69984-73-2

Usage

Uses

n-Nonyl-beta-D-glucopyranoside is a nonionic surfactant.

Purification Methods

Purify nonyl--D-glucopyranoside by recrystallisation from Me2CO or hexane/Et2O and store it in well-stoppered containers as it is hygroscopic. [Pigman & Richtmyer J Am Chem Soc 64 369 1942.] It is a UV transparent non-ionic detergent for solubilising membrane proteins [Schwendener et al. Biochem Biophys Res Commun 100 1055 1981]. [Beilstein 17 III/IV 2937, 17/7 V 39.]

InChI:InChI=1/C15H30O6/c1-2-3-4-5-6-7-8-9-20-15-14(19)13(18)12(17)11(10-16)21-15/h11-19H,2-10H2,1H3/t11-,12-,13+,14-,15-/m1/s1

Upstream product

• 2280-44-6 D-Glucose 
• 143-08-8 nonyl alcohol 
• 330477-04-8 1-n-nonyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 492-61-5 β-D-glucose 
• 25320-96-1 O-n-pentyl β-D-glucopyranoside 
• 39824-11-8 n-hexyl-β-D-glucopyranoside 
• 58846-77-8 n-decyl β-D-glucopyranoside 
• 78617-12-6 n-heptyl beta-D-glucopyranoside 
• 56401-20-8 α-D-Glucopyranoside 1-(disodium phosphate) 
• 25320-91-6 propyl β-D-glucopyranoside 
• 5391-18-4 n-butyl β-D-glucopyranoside 
• 29836-26-8 n-octyl β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 492-61-5 β-D-glucose 
• 143-08-8 nonyl alcohol 
• 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 
• 25320-91-6 propyl β-D-glucopyranoside 
• 5391-18-4 n-butyl β-D-glucopyranoside 
• 29836-26-8 n-octyl β-D-glucopyranoside 

Relevant academic research and scientific papers

N-alkyl - β - D - glucopyranoside synthetic method

The invention discloses a synthesizing method of n-alkyl-beta-D-glucopyranoside. The method includes the following steps of dissolving fully-acetylated glucopyranose, n-alkyl alcohol and anhydrous stannic chloride in anhydrous methylene dichloride, stirring the mixture to have a reaction for 20 min to 70 min at the room temperature, washing the mixture through a saturated sodium carbonate solution, collecting organic phases, conducting reduced pressure distillation to obtain 1-n-alkyl-2,3,4,6-tetraacetyl-beta-D-glucopyranoside, dissolving the 1-n-alkyl-2,3,4,6-tetraacetyl-beta-D-glucopyranoside in methyl alcohol, adding sodium methylate to adjust the pH value to 9, having a reaction for 1.5 h at the room temperature, adjusting the pH value to be neutral through strong acid cation exchange resin, conducting filtering, steaming filtrate to obtain solvent, and drying the solvent to obtain the n-alkyl-beta-D-glucopyranoside. The n-alkyl is n-alkyl of C8-C12. The method is simple, raw materials are easy to obtain, cost is low, reaction temperature is moderate and easy to control, the method is environmentally friendly, and the prepared beta-configuration glucopyranoside is high in purity.

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.

Significantly Improved Equilibrium Yield of Long-Chain Alkyl Glucosides via Reverse Hydrolysis in a Water-Poor System Using Cross-Linked Almond Meal as a Cheap and Robust Biocatalyst

An array of ten β-D-glucopyranosides with varied alkyl chain lengths were enzymatically synthesized. It was found that for longer alkyl chains a lower initial rate and final yield of glucoside was obtained except for methyl glucoside because of the severe toxicity of methanol to the enzyme. From a thermodynamics point of view, the equilibrium constant and Gibbs free energy variation of the glucoside syntheses were systematically investigated. To improve the final yields of the glucosides containing long alkyl chains the equilibrium of the enzymatic glucoside synthesis was altered. The equilibrium yield of decyl β-D-glucoside increased from 1.9% to 6.1% when the water content was reduced from 10% to 5% (v/v) using tert-butanol as a cosolvent and 0.10 mol/L of glucose as a substrate. As for the other longer alkyl chain glucosides, heptyl β-D-glucoside was found to have significant surface activity as well.

