CBD hydroxyquinone photo-isomerises to a highly reactive intermediate

Brodie. J. Thomson, Summer Hanna, Adrian Schwarzenberg,Pirouz Kiani, Dan Bizzotto,Pierre Kennepohl,Ashley Davies,Markus Roggen,Glenn M. Sammis

Scientific Reports(2023)

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摘要
The legalisation of hemp has led to wide commercial availability of cannabidiol (CBD)-containing products. Here we show that the CBD-hydroxyquinone (HU-331), a readily formed oxidation product and common impurity in CBD isolates, undergoes a previously unknown photo-isomerisation to produce a highly reactive intermediate in solution. Studies supported by calculations indicate that this intermediate rapidly reacts with oxygen to form a multitude of cannabinoid products. The purple colour observed in light-aged CBD-containing solutions is largely due to the anions of these by-products and is not significantly due to the HU-331 anion. Our findings suggest that these uncharacterized cannabinoid derivatives can be present in CBD-containing e-liquids and solutions that have been stored under ambient light conditions, calling for quality control processes that manage HU-331 contamination.
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photo-isomerises
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