Wuttichai Jaidee1,2, Ittipon Siridechakorn1, Siwames Nessopa1, Vanuchawan Wisuitiprot1, Nathareen Chaiwangrach3, Kornkanok Ingkaninan1,3, Neti Waranuch1,4. 1. Cosmetics and Natural Products Research Center, Faculty of Pharmaceutical Sciences, Naresuan University, Phitsanulok, Thailand. 2. Medicinal Plant Innovation Center of Mae Fah Luang University, Mae Fah Luang University, Chiang Rai, Thailand. 3. Center of Excellence in Cannabis Research, Faculty of Pharmaceutical Sciences, Naresuan University, Phitsanulok, Thailand. 4. Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences and Center of Excellence for Innovation in Chemistry, Naresuan University, Phitsanulok, Thailand.
Abstract
Introduction: Cannabidiol (CBD), cannabinol (CBN), and Δ9-tetrahydrocannabinol (Δ9-THC) are major cannabinoids in cannabis resin and products. The kinetic of the chemical reaction of resin cannabis is important for product development and storage. A few reports are available in the literature on the rate of CBD and Δ9-THC degradation, and CBN formation in dried resin and solutions of various pH. Materials and Methods: Thermal degradation of CBD, Δ9-THC, and formation of CBN was studied at 50°C, 60°C, 70°C, and 80°C for dried cannabis resin. The effect of pH and temperature on cannabinoids transformation in cannabis solution was also examined at pH 2, 4, 6, 8, 10, and 12 and at 40°C, 50°C, 60°C, and 70°C. High-performance chromatography coupled with diode-array detection (HPLC-DAD) was used for the analysis of CBD, CBN, and Δ9-THC transformation. The values of activation energies (Ea), shelf-life (t90% - t110%), and rate constant (k) were calculated for the CBD, Δ9-THC, and CBN. The effect of temperature and pH on the dried cannabis resin was adequately modeled with the Arrhenius equation. Results: The results indicated that the chemical kinetics in the thermal degradation of CBD, Δ9-THC, and formation of CBN were the zero-order, pseudo-zero-order, and first-order reactions, respectively, in cannabis resin. The first-order and pseudo-first-order degradation kinetics were evidenced for CBD and Δ9-THC, respectively, in cannabis solutions, whereas the zero-order formation kinetic was detected for the CBN. The transformation rate of the CBD, CBN, and Δ9-THC increased with increasing temperature, especially as temperature increased to 70°C at pH 2.0. The optimum pH for CBD stability was between pH 4 and 6, whereas the optimum pH for Δ9-THC stability was between pH 4 and 12. Conclusion: The major cannabinoids (CBD, CBN, and Δ9-THC) reacted more quickly at high temperature and in an acidic solution. Especially, the minimum transformation of CBD, CBN, and Δ9-THC was achieved by using on a low temperature, slightly to moderately acidic pH values, and short-time processing. These results may help to improve the storage condition of CBD, CBN, and Δ9-THC products and in the manufacturing process.
Introduction: Cannabidiol (CBD), cannabinol (CBN), and Δ9-tetrahydrocannabinol (Δ9-THC) are major cannabinoids in cannabis resin and products. The kinetic of the chemical reaction of resin cannabis is important for product development and storage. A few reports are available in the literature on the rate of CBD and Δ9-THC degradation, and CBN formation in dried resin and solutions of various pH. Materials and Methods: Thermal degradation of CBD, Δ9-THC, and formation of CBN was studied at 50°C, 60°C, 70°C, and 80°C for dried cannabis resin. The effect of pH and temperature on cannabinoids transformation in cannabis solution was also examined at pH 2, 4, 6, 8, 10, and 12 and at 40°C, 50°C, 60°C, and 70°C. High-performance chromatography coupled with diode-array detection (HPLC-DAD) was used for the analysis of CBD, CBN, and Δ9-THC transformation. The values of activation energies (Ea), shelf-life (t90% - t110%), and rate constant (k) were calculated for the CBD, Δ9-THC, and CBN. The effect of temperature and pH on the dried cannabis resin was adequately modeled with the Arrhenius equation. Results: The results indicated that the chemical kinetics in the thermal degradation of CBD, Δ9-THC, and formation of CBN were the zero-order, pseudo-zero-order, and first-order reactions, respectively, in cannabis resin. The first-order and pseudo-first-order degradation kinetics were evidenced for CBD and Δ9-THC, respectively, in cannabis solutions, whereas the zero-order formation kinetic was detected for the CBN. The transformation rate of the CBD, CBN, and Δ9-THC increased with increasing temperature, especially as temperature increased to 70°C at pH 2.0. The optimum pH for CBD stability was between pH 4 and 6, whereas the optimum pH for Δ9-THC stability was between pH 4 and 12. Conclusion: The major cannabinoids (CBD, CBN, and Δ9-THC) reacted more quickly at high temperature and in an acidic solution. Especially, the minimum transformation of CBD, CBN, and Δ9-THC was achieved by using on a low temperature, slightly to moderately acidic pH values, and short-time processing. These results may help to improve the storage condition of CBD, CBN, and Δ9-THC products and in the manufacturing process.
Entities:
Keywords:
Arrhenius equation; activation energies; cannabis resin; degradation; order reaction
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