273406-45-4Relevant academic research and scientific papers
α- and β-thujones (herbal medicines and food additives): Synthesis and analysis of hydroxy and dehydro metabolites
Sirisoma, Nilantha S.,Hoeld, Karin M.,Casida, John E.
, p. 1915 - 1921 (2007/10/03)
Essential oils containing α- and β-thujones are important herbal medicines and food additives. The thujone diastereomers are rapidly metabolized convulsants acting as noncompetitive blockers of the γ-aminobutyric acid-gated chloride channel. Synthesis and analysis of the metabolites are essential steps in understanding their health effects. Oxidation of α- and β-thujones as their 2,3-enolates with oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide) gave the corresponding (2R)-2-hydroxythujones assigned by 1H and 13C NMR and X-ray crystallography, α-Thujone was converted to 4-hydroxy-α- and -β-thujones via the 3,4-enol acetate on oxidation with peracid and osmium tetroxide, respectively. Ozonation provided 7-hydroxy-α- and -β-thujones, and by dehydration provided the 7,8-dehydro compounds. 4,10-Dehydrothujone was prepared from sabinene via sabinol. The hydroxy and dehydro derivatives are readily identified and analyzed by GC/MS as the parent compounds and trimethylsilyl and methyloxime derivatives. A separate study established that all of these compounds are metabolites of α- and β-thujones.
