41444-57-9

Basic information

• Product Name: BUTYL GLUCOSIDE
• Synonyms: BUTYL GLUCOSIDE
• CAS NO: 41444-57-9
• Molecular Formula: C10H20O6
• Molecular Weight: 236.2622
• Mol File: 41444-57-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BUTYL GLUCOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BUTYL GLUCOSIDE(41444-57-9)
• EPA Substance Registry System: BUTYL GLUCOSIDE(41444-57-9)

Safety Data

• Hazardous Substances Data: 41444-57-9(Hazardous Substances Data)

Upstream product

• 6697-88-7 2,3,4,6-tetra-O-acetyl-1-n-butyl-β-D-glucopyranoside 
• 498-07-7 levoglucosan 
• 71-36-3 butan-1-ol 
• 5391-18-4 butyl-α-D-glucopyranoside 
• 1464-44-4 phenyl-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 604-69-3 β-D-glucose pentaacetate 
• 57-50-1 Sucrose 
• 50-99-7 D-glucose 
• 9004-34-6 cellulose 
• 492-61-5 β-D-glucose 
• 25320-91-6 propyl β-D-glucopyranoside 
• 69984-73-2 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-nonyloxy-tetrahydro-pyran-3,4,5-triol 
• 54623-03-9 butyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 

Downstream Products

• 153323-26-3 butyl 6-O-stearoyl-α-D-glucopyranoside 

Relevant articles and documents

Preparation of Long-Chain Alkyl Glucoside Surfactants by One-Step Direct Fischer Glucosidation, and by Transacetalation of Butyl Glucosides, on Beta Zeolite Catalysts

Long-chain alkyl glucoside surfactants have been obtained with good conversions and selectivities by the transacetalation of butyl glucosides with different fatty alcohols as well as by one-step direct glycosidation, using H-Beta zeolites as catalyst. The influence of the different process variables such as temperature, molar ratio of reactants, and fatty alcohol chain length has been investigated. Moreover, the study of the transacetalation process in the presence of H-Beta zeolites with different hydrophobic-hydrophilic properties has shown the strong influence of this zeolite property on catalyst deactivation. The rate of decay is lower for the more hydrophobic Beta Samples.

Bio-based Surfactants

Bio-based surfactants have great opportunity for use in a variety of applications such as laundry detergents, industrial cleaners, adjuvants, and oil and gas. Surfactants in these applications can be nonionic, anionic, cationic, or amphoteric. Utilizing high oleic soybean oil as a platform chemical, a variety of surfactants and properties can be produced. While early work focused solely on surfactant use in laundry cleaning and fracking, recent work has expanded functional groups and application evaluations in hard surface cleaning. The current invention expands on Battelle's high oleic soybean oil (HOSO) surfactant technology. Use of HOSO overcomes the limitations of regular soybean oil and significantly reduces or eliminates undesirable byproducts in most chemistries. However, with use of select reagents, a few candidates were achievable with regular epoxidized soybean oil (ESO). The HOSO surfactant platform offers several key advantages including: a highly water miscible (not typical of C18 surfactants) and water stable surfactant; ability to adjust and vary hydrophilic-lipophilic (HLB) values for stain removal performance; and increased biodegradability without toxic or persistent by-products.

Selective Primary Alcohol Oxidation of Lignin Streams from Butanol-Pretreated Agricultural Waste Biomass

Chemically modified lignins are important for the generation of biomass-derived materials and as precursors to renewable aromatic monomers. A butanol-based organosolv pretreatment has been used to convert an abundant agricultural waste product, rice husks, into a cellulose pulp and three additional product streams. One of these streams, a butanol-modified lignin, was oxidized at the γ position to give a carboxylic acid functionalized material. Subsequent coupling of the acid with aniline aided lignin characterization and served as an example of the flexibility of this approach for grafting side chains onto a lignin core structure. The pretreatment was scaled up for use on a multi-kilogram scale, a development that enabled the isolation of an anomeric mixture of butoxylated xylose in high purity. The robust and scalable butanosolv pretreatment has been developed further and demonstrates considerable potential for the processing of rice husks.

