Mid-infrared spectroscopy as process analytical technology tool for estimation of THC and CBD content in Cannabis flowers and extracts

Geškovski, Nikola; Stefkov, Gjoše; Gigopulu, Olga; Stefov, Stefan; Huck, Christian W.; Makreski, Petre

doi:10.1016/j.saa.2020.119422

Cited by 40 publications

(26 citation statements)

References 24 publications

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“…This band should be ascribed to the phenolic stretching C-O band and nicely complement to the tentative assignment proposed from the Raman results [20]. The spectral band around 1120 cm -1 , also found discriminating among the CBDA and THCA cannabinoids and attributed to the symmetric alkyl-aryl ether group [14], was another fingerprint to distinguish between the THCA and THC due to the its intensity loss related to the interconversion process (Table 2, Fig. 3).…”

Section: This Work Tentative Ir Assignmentssupporting

confidence: 78%

“…Here, it is worth emphasizing that the assignment of the bands were tentative and delivered in close resemblance to the scarce available literature results for cannabis and hemp samples [14], [18]- [20] because literature lacks detailed theoretical vibrational (infrared and Raman) band assignments for THCA and THC species. Further aim of the work was to compare the CO2 elimination reaction that took place in the THCA standard and in the cannabis flower sample.…”

Section: This Work Tentative Ir Assignmentssupporting

confidence: 59%

“…Principal component analysis (PCA) was employed to identify the MIR spectral changes due to the THCA decarboxylation in the standard and in the cannabis flower. Since the most specific THCA/THC bands appear bellow 1700 cm -1 (see the previous discussion) [14], the MIR spectral region for statistical analysis was narrowed to 1700-400cm -1 . The 75 spectra recorded in the t-ATR MIR experiments of THCA standard in the 25-160 ºC temperature range, were SNV transformed and subjected to PCA.…”

Section: Statistical Models For Decarboxylation Of Thca Standard and Cannabis Flower And Kinetic Analysismentioning

confidence: 99%

“…Attenuated total reflectance Fourier-transform infrared (ATR FTIR) spectroscopy is a widely used technique for chemical analysis of biological materials [12]. The ability to provide qualitative and quantitative data on the chemical reactions further processed using multivariate analysis, is important for its adaptation as a PAT [13] that was recently shown in our previous spectroscopic work aimed at Cannabis processing [14].…”

Section: Introductionmentioning

confidence: 99%

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Synergistic Use of FTIR Spectroscopy and TG to Elucidate the Solid State THCA Decarboxylation Reaction Kinetics in THCA Standard and Cannabis Flower

Gigopulu¹,

Geškovski

Stefkov³

et al. 2021

Preprint

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<p>The decarboxylation of Δ9-tetrahydrocannabinolic acid (THCA) plays pivotal role in the potency of medical cannabis and its extracts. However, the literature data point out substantial variations in the process reaction rate and conversion efficacy due to variability of the temperature, heat transfer efficacy, raw material attributes, consequently resulting in incomplete decarboxylation, cannabinoid content decrease due to decomposition, evaporation, and possible side reactions. Our present work aims to draw attention to mid-infrared (MIR) spectroscopy for in-situ monitoring and decipher the THCA decarboxylation reaction in the solid state. The initial TG/DTG curves of THCA, for a first time outlined the solid-solid decarboxylation dynamics, defined the endpoint of the process and the temperature of the maximal conversion rate, which aided in the design of the further IR experiments. Temperature controlled IR spectroscopy experiments were performed on both THCA standard and cannabis flower by providing detailed band assignment and conducting spectra-structure correlations, based on the concept of functional groups vibrations. Moreover, a multivariate statistical analysis was employed to depict the spectral regions of utmost importance for the THCA→THC interconversion process. The principal component analysis model was reduced to two PCs, where PC1 explained 94.76% and 98.21% of the total spectral variations in the THCA standard and in the plant sample, respectively. The PC1 plot score of the THCA standard, as a function of the temperature, neatly complemented to the TG/DTG curve and enabled determination of rate constants for the decarboxylation reaction undertaken on several temperatures. Consequently, a progress in elucidation of kinetic models of THCA decarboxylation, fitting experimental data for both, solid state standard substance and a plant flower, was achieved. The results open the horizon to promote an appropriate process analytical technology (PAT) in the outgrowing medical cannabis industry.</p>

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Section: This Work Tentative Ir Assignmentssupporting

confidence: 78%

Section: This Work Tentative Ir Assignmentssupporting

confidence: 59%

Section: Statistical Models For Decarboxylation Of Thca Standard and Cannabis Flower And Kinetic Analysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synergistic Use of FTIR Spectroscopy and TG to Elucidate the Solid State THCA Decarboxylation Reaction Kinetics in THCA Standard and Cannabis Flower

