Lu Huiling, Pourceau Gwladys, Briou Benoit, Wadouachi Anne, Gaudin Théophile, Pezron Isabelle, Drelich Audrey
Université de Technologie de Compiègne, ESCOM, TIMR (Transformations Intégrées de la Matière Renouvelable), Centre de Recherche Royallieu-CS 60 319, 60203 Compiègne Cedex, France.
Laboratoire de Glycochimie, et des Agroressources d'Amiens (LG2A), UR 7378-Institut de Chimie de Picardie, Université de Picardie Jules Verne, 33 rue Saint Leu, 80039 Amiens Cedex, France.
Molecules. 2024 May 16;29(10):2338. doi: 10.3390/molecules29102338.
Two series of sugar esters with alkyl chain lengths varying from 5 to 12 carbon atoms, and with a head group consisting of glucose or galactose moieties, were synthesized. Equilibrium surface tension isotherms were measured, yielding critical micellar concentration (CMC) surface tensions at CMC (γcmc) and minimum areas at the air-water interface (Amin). In addition, Krafft temperatures (Tks) were measured to characterize the ability of molecules to dissolve in water, which is essential in numerous applications. As a comparison to widely used commercial sugar-based surfactants, those measurements were also carried out for four octyl d-glycosides. Impacts of the linkages between polar and lipophilic moieties, alkyl chain lengths, and the nature of the sugar head group on the measured properties were highlighted. Higher Tk and, thus, lower dissolution ability, were found for methyl 6--acyl-d-glucopyranosides. CMC and γcmc decreased with the alkyl chain lengths in both cases, but Amin did not appear to be influenced. Both γcmc and Amin appeared independent of the ester group orientation. Notably, alkyl (methyl α-d-glucopyranosid)uronates were found to result in noticeably lower CMC, possibly due to a closer distance between the carbonyl function and the head group.
合成了两类糖酯，其烷基链长度在5至12个碳原子之间变化，且头基由葡萄糖或半乳糖部分组成。测量了平衡表面张力等温线，得到了临界胶束浓度（CMC）、CMC时的表面张力（γcmc）以及气-水界面的最小面积（Amin）。此外，还测量了克拉夫特温度（Tks），以表征分子在水中的溶解能力，这在众多应用中至关重要。作为与广泛使用的商业糖基表面活性剂的比较，也对四种辛基d-糖苷进行了这些测量。突出了极性和亲脂性部分之间的连接、烷基链长度以及糖头基的性质对所测性质的影响。对于6-酰基-d-葡萄糖吡喃糖苷甲基酯，发现其Tk较高，因此溶解能力较低。在两种情况下，CMC和γcmc均随烷基链长度的增加而降低，但Amin似乎不受影响。γcmc和Amin似乎均与酯基取向无关。值得注意的是，发现烷基（甲基α-d-葡萄糖吡喃糖苷）uronates会导致CMC明显降低，这可能是由于羰基官能团与头基之间的距离更近。
