Triolein

Category

Emollient; Penetration enhancer; Solubilizing Agents; Solvent

Molecular Formula

C57H104O6

Molecular Weight

885.43

Grade

Pharmceutical Excipients

Description

Triolein occurs as a clear, colorless to yellowish oily liquid, and is tasteless and odorless.

UNII

O05EC62663

CAS Number

122-32-7

Synonyms

Captex GTO; glycerol trielaidate; glyceryl trioleate; 9-octadecenoic acid-1, 2, 3-propanetriyl ester; olein; 1, 2, 3-propanetriyl tris((E)-9-octadecenoate); trielaidin; trielaidoylglycerol; 1, 2, 3-tri(cis-9-ctadecenoyl) glycero

Administration route

Injection

Dosage Form

liposomal suspension for epidural injections

Stability and Storage Conditions

Triolein is classified as a stable compound but is sensitive to air and light. It should be stored in tightly sealed containers in a dry area at 2-8℃. Thermal decomposition of triolein may lead to release of irritating gases and vapors such as carbon oxides. Exposure to air and moisture over prolonged periods should be avoided.

Source and Preparation

Triolein is manufactured by the esterification of fractionated fatty acids, mainly oleic acid and glycerin.

Applications

Triolein is used as a solubilizer and solvent in injectable preparations. It has been used in marketed preparations of sustained-release injections of cytarabine and multivesicular liposomal injections of morphine sulfate. It has also been used in enteric coatings for oral preparations in combination with other enteric coating excipients to protect against degradation by pancreatic lipase. Triolen is used in personal care products as a skin-conditioning and viscosity-controlling agent.

Safety

Triolein is used in injectable preparations, in enteric coatings for oral preparations, and in personal care products. Chronic exposure may cause nausea and vomiting, and higher exposures may cause unconsciousness. The Cosmetic Ingredient Review (CIR) Expert Panel found that dermal application of triolein was not associated with significant irritation, and no evidence of sensitization or photosensitization was observed.Ocular exposures were found to be only mildly irritating to eyes. Triolein has not been found to be genotoxic in a number of in vitro and in vitro assay systems. Subcutaneous injections of triolein in rats showed no tumors at the injection site. The CIR Expert Panel also noted that metabolism data indicated that glyceryl triesters (including triolein) followed the same metabolic pathways as fats in food. They were split into monoglycerides, free fatty acids, and glycerol, all of which were absorbed into the intestinal mucosa and metabolized further.Therefore, oral exposure to these compounds was not found to be a concern. A triolein-based amphotericin emulsion showed better safety with a higher LD50 in rats as compared with the conventional amphotericin deoxycholate.

Incompatibilities

Triolein is incompatible with strong oxidizing agents and spontaneously flammable products. Being a triglyceride ester, triolein can be hydrolyzed by strong acids, and particularly by strong bases. It is possible for primary amines to form an adduct across the olefinic double bonds (analogous to a Michael addition).