Name: Ethyl Oleate
CAS No: (Z)-9-Octadecenoic acid, ethyl ester [111-62-6]
Crodamol EO; ethylis oleas; ethyl 9-octadecenoate; Kessco EO; oleic acid, ethyl ester
(Z)-9-Octadecenoic acid, ethyl ester [111-62-6]
C20H38O2,310.51
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(1) and in the preparation of microemulsions containing cyclosporin(2) and norcantharidin.(3) Microemulsion formulations containing ethyl oleate have also been proposed for topical(4) and ocular(5) delivery, and for liver targeting following parenteral administration.(6) Ethyl oleate has been used in topical gel formulations,(7) and in self-microemulsifying drug delivery systems for oral administration.(8) 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.(9) Ethyl oleate has also been evaluated as a vehicle for subcutaneous injection.(
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 USP32–NF27 as consisting of esters of ethyl alcohol and high molecular weight fatty acids, principally oleic acid. A suitable antioxidant may be included.
See Table I.
Boiling point 205–2088C (some decomposition) Flash point 175.38C Freezing point 328C Moisture content At 208C and 52% relative humidity, the equilibrium moisture content of ethyl oleate is 0.08%. Solubility Miscible with chloroform, ethanol (95%), ether, fixed oils, liquid paraffin, and most other organic solvents; practically insoluble in water. Surface tension 32.3 mN/m (32.3 dynes/cm) at 258C(9) Viscosity (dynamic) 3.9 mPa s (3.9 cP) at 258C(9) Viscosity (kinematic) 0.046 mm2 /s (4.6 cSt) at 258C(9)
Ethyl oleate should be stored in a cool, dry place in a small, wellfilled, 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 58C, 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.(11,12) 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.(12) Ethyl oleate may be sterilized by heating at 1508C for 1 hour
Ethyl oleate dissolves certain types of rubber and causes others to swell.(13,14) It may also react with oxidizing agents.
Ethyl oleate is prepared by the reaction of ethanol with oleoyl chloride in the presence of a suitable hydrogen chloride acceptor.
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.(15) No reports of intramuscular irritation during use have been recorded
Observe normal precautions appropriate to the circumstances and quantity of material handled. Eye protection and nitrile gloves are recommended. Ethyl oleate is flammable.
Included in the FDA Inactive Ingredients Database (transdermal preparation). Included in parenteral (intramuscular injection) and nonparenteral (transdermal patches) medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Methyl oleate; oleic acid. Methyl oleate Empirical formula C19H36O2 Molecular weight 296.49 CAS number [112-69-9] Synonyms Methyl 9-octadecenoate; (Z)-9-octadecenoic acid, methyl ester. Boiling point 168–1708C Density 0.879 g/cm3 Iodine number 85.6 Refractive index n D 26 = 1.4510 Solubility Miscible with ethanol (95%) and ether. Comments Prepared by refluxing oleic acid with p-toluenesulfonic acid in methanol.
The EINECS number for ethyl oleate is 203-889-5. The PubChem Compound ID (CID) for ethyl oleate includes 8123 and 5364430