Eleven cannabinoids, namely cannabidivann (CBDV), tetrahydrocannabivarin (THCV), cannabidiol (CBD) with 99.66% purity (Lot: FE08071702), cannabigerol (CBG) with 98.98% purity (Lot: FE06241604), cannabidiolic acid (CBDA) with 98.3% purity (Lot: FE12011601), cannabigerolic acid (CBGA), cannabinol (CBN) with 99.37% purity (Lot: FE06131701), delta 9-tetrahydrocannabinol (Δ9-THC) with 97.66% purity (Lot: FE1041701), delta 8-tetrahydrocannabinol (Δ8-THC), cannabichomene (CBC) with 97.60% purity (Lot: FE10011502), and delta 9-Tetrahydrocannabinol acid (THCA-A) with 99.18% purity (Lot: FE12121601) stock solution with the concentration of 1000 µg/mL in acetonitrile or methanol (acid forms) as reference standards were purchased from Cerilliant, a Sigma Aldrich company (Kinesis Australia Pty Ltd., Redland Bay, QLD, and Novachem Pty Lt, Victoria, Australia). All other solvents (methanol, acetonitrile, and phosphoric acid) were purchased from Merck.
Cannabidiolic acid
Manufactured by Cerilliant
Sourced in United States
Cannabidiolic acid is a cannabinoid compound found in cannabis plants. It is the precursor to cannabidiol (CBD) and is present in the plant material prior to decarboxylation. Cannabidiolic acid is a naturally occurring chemical substance.
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Lab products found in correlation
Cannabigerolic acid, by Cerilliant (9 mentions)
Cannabigerol, by Cerilliant (8 mentions)
Cannabidiol, by Cerilliant (6 mentions)
Cannabichromene, by Cerilliant (5 mentions)
Cannabinol, by Cerilliant (4 mentions)
Tetrahydrocannabivarin, by Cerilliant (3 mentions)
Milli q plus185 system, by Merck Group (3 mentions)
Formic acid, by Thermo Fisher Scientific (2 mentions)
Barnstead smart2pure nanopure system, by Thermo Fisher Scientific (2 mentions)
Tetrahydrocannabinolic acid, by Cerilliant (2 mentions)
δ9 thc, by Cerilliant (2 mentions)
Sucrose, by Merck Group (2 mentions)
Hplc grade water, by Merck Group (2 mentions)
Cannabidivarin, by Cerilliant (2 mentions)
Delta 9 tetrahydrocannabinol, by Cerilliant (1 mentions)
Acetonitrile, by Avantor (1 mentions)
Hplc grade methanol, by Avantor (1 mentions)
Ammonium formate, by Merck Group (1 mentions)
δ8 thc, by Cerilliant (1 mentions)
Cannabigerolic acid cbga, by Cerilliant (1 mentions)
12 protocols using cannabidiolic acid
1
Comprehensive Cannabinoid Reference Standards
2
Analytical HPLC Protocol for Cannabinoids
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HPLC grade methanol and acetonitrile were purchased from VWR International. Water was deionized and purified to 18.2 MΩ using a Barnstead Smart2Pure nanopure system (Thermo Scientific). Ammonium formate, HPLC grade (> 99.0 %), was purchased from Sigma-Aldrich and formic acid (98 %) was HPLC grade and purchased from Fisher Scientific. Cannabinoid certified reference material standards purchased as 1 mL solutions in ampules were purchased from Cerilliant Corp. They included tetrahydrocannabinolic acid (THCA, 1.000 mg/mL), Δ9-tetrahydrocannabinol (THC, 1.001 mg/mL), cannabidiolic acid (CBDA, 1.000 mg/mL), cannabidiol (CBD, 1.000 mg/mL), cannabigerol (CBG, 1.000 mg/mL), cannabichromene (CBC, 1.000 mg/mL), tetrahydrocannabivarin (THCV, 1.00 mg/mL), and cannabinol (CBN, 1.000 mg/mL). Additional standards were purchased for peak identification from Cerilliant Corp., which included Δ8-THC (1.000 mg/mL), cannabi-▶ Table 3 Reported activities of monoterpenes and sesquiterpenes identified in Cannabis through in vitro cell-based models, in vivo animal models, and clinical data.
