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Updated: Jun 20, 2026

A Toolkit to Enable Hydrocarbon Conversion in Aqueous Environments
Published on: October 2, 2012
Hydroxylation and further oxidation of delta9-tetrahydrocannabinol by alkane-degrading bacteria
Hassan Rashidi1, Muhammad T Akhtar, Frank van der Kooy
1Department of Pharmacognosy, IBL Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Abstract:
The microbial biotransformation of Delta(9)-tetrahydrocannabinol was investigated using a collection of 206 alkane-degrading strains. Fifteen percent of these strains, mainly gram-positive strains from the genera Rhodococcus, Mycobacterium, Gordonia, and Dietzia, yielded more-polar derivatives. Eight derivatives were produced on a mg scale, isolated, and purified, and their chemical structures were elucidated with the use of liquid chromatography-mass spectrometry, (1)H-nuclear magnetic resonance (1H-NMR), and two-dimensional NMR (1H-1H correlation spectroscopy and heteronuclear multiple bond coherence). All eight biotransformation products possessed modified alkyl chains, with hydroxy, carboxy, and ester functionalities. In a number of strains, beta-oxidation of the initially formed C5 carboxylic acid led to the formation of a carboxylic acid lacking two methylene groups.
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