Comprehensive cannabinoid profiling of acid-treated CBD samples and Δ8-THC-infused edibles

Si Huang; Teris A van Beek; Frank W Claassen; Hans-Gerd Janssen; Ming Ma; Bo Chen; Han Zuilhof; G Ij Salentijn

doi:10.1016/j.foodchem.2023.138187

Comprehensive cannabinoid profiling of acid-treated CBD samples and Δ⁸-THC-infused edibles

Food Chem. 2024 May 15:440:138187. doi: 10.1016/j.foodchem.2023.138187. Epub 2023 Dec 14.

Authors

Si Huang¹, Teris A van Beek², Frank W Claassen², Hans-Gerd Janssen³, Ming Ma⁴, Bo Chen⁵, Han Zuilhof⁶, G Ij Salentijn⁷

Affiliations

¹ Key Laboratory of Phytochemical R&D of Hunan Province and Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research of Ministry of Education, Hunan Normal University, No.36, Lushan Road, 410081 Changsha, China; Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708 WE Wageningen, The Netherlands.
² Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708 WE Wageningen, The Netherlands.
³ Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708 WE Wageningen, The Netherlands; Unilever Foods Innovation Centre - Hive, Bronland 14, 6708 WH Wageningen, The Netherlands.
⁴ Key Laboratory of Phytochemical R&D of Hunan Province and Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research of Ministry of Education, Hunan Normal University, No.36, Lushan Road, 410081 Changsha, China.
⁵ Key Laboratory of Phytochemical R&D of Hunan Province and Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research of Ministry of Education, Hunan Normal University, No.36, Lushan Road, 410081 Changsha, China. Electronic address: [email protected].
⁶ Key Laboratory of Phytochemical R&D of Hunan Province and Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research of Ministry of Education, Hunan Normal University, No.36, Lushan Road, 410081 Changsha, China; Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708 WE Wageningen, The Netherlands. Electronic address: [email protected].
⁷ Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708 WE Wageningen, The Netherlands; Wageningen Food Safety Research (WFSR), Wageningen University & Research, P.O. Box 230, 6700 AE Wageningen, The Netherlands. Electronic address: [email protected].

PMID: 38134831
DOI: 10.1016/j.foodchem.2023.138187

Abstract

Δ⁸-Tetrahydrocannabinol (Δ⁸-THC) is increasingly popular as a controversial substitute for Δ⁹-tetrahydrocannabinol (Δ⁹-THC) in cannabinoid-infused edibles. Δ⁸-THC is prepared from cannabidiol (CBD) by treatment with acids. Side products including Δ⁹-THC and other isomers that might end up in Δ⁸-THC edibles are less studied. In this paper, three orthogonal methods, namely reversed-phase (RP)-UHPLC-DAD/HRMS, normal-phase/argentation (silica-Ag(I))-HPLC-DAD/MS, and GC-FID/MS were developed for analysis of cannabinoid isomers, namely Δ⁸-THC, Δ⁹-THC, CBD, Δ⁸-iso-THC, Δ⁽⁴⁾⁸-iso-THC, and hydrated THC isomers. Eight acid-treated CBD mixtures contained various amounts of Δ⁸-THC (0-89%, w/w%), high levels of Δ⁹-THC (up to 49%), Δ⁸-isoTHC (up to 55%), Δ⁽⁴⁾⁸-iso-THC (up to 17%), and three hydrated THC isomers. Commercial Δ⁸-THC gummies were also analyzed, and issues like overclaimed Δ⁸-THC, excessive Δ⁹-THC, undeclared Δ⁸-iso-THC, and Δ⁽⁴⁾⁸-iso-THC were found. These findings highlight the urgency of improving regulations towards converting CBD to Δ⁸-THC for use as food ingredients.

Keywords: CBD conversion; Cannabinoids isomers; Chromatographic analysis; Δ(8)-THC; Δ(8)-THC gummies.

MeSH terms

Cannabidiol*
Cannabinoids* / analysis
Cannabis*
Dronabinol / analysis
Gas Chromatography-Mass Spectrometry
Liquid Chromatography-Mass Spectrometry

Substances

Cannabinoids
Cannabidiol
Dronabinol