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Terpenes Analysis in Cannabis Products by Liquid Injection Using the Agilent Intuvo 9000/5977B GC/MS System

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Terpenes Analysis in Cannabis Products by Liquid Injection Using the Agilent Intuvo 9000/5977B GC/MS System Application Note Cannabis & Hemp Testing Terpenes Analysis in Cannabis Products by Liquid Injection using the Agilent Intuvo 9000/5977B GC/MS System Authors Abstract Jeffery S. Hollis1, Terpenes are volatile and semivolatile chemicals that engender flavor and Terry Harper1, and aroma organoleptic properties to cannabis and cannabinoid products. Cannabis Anthony Macherone1,2 growers and producers use terpene profiles to characterize specific strains of 1 Agilent Technologies, Inc. cannabis and hemp. To this end, a robust analytical method is necessary to 2 Johns Hopkins University chemically profile terpenes in cannabis and cannabinoid products prior to use in School of Medicine medicinal and recreational marijuana programs. Although regulatory agencies such as the California Bureau of Cannabis Control (BCC) do not regulate terpene content unless there is a specific label claim, terpenes are commonly analyzed in regulatory laboratories.1 The most common approach to terpenes analyses in these laboratories is headspace gas chromatography (GC) with flame ionization detection (FID), mass spectrometry (MS), or both (FID/MS). Over the past several years, issues such as losses of sesquiterpenoids like α-bisabolol have been observed in high-potency cannabis samples with headspace methodologies. This has led to a need for liquid injection terpenes analysis. In this application note, we demonstrated a selective, sensitive, and robust method for the analysis of 40 chromatographically resolved terpenes common to Cannabis spp. using liquid injection GC/MS. Introduction In two separate polyketide pathways, Many terpenes exist as enantiomers: GPP is the substrate for geranylpyro- nonsuperimposable, mirror images Terpenes in cannabis phosphate:olivetolate geranyltransferase of one another. These terpenes are Terpenes are n-mers of isoprene that synthesizes cannabigerovarinic comprised of the same atoms with acid (CBGVA) and cannabigerolic acid the same connectivity but differ in (C5H8). Approximately 35,000 terpenes have been identified, but the biological (CBGA). In these pathways, CBGVA three-dimensional configuration. functions of most have not been and CBGA are the precursors for six Enantiomers have identical physical determined.2 Common terpenes found acid phytocannabinoids through the properties such as chromatographic in Cannabis spp. include monoterpenes action of three acid phytocannabinoid retention time, acidity, and melting 6-8 and sesquiterpenes. Monoterpenes synthases. point, and are optically active i.e., have the general empirical formula rotate plane polarized light in either a Stereochemistry of terpenes 9 C H (e.g., limonene), and the general clockwise or counterclockwise direction. 10 16 Terpenes exist in nature in diverse empirical formula for sesquiterpenes Clockwise rotation is designated (+) and configurations that give rise to is C H (e.g., farnesene). Terpenoids counterclockwise as (–). An obsolete 15 24 stereoisomers and chemical properties and sesquiterpenoids are functionalized but still used system of optical rotation such as optical rotation. Examples terpenes that contain other elements nomenclature is dextrorotatory (d) of configurational isomerism are such as oxygen (e.g., camphor). and levorotatory (l), but this usage is the sesquiterpenoids Z-nerolidol The chemical profile of terpenes is discouraged by the International Union and E-nerolidol, shown in Figure 1. 10 a variable phenotypic trait across of Pure and Applied Chemistry (IUPAC). Compounds such as these, which Cannabis spp. Common terpenes include The stereodescriptors d and l are in are not mirror images of one another, β-caryophyllene, α-pinene, β-myrcene, lower case, but sometimes capital D and are known as diastereomers. Z and E α-humulene, (+)-limonene, linalool, L are used, leading to much confusion. diastereomers tend to have different α-bisabolol, and (E)-β-farnesene.3 This The D and L designation arose from chemical properties that allow them to application note, along with additional the Fischer-Rosanoff convention where be chromatographically separated. information, and ready-to-run acquisition (+)-glyceraldehyde was arbitrarily and quantitation methods, are available described as D-glyceraldehyde and its as eMethod G5282AA#010, Terpenes enantiomer as L-glyceraldehyde (Moss, 1996). In this case, the D and L usage analysis in cannabis products using HO liquid injection with the Intuvo/5977 was referring to absolute configuration GC/MS system. of the molecules. The use of D and L is discouraged by IUPAC in favor of R and Terpene biosynthesis S stereodescriptors to define absolute Terpenes are