Surface Activity of Alkoxy Ethoxyethyl β-d-Glucopyranosides

Abstract

Dioxyethene fragment (−(OCH2CH2)2−) was introduced into traditional alkyl β-d-glucopyranosides to ameliorate the water solubility, and eight nonionic surfactants, that is, alkoxy ethoxyethyl β-d-glucopyranosides with alkyl chain lengths (n = 6–16), were synthesized and characterized. Their hydrophilic and lipophilic balance number, water solubility, critical micelle concentration (cmc), γcmc, Γmax, and hygroscopic rate decreased with an increase in the alkyl chain length. Hexadecoxy ethoxyethyl β-d-glucopyranoside had no water solubility at 25 °C. Decoxy ethoxyethyl β-d-glucopyranoside had the best emulsifying property in the toluene/water and n-octane/water systems and the strongest foaming property, whereas dodecoxy ethoxyethyl β-d-glucopyranoside had the best emulsifying property in the rapeseed oil/water system. Such β-d-glucopyranosides (n = 6–12) exhibited excellent surface activity. In addition, for the binary mixture of alkoxy ethoxyethyl β-d-glucopyranosides (n = 8, 10, 12) and sodium dodecyl sulfate or cetyl trimethyl ammonium chloride, their cmc values were lower than the pure β-d-glucopyranosides, indicating that they had synergistic interactions. The fan focal conic textures of alkoxy ethoxyethyl β-d-glucopyranosides (n = 7–16) were observed during the cooling process under a polarizing optical microscope. Alkoxy ethoxyethyl β-d-glucopyranosides (n = 14, 16) had the related melting points and the clear points with differential scanning calorimetry. With β-d-glucopyranosides (n = 6–16) and n-butanol as the surfactant and cosurfactant, respectively, and with cyclohexane as the oil phase, the related microemulsion areas in their pseudoternary phase diagram system were investigated with the visual observation at 25 °C. Along with the slashing requirements of petroleum consumption, environmental protection, and green and sustainable development, nonionic sugar-based alkoxy ethoxyethyl β-d-glucopyranosides should be expected to have their potential practical application because of their strengthened hydrophilicity, improved water solubility, and enhanced surface activity.

Surface Properties and Liquid Crystal Properties of Alkyltetra(oxyethyl) β-d-Glucopyranoside

“…It is usually used to predict the migration and distribution of compounds in the environment, the accumulation and expansion in organisms, and the study of compound activity (or toxicity), which has special significance in environmental and medical research. , Herein, ChemBioDraw (Ultra 14.0) software could be used to estimate the log P value of 4a – 4g . The water solubility of the dried 4a – 4g was measured at 25 °C …”

“…Studies have shown that the phase behaviors should greatly depend on hydrophilic sugar head and hydrophobic alkyl chains. , For example, it has been shown that increasing the alkyl chain length leads to higher thermal stability of the thermotropic and lyotropic phases, because long-chain alkyl glycosides have stronger van der Waals interactions and require more energy to melt them. ,, In recent years, the application of sugar-based nonionic surfactants has become more widespread, which greatly increases the possibility of them entering the environment and industrial and household waste . More importantly, their biological and industrial importance has encouraged the development and application of many synthetic glycolipids and their derivatives; the well-known APGs should be the most important, which have been found to be used in many fields. , It is reported that although long-chain APGs and AGs with 1,2-cis or 1,2-trans anomeric pure have high surface activity, they have a fatal weakness, that is, weak hydrophilicity and poor or even no water solubility, which has brought great limitations to its commercial application . Therefore, the research on their preparation, characterization, derivatization, reconstruction, physicochemical characteristics, and application should be crucial .…”

“…Such modification might tendentiously trigger or claim or promote, or even encourage the extensive research, safety, availability, and scale development of various highly efficient and novel mRNA vaccines to curtail the epidemic, seasonal epidemic, or pandemic with the related progress of seasonal/local/global vaccination until an end to the devastating effects of the related epidemics nowadays and in the future . In fact, ethoxylation should be one of the most important reactions to produce synthetic surfactants involving the required surface activity within the preferred/optimized range of the hydrophilic and lipophilic balance (HLB) and octanol–water partition coefficient (log P). ,, With the progress of environmental legislation and international/governmental restrictions of carbon neutralization, it is a great opportunity for the surfactant researchers to move perfectly away from PEGylation or ethoxylation to adjust the relevant strategy actively through introducing hydrophilic head (such as sustainable sugar head), and controlling the length of the hydrophilic spacer to obtain tensioactive molecules to meet the needs of practical, renewable, sustainable, and green surfactants with the required surface activity to a certain extent …”

Surfactant‐modified parathyroid hormone fragments with high potency and prolonged action: Structure‐informed design using glycolipid surfactant conjugation

“…For the parent surfactants, it is well known that the length and hydrophobicity of the alkyl chains vary the general physical and surfactant properties [35,36] such as solubility in water, liquid crystal behavior, critical micelle concentration (CMC), micelle size, affinity for SA, and so on. [37] By extension, these properties are expected to the extend to the peptide conjugates (to a greater or lesser extent, depending on peptide size and placement) with clear potential to substantially affect, in a tunable way, solubility in presence of SA, PK/PD behavior in vivo, receptor affinity and kinetics, protease resistance, permeability across mucosal membranes, and so on. It was not feasible to investigate all of these aspects at this stage of preliminary proof-of-concept…”

“…The objective with these modifications was to demonstrate the effect of varying the chain length of the surfactant as this is known to affect the CMC, solubility and micellar behavior of such surfactants. [36,37] The duration of action in vivo is anticipated to vary with chain length, with longer chains expected to show slower uptake and tighter binding to SA, resulting in lower Cmax and longer T 1/2 , although this has not yet been evaluated in detail for this series due to funding limits. Further variation in physical properties and PK profile are possible by variation of the surfactant head group (e.g., mono vs disaccharide; α or β configuration) and alkyl tail group functionalization.…”