivery systems for oral administration. Ethyl oleate is a suitable solvent for steroids and other lipophilic drugs. Its properties are similar to those of almond oil and peanut oil. However, it has the advantage that it is less viscous than fixed oils and is more rapidly absorbed by body tissues. Ethyl oleate has also been evaluated as a vehicle for subcutaneous injection.

Safety

Ethyl oleate is generally considered to be of low toxicity but ingestion should be avoided. Ethyl oleate has been found to cause minimal tissue irritation.No reports of intramuscular irritation during use have been recorded.

Incompatibilities

Ethyl oleate dissolves certain types of rubber and causes others to swell. It may also react with oxidizing agents.