primarily synthesized in the configuration. An example of R and trichomes of Cannabis spp. inflorescence S enantiomers are given in Figure 2 where acid phytocannabinoids are also Z-Nerolidol for linalool. synthesized; the latter are sometimes referred to as terpenophenols.4 The plastidial methylerythritol phosphate HO OH (MEP) and the cytosolic mevalonate (MEV) pathways synthesize dimethylallyl HO diphosphate (DMAPP) and isopentenyl E-Nerolidol diphosphate (IPP). Geranyl diphosphate synthase (GPPS) and farnesyl Figure 1. Z-nerolidol and E-nerolidol. Z (zussammen) means together or on the same diphosphate synthase (FPPS) combine side. E (entgegen) means opposite sides. The one molecule of IPP and one or two nomenclature cis and trans also refers to the same (S)-(+)-Linalool (R)-(–)-Linalool molecules of DMAPP to synthesize or opposite sides, respectively of a molecule but the 10-carbon monoterpene precursor are generally ambiguous identifiers for alkenes. Figure 2. Linalool enantiomers. geranyl diphosphate (GPP) and the 15-carbon sesquiterpene precursor farnesyl diphosphate (FPP), respectively.5 2 Commercially available enantiomeric O reference standards may be obtained O OH as a pure enantiomer (+) or (–), or as a racemic mixture (±) of both enantiomers. In this latter case, if the enantiomers or not present in a 50/50 ratio, the (±)-Camphor (±)-Borneol (±)-Fenchone Chemical formula: C H O Chemical formula: C H O Chemical formula: C H O enantiomeric excess (EE) of the higher 10 16 10 18 10 16 Molecular weight: 152.2370 Molecular weight: 154.2530 Molecular weight: 152.2370 concentration enantiomer should be reported if known. Examples of racemic Figure 3. Racemic mixtures of terpenes. terpenes are given in Figure 3. Materials and methods Table 1. Agilent 7650A autosampler. Parameter Value Hardware and software Syringe Size 10 µL An Agilent Intuvo 9000 gas Injection Volume 1.0 µL chromatograph (G3950A) configured Air Gap 0.2 µL with a mid-column backflush Flow-Chip Solvent A Washes (Ethyl Acetate) 3 times post injection with 3.0 µL (option 881), a multimode inlet (MMI) Solvent B Washes (Ethyl Acetate) 3 times post injection with 3.0 µL and Guard Chip (G4587-60665) was Sample Washes 3 times with 3.0 uL used. Note that a split/splitless inlet (S/SL) can be used as an alternative (the Table 2. Agilent Intuvo 9000 GC. Table 3. Agilent 5977B MS. Guard Chip part number for the S/SL Parameter Value Parameter Value is G4587-60565). The Agilent 7650A Flow Rate Column 1 2.0 mL/min Solvent Delay 14 minutes 50-position automatic liquid sampler Flow Rate Column 2 2.2 mL/min Acquisition Mode SIM (ALS) configured with a 10.0 µL syringe Initial Oven Temperature 35 °C EM Setting mode Gain Variable per SIM segment was installed. (G4567A). Optionally, the Inlet Temperature 250 °C Source Temperature 300 °C Agilent XLSI weldment may be used Inlet Mode Split Quadrupole Temperature 200 °C for side mount of the Agilent 7697A Split Ratio 150:1 headspace autosampler transfer line Trace Ion Detection On On after 3 minutes (G3969A) if the headspace system Gas Saver MS Tuning AUTOTUNE [ATUNE.U] is attached. A 4 mm Ultra Inert, low Initial Oven Temperature 75 °C Number of SIM Groups 20 pressure drop, glass wool split liner Initial Hold Time 1 minute Run Time 30 minutes (5190-2295) and two DB-Select 624 Ramp Rate 1 5 °C/min Ultra Inert columns (30 m × 0.25 mm id, Final Temperature 165 °C 1.4 µm film thickness, 122-0334UI-INT) Hold Time 0 minutes were used for all analyses. The GC Ramp Rate 2 175 °C/min system was connected to an Agilent Final Temperature 2 250 °C 5977B mass selective detector (MSD) Final Hold 10.514 minutes with EI Extractor source (G7077BA EI Total Run Time 30.0 minutes InertPlus Turbo with 9 mm extractor Post Run Backflush 3.236 minutes lens). Data were collected using Agilent MassHunter B.10 GC/MS Acquisition software. All data analyses were performed using MassHunter Quantitative Software B.10.1. Tables 1 to 4 provide the GC/MS parameters. 3 Table 4. MS SIM parameters. SIM Group (Mass, Dwell) SIM Group (Mass, Dwell) SIM Group (Mass, Dwell) Group 1 Group 7 Group 13 Resolution HIGH Resolution HIGH Resolution HIGH Gain Factor 10 Gain Factor 15 Gain Factor 20 Group Start Time 14 Group Start Time 20.8 Group Start Time 25.2 Number of Ions 3 Number of Ions 6 Number of Ions 3 (77.00, 75) (91.00, 75) (80.00, 37) (81.00, 37) (80.00, 75) (93.00, 75) (Mass, Dwell) In Group (Mass, Dwell) In Group (93.00, 75) (Mass, Dwell) In Group (111.00, 37) (121.00, 37) (121.00, 75) (136.00, 37) (154.00, 37) Group 2 Group 14 Group 8 Resolution HIGH Resolution HIGH Resolution HIGH Gain Factor 10 Gain Factor 20 Gain Factor 10 Group Start Time 15.25 Group Start Time 25.7 Group Start Time 21.45 Number of Ions 3 Number of Ions 3 Number of Ions 12 (93.00, 75) (107.00, 75) (161.00, 75) (189.00, 75) (Mass, Dwell) In Group (Mass, Dwell) In Group (136.00, 75) (59.00, 18) (71.00, 18) (204.00,
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