Type: Synthesis Essays
Sample donated: Glenda Adkins
Last updated: August 19, 2019
Thepowerful antioxidant, oleacein, is a compound involved in the production ofextra virgin olive oil, and is associated with numerous health benefits.
Introducingoleacein into other edible oils may enhance the health properties of theseproducts, and provides motivation for developing simple and effective methodsof oleacein synthesis. Existing methods of oleacein synthesis include a one-stepdecarboalkoxylationof oleuropein sourced from black olives, or alternatively the decarboxylationof demethyl oleuropein. However, these methods give oleacein in low yield and requireeither harsh reaction conditions or involve extractions from black olivedrupes, which are only seasonally available and produce limited quantities of oleuropein. Here we show a newmethod to synthesize oleacein in high yield using oleuropein naturally sourcedfrom olive leaves. We found that the oleacein yield doubled when the use ofDMSO as a reaction solvent was replaced for water, and conventional refluxheating was replaced for the use of a microwave. Furthermore, we found that thereaction profile was enhanced using aqueous NaCl as a decarboxylation catalyst.
Our results demonstrate that an aqueousadaption of the decarboxylationreaction minimized hindering side reactions that had been facilitated by DMSO.This newly improved synthetic route is the first method to give oleacein in goodyield in a simple and sustainable manner. These findings have made oleaceinwidely accessible and could lead to the production of healthier commercial oils.