Abstract
Four major phytocannabinoids (∆8-tetrahydrocannabinol, ∆9-tetrahydrocannabinol, cannabidiol, and cannabinol, 100 mg each) were dissolved in Duquenois reagent containing vanillin and acetaldehyde in ethanol, and concentrated hydrochloric acid was added. The chromophores derived from the four cannabinoids were characterized by mass spectrometry after dichloromethane extraction and partial purification by Florisil column chromatography with dichloromethane-ethanol solutions, using a unique replacement technique, which caused various modes of peak shifts in mass spectra giving information for structural elucidation. It was disclosed that there were three types of condensates, among which the structures of two condensates could be delineated, but one condensate remains to be clarified. To our knowledge, this is the first report to simultaneously propose the structures of the Duquenois reaction chromophores for the four major phytocannabinoids.
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A part of this work was supported by the Specific Research Fund of Hokuriku University.
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Watanabe, K., Honda, G., Miyagi, T. et al. The Duquenois reaction revisited: mass spectrometric estimation of chromophore structures derived from major phytocannabinoids. Forensic Toxicol 35, 185–189 (2017). https://doi.org/10.1007/s11419-016-0337-6
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DOI: https://doi.org/10.1007/s11419-016-0337-6