Trimyristin from nutmeg

Trimyristin, or glyceryl trimyristate, is an interesting triglyceride that occurs naturally in nutmeg. It doesn't have many uses except in scientific research. Trimyristin can be hydrolysed to glycerol and myristic acid, and in the future I plan to try this out. Ground dry nutmeg typically contains about 25% trimyristin (by weight) so this is a great source of the compound.

The extraction of trimyristin from nutmeg is a classic experiment. Usually diethyl ether is used as the extraction solvent, but I tried using a different method.

To a 250ml conical flask, I added 40g of dry ground nutmeg. To this I added 100ml of hot (nearly boiling) ethanol and stirred vigorously for 15 seconds. I then immediately filtered the mixture through a cloth, collecting the orange filtrate in a 200ml conical flask. I washed the nutmeg on the filter with 25ml more hot ethanol. It's important that the whole filtering process is performed quickly while the ethanol is still hot, otherwise the trimyristin will start crystallizing out. Anyway, the 200ml conical flask containing the filtrate (already starting to precipitate some product) was chilled to about 2 C. A lot more trimyristin crystallized out and the mixture was filtered to collect it.

After filtration, I was left with fine crystals of almost white trimyristin. I decided to perform a recrystallization from ethanol to purify my product. After recrystallization, I was left with 0.84g of trimyristin as very fine white crystals. The product was easily melted by hot water, which is a good sign as trimyristin is said to melt at about 56 C. My guess is the trimyristin isn't extremely pure but still definitely usable for most things.

Left = recrystallized trimyristin   Right = ground nutmeg

This extraction was poorly planned and performed. I probably could have gotten more product by boiling the nutmeg in ethanol at the start. My procedure was loosely based on this.