Isolation of Trimyristin from Nutmeg and Its
Hydrolysis to Myristic Acid
Compounds having complex molecular structures can be separated from natural materials.
Usually they are
components of very complex mixtures.
To obtain pure compounds, long, tedious separation and purification
procedures are often required.
The triester, trimyristin, is however an exception and can be extracted from
ground nutmeg seeds with tert-butyl methyl ether.
Crystallization from acetone yields the pure compound.
Most of the numerous other ether soluble components of nutmeg remain in the acetone solution.
triesters of glycerol, such as trimyristin,
in which the carboxylic acid portion of the molecule is unbranched
and contains 14 or more carbon atoms, are also known as fats or triglycerides and are components of food.
A significant part of the structure proof of many natural products is their degradation by chemical reactions
to simpler structures.
When trimyristin is refluxed with NaOH in aqueous ethanol and then acidified, the
carboxylic acid, along with glycerol, is obtained.
As part of your prelab outline, prepare a table of relevant physical properties of all reactants, products, and
solvents, along with quantities of each (see Sample Table on Handouts page of website). This lab will take
most of four hours, so be well prepared and get started as soon as possible.
As always, as part of your prelab outline, prepare a table of reactants, products, and solvents (see website for
This lab will take most of four hours, so be well prepared and get started as soon as possible.
Set your sand bath to about 20% (turn to 30, then down; make sure yellow power light is on).
Weigh 1.00 g (± 0.05 g) of ground nutmeg onto weighing paper and transfer the nutmeg to the microscale
round-bottomed (RB) flask, using the plastic funnel to assist in the transfer.
Add 3 mL of tert-butyl methyl
ether and two or three boiling chips to the flask and, using the black plastic connector, connect the
distillation column/air condenser (not the longer chromatography column) to the flask.
Be sure that the
connector is not too frayed.
Clamp the flask to a ring stand using the small three-pronged clamp and slowly
lower the flask into a slight depression in the sand, without actually touching the flask to the sand. Carefully
adjust the position of the flask so that the mixture boils very gently.
The finely divided nutmeg causes the
mixture to bump (boil violently).
Excessive heating may cause some of the mixture to bump out of the flask;
bumping is minimized by heating very gently.
Heat just at the boiling point for 10 minutes, remove from the
heat, and allow the suspended solids to settle for a few minutes.
In the following transfer procedure the idea is to leave behind as much solid as possible before adding the