3
HPLC Analysis of Cannabinoid Standards
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The standards of cannabinoids purchased as solutions were used for HPLC analysis as follows: cannabidiol (CBD) (Dr. Ehrenstorfer GmbH, Augsburg, Germany), 100 µg/mL in methanol; cannabidiolic acid (CBDA) (Dr. Ehrenstorfer GmbH, Augsburg, Germany), 100.0 µg/mL in acetonitrile; cannabidivarinic acid (CBDVA), 100.0 µg/mL in acetonitrile; cannabidiolic acid (CBDA) (Cerilliant Corporation, Texas, TX, USA), 500 µg/mL in acetonitrile; cannabigerolic acid (CBGA) (Cerilliant Corporation, Texas, TX, USA), 500 µg/mL in acetonitrile; tetrahydrocannabivarinic acid (THCVA) (Cerilliant Corporation, Texas, TX, USA), 500 µg/mL in acetonitrile; tetrahydrocannabinolic acid (THCA-A) (Cerilliant Corporation, Texas, TX, USA), 500 µg/mL in acetonitrile; cannabinol (CBN) (Dr. Ehrenstorfer GmbH, Augsburg, Germany), 100 µg/mL in methanol; cannabichromene (CBC) (Dr. Ehrenstorfer GmbH, Augsburg, Germany), 100 µg/mL in methanol; cannabigerol (CBG) (Dr. Ehrenstorfer GmbH, Augsburg, Germany), 100 µg/mL in methanol; and (-)-delta9-THC solution (THC) (Cerilliant Corporation, Texas, TX, USA), 1.0 mg/mL in methanol. All solvents and chemicals used were of analytical grade.
4
Analytical Standards for Cannabis Compounds
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cannabidiolic acid (CBDA), cannabigerolic acid (CBGA), cannabigerol (CBG), and cannabidiol (CBD) standard solutions (1 mg/mL in methanol or acetonitrile) were purchased from Cerilliant (Round Rock, TX, USA). Chrysoeriol was purchased from Sigma-Aldrich (Milan, Italy), while canniprene was kindly provided by Dr. Federica Pollastro of the Department of Drug Sciences of the University of Piemonte Orientale (Novara, Italy). Formic acid (HCOOH) and HPLC-grade solvents, including EtOH, MeOH, ACN, acetone, EtOAc, n-hexane, DCM, ethyl ether and toluene, were from VWR (Milan, Italy). H2O was purified by using a Milli-Q Plus185 system from Millipore (Milford, MA, USA).
5
Cannabinoid Stock Solutions Preparation
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Stock methanolic solutions (1.0 mg/ml) of, cannabidiol (CBD), cannabigerol (CBG) and cannabinol (CBN) and stock Acetonitrile solutions (1.0 mg/ml) of cannabidiolic acid (CBDA) and cannabigerolic acid (CBGA) were purchased from Cerilliant Corporation (Round Rock, TX, USA). CBD, CBG and CBN stock solutions were stored at −20°C, while CBDA and CBGA solutions were stored at −80°C.
Acetonitrile (ACN), absolute ethanol (EtOH), methanol (MeOH), formic acid (HCOOH), dimethyl sulfoxide (DMSO), 10,000 UI penicillin ‐ 10 mg/ml streptomycin association, cell counting kit‐8 and imatinib were purchased from Sigma Aldrich s.r.l. (Milan, Italy). Water (H2O) was purified by using a Milli‐Q Plus185 system from Millipore (Milford, MA, USA). Dulbecco's Modified Eagle's Medium (DMEM) was purchased from PAN Biotech (Aidenbach, Germany). Roswell Park Memorial Institute (RPMI) media were from EuroClone s.p.a. (Milan, Italy). Bio Whittaker foetal bovine serum (FBS) was acquired from Lonza. Glutamine was from Invitrogen s.r.l. (San Giuliano Milanese, MI, Italy).
Acetonitrile (ACN), absolute ethanol (EtOH), methanol (MeOH), formic acid (HCOOH), dimethyl sulfoxide (DMSO), 10,000 UI penicillin ‐ 10 mg/ml streptomycin association, cell counting kit‐8 and imatinib were purchased from Sigma Aldrich s.r.l. (Milan, Italy). Water (H2O) was purified by using a Milli‐Q Plus185 system from Millipore (Milford, MA, USA). Dulbecco's Modified Eagle's Medium (DMEM) was purchased from PAN Biotech (Aidenbach, Germany). Roswell Park Memorial Institute (RPMI) media were from EuroClone s.p.a. (Milan, Italy). Bio Whittaker foetal bovine serum (FBS) was acquired from Lonza. Glutamine was from Invitrogen s.r.l. (San Giuliano Milanese, MI, Italy).
6
Cannabinoid Standards Procurement and Characterization
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Cannabinol (CBN), cannabichromenic acid (CBCA), cannabichromene (CBC), cannabigerolic acid (CBGA), CBG, cannabidiolic acid (CBDA), CBD, Δ9tetrahydrocannabinoic acid (THCA), and Δ9-THC were purchased from Cerilliant (Cerilliant Corporation, Round Rock, TX). Cannabidivarinic acid (CBDVA), cannabidivarin (CBDV), tetrahydrocannabivarin (THCV), and Δ8-THC were purchased from Restek (Bellefonte, PA). All cannabinoid standards are CRM standards, at 1000 μg/mL in methanol.