Significantly improved equilibrium yield of long-chain alkyl glucosides via reverse hydrolysis in a water-poor system using cross-linked almond meal as a cheap and robust biocatalyst

An array of ten β-D-glucopyranosides with varied alkyl chain lengths were enzymatically synthesized. It was found that for longer alkyl chains a lower initial rate and final yield of glucoside was obtained except for methyl glucoside because of the severe toxicity of methanol to the enzyme. From a thermodynamics point of view, the equilibrium constant and Gibbs free energy variation of the glucoside syntheses were systematically investigated. To improve the final yields of the glucosides containing long alkyl chains the equilibrium of the enzymatic glucoside synthesis was altered. The equilibrium yield of decyl β-D-glucoside increased from 1.9 to 6.1 when the water content was reduced from 10 to 5 (v/v) using tert-butanol as a cosolvent and 0.10 mol/L of glucose as a substrate. As for the other longer alkyl chain glucosides, heptyl β-D-glucoside was found to have significant surface activity as well.

A convenient stereoselective synthesis of β-D-glucopyranosides

The Koenigs-Knorr method plays a prominent role in the stereoselective synthesis of alkyl D-glucopyranosides via glycosidic linkage. Such an approach requires costly and toxic promoter salts of silver or mercury, which have additional separation problems. In a novel method a less toxic promoter salt like LiCO3 is used for glycosidation of several fatty alcohols including an aromatic alcohol. LiCO3 can be easily separated from the reaction mass and gives good yield.

Novel reaction systems for the synthesis of O-glucosides by enzymatic reverse hydrolysis

Our studies are presented to replace alcohols as solvents in reverse hydrolytic reactions catalyzed by immobilized β-glucosidase to synthesize O-substituted β-D-glucopyranosides in preparative-scale. We found that 1,2-diacetoxyethane is a suitable solvent and O-alkyl or aryl β-D-glucosides were synthesized in moderate yields (after isolation 12-19%). In these reactions proportion of glucose and glucosyl acceptor hydroxy compounds was 1:20. We suggest that 1,2-diacetoxyethane can be useful not only for alcohols but for other glucosyl donor compounds unsuitable for the role of solvent (e.g., phenols) in the synthesis of O-β-D-glucosides by reverse hydrolysis.

BF3 etherate-induced formation of C7-C 16-alkyl β-D-glucopyranosides

BF3 etherate-induced formation of C7-C 16-alkyl D-glucopyranosides is used as the key step in their synthesis from glucose and C7-C16-alkanols.

Synthesis of C7-C16-alkyl glycosides: Part I - Synthesis of alkyl D-glucopyranosides in the presence of tin (IV) chloride as a Lewis acid catalyst

The Lewis acid catalyzed glycosylation reaction of β-peracetylated sugar derivative (glucose) with fatty alkanols is used in a synthesis of C7-C16-alkyl glucopyranosides. The process occurs under the influence of tin (IV) chloride.

Preparation of alkyl α- and β-D-glucopyranosides, thermotropic properties and X-ray analysis

Monohydrates of heptyl to decyl α-D-glucopyranosides as obtained from product mixtures of the Fischer glucosylation were crystallized from water at the Krafft point. The results of the single-crystal X-ray analysis of anhydrous α anomers and their monohydrates provide for a better understanding of crystal formation and stability of their hydrates. The preparation of alkyl β-D-glucopyranosides-without concomitant formation of α anomers as by-products-has been described. The thermotropic properties have been investigated for the α compounds and their monohydrates, and for the β-D-glucopyranosides. Copyright (C) 1998 Elsevier Science Ltd.