Improved method for the synthesis of trans-feruloyl-beta-sitostanol

Auteur(s) :
Baker DC., Condo AM., Hicks KB., Moreau RA.
Date :
Oct, 2001
Source(s) :
Journal of agricultural and food chemistry. #49:10 p4961-4964
Adresse :
"BAKER DC,UNIV TENNESSEE,DEPT CHEM; KNOXVILLE TN 37996, USA.dcbaker@utk.edu "

Sommaire de l'article

Phytosterols and phytostanols are known to lower low-density lipoprotein-cholesterol (LDL-C) levels in humans by up to 15%, and at least two products, Benecol and Take Control, are now on the market as naturally derived fatty acid esters of phytostanols (stanol esters) and phytosterols (sterol esters), respectively. A synthetic process was developed to synthesize gram quantities of transferuloyl-beta -sitostanol from ferulic acid and beta -sitostanol, with high purity and yields of similar to 60%. The process involves (a) condensation of trans-4-O-acetylferulic acid with the appropriate phytostanol or phytostanol mixture in the presence of N,N-dicyclohexylcarbodiimide and 4-(dimethylamino)pyridine, (b) separation of the trans-4-O-acetylferuloyl products by preparative liquid chromatography, (c) selective deacetylation of the feruloyl acetate, and (d) chromatographic purification of the feruloylated phytostanols. The process was successfully applied to synthesize stanol trans-feruloyl esters from "Vegetable Stanols", a mixture of similar to 70:30 beta -sitostanol and beta -campestanol, in comparable purity and yield.

Source : Pubmed
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