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Purification of Commercially Available β‐Sitosterol via Chemical Synthesis
Author(s) -
Zmysłowski Adam,
Sitkowski Jerzy,
Michalska Katarzyna,
Szterk Arkadiusz
Publication year - 2021
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.202000331
Subject(s) - stigmasterol , phytosterol , chemistry , sterol , chromatography , reagent , dihydroxylation , organic chemistry , enantioselective synthesis , cholesterol , biochemistry , catalysis
Abstract β‐Sitosterol, a plant sterol, is found to be useful in the nutraceutical and pharmaceutical industries, but is also frequently employed in biological research. In addition to stigmasterol, phytosterols are available as mixtures, and it is challenging to obtain highly pure β‐sitosterol in larger quantities. Two methods for the purification of β‐sitosterol from commercially available phytosterols are presented. Both methods are based on increasing the polarity by either epoxidation or dihydroxylation reactions with the Δ 5–6 double bond of the sterol. The synthesis methods and purification are chosen to be simple with inexpensive and easily obtained reagents and equipment in the laboratory. The purifications described afford β‐sitosterol in gram quantities with high purity (>95%) at 37–39% and 32% yields for epoxidation and dihydroxylation reactions, respectively. The highly pure β‐sitosterol is only available in small quantities, which makes it expensive. The presented methods can be used for obtaining the pure β‐sitosterol in large scale using relatively simple organic chemistry and preparative chromatography. The use of the method may significantly increase the quantity available, which causes a reduction in price and, consequently, increases the number of research and applications available with the use of β‐sitosterol.