A low-toxicity method for the separation of lanosterol and dihydrolanosterol from commercial mixtures.
We describe an inexpensive, low-toxicity and high-yielding method for the production of pure lanosterol and dihydrolanosterol from the commercially available mixture. Optimum conditions are presented for the one-pot production of the intermediate 24,25 vicinal diol of lanosterol acetate (via either epoxidation or hydroxyhalogenation) which is readily separated from the unreacted dihydrolanosterol acetate. The lanosterol diol can then be converted to pure (>97%) lanosterol. Hypophosphorous acid was used for both the conversion of the epoxide to the diol, and as a catalyst for the hydroxyhalogenation by N-halosuccinimides of the olefinic bond.
Chemistry Department, University of Waikato, Private Bag 3105, Hamilton, New Zealand.
Levan K
LK
Kavtaradze
Merilyn
M
Manley-Harris
Brian K
BK
Nicholson
D000107:Acetylation; D004852:Epoxy Compounds / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006219:Halogens / Q000737:chemistry; D007810:Lanosterol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D004852:Epoxy Compounds; D006219:Halogens; D007810:Lanosterol; C015316:lanostenol