7
Development of CBD-Enriched Emulsions
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200V (14–16 wt% quillaja saponin; Ingredion, New Jersey) was used as received. Soybean oil was sourced from Jeen International Corporation (New Jersey) and used without further purification. CBD-enriched cannabis distillate (CDCBD) was donated by XTRX (Ontario, Canada) and was used as received; the cannabinoid composition of the CDCBD may be found in Table S1 (SI). The preservative potassium sorbate (Nantong Acetic Acid Chemical Co., China) was added to the coarse emulsions prior to high pressure homogenization. HPLC grade water (EMD Millipore) was used in all experiments. Sucrose and CaCl2 were purchased from Sigma Aldrich. For the measurement of pH, a freshly calibrated pH-meter (Milwaukee MW102 PRO+) was used. For the HPLC analysis, 1 mg/mL stock solution of each of the following cannabinoids was obtained from Cerilliant: cannabidiolic acid (CBD-A), tetrahydrocannabinolic acid (THC-A), cannabidiol (CBD), cannabigerolic acid (CBG-A), cannabigerol (CBG), cannabichromene (CBC), cannabinol (CBN), and delta-9 tetrahydrocannabinol (THC).
8
Quantitative Analysis of Cannabinoids
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Certified cannabinoid reference standards (at 1 mg/mL in methanol) including cannabidiolic acid (CBDA), cannabigerolic acid (CBGA), cannabigerol (CBG), CBD, tetrahydrocannabivarin, cannabinol (CBN), Δ9-THC, cannabichromene (CBC), cannabidivarin (CBDV), and Δ9-tetrahydrocannabinolic acid-A (THCA) were purchased from Cerilliant (Round Rock, TX). Second-source standards of CBN, CBD, and Δ9-THC were from Restek (Bellefonte, PA). CBD hemp oil was purchased from HempMeds (Poway, CA). Norgestrel, 4-pentylphenyl 4-methylbenzoate (PPMB), ammonium formate, formic acid, and sesame oil were from Sigma-Aldrich (St. Louis, MO). Medium-chain triglyceride (MCT) oil was from Warner Graham (Cockeysville, MD). Propylene glycol was from J.T. Baker (Central Valley, PA). Ammonium formate, formic acid, methanol, acetonitrile, and water were HPLC grade. All other reagents used were analytical grade. Bulk cannabis plant material was obtained from the National Institute on Drug Abuse (NIDA), National Institutes of Health, Bethesda, MD.
9
Characterization of THC-enriched Cannabis Distillate
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THC-enriched cannabis distillate (CD T HC ) was donated by XTRX (Ontario, Canada) and was used without any purification. Polysorbate-60 (Jeesorb S-20 NF, Charles Tennant and Company Ltd, Canada) and soy lecithin (Charles Tennant and Company Ltd, Canada) were used as received. Medium chain triglycerides (MCT oil, Charles Tennant and Company Ltd, Canada) were used as the carrier oil. HPLC grade water (EMD Millipore) was used for all experiments. Anhydrous food-grade ethanol was purchased from Greenfield (Chatham, ON, Canada), and sucrose was purchased from Sigma Aldrich. A calibrated pH-meter (Milwaukee MW102 PRO+) was used to measure the pH. A BUCHI R-200 Rotary evaporator was used for ethanol removal. Maltodextrin (MD) and xylitol (XT) were sourced from Bulk Barn (Aurora, ON, Canada). For the HPLC analysis, a mg•mL -1 stock solution of each of the following cannabinoids was obtained from Cerilliant: cannabidiolic acid (CBD-A), tetrahydrocannabinolic acid (THC-A), cannabidiol (CBD), cannabigerolic acid (CBG-A), cannabigerol (CBG), cannabichromene (CBC), cannabinol (CBN), and ∆ 9 tetrahydrocannabinol (THC).
10
Quantitative Cannabinoid Analysis via HPLC
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Methanol, acetonitrile, ammonium formate and formic acid (98%) were HPLC grade. Water was deionized and purified to 18.2 MΩ using a Barnstead Smart2Pure nanopure system (Thermo Scientific). Cannabinoid standards for quantification were purchased from Cerilliant Corp. (Round Rock, TX) for tetrahydrocannabinolic acid (THCA), THC, cannabidiolic acid (CBDA), CBD, cannabigerol (CBG), cannabichromene (CBC), tetrahydrocannabivarin (THCV) and cannabinol (CBN), Δ8-THC, cannabidivarinic acid (CBDVA), cannabidivarin (CBDV), cannabigerolic acid (CBGA) and cannabicyclol (CBL). All standards were provided as 1.0 mg/mL solutions in either methanol or acetonitrile.
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