What topics does this cannabis study cover?

This study covers research on: THC, CBD.

Where was this research published?

Published in Organic & biomolecular chemistry on July 20, 2026.

THC CBD

How reaction conditions steer CBD toward different THC isomers

Q: What did this research study find?

**Lower temperatures favor *Δ9-THC* formation** under both Brønsted and Lewis acid catalysis.

Regioselective acid-catalyzed conversion of cannabidiol into THC isomers: experimental and computational elucidation.

Organic & biomolecular chemistry • July 20, 2026 • Highly Relevant

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AI Summary

This study examined how cannabidiol (CBD) can be converted into different THC isomers—Δ9-THC, Δ8-THC, and iso-Δ8-THC—using acid catalysts. The researchers found that product formation depends strongly on temperature and catalyst type. Lower temperatures favored Δ9-THC with both catalysts, while harsher p-TsOH conditions promoted conversion toward Δ8-THC. With BF3, higher temperatures and longer reaction times favored iso-Δ8-THC.

Computational results suggest that Δ9-THC is the kinetic product, meaning it forms through the easiest initial reaction pathway. In contrast, Δ8-THC and iso-Δ8-THC are more thermodynamically favored under the respective acid conditions. The findings help explain why different chemical processes produce different THC isomer mixtures, but the abstract does not report clinical effects, consumer safety, or quantitative product yields.

💡 Key Findings

Lower temperatures favor Δ9-THC formation under both Brønsted and Lewis acid catalysis.

Good

70%

Under p-TsOH, harsher conditions promote Δ9-THC/Δ8-THC interconversion and enrichment of ** Δ8-THC **.

Good

70%

BF3 favors ** iso-Δ8-THC ** at higher temperatures and longer reaction times.

Good

70%

Computational modeling indicates that Δ9-THC is the kinetic product, while Δ8-THC and iso-Δ8-THC are thermodynamically favored under their respective acid conditions.

Good

75%

The study shows that catalyst type and temperature determine regioselectivity, helping explain how different THC isomer mixtures arise during chemical conversion of CBD.

High

80%

📄 Original Abstract

Cannabis sativa is a major source of phytocannabinoids, with cannabidiol (Δ9-CBD) serving as a key precursor to THC-type cannabinoids through acid-catalyzed intramolecular cyclization. However, the origin of regioselectivity under different conditions remains unclear. Herein, combined experimental and theoretical approaches were employed to elucidate the pathways leading to Δ9-THC, Δ8-THC, and iso-Δ8-THC under Brønsted (p-TsOH) and Lewis (BF3) acid catalysis in batch and continuous-flow systems, respectively. Experimentally, product distribution is strongly temperature-dependent. Under both catalytic conditions, lower temperatures favor Δ9-THC formation. Under p-TsOH, harsher conditions promote Δ9-THC/Δ8-THC interconversion and enrichment of Δ8-THC, whereas BF3 favored formation of iso-Δ8-THC at higher temperatures and longer reaction times. Computational simulations reveal that BF3 promotes parallel cyclization pathways leading to Δ9-THC and iso-Δ8-THC, whereas p-TsOH follows a sequential mechanism involving cyclization followed by double-bond isomerization. The calculations further indicate that Δ9-THC is the kinetic product, formed through lower activation barriers (ΔG‡), whereas Δ8-THC and iso-Δ8-THC are thermodynamically favored under Brønsted and Lewis conditions, respectively, displaying lower final free energies (ΔG). Overall, regioselectivity emerges from the interplay between temperature and catalyst type, with dual Lewis-Brønsted activation by BF3 driving rapid cyclization and suppressing isomerization pathways, as supported by DFT calculations.

Paper Type

📄 Research

Publication

Journal: Organic & biomolecular chemistry
Published: July 20, 2026
PMID: 42475118
DOI: 10.1039/d6ob00784h

Authors (6)

Patrick de L Barbosa Research Group on Structure and Reactivity of Organic Compounds - Department of Organic Chemistry, Institute of Chemistry, Universidade Federal Fluminense - UFF, Niteroi, Rio de Janeiro, 24020-141, Brazil. rodolfofiorot@id.uff.br.
Felipe Lopes N da Silva Biocatalysis and Organic Synthesis Group - Institute of Chemistry, Universidade Federal do Rio de Janeiro - UFRJ, Cidade Universitária, Rio de Janeiro 21941-909, Brazil.
Diogo R Ramos Biocatalysis and Organic Synthesis Group - Institute of Chemistry, Universidade Federal do Rio de Janeiro - UFRJ, Cidade Universitária, Rio de Janeiro 21941-909, Brazil.
João G H Rosa Biocatalysis and Organic Synthesis Group - Institute of Chemistry, Universidade Federal do Rio de Janeiro - UFRJ, Cidade Universitária, Rio de Janeiro 21941-909, Brazil.
Rodrigo O M A de Souza Biocatalysis and Organic Synthesis Group - Institute of Chemistry, Universidade Federal do Rio de Janeiro - UFRJ, Cidade Universitária, Rio de Janeiro 21941-909, Brazil.
+1 more authors