Gigopulu¹,

Geškovski

Stefkov³

et al. 2021

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

“…However, the interest in qualitative profiling of cannabis (identification/classification) and quantitative profiling of the main phytocannabinoids is slowly gaining momentum in the last few years (Supporting information, Table S3 ). A recent study for ATR mid-IR quantification of Δ 9 -THC and CBD in cannabis flowers and extracts described a stepwise approach in developing multivariate quantification models accompanied by detailed band assignment of the mentioned phytocannabinoids, both for pure compounds and analysed samples (complex matrices) [ 21 ]. In a further study by the same group, the potential of ATR mid-IR as a process analytical tool (PAT) for continuous monitoring of Δ 9 -THCA decarboxylation was showcased [ 22 ].…”

Section: Analytical Methods For Phytocannabinoid Profilingmentioning

confidence: 99%

Analytical Techniques for Phytocannabinoid Profiling of Cannabis and Cannabis-Based Products—A Comprehensive Review

et al. 2022

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Cannabis is gaining increasing attention due to the high pharmacological potential and updated legislation authorizing multiple uses. The development of time- and cost-efficient analytical methods is of crucial importance for phytocannabinoid profiling. This review aims to capture the versatility of analytical methods for phytocannabinoid profiling of cannabis and cannabis-based products in the past four decades (1980–2021). The thorough overview of more than 220 scientific papers reporting different analytical techniques for phytocannabinoid profiling points out their respective advantages and drawbacks in terms of their complexity, duration, selectivity, sensitivity and robustness for their specific application, along with the most widely used sample preparation strategies. In particular, chromatographic and spectroscopic methods, are presented and discussed. Acquired knowledge of phytocannabinoid profile became extremely relevant and further enhanced chemotaxonomic classification, cultivation set-ups examination, association of medical and adverse health effects with potency and/or interplay of certain phytocannabinoids and other active constituents, quality control (QC), and stability studies, as well as development and harmonization of global quality standards. Further improvement in phytocannabinoid profiling should be focused on untargeted analysis using orthogonal analytical methods, which, joined with cheminformatics approaches for compound identification and MSLs, would lead to the identification of a multitude of new phytocannabinoids.

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Novel fluorescence spectroscopy method coupled with N‐PLS‐R and PLS‐DA models for the quantification of cannabinoids and the classification of cannabis cultivars

Birenboim

Kenigsbuch

Shimshoni

2023

Phytochemical Analysis

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Introduction: Cannabis sativa L. inflorescences are rich in secondary metabolites, particularly cannabinoids. The most common techniques for elucidating cannabinoid composition are expensive technologies, such as high-pressure liquid chromatography (HPLC).Objectives: We aimed to develop and evaluate the performance of a novel fluorescence spectroscopy-based method coupled with N-way partial least squares regression (N-PLS-R) and partial least squares discriminant analysis (PLS-DA) models to replace the expensive chromatographic methods for preharvest cannabinoid quantification.Methodology: Fresh medicinal cannabis inflorescences were collected and ethanol extracts were prepared. Their excitation-emission spectra were measured using fluorescence spectroscopy and their cannabinoid contents were determined by HPLC-PDA. Subsequently, N-PLS-R and PLS-DA models were applied to the excitation-emission matrices (EEMs) for cannabinoid concentration prediction and cultivar classification, respectively. Results:The N-PLS-R model was based on a set of EEMs (n = 82) and provided good to excellent quantification of (À)-Δ9-trans-tetrahydrocannabinolic acid, cannabidiolic acid, cannabigerolic acid, cannabichromenic acid, and (À)-Δ9-transtetrahydrocannabinol (R 2 CV and R 2 pred > 0.75; RPD > 2.3 and RPIQ > 3.5; RMSECV/ RMSEC ratio < 1.4). The PLS-DA model enabled a clear distinction between the four major classes studied (sensitivity, specificity, and accuracy of the prediction sets were all ≥0.9). Conclusions:The fluorescence spectral region (excitation 220-400 nm, emission 280-550 nm) harbors sufficient information for accurate prediction of cannabinoid contents and accurate classification using a relatively small data set.

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Mid-infrared spectroscopy as process analytical technology tool for estimation of THC and CBD content in Cannabis flowers and extracts

Cited by 40 publications

References 24 publications

Synergistic Use of FTIR Spectroscopy and TG to Elucidate the Solid State THCA Decarboxylation Reaction Kinetics in THCA Standard and Cannabis Flower

Synergistic Use of FTIR Spectroscopy and TG to Elucidate the Solid State THCA Decarboxylation Reaction Kinetics in THCA Standard and Cannabis Flower

Analytical Techniques for Phytocannabinoid Profiling of Cannabis and Cannabis-Based Products—A Comprehensive Review

Novel fluorescence spectroscopy method coupled with N‐PLS‐R and PLS‐DA models for the quantification of cannabinoids and the classification of cannabis cultivars

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