Carbohydrates are interesting starting materials for scientific and industrial syntheses as they allow a versatile chemistry. Moreover, they are of natural origin and environmentally benign. During the past few years, inositol, a rather "exotic" carbohydrate, and its derivatives have gained increasing attention. Here, we describe the syntheses of new regiochemically defined inositol monoethers and monoesters as well as regioisomeric inositol ester mixtures and investigate their amphitropic liquid crystallinity. Furthermore, first results on their surface activity in aqueous solutions are given and compared with classical sugar surfactants.