Volume: 5, 2026
5th International PhD Students’ Conference at the University of Life Sciences in Lublin, Poland:
ENVIRONMENT – PLANT – ANIMAL – PRODUCT
Abstract number: H022
DOI: https://doi.org/10.24326/ICDSUPL5.H022
Published online: 22 April 2026
Epoxidation and amine-mediated nucleophilic opening of the oxirane ring in acylated derivatives of CBD and CBG
Hubert Wólczyński*1, Rafał Typek1 and Marek Stankevič2
1 Department of Chromatography, Maria Curie-Skłodowska University, 2 Maria Curie-Skłodowska Sq., 20-031 Lublin, Poland
2 Department of Organic Chemistry and Crystal Chemistry, Maria Curie-Skłodowska University, 33 Gliniana St., 20-613 Lublin, Poland
* Corresponding author: wolczynski.hubert@gmail.com
The aim of this study was the synthesis of novel nitrogen-containing derivatives of the cannabinoids cannabidiol (CBD) and cannabigerol (CBG) through a reaction sequence of epoxidation followed by nucleophilic oxirane ring opening. In the first stage, acylated derivatives of CBD and CBG were prepared to protect the hydroxyl groups and enhance the lipophilicity of the starting materials. The key modification step involved the epoxidation of the unsaturated bonds using meta-chloroperoxybenzoic acid (m-CPBA). The process was conducted in the presence of potassium carbonate (K2CO3), which served as a buffering agent to neutralize the resulting meta-chlorobenzoic acid. This prevented acid-catalyzed hydrolysis and unwanted rearrangements of the sensitive cannabinoid skeleton. The obtained epoxides were subsequently reacted with selected primary and secondary amines. The nucleophilic opening of the oxirane ring led to the formation of a series of new â-amino alcohols with potential biological activity. The structures of the synthesized compounds were confirmed using spectroscopic methods (NRM, MS). The developed synthetic pathway represents an efficient method for the functionalization of natural cannabinoids, enabling the introduction of pharmacophoric amine groups into their structure, which opens new perspectives for research into their pharmacological properties.
Keywords: aminolysis; cannabinoids; CBD; CBG; oxirane ring opening
How to cite
Wólczyński H., Typek R., Stankevič M., 2026. Epoxidation and amine-mediated nucleophilic opening of the oxirane ring in acylated derivatives of CBD and CBG. In: 5th International PhD Students’ Conference at the University of Life Sciences in Lublin, Poland: Environment – Plant – Animal – Product. https://doi.org/10.24326/ICDSUPL5.H022