The novel heptyl phorolic acid cannabinoids content in different Cannabis sativa L. accessions

The recent discovery of the novel heptyl phytocannabinoids cannabidiphorol (CBDP) and Delta 9-tetrahydrocannabiphorol (Delta 9-THCP) raised a series of questions relating to the presence and abundance of these new unorthodox compounds in cannabis inflorescence or derived products. As fresh inflorescence contains mainly their acid precursors, which are not commercially available, an ad hoc stereoselective synthesis was performed in order to obtain cannabidiphorolic acid (CBDPA) and Delta 9-tetrahydrocannabiphorolic acid (THCPA) to be used as analytical standards for quantitative purposes. The present work reports an unprecedented targeted analysis of both pentyl (C5) and heptyl (C7) CBD- and THC-type compounds in forty-nine cannabis samples representing four different chemotypes. Moreover, the ultrahigh performance liquid chromatography coupled to highresolution mass spectrometry-based method was applied for the putative identification of other heptyl homologs of the most common phytocannabinoid acids, including cannabigerophorolic acid (CBGPA), cannabichromephorolic acid (CBCPA), cannabinophorolic acid (CBNPA), cannabielsophorolic acid (CBEPA), cannabicyclophorolic acid (CBLPA), cannabitriophorolic acid (CBTPA), and cannabiripsophorolic acid (CBRPA).

Automated summary

The recent discovery of CBDP and Delta 9-THCP has raised questions about their presence and abundance in cannabis, leading to the synthesis of CBDPA and THCPA for quantitative analysis. A targeted analysis of CBD- and THC-type compounds in different cannabis samples was conducted, along with the identification of other heptyl homologs using ultrahigh performance liquid chromatography coupled to high-resolution mass spectrometry.