Formation of micelles and liposomes from carnitine amphiphiles.

Esterification of the carboxy and/or the hydroxy groups of (R)-carnitine (3-hydroxy-4-trimethylammonium butanoate) produces interesting classes of (cationic or zwitterionic) surfactants whose CMC values are in general predictable from their molecular structure. In fact similar relationships between CMC and the number of carbon atoms, Cn, have been found for three classes of such surfactants. However the sensitivity of CMC to Cn for the diesters is considerably lower than that calculated from literature values for the monoesters (either in their cationic or zwitterionic forms).

Effect of the addition of electrolytes on the partition coefficients, activity coefficients, and acid dissociation constants of carnitine and its acetyl and propionyl derivatives.

The partition coefficients, P, between n-octanol and water of carnitine, acetylcarnitine, propionylcarnitine, and tetraethylammonium pentacyanopropenides have been determined spectrophotometrically at 20 degrees C. The value of P increases upon addition of electrolytes, the increase produced by LiCl being particularly high. The carnitine cations are 'salted-out' by electrolytes as shown by the variation of their 'single-ion' activity coefficients (relative to that of the tetraethylammonium ion) with electrolyte concentration.