Solid acid-catalyzed one-step synthesis of oleacein from oleuropein.

ABSTRACT: In this study, we developed a new synthetic strategy to convert secoiridoid glucosides into unique dialdehydic compounds using solid acid catalysts. Specifically, we succeeded in the direct synthesis of oleacein, a rare component of extra-virgin olive oil, from oleuropein, which is abundant in olive leaves. Whereas the conventional total synthesis of oleacein from lyxose requires more than 10 steps, these solid acid catalysts enabled the one-step synthesis of oleacein from oleuropein. A key step in this synthesis was the selective hydrolysis of methyl ester. Density functional theory calculations at the B3LYP/631+G (d) level of theory revealed the formation of a tetrahedral intermediate bonded to one H₂O molecule. These solid acid catalysts were easily recovered and reused at le

SUBMITTER: Shimamoto Y 

PROVIDER: S-EPMC10203140 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature