Name: Triolein
CAS No: 2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate [122-32-7]
None adopted.
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-octadecenoyl) glycerol.
2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate [122-32-7]
C57H104O6 885.43
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.(1) Triolen is used in personal care products as a skin-conditioning and viscosity-controlling agent.
Triolein occurs as a clear, colorless to yellowish oily liquid, and is tasteless and odorless.
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Boiling point 235–2408C Density 0.915 g/cm3 Flash point 3308C Free fatty acids 40.1% Iodine value 80–100 Melting point 5 to 48C Peroxide value 42 Refractive index nD 20 = 1.4676; nD 60 = 1.4561. Solubility Soluble in chloroform, ether, carbon tetrachloride; slightly soluble in ethanol (95%); practically insoluble in water. Specific gravity 0.9 at 258C (water = 1) Vapor density >1 (air = 1) Vapor pressure <133.3 Pa (<1mmHg) at 258C Viscosity (kinematic) 74mm2/s (74 cSt) at 258C
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 2–88C. 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.
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).
Triolein is manufactured by the esterification of fractionated fatty acids, mainly oleic acid and glycerin.
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.(2) 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.(2) A triolein-based amphotericin emulsion showed better safety with a higher LD50 in rats as compared with the conventional amphotericin deoxycholate.(3)
Observe normal precautions appropriate to the circumstances and quantity of the material handled. Use of a mask and/or respirator is recommended in case aerosol/dust is formed. Ventilation is recommended to control dust or fumes from the material. For eye protection, safety glasses with side shields are recommended. For hand protection, PVC or other plastic material gloves are recommended.
Included in the FDA Inactive Ingredients Database (liposomal suspension for epidural injections). Included in parenteral medicines (suspension for intrathecal injection) licensed in the UK. Triolein is included in the CIR category as safe for use in cosmetics and personal care products. Its use as an indirect food additive has been approved by the FDA.
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Triolein enhances the transfection efficiency of polycation nanostructured lipid carrier.(4) Transferrin-conjugated solid lipid nanoparticles containing triolein were found to enhance the delivery of quinine dihydrochloride to the brain for the treatment of cerebral malaria.(5) A nanoemulsion lipoprotein delivery system, comprising triolein in its oily phase, has been found to show lower cytotoxicity than conventional systems in in vitro gene transfection in human glioma cells.(6) Gadolinium-containing lipid nanoemulsions have also been prepared using triolein.(7) A w/o/w insulin emulsion system containing triolein in its oily phase has demonstrated strong hypoglycemic effects.(8) The use of multivescicular liposomes of breviscapine from a triolein/tricaprylin system as an intramuscular injection for sustained delivery has been reported.(9) A paclitaxel prodrug has been incorporated into a lipid nanoparticle formulation comprising triolein in a mixture of lipids and has shown promising results in the treatment of folate receptor tumors.(10) Improved drug distribution to the tumor has been reported with parenteral administration of a submicrometer lipid emulsion of paclitaxel with triolein as the oily core.(11) Folate receptor-targeted solid lipid nanoparticles of hematoporphyrin containing triolein have also shown specific receptor binding and potential as a targeted drug delivery system.(12) The EINECS number for triolein is 204-534-7. The PubChem Compound ID (CID) for triolein is 5497163.