Isolating Trimyristin from Nutmeg and Preparing Myristic Acid

Introduction

Natural products chemistry is the process of isolating organic compounds from plants. Trimyristin is found in nutmeg in large quantities and be isolated from nutmeg by extraction. Extraction generally follows the techniques of moving the solid phase to a liquid and purify it by recrystallization. Once in isolated form, the melting point can be taken of the product to compare it to literature values to determine how pure the sample is and if the process was done correctly or not. The melting point of a crystallized solid is the temperature it becomes a liquid at normal atmospheric pressure and it can be reported as a range. The length of this range can determine if a sample if pure or not. Broad ranges indicated an impure sample while narrow, sharp ranges indicate a pure sample.

The concept of a broad range vs narrow range can be seen in part two of lab when the mixture’s melting point is determined to see if hydrolysis was done correctly and if the sample contains only myristic acid or not. The myristic acid is produced by the hydrolysis of trimyristin when it hydrolyzes to its salt which will then be acidified after refluxing. Esters can also undergo hydrolysis in order to form an alcohol group and a carboxylic acid anion. The reaction mechanism from lab lecture of the preparation of myristic acid from trimyristin is listed below. An undesired side reaction that can occur during hydrolyzation of trimyristin from lab lecture.

Discussion

When comparing the melting points to the literature values, the experimentally obtained values are close to the literature values. The literature value of trimyristin is 56-58˚C and the experimentally obtained value is the same. The literature value of the myristic acid is 54-55˚C and the experimentally obtained value is 50-56˚C which is very close to the literature value. When obtaining the pure compound of trimyristin, only. 06 g was recovered from the original. 4 g of nutmeg which is a 15% recovery which is low. The percent yield for myristic acid was 48% which is very close to 50%. Reasons that it was not 50% could be attributed to a possibility of the side reaction occurring as well as human error in over evaporating the solvent. The mixture melting point is 50-60˚C which is a narrow range that aligns with the other melting points which means that the hydrolysis was completed successfully, and the sample was pure myristic acid, thus trimyristin did not form in a 50:50 ratio with myristic acid.

Conclusion

As seen by the over successful results, the theory and results are connected, and the lab did set out what it was supposed to do. The melting points of each product were close, or exact, to the literature values and the mixture’s melting point was a narrow, sharp range which indicts that pure myristic acid was formed and not trimyristin proving that the isolation and hydrolysis were successful. Another evidence of this is the 48% recovery of myristic acid which is very close to 50%. The techniques of this lab can also be seen in the application of natural products chemistry in drug discovery by using methods similar to this. Interest in drug recovery via natural products has increased due to big pharmacy drug failures in immunosuppression and anti-infections.