41444-55-7

Upstream product

• 103168-14-5 n-decyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 112-30-1 1-Decanol 
• 31387-97-0 n-butyl D-glucoside 
• 492-61-5 β-D-glucose 
• 25320-96-1 O-n-pentyl β-D-glucopyranoside 
• 39824-11-8 n-hexyl-β-D-glucopyranoside 
• 78617-12-6 n-heptyl beta-D-glucopyranoside 
• 92052-29-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate 
• 83-87-4 D-glucose pentaacetate 
• 103168-14-5 Decyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 2816-24-2 o-nitrophenyl D-galactopyranoside 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 25878-60-8 D-galactose pentaacetate 

Downstream Products

• 25320-96-1 O-n-pentyl β-D-glucopyranoside 
• 39824-11-8 n-hexyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Antimicrobial activity of mannose-derived glycosides

A set of 14 synthetic mannolipid-mimicking O-mannosides, S-mannosides, and mannosylsulfones varying in aglycone length were evaluated for their antimicrobial activity towards yeast Candida albicans as well as Gram-positive and Gram-negative bacteria, Staphylococcus aureus and Escherichia coli, respectively. S. aureus was the most susceptible to dodecyl α-d-mannopyranoside showing MIC value of 78 μM, while dodecyl α-d-thiomannopyranoside was superior yeast inhibitor exhibiting twofold lower MIC value. On the other hand, E. coli was resistant to both dodecyl glycosides. Mannosides exposure on RAW 264.7 cell line murine macrophages revealed the tight structure - immunobiological activity pattern. No significant cytotoxic effect and suppression of proliferation as a consequence of cell injury following 24 h exposure with 1-100 μg/cm3 mannosides were observed.

Decyl glucoside synthesized by direct glucosidation of d-glucose over zeolite catalysts and its estrogenicity as non-endocrine disruptive surfactant

The estrogenicity of decyl glucoside was asserted as a non-endocrine disruptive surfactant with its preparation method using zeolite catalysts. Its estrogenicity was estimated using E-Assay method. The decyl glucoside was synthesized by direct glucosidation from D-glucose with 1-decanol. The conversion and yield were improved with increasing of amount of acid sites of the zeolite catalysts. The decyl glucopyranoside is more hydrophilic than nonylphenol and has a high wettability. The decyl glucopyranosides exhibited extremely lower proliferation of estrogenic cell compared with nonylphenol.

Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics

A series of 19 synthetic alkyl and thioalkyl glycosides derived from D-mannose, D-glucose and D-galactose and having C10–C16 aglycone were investigated for cytotoxic activity against 7 human cancer and 2 non-tumor cell lines as well as for antimicrobial potential on 12 bacterial and yeast strains. The most potent compounds were found to be tetradecyl and hexadecyl β-D-galactopyranosides (18, 19), which showed the best cytotoxicity and therapeutic index against CCRF-CEM cancer cell line. Similar cytotoxic activity showed hexadecyl α-D-mannopyranoside (5) but it also inhibited non-tumor cell lines. Because these two galactosides (18, 19) were inactive against all tested bacteria and yeast strains, they could be a target-specific for eukaryotic cells. On the other hand, β-D-glucopyranosides with tetradecyl (11) and hexadecyl (12) aglycone inhibited only Gram-positive bacterial strain Enterococcus faecalis. The studied glycosides induce changes in the lipid bilayer thickness and lateral phase separation at high concentration, as derived from SAXS experiments on POPC model membranes. In general, glucosides and galactosides exhibit more specific properties. Those with longer aglycone show high cytotoxicity and therefore, they are more promising candidates for cancer cell line targeted inhibition.

Method for preparing alkyl glycoside

The invention provides a method for preparing alkyl glycoside. The method comprises the following steps: providing a deep-eutectic solvent as a catalyst, wherein the deep-eutectic solvent consists ofcholine chloride and hydrogen-bond donors, and the structural formula of the choline chloride is shown as the formula (I) in the original specification; performing a reaction on the deep-eutectic solvent, glucose and fatty alcohol, so as to generate the alkyl glycoside, wherein the molar ratio of the choline chloride and the hydrogen-bond donors is 1: 1. Therefore, by utilizing the characteristicsof the deep-eutectic solvent of being uneasy in volatilization and combustion, good in heat stability and solubility, easy in recovery, repeatable in use and the like, the reaction is performed on the deep-eutectic solvent, the glucose and the fatty alcohol to generate the alkyl glycoside, the utilization rate of atoms in a synthesis process is as high as 100%, and the alkyl glycoside is low in toxicity and is biodegradable.

Sweet surfactants: Packing parameter-invariant amphiphiles as emulsifiers and capping agents for morphology control of inorganic particles

Surfactants are not only pivotal constituents in any biological organism in the form of phospholipids, they are also essential for numerous applications benefiting from a large, internal surface, such as in detergents, for emulsification purposes, phase transfer catalysis or even nanoparticle stabilization. A particularly interesting, green class of surfactants contains glycoside head groups. Considering the variability of glycosides, a large number of surfactant isomers become accessible. According to established models in surfactant science such as the packing parameter or the hydrophilic lipophilic balance (HLB), they do not differ from each other and should, thus, have similar properties. Here, we present the preparation of a systematic set of glycoside surfactants and in particular isomers. We investigate to which extent they differ in several key features such as critical aggregation concentration, thermodynamic parameters, etc. Analytical methods like isothermal titration calorimetry (ITC), tensiometry, dynamic light scattering (DLS), small angle-X-ray scattering (SAXS), transmission electron microscopy (TEM) and others were applied. It was found that glycosurfactant isomers vary in their emulsification properties by up to two orders of magnitude. Finally, we have investigated the role of the surfactants in a microemulsion-based technique for the generation of zinc oxide (ZnO) nanoparticles. We found that the choice of the carbohydrate head has a marked effect on the shape of the formed inorganic nanocrystals.

