Trimyristin Isolation

In this lab, trimyristin was isolated from ground nutmeg and recrystallized to get a percent yield of 72.91%, as well as hydrolyzed to produce myristic acid in a 79.03% yield. The ground nutmeg seeds were refluxed with tert-butyl methyl ether to extract the crude trimyristin which was then recrystallized with acetone to purify the trimyristin product. The other soluble components of the nutmeg remain in the acetone solution while trimyristin recrystallizes out. Trimyristin is a triglyceride, which is a triester of the trialcohol glycerol and a long chain, unbranched carboxylic acid. Hydrolysis of a triglyceride yields one glycerol molecule and three carboxylic acid molecules for every molecule of fat. When trimyristin is converted into glycerol and myristic acid through saponification, the addition of the sodium hydroxide creates glycerol and sodium myristate and with the addition of acid to the sodium myristate causes a change to a carboxylic acid, thus forming myristic acid in this lab. The addition of acid causes the sodium salt to leave the sodium myristate and allows for the hydration of the now unbound oxygen which provides the mechanism for the alcohol group formation on the carboxylic acid.