Potentiometric determination of octanol–water and liposome–water partition coefficients (log P) of ionizable organic compounds

The logarithm of the octanol–water partition coefficient, log P, is a key physicochemical property for both pharmaceutical drugs and agrochemicals. It is also required by legislation as part of the physicochemical properties profile for high volume production chemicals. This Letter describes a simpl...

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Bibliographic Details
Published in:Tetrahedron letters 2007-05, Vol.48 (19), p.3337-3341
Main Authors: Barzanti, Claire, Evans, Rebecca, Fouquet, Jérémy, Gouzin, Léonard, Howarth, Nicola M., Kean, Gary, Levet, Emilie, Wang, Daniel, Wayemberg, Estelle, Yeboah, Agnes A., Kraft, Arno
Format: Article
Language:English
Subjects:
Ionization constant
Liposomes
Octanol
Partition coefficient
Potentiometric titration
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Summary:The logarithm of the octanol–water partition coefficient, log P, is a key physicochemical property for both pharmaceutical drugs and agrochemicals. It is also required by legislation as part of the physicochemical properties profile for high volume production chemicals. This Letter describes a simple method for determining log P values (over a wide range from −0.8 to 5.3) for 12 organic weak acids and bases using potentiometric titrations, with octanol or phosphatidyl choline liposomes as the partitioning medium. Such titrations take comparatively little time (about 30–45 min per titration), are easy to implement, and can be carried out with an inexpensive laboratory titrator.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.03.085