41444-50-2

Usage

InChI:InChI=1/C14H28O6/c1-2-3-4-5-6-7-8-19-14-13(18)12(17)11(16)10(9-15)20-14/h10-18H,2-9H2,1H3/t10-,11-,12+,13-,14?/m1/s1

Upstream product

• 2280-44-6 D-Glucose 
• 111-87-5 octanol 
• 9004-34-6 cellulose 

Downstream Products

• 695228-29-6 n-octyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 38954-67-5 octyl (2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside 
• 102935-48-8 octyl (2,3,4,6-tetra-O-acetyl)-α-D-glucopyranoside 
• 29836-26-8 n-octyl β-D-glucopyranoside 

Relevant academic research and scientific papers

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.

Efficient production and separation of biodegradable surfactants from cellulose in 1-butyl-3-methylimidazolium chloride

Alkyl glycoside biodegradable surfactants were produced from cellulose and 1-octanol or 1-dodecanol in a one-pot, two-step (hydrolysis-glycosidation) process in 1-butyl-3-methylimidazolium chloride. Both surfactant productivity and separation efficiencies have been strikingly enhanced compared to other previously reported ionic liquid processes. Production temperatures were decreased to limit the extent of glucose dehydration and further degradation processes, but the conversions remained high. Surfactant molar yields up to 72% were achieved by operating at 70°C. Several separation procedures were tested to achieve high recoveries of both surfactant and ionic liquid. The use of a silica stationary phase was useful for isolation of the surfactant, whereas crystallization of the ionic liquid improved its separation efficiency. Finally, the precipitation of dodecyl glycosides in aqueous media was highly efficient for their isolation and for the recovery (> 99 %) of the ionic liquid by using only water as the solvent for separation.

Transformation of cellulose into biodegradable alkyl glycosides by following two different chemical routes

The transformation of cellulose into long-chain alkyl glycoside surfactants has been carried out following two different routes: (1) Direct transformation of cellulose to butyl-, hexyl-, octyl-, decyl- and dodecyl-α,β- glycosides in an ionic liquid media and Amberlyst-15Dry as catalysts, with mass yield of up to 82%; and (2) two steps reaction with transformation of cellulose into methyl glucosides, with a procedure described by Zhang et al., followed by transacetalation with 1-octanol and 1-decanol in the presence of Amberlyst-15Dry. A kinetic study for the direct transformation of cellulose using 1-octanol has shown that depolymerisation of cellulose continues during the Fischer glycosidation. Increasing the chain length of the alcohol decreases the global reaction rate owing to an increase in the lipophilicity of the alcohol that decreases its contact with the carbohydrates. Finally, several acid catalysts were tested and the best results were obtained with Amberlyst-15Dry.

Direct conversion of xylan into alkyl pentosides

Xylan has been used as a raw material in the synthesis of butyl, octyl and decyl glycosides. Mixtures of d-xylose-, l-arabinose- and d-glucose-based surfactants were obtained under smooth conditions with high yields in a one-pot process. The surface activities of octyl and decyl glycosides thus obtained have been studied and compared with that of pure alkyl d-xylosides. The results have confirmed that the new synthetic approach described in this paper is a potentially economical and efficient method for the preparation of environmentally friendly surfactants.

One pot catalytic conversion of cellulose into biodegradable surfactants

Cellulose has been directly converted into environmentally friendly alkyl glycoside surfactants in a one pot transformation. By working in ionic liquid media with Amberlyst 15Dry (A15) as catalyst and coupling the rate of cellulose hydrolysis and the rate of glycosidation of the monosaccharides formed with C4 to C8 alcohols, it was possible to obtain 82% mass yield of octyl-α,β-glucoside plus octyl-α,β-xyloside.

Montmorillonite K-10 as a reusable catalyst for fischer type of glycosylation under microwave irradiation

Montmorillonite K-10-catalyzed Fischer type glycosylation was studied for various monosacharides with different alcohols under microwave irradiation. The method was found to be efficient, economic, simple, and time saving and the catalyst montmorillonite K-10 was reused three times without loss of catalytic activity and anomeric selectivity. With glycerol, the method gave products glycosylated at primary alcohols only.

Sulfuric acid immobilized on silica: an excellent catalyst for Fischer type glycosylation

Fischer glycosylation, a widely used technique for the preparation of simple alkyl or aryl glycosides, has a few drawbacks including the use of strong mineral acids, excess alcohols, high temperature and long reaction times. This manuscript highlights a modification using sulfuric acid immobilized on silica as catalyst for the preparation of glycosides from free sugars such as d-glucose, d-galactose, d-mannose, l-rhamnose, l-fucose, N-acetyl-d-glucosamine and d-maltose with a diverse range of alcohols to afford a series of useful sugar derivatives in good to excellent yields.

Angiogenic and blood perfusion inducing properties of amphiphilic compounds

A method for enhancing angiogenesis and/or blood vascular perfusion in mammals by administering a pharmacologically effective amount of specific angiogenically active non-ionic, anionic, cationic and zwitterionic amphiphilic compounds. An angiogenically effective amount of the angiogenically active compound digitonin is in the range of at least 1.25 microgram to at least 200 microgram of digitonin. The range including enhancement of vascular perfusion is up to 50 mg of digitonin.