McCarthy, F. O. and Chopra, J. and Ford, A. and Hogan, S. A. and Kerry, J. P. and O'Brien, N. M. and Ryan, E. and Maguire, A. R.

2005

Organic & Biomolecular Chemistry

Synthesis, isolation and characterisation of beta-sitosterol and beta-sitosterol oxide derivatives

Validated

()

3

16

3059

3065

beta-Sitosterol is the most prevalent plant cholesterol derivative (phytosterol) and can undergo similar oxidation to cholesterol, leading to beta-sitosterol oxides. The biological impact of phytosterol oxides has only been evaluated in a phytosterol blend (usually of beta-sitosterol, campesterol, stigmasterol and dihydrobrassicasterol). The lack of pure phytosterols, including beta-sitosterol, hinders the collection of significant toxicity data on the individual beta-sitosterol oxides. An efficient synthetic route to multi-gram quantities of pure beta-sitosterol is described here, together with the first syntheses and characterisation of pure beta-sitosterol oxides.