Curcumin is the active ingredient in turmeric that consists of an acetylacetone central linker and two side-arms of benzaldehyde derivatives. Curcumin has demonstrated a broad spectrum of biological activity. Curcumin is known for its anti-cancer, anti-viral, anti-inflammatory, and anti-oxidizing effects. However, curcumin is not a good pharmaceutical candidate because when ingested, it quickly decomposes due to its poor stability. In addition, curcumin has low water solubility. These factors severely hinder the pharmaceutical use of curcumin itself. The stability of curcumin has been linked to the flexibility of the central core while the solubility in large depends on the functional groups present at side arms. It was previously suggested that increasing the rigidity of the central linker could provide curcuminoids with improved biological stability. In this study, we have substituted acetylacetone with rigid 2-acetylcyclohexanone. We conducted our study using a combination of computational modeling and 1H NMR experiments. As a result of our efforts, we developed a versatile green method towards 2-acetylcyclohexanone-based asymmetric curcuminoids. We were able to elucidate the mechanism of their formation and develop a simple two-step purification procedure that does not require column chromatography or extensive recrystallization or extractions. Our method provides desired compounds using one general procedure for a variety of curcuminoids with modified side arms. All new compounds demonstrate a high level of purity using 1H and 13C NMR spectroscopic data and elemental analysis.

Asymmetric curcuminoids: Mechanistic study, computational modeling, and green synthesis

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.