Cannabigerolic acid

(1) Terpene profiling. Terpenoid analyses (DigiPath Laboratories) were carried out on an Agilent 7890B GC/7697A Headspace/5977A mass spectrophotometer with a DB-624UI and Agilent 5181–8818 split/splitless liner. Injector port temperature was 250°C with a transfer line, valve oven and needle temperature of 180°C. Carrier gas was helium at a flow of 33.0 cm/s. The MS detector was set to scan with a range from 50 to 300 m/z. The instrument was controlled by Agilent Masshunter quantitative analysis (Vers. B.08.00 Build 8.0.593.0). Certified reference standards were from Restek (Bellefonte, PA) with Masshunter library confirmation.
(2) Strain-inspired mixture: Cannabidivarin (CBDV), Cannabichromene (CBC), Cannabidiol (CBD), Cannabidiolic Acid (CBDA), Cannabigerol (CBG), Cannabigerolic Acid (CBGA), Cannabinol (CBN), alpha-Bisabolol, alpha-Humulene, alpha-Pinene, beta-Caryophyllene, beta-Myrcene, (+)-beta-Pinene, Camphene, Limonene, Linalool, Nerolidol. (3) Cannabinoid mixture: Cannabidivarin (CBDV), Cannabichromene (CBC), Cannabidiol (CBD), Cannabidiolic Acid (CBDA), Cannabigerol (CBG), Cannabigerolic Acid (CBGA), Cannabinol (CBN). (4) Terpene mixture: alpha-Bisabolol, alpha-Humulene, alpha-Pinene, beta-Caryophyllene, beta-Myrcene, (+)-beta-Pinene, Camphene, Limonene, Linalool, Nerolidol.

Acetonitrile, anhydrous ammonium formate, ethanol, and formic acid were obtained from Sigma-Aldrich (HPLC grade, Saint Louis, MO, USA). Ultra-pure water was provided by the Milli-Q Plus system (Millipore Corp., Billerica, MA, USA). Cannabinoid analytical standards were purchased from RESTEK (RESTEK, Bellefonte, PA, USA): cannabidivarinic acid (CBDVA), cannabidiolic acid (CBDA), cannabigerolic acid (CBGA), cannabigerol (CBG), cannabidiol (CBD), (−)-Δ9-trans-tetrahydrocannabivarinic acid (THCVA), cannabinol (CBN), (−)-Δ9-trans-tetrahydrocannabinol (Δ-9-THC), (−)-Δ8-trans-tetrahydrocannabinol (Δ-8-THC), (−)-Δ9-trans-tetrahydrocannabinolic acid (THCA), and cannabichromenic acid (CBCA). Each of those standards was obtained at a stock concentration of 1000 µg/mL except CBLA, which was obtained at a stock concentration of 500 µg/mL. Terpene standard mix, at a stock concentration of 2500 µg/mL from each terpene, and which contains the following terpenes—α-pinene, camphene, (−)-β-pinene, β-myrcene, δ-3-carene, α-terpinene, p-cymene, d-limonene, ocimene, γ-terpinene, terpinolene, linalool, (−)-isopulegol, geraniol, β-caryophyllene, α-humulene, nerolidol, (−)-guaiol, and (−)-α-bisabolol—was obtained from RESTEK (RESTEK, Bellefonte, PA, USA).