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Synthesis of betulin derivatives and the determination of their relative lipophilicities using reversed‐phase thin‐layer chromatography
Author(s) -
AchremAchremowicz Jacek,
Kępczyńska Elżbieta,
Żylewski Marek,
Janeczko Zbigniew
Publication year - 2010
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/bmc.1282
Subject(s) - chemistry , lipophilicity , betulin , chromatography , thin layer chromatography , partition coefficient , phase (matter) , analytical chemistry (journal) , organic chemistry
A series of superlipophilic or highly lipophilic semisynthetic betulin derivatives was prepared and their relative lipophilicity was measured by reversed‐phase thin‐layer chromatography (RP‐TLC) at different pH values using 1,4‐dioxane–acetate buffer mixtures as mobile phases. Cholesterol, 17β‐estradiol and pure betulin were used as the reference compounds. Linear relationships were found between R M values and 1,4‐dioxane concentrations in the mobile phases. Log P values were also calculated with computer programs ACD/LogP (ChemSketch 11.0, Advanced Chemistry Development Inc.) and C log P (Daylight Chemical Information Systems Inc.). The empirical and theoretical data were compared, and the R M0 values correlated well with log P . Two of the synthesized betulin derivatives are reported for the first time. Copyright © 2009 John Wiley & Sons, Ltd.