Micellar effect on the direct Fischer synthesis of alkyl glucosides

This manuscript presents results from the investigation on the synthesis of alkyl glucosides by the novel, very efficient and environmentally friendly protocol of the Fischer-type synthesis from unprotected glucose and aliphatic alcohols. The use of the dual functionality catalysts (surfactant?+?acid catalyst) and micellar reaction system are the main novelty of described method. It has been found, that in developed method of synthesis the reaction of unprotected glucose with aliphatic alcohols carried out with significantly different route, than the normal (classical) route and leads to alkyl glucopyranoside derivatives with high yields. In progress analyses by DLS, HPLC and GC/MS confirm the general postulated pathway of developed method.

manufacturing method of decyl glucoside using zeolite catalyst

The invention relates to a zeolite catalyst using it will be burntcauchy writing base [tu[tu] manufacturing method is provided, more particularly zeolite catalyst to improve yield cauchy writing base [tu[tu]it will be burnt using specific and for improving product yields can be cauchy writing base [tu[tu]it will be burnt which selectively adjusts the method are disclosed. The present invention relates to glucose (glucose) 100 parts by weight of 200 to 3000 parts by weight of glass space this year (decanol) input and a reactor, reacting the glucose (decyl glucopyranoside) and it will be burntthe writing base nose ladle presbyopia [tu[tu]writing base nose bleed presbyopia [tu[tu]it will be burntspace this year zeolite catalyst under reaction to produce (decyl glucofuranoside) comprising the following steps. (by machine translation)

Synthesis and Properties of Alkyl β-d-Galactopyranoside

A series of alkyl β-d-galactopyranosides were prepared by the trichloroacetimidate method with d-galactose and alcohols with different chain lengths as raw materials. Their solubility, surface tension, emulsification, foaming, wettability, thermotropic liquid crystalline properties, and thermal stability were investigated. Alkyl β-d-galactopyranosides are soluble in water and ethanol, and the solubility decreases with increasing alkyl chain length. Decyl β-d-galactopyranoside was insoluble in water, but soluble in ethanol. Dissolution of alkyl β-d-galactopyranoside in water is an endothermic process with dissolution enthalpies greater than zero. Nonyl β-d-galactopyranoside had an excellent emulsifying?property, better foaming ability and the best foam stability. The CMC values of alkyl β-d-galactopyranosides decrease with increasing of alkyl chain length. Alkyl β-d-galactopyranosides are thermally stable up to 270?°C. Alkyl β-d-galactopyranosides show the distinctive optical texture of a thermotropic liquid crystal smectic A type phase. Decyl β-d-galactopyranoside showed the strongest wettability.

Method for preparing alkyl polyglycoside through concerted catalysis of ionic liquid compounding system

The invention belongs to a preparation method of alkyl polyglycoside, and particularly relates to a method for preparing the alkyl polyglycoside through concerted catalysis of an ionic liquid compounding system. According to the method disclosed by the invention, ionic liquid with catalytic activity is compounded with one or two of sulphuric acid, phosphoric acid, p-toluene sulfonic acid and dodecylbenzene sulfonic acid so that a novel catalysis system is formed, and the alkyl polyglycoside is prepared through the concerted catalysis of the novel catalysis system. The technology of the method disclosed by the invention has the advantages that the reaction efficiency of a unit catalyst is high and the reaction time is short.

Chemoenzymatic synthesis of β-D-glucosides using cellobiose phosphorylase from Clostridium thermocellum

Abstract Over the past decade, disaccharide phosphorylases have been successfully applied for the synthesis of numerous α-glucosides. In contrast, much less research has been done with respect to the production of β-glucosides. Although cellobiose phosphorylase was already successfully used for the synthesis of various disaccharides and branched trisaccharides, its glycosylation potential towards small organic compounds has not been explored to date. Unfortunately, disaccharide phosphorylases typically have a very low affinity for non-carbohydrate acceptors, which urges the addition of solvents. The ionic liquid AMMOENGTM 101 and ethyl acetate were identified as the most promising solvents, allowing the synthesis of various β-glucosides. Next to hexyl, heptyl, octyl, nonyl, decyl and undecyl β-D-glucopyranosides, also the formation of vanillyl 4-O-β-D-glucopyranoside, 2-phenylethyl β-D-glucopyranoside, β-citronellyl β-D-glucopyranoside and 1-O-β-D-glucopyranosyl hydroquinone was confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry. Moreover, the stability of cellobiose phosphorylase could be drastically improved by creating cross-linked enzyme aggregates, while the efficiency of the biocatalyst for the synthesis of octyl β-D-glucopyranoside was doubled by imprinting with octanol. The usefulness of the latter system was illustrated by performing three consecutive batch conversions with octanol imprinted cross-linked enzyme aggregates, yielding roughly 2 g of octyl β-D-glucopyranoside.