烷基-α-D-吡喃葡萄糖苷的合成与性能

doi:10.11944/j.issn.1000-0518.2016.11.160017

摘要/Abstract

摘要：

以D-葡萄糖为原料,经全乙酰化、在SnCl₄催化下与脂肪醇糖苷化、脱保护3步反应合成了7种不同碳链长度的烷基-α-D-吡喃葡萄糖苷。利用核磁共振、表面张力仪和偏光显微镜等对其进行结构、表面张力和热致液晶等性能测试,结果表明,当烷基-α-D-吡喃葡萄糖苷烷基链长(n)为6~9时,均有发泡和乳化性能,其中正壬基-α-D-吡喃葡萄糖苷具有最佳的发泡和乳化性能;烷基糖苷(n=6~9)的表面张力(γ_CMC)及临界胶束浓度(CMC)均比较低;饱和吸附量(Γ_max)随烷基链的增长而减小,饱和吸附面积(A_min)随烷基链增长而增大;形成胶束时的标准自由能(ΔG_mic)和吸附自由能(ΔG_ads)均为负值,其绝对值随烷基链增长而越来越大,其中正辛基-α-D-吡喃葡萄糖苷的表面活性最好;烷基糖苷(n=4~9)对皮肤均无急性刺激作用;所合成的烷基糖苷均具有热致液晶行为,随烷基链长的增加,液晶相的温度范围变宽,液晶相的稳定性越好。

关键词: D-葡萄糖, 烷基-α-D-吡喃葡萄糖苷, SnCl₄, 表面性能, 热致液晶

Abstract:

Alkyl α-D-glucopyranosides were synthesized with D-glucose as the raw material by three reactions involving acetylation, SnCl₄ catalyzing glycosylation with the aliphatic alcohols and deacetylation. The structures of alkyl α-D-glucopyranosides, their surface properties and thermotropic liquid crystalline properties were determined through NMR, surface tensiometer, polarization microscope and so on. The results show that alkyl α-D-glucopyranosides possess foaming and emulsifying power as their hydrophobic alkyl chain length n=6~9, wherein n-nonyl α-D-glucopyranoside has rather superior foaming and emulsifying power. The values of the surface tension(γ_CMC) and the critical micelle concentration(CMC) of the alkyl glycosides(n=6~9) are very low, their saturated adsorption capacity(Γ_max) decreases with increasing alkyl chain length, and their saturation adsorption area(A_min) increases with the increase of alkyl chain lengths. The standard free energy of micellization(ΔG_mic) and standard free energy of adsorption(ΔG_ads) for alkyl glycosides(n=6~9) are all less than zero, and the values of ΔG_mic and ΔG_ads are more negative with the increase of the alkyl chain length. The n-octyl α-D-glucopyranoside has the best surface activity. Furthermore, the alkyl glucosides(n=4~9) does not have any skin irritation. Finally, all of alkyl α-D-glucopyranosides exhibit thermotropic liquid crystalline behavior, the temperature range of the thermotropic liquid crystalline phase becomes broader, and the stability of the thermotropic liquid crystalline phase becomes stronger with the increase of alkyl chain length.

Key words: D-glucose, alkyl α-D-glucopyranoside, SnCl₄, surface performance, thermotropic liquid crystallline

李贞操, 陈国勇, 陈朗秋, 申望珍, 季善伟. 烷基-α-D-吡喃葡萄糖苷的合成与性能[J]. 应用化学, 2016, 33(11): 1265-1273.

LI Zhencao, CHEN Guoyong, CHEN Langqiu, SHEN Wangzhen, JI Shanwei. Synthesis and Properties of Alkyl α-D-Glucopyranosides[J]. Chinese Journal of Applied Chemistry, 2016, 33(11): 1265-1273.

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