CBD hydroxyquinone photo-isomerises to a highly reactive intermediate
Abstract 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...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2023-04-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-023-33815-7 |
| _version_ | 1827956807104987136 |
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| author | Brodie. J. Thomson Summer Hanna Adrian Schwarzenberg Pirouz Kiani Dan Bizzotto Pierre Kennepohl Ashley Davies Markus Roggen Glenn M. Sammis |
| author_facet | Brodie. J. Thomson Summer Hanna Adrian Schwarzenberg Pirouz Kiani Dan Bizzotto Pierre Kennepohl Ashley Davies Markus Roggen Glenn M. Sammis |
| author_sort | Brodie. J. Thomson |
| collection | DOAJ |
| description | Abstract 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. |
| first_indexed | 2024-04-09T15:09:37Z |
| format | Article |
| id | doaj.art-2a41e22085f94d72a300d5c37586f8c4 |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-04-09T15:09:37Z |
| publishDate | 2023-04-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-2a41e22085f94d72a300d5c37586f8c42023-04-30T11:15:30ZengNature PortfolioScientific Reports2045-23222023-04-011311910.1038/s41598-023-33815-7CBD hydroxyquinone photo-isomerises to a highly reactive intermediateBrodie. J. Thomson0Summer Hanna1Adrian Schwarzenberg2Pirouz Kiani3Dan Bizzotto4Pierre Kennepohl5Ashley Davies6Markus Roggen7Glenn M. Sammis8Department of Chemistry, University of British ColumbiaGroup Research and Development Centre, BAT Investments LimitedGroup Research and Development Centre, BAT Investments LimitedDepartment of Chemistry, University of CalgaryDepartment of Chemistry, University of British ColumbiaDepartment of Chemistry, University of CalgaryGroup Research and Development Centre, BAT Investments LimitedDELIC LabsDepartment of Chemistry, University of British ColumbiaAbstract 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.https://doi.org/10.1038/s41598-023-33815-7 |
| spellingShingle | Brodie. J. Thomson Summer Hanna Adrian Schwarzenberg Pirouz Kiani Dan Bizzotto Pierre Kennepohl Ashley Davies Markus Roggen Glenn M. Sammis CBD hydroxyquinone photo-isomerises to a highly reactive intermediate Scientific Reports |
| title | CBD hydroxyquinone photo-isomerises to a highly reactive intermediate |
| title_full | CBD hydroxyquinone photo-isomerises to a highly reactive intermediate |
| title_fullStr | CBD hydroxyquinone photo-isomerises to a highly reactive intermediate |
| title_full_unstemmed | CBD hydroxyquinone photo-isomerises to a highly reactive intermediate |
| title_short | CBD hydroxyquinone photo-isomerises to a highly reactive intermediate |
| title_sort | cbd hydroxyquinone photo isomerises to a highly reactive intermediate |
| url | https://doi.org/10.1038/s41598-023-33815-7 |
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