Characterization and Synthesis of Cannabinoid Derivatives

THC (lot no. ZL20180816, purity 99.08%) was obtained from the Zhonglan industry (Zhonglan Industry, Shandong, China). TDG (purity 99.71%) was synthesized and characterized as previously reported [21 (link)]. Tetrahydrocurcumin-monoglutaric acid (TMG) was synthesized and assayed for purity (see Supplementary Materials, Figure S1). All reagents were at least of analytical grade and were procured from commercial sources. Formic acid was obtained from Carlo Erba (Val de Reuil, France). The HPLC grade of acetonitrile (ACN) was purchased from Fisher Scientific (Soul, South Korea). Hydrochloric acid and sodium hydroxide were obtained from QRëc (Auckland, New Zealand) and Carlo Erba (Val de Reuil, France), respectively. Bile, bovine serum albumin, lipase, mucin, pancreatin, α-amylase, and pepsin were obtained from Sigma-Aldrich Co., Ltd. (St. Louis, MO, USA). Calcium chloride anhydrous powder was purchased from Carlo-Erba (Val de Reuil, France). The ultrapure water (18.2 MΩ-cm) used throughout the study was produced in-house using a Milli-Q^® integral water purification system (Millipore, S.A.S, France).