Direct de/carboxylation of cannabidiolic acid (CBDA) and cannabidiol (CBD) from hemp plant material under supercritical CO₂

Abstract

Many organic reactions rely on CO₂ sources to generate important structural units and valuable chemicals. In this study, we compared the effects of cannabidiol (CBD) and cannabidiolic acid (CBDA) on the supercritical CO₂ (scCO₂)-induced de/carboxylation reaction. The results showed that CBD was directly carboxylated in the ortho-position to form CBDA with up to 62% conversion. Meanwhile, CBDA decarboxylation occurred on hemp plant material via varying composition. Mechanistic studies revealed that CBD carboxylation was influenced not only by the physical properties of scCO₂, but also by the vegetable matrix.

GRAPHICAL ABSTRACT

Keywords:

• Supercritical CO₂ (scCO₂)
• cannabidiol (CBD)
• cannabidiolic acid (CBDA)
• decarboxylation
• carboxylation

Acknowledgements

The authors acknowledge the Analytical and Testing Center of Daqing Branch of Heilongjiang Academy of Sciences for the HPLC and LC-MS measurements.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was financially supported by the Heilongjiang Provincial Natural Science Foundation of China [LH2020B022]; Dean Foundation of Heilongjiang Academy of Sciences [YZ2022DQ01]; The Financial Support of the Institutes Scientific Research Foundation of Heilongjiang Provincial Scientific Research [YS2023DQ02]; and the Shuangtiyanzhen Special Plan Foundation of Heilongjiang Academy of Sciences [YZQY2023DQ01].