Neimert-Andersson Kristina, Sauer Sven, Panknin Olaf, Borg Tessie, Söderlind Erik, Somfai Peter
KTH Chemical Science and Engineering, Organic Chemistry, S-100 44 Stockholm, Sweden.
J Org Chem. 2006 Apr 28;71(9):3623-6. doi: 10.1021/jo051904b.
The synthesis of four sugar-based surfactants derived from glucose and (R)-12-hydroxystearic acid is described. The surfactants have a hydroxy group in the hydrophobic part, which is either free or acylated using acetyl chloride, hexanoyl chloride, or myristoyl chloride. Three of the synthesized surfactants are water-soluble and are evaluated with respect to their CMCs and hemolytic activities. The fourth surfactant has limited water solubility and is not further included in the study. The investigated surfactants are all hemolytic close to their respective CMC indicating that their use in parenteral formulations may be limited. Nevertheless, surfactants having the proposed structure appear as promising alternatives to existing solubilizing agents for pharmaceutical applications.
