Auto-oxidation of Ent-beyer-15-en-19-al isolated from the essential oil of the heartwood of Erythroxylum monogynum Roxb.: formation of 15,16-epoxy-ent-beyeran-19-oic acid and other products.

ABSTRACT: Chemical investigation of the essential oil obtained from the heartwood of Erythroxylum monogynum Roxb. yielded three beyerene type diterpenoids ent-beyer-15-ene (1), ent-beyer-15-en-19-ol (erythroxylol A) (2) and ent-beyer-15-en-19-al (3). Ent-beyer-15-en-19-al (3) was found to be unstable at room temperature, giving rise to hitherto unknown 15,16-epoxy-ent-beyeran-19-oic acid (4). This conversion involves the auto-oxidation of a C-4 axial aldehyde group of an ent-beyer-15-ene diterpenoid with the concurrent epoxidation of the C-15 double bond. This is the first report of the auto-oxidation of an aldehyde group to a carboxylic acid group with the concurrent epoxidation of a double bond in the same compound. Further investigation of this observation under controlled conditions resulted in

SUBMITTER: Tennakoon TMSG 

PROVIDER: S-EPMC7071572 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature