- Simple preparation method of alkyl maltoside surfactant
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The invention belongs to the technical field of fine chemicals, and specifically discloses a preparation method of sugar-based nonionic surfactant alkyl-beta-D-maltoside. The preparation method includes the steps of performing an acylation reaction on maltose to obtain octa-O-acetyl-D-maltose, performing condensation on the octa-O-acetyl-D-maltose and fatty alcohol, and performing deprotection toobtain the alkyl-beta-D-maltoside. The preparation method provided by the invention is simple and easy to implement, has the advantages of mild and controllable conditions, low costs, and practicability.
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Paragraph 0027; 0029
(2020/06/09)
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- Solution Properties of Alkyl β-D-Maltosides
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Alkyl β-D-maltosides are an important class of sugar-based nonionic surfactants and have been widely studied. Nevertheless, it is still necessary to investigate further their amphiphilic structure-surface property relationships. In this article, we reported a series of properties of synthetic alkyl β-D-maltosides (6a–6i, n = 6–18) including their hydrophilic–lipophilic balance (HLB) number, water solubility, hygroscopicity, moisture-retention capacity, foaming ability, surface tension, thermotropic phase behavior, and skin irritation. Their HLB number and water solubility decreased with increasing alkyl chain length. Hexyl β-D-maltoside exhibited the strongest hygroscopicity and moisture-retention capacity. Decyl β-D-maltoside and dodecyl β-D-maltoside possessed excellent foaming power and foaming stability. Furthermore, the critical micelle concentration (CMC) of alkyl β-D-maltoside (6a–6g, n = 6–14) and their surface tension at CMC decreased with increasing alkyl chain length. At last, alkyl β-D-maltosides (6a–6g) should be considered as safe surfactants by the skin irritation assessment.
- Li, Zhencao,Chen, Guoyong,Chen, Langqiu,Zhang, Yanhua,Dai, Zhiyong
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p. 731 - 742
(2019/04/10)
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- Alkyl melibioside and alkyl cellobioside surfactants: Effect of sugar headgroup and alkyl chain length on performance
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The potential of glycolipid surfactants, composed of a sugar headgroup and lipid tail, as highly biodegradable and less toxic alternatives to commonly used surfactants motivates the systematic study of structure-function relationships of various glycolipid surfactants. Advances in the efficient synthesis of high purity amphipathic glycolipid surfactants enable the analysis of a diverse set of glycolipids. The solution phase properties of two suites of glycolipid surfactants, n-alkyl-O-melibiosides and n-alkyl-O-cellobiosides, with varying straight-chain alkyl tails of 8, 10 and 12 carbons are investigated in this work. This study substantiates their efficient surfactant performance and reveals their aggregate structure and microenvironment as it relates to molecular structure. Surface tensiometry demonstrates critical micelle concentrations of 0.2-40 mM with minimum surface tension values of 36-40 mN m-1. Time resolved fluorescence quenching (TRFQ) spectroscopy is used to calculate micelle aggregation number (12-70 molecules per micelle) and assess relative micropolarity and microfluidity within the aggregates. The average aggregation numbers determined by TRFQ and apparent hydrodynamic radii determined by dynamic light scattering vary with alkyl chain length and headgroup size, but these properties are relatively insensitive to changes in concentration. The aggregates form nearly spherical, tightly-packed micelles with a small population of vesicles and polydispersity present at low concentrations or with short alkyl chain length.
- Kegel, Laurel L.,Szabó, Lajos Z.,Polt, Robin,Pemberton, Jeanne E.
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p. 4446 - 4460
(2016/08/18)
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- Specific maltose derivatives modulate the swarming motility of nonswarming mutant and inhibit bacterial adhesion and biofilm formation by pseudomonas aeruginosa
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We have demonstrated that specific synthetic maltose derivatives activate the swarming motility of a Pseudomonas aeruginosa nonswarming mutant (rhlA) at low concentration, but inhibit it at high concentration. Although these molecules are not microbicidal, active maltose derivatives with bulky hydrocarbon groups inhibited bacterial adhesion, and exhibited biofilm inhibition and dispersion (IC50 ~20 μM and DC50 ~30 μM, respectively). Because the swarming motility of the rhlA mutant is abolished by the lack natural rhamnolipids, the swarming activation suggests that maltose derivatives are analogues of rhamnolipids. Together, these results suggest a new approach of controlling multiple bacterial activities (bacterial adhesion, biofilm formation, and swarming motility) by a set of disaccharide-based molecules.
- Shetye, Gauri S.,Singh, Nischal,Jia, Changqing,Nguyen, Chan D.K.,Wang, Guirong,Luk, Yan-Yeung
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p. 1514 - 1523
(2014/07/21)
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- SYNTHESIS OF CARBOHYDRATE-BASED SURFACTANTS
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The present invention provides carbohydrate-based surfactants and methods for producing the same. Methods for producing carbohydrate-based surfactants include using a glycosylation promoter to link a carbohydrate or its derivative to a hydrophobic compound.
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- Minimally competent lewis acid catalysts: Indium(III) and bismuth(III) salts produce rhamnosides (=6-deoxymannosides) in high yield and purity
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Glycosylation of decan-1-ol (2), (±)-decan-2-ol (3), and (±)-methyl 3-hydroxydecanoate (4) with L-rhamnose peracetate 5 to produce rhamnosides (=6-deoxymannosides) 6, 7, and 8 in the presence of Lewis acids BF3×Et2O, Sc(OTf)3/s
- Coss, Clifford,Carrocci, Tucker,Maier, Raina M.,Pemberton, Jeanne E.,Polt, Robin
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p. 2652 - 2659
(2013/03/28)
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- Synthesis of C7-C16-Alkyl maltosides in the presence of tin(IV) chloride as a lewis acid catalyst
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The synthesis of C7- to C16-alkyl maltosides in the presence of tin(IV) chloride as Lewis acid catalyst was performed. The characterization of the products and theoretical investigation of the crucial step in the synthesis were carried out. The preparation of the β-maltosides required reaction time of 1 h, and that of the α-maltosides was 72 h. The side products were the α-D-maltosidechloride and 2-hydroxy-β-maltoside, respectively. The PM3 calculation confirmed the formation of the kinetically controlled β-product.
- Markovic, Zoran,Predojevic, Jasmina,Manojlovic, Nedeljko T.
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experimental part
p. 83 - 90
(2012/05/20)
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- Specific fixed aqueous layer of three-component hybrid liposomes related to inhibition of hepatoma cells growth
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It is noteworthy that the thickness of fixed aqueous layer (TFAL) of three-component hybrid liposomes (THL) composed of L-α- dimyristoylphosphatidylcholine (DMPC), polyoxyethylene (20) sorbitan monolaurate (Tween 20), and decyl-β-lactopranoside (LactCsub
- Matsumoto, Yoko,Tanaka, Yoshihiro,Goto, Koichi,Ueoka, Ryuichi
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p. 118 - 119
(2008/09/20)
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- Thermotropic Liquid Crystals Based on Oligosaccharides. n-Alkyl 1-O-β-D-Cellobiosides
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n-Alkyl 1-O-β-D-cellobiosides with an alkyl length ranging from 7 to 18 in carbon number m were synthesized, and their thermal properties were studied in comparison with those of the already-known monosaccharide homologues, n-alkyl 1-O-β-D-glucopyranosides.The cellobiosides were found to exhibit a thermotropic mesophase at higher temperatures than the glucopyranosides.Depending on m and thermal history, the cellobiosides showed various textures such as homeotropic, transient batonnets, polygonal, and fan-shaped textures.Like in the case of the monosaccharide homologues, the difficulty of aligning the samples prohibited a full classification of the mesophase, but the X-ray diffractograms of the unaligned cellobiosides indicated that their mesophase belongs to smectic A (or less possibly, smectic C).The m dependence of the lamella thickness was much weaker than (about half) that of the monosaccharide homologues.Possible molecular arrangements of the cellobiosides in the mesophase were presented.
- Ma, Yung-Dae,Takada, Akihiko,Sugiura, Makoto,Fukuda, Takeshi,Miyamoto, Takeaki,Watanabe, Junji
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p. 346 - 351
(2007/10/02)
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