Triacetin
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Triacetin is the organic compound with the formula Template:Chem2. It is classified as a triglyceride, i.e., the triester of glycerol with acetic acid.[1] It is a colorless, viscous, and odorless liquid with a high boiling point and a low melting point. It has a mild, sweet taste in concentrations lower than 500 ppm, but may appear bitter at higher concentrations.[2] It is one of the glycerine acetate compounds.
Uses
Triacetin is a common food additive, for instance as a solvent in flavorings, and for its humectant function, with E number E1518 and Australian approval code A1518. It is used as an excipient in pharmaceutical products, where it is used as a humectant, a plasticizer, and as a solvent.[3]
Potential uses
The plasticizing capabilities of triacetin have been utilized in the synthesis of a biodegradable phospholipid gel system for the dissemination of the cancer drug paclitaxel (PTX).[4] In the study, triacetin was combined with PTX, ethanol, a phospholipid and a medium chain triglyceride to form a gel-drug complex. This complex was then injected directly into the cancer cells of glioma-bearing mice. The gel slowly degraded and facilitated sustained release of PTX into the targeted glioma cells.
Triacetin can also be used as a fuel additive as an antiknock agent which can reduce engine knocking in gasoline, and to improve cold and viscosity properties of biodiesel.[5]
It has been considered as a possible source of food energy in artificial food regeneration systems on long space missions. It is believed to be safe to get over half of one's dietary energy from triacetin.[6]
Synthesis
Triacetin was first prepared in 1854 by the French chemist Marcellin Berthelot.[7] Triacetin was prepared in the 19th century from glycerol and acetic acid.[8]
Its synthesis from acetic anhydride and glycerol is simple and inexpensive.
- 3 Template:Chem2 + 1 Template:Chem2 → 1 Template:Chem2 + 3 Template:Chem2
This synthesis has been conducted with catalytic sodium hydroxide and microwave irradiation to give a 99% yield of triacetin.[9] It has also been conducted with a cobalt(II) Salen complex catalyst supported by silicon dioxide and heated to 50 °C for 55 minutes to give a 99% yield of triacetin.[10]
Safety
The US Food and Drug Administration has approved it as generally recognized as safe[11] food additive and included it in the database according to the opinion from the Select Committee On GRAS Substances (SCOGS). Triacetin is included in the SCOGS database since 1975.[12]
Triacetin was not toxic to animals in studies of exposure through repeated inhalation over a relatively short period.[13]
References
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