Preparation of salidroside with n-butyl β-D-glucoside as the glycone donor via a two-step enzymatic synthesis catalyzed by immobilized β-glucosidase from bitter almonds

β-Glucosidase from bitter almonds was immobilized on epoxy group-functionalized beads for catalyzing salidroside synthesis in a two-step process with n-butyl-β-D-glucoside (BG) as the glucosyl donor. The formation of salidroside ((0.59 ± 0.02) M) at a yield of 39.04%±1.25% was accomplished in 8 h by the transglucosylation of immobilized β-glucosidase at pH?8.0 and 50 °C when the ratio of BG to tyrosol was 1:2 (mol/mol). A study on the influence of different glycosyl acceptors demonstrated that the yield of the glucosylation reaction of phenylmethanol and cyclohexanol was higher than that of either phenol or cyclohexanol. This may account for the selectivity of the immobilized enzyme towards the alcoholic hydroxyl group of tyrosol in the salidroside synthesis reaction. A study on the synthesis of BG via the reverse hydrolysis of immobilized β-glucosidase showed that a yield of 78.04%±2.2% BG can be obtained with a product concentration of (0.23 ± 0.015) M.

Influence of acyl groups on glucopyranoside reactivity in Lewis acid promoted anomerisation

Lewis acid promoted anomerisation has potential in O- or S-glycoside synthesis. Herein, the anomerisation kinetics of thirty-one β-D-glucopyranosides was determined to determine how particular acyl protecting groups and their location influence reactivity towards a Lewis acid promoted reaction. The replacement of acetyl groups with benzoyl groups led to reduced reactivity when located at O-3, O-4 and O-6. However a reactivity increase was observed when the acetyl group was replaced by a benzoyl group at O-2. The 2,3,4,6-tetra-O-(4-methoxy)benzoate had an ～2-fold increase in rate when compared to the tetrabenzoate.

Stereoselective Construction of β-Mannopyranosides by Anomeric O-Alkylation: Synthesis of the Trisaccharide Core of N-linked Glycans

A new and efficient approach for direct and stereoselective synthesis of β-mannopyranosides by anomeric O-alkylation has been developed. This anomeric O-alkylation of mannopyranose-derived lactols is proposed to occur under synergistic control of a kinetic anomeric effect and metal chelation. The presence of a conformationally flexible C6 oxygen atom in the sugar-derived lactol donors is required for this anomeric O-alkylation to be efficient, probably because of its chelation with cesium ion. In contrast, the presence of a C2 oxygen atom plays a minor role. This glycosylation method has been successfully utilized for the synthesis of the trisaccharide core of complex N-linked glycans. Lactol in control: The title reaction is believed to occur under synergistic control of a kinetic anomeric effect and metal chelation. The presence of a conformationally flexible C6 oxygen atom in the lactol is required for the reaction to be efficient, probably due to its chelation with cesium ion. This glycosylation method was successfully utilized for the synthesis of the trisaccharide core of complex N-linked glycans.

Acid-Assisted Ball Milling of Cellulose as an Efficient Pretreatment Process for the Production of Butyl Glycosides

Ball milling of cellulose in the presence of a catalytic amount of H2SO4 was found to be a promising pre-treatment process to produce butyl glycosides in high yields. Conversely to the case of water, n-butanol has only a slight effect on the recrystallization of ball-milled cellulose. As a result, thorough depolymerization of cellulose prior the glycosylation step is no longer required, which is a pivotal aspect with respect to energy consumption. This process was successfully transposed to wheat straw from which butyl glycosides and xylosides were produced in good yields. Butyl glycosides and xylosides are important chemicals as they can be used as hydrotropes but also as intermediates in the production of valuable amphiphilic alkyl glycosