Syntheses, Amphitropic Liquid Crystallinity, and Surface Activity of New Inositol-Based Amphiphiles

Abstract

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.

Partition coefficients of nonionic surfactants in water/n-alkane systems

“…The equilibrium surface tension isotherms which were used as reference curves for the K p calculation were measured in our group or by collaborators and published elsewhere: C 10 DMPO [17], C 12 DMPO [18], C 14 DMPO [17], C 10 E 4 [19], C 10 E 6 [20], C 12 E 6 [21], b-C 10 G 1 [22], b-C 10 G 2 [22], b-C 12 G 2 [23], 818 UP [24]. All curves were fitted to a 2nd order polynomial function.…”

Mixtures of n-dodecyl-β-d-maltoside and hexaoxyethylene dodecyl ether — Surface properties, bulk properties, foam films, and foams

“…Inositols differ from other carbohydrates as, due to their molecular constitution, they allow different types of symmetry, including meso-structures. This unique structural situation allows detailed structure/property studies on various aspects of supramolecular interactions including the influence of the molecular symmetry, which is not possible with other carbohydrates [71,72].…”

“…A surfactant with a head group consisting of three ethylene oxide units and an inositol unit is an interesting alternative to the classical glucose units as it has the same molecular formula as conventional hexoses C 6 H 12 O 6 , but a different molecular structure (see Section 6.3 for details). Surface tension studies on this surfactant revealed that its surface activity is "between" that of the pure C 12 E 6 and β-C 12 G 2 , respectively [73], which is a very nice example of a "structureproperty-relationship" and opens the arena for a new family of surfactants [71,72]. Molecular simulation techniques cannot only be used to complement these studies but they also offer a more time and cost effective means compared with experiment.…”

Synthesis and application of non-bioaccumulable fluorinated surfactants: a review

“…Presently, this sort of fluorinated surfactants containing multiplehydroxyl natural product groups are mainly used in handling membrane proteins (see 3.2 section for details). Moreover, it is should be noted that the water solubility of the some surfactants bearing only one natural product hydrophilic unit is poor [64,65]. The introduction of oxyethene fragments (−OCH 2 CH 2 -) or the multiple natural product hydrophilic units into the hydrophilic moiety can improve the water solubility of the entire surfactant molecule.…”