Theoretical exploration and experimental regulation of the degradation of Δ9-tetrahydrocannabinol in hemp seed oil by density functional theory

Δ⁹-tetrahydrocannabinol (Δ⁹-THC) in hemp seed oil is a psychoactive cannabinoid, and the content of Δ⁹-THC can be reduced. Density functional theory (DFT) was used to simulate the degradation path of Δ⁹-THC, and the ultrasonic treatment was used to degrade the Δ⁹-THC in hemp seed oil. Results found that the reaction of Δ⁹-THC degradation to cannabinol (CBN) was a spontaneous exothermic reaction, which required a certain amount of external energy to initiate reaction process. Through the surface electrostatic potential analysis, the minimum value of electrostatic potential of Δ⁹-THC was -37.68 kcal/mol, and the maximum value was 40.98 kcal/mol. The frontier molecular orbitals analysis found that the energy level difference of Δ⁹-THC was lower than that of CBN, indicating that the reactivity of Δ⁹-THC was stronger. The degradation process of Δ⁹-THC could be divided into two stages, which needed to cross the reaction energy barriers of 3197.40 and 3087.24 kJ/mol, respectively. Ultrasonic treatment was used to degrade Δ⁹-THC standard solution, it was found that Δ⁹-THC can be effectively degraded into CBN through intermediate. Subsequently, ultrasonic technology was applied to hemp seed oil, under the conditions of ultrasonic power 150 W and ultrasonic time 21 min, the Δ⁹-THC was degraded to 10.00 mg/kg.