Water Solubility and Surface Property of Alkyl Di-/Tri-/Tetraoxyethyl β-d-Xylopyranosides

Abstract

Alkyl di-/tri-/tetraoxyethyl β-D-xylopyranosides as derivatives of alkyl xylosides are a class of non-ionic sugarbased surfactants. They were stereoselectively synthesized by the Helferich method. Their properties including hydrophilic− lipophilic balance number, water solubility, surface property, foam property, emulsifying property, and thermotropic liquid crystal property were mainly investigated. The results showed that their water solubility decreased with increasing the alkyl chain length and increasing the number of the oligooxyethyl fragment. The critical micelle concentration had a monotonous decreasing trend with increasing the alkyl chain length. Nonyl di-/tri-/tetraoxyethyl β-D-xylopyranosides [−(OCH 2 CH 2 ) m −, where m = 2, 3, and 4] exhibited the most excellent foaming ability and foam stability. In the n-octane/water system, dodecyl tetraoxyethyl β-D-xylopyranosides and tetradecyl tetraoxyethyl β-D-xylopyranosides had the strongest emulsion ability. In addition, some alkyl di-/tri-/tetraoxyethyl β-D-xylopyranosides had thermotropic liquid crystal properties. Such sugar-based surfactants, alkyl di-/tri-/tetraoxyethyl β-D-xylopyranosides, will be expected to develop for a variety of practical application.

d-Mannitol based surfactants for cosmetic and food applications and hydrogels to produce stabilized Ag nanoparticles

“…Increasing the hydrocarbon chain length reduces the solubility in water, which is reflected in their foaming ability (Table 2). 34,35 Thus, among the series of amphiphiles, the foaming ability of M12 is excellent and comparable to a widely used commercial detergent sodium dodecyl sulfate (SDS). Hence, M12, a surfactant primarily based on renewable resources, might be a valuable alternative to SDS, which causes undesirable side effects.…”

Surface Activity of Alkoxy Ethoxyethyl β-d-Glucopyranosides

“…The foam volume (H 5 ) was subsequently rerecorded after being left for 5 min, and the foam vanishing rate (ν) was calculated according to formula 2. 27,28…”

“…The theoretical analysis showed that the hydrophilic and lipophilic balance (HLB) number of the longchain glycosides indeed is smaller than the HLB number of the short-chain glycosides such that the long alkyl group would reduce the hydrophilicity and weaken the water solubility and even damage their practical values. 28 As an important part and effective extension of the research project, an oxyethylene fragment as a hydrophilic spacer was already introduced into traditional alkyl β-D-glucopyranosides to successfully obtain alkoxyethyl β-D-glucopyranosides and alkoxyethyl β-D-xylopyranosides with improving related water solubility. 27,28 The research triggered us to take the investigation further.…”

“…28 As an important part and effective extension of the research project, an oxyethylene fragment as a hydrophilic spacer was already introduced into traditional alkyl β-D-glucopyranosides to successfully obtain alkoxyethyl β-D-glucopyranosides and alkoxyethyl β-D-xylopyranosides with improving related water solubility. 27,28 The research triggered us to take the investigation further. In this article, dioxyethylene fragment (−(OCH 2 CH 2 ) 2 −) as a stronger hydrophilic spacer was further introduced into alkyl β-D-glucopyranosides to prepare effectively alkoxy ethoxyethyl β-D-glucopyranosides (4a−4h n = 6−16) (Figure 1) with strengthening hydrophilicity and improving water solubility and disclose the relationships between the quantitative structure and physicochemical property involving surface activity and liquid-crystalline behavior.…”

“…29 The water solubility of the dried alkoxy ethoxyethyl β-D-glucopyranosides (4a−4h) was measured at 25 °C. 27,28 2.3. Emulsification Power.…”