TRIMYRISTIN

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Trimyristin, is the triglyceride of myristic acid, which is found naturally in many vegetable fats and oils. It can be used for the preparation of Solid lipid nanoparticles (SLN) composed of trimyristin (solid lipid) and poloxamer 407 (surfactant).

ChEBI: A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by myristic (tetradecanoic) acid.

Not classified

Trimyristin is prepared by the esterification of glycerol with myristic acid under acidic conditions, or isolated from nutmeg through chloroform maceration[1-2].
Chemical synthesis of trimyristin: Myristic acid (13.7 g, 60 mmol), glycerol (0.9 g, 10 mmol), and a 5% wt sulfuric acid solution (0.7 mL) were reacted at 393 K for 3 h. Chloroform (96 mL) was added into the solution and stirred at 343 K for 30 min. A 10% wt NaOH solution was added into the mixture until the pH of the mixture reached 13. The product was extracted with n-hexane and the organic layer was washed with distilled water until neutral. The organic phase was dried over anhydrous sodium sulfate to obtain 9.62 g of trimyristin as a yellowish solid (54% yield).

Crystallise it from diethyl ether. [Beilstein 2 IV 1135.]

[1] Jumina, Nurmala, A., Fitria, A., Pranowo, D., Sholikhah, E. N., Kurniawan, Y. S., Kuswandi, B. (2018). Monomyristin and Monopalmitin Derivatives: Synthesis and Evaluation as Potential Antibacterial and Antifungal Agents. Molecules, 23(12), 3141. https://doi.org/10.3390/molecules23123141
[2] Kapelle, I. B. D. Laratmase, M. S. (2014). Trimyristin Isolation From Nutmeg And Synthesis Of Methylester Using Heterogen Catalyst. Indonesian Journal of Chemical Research, 2(1), 160–165. https://doi.org/10.30598/ijcr.2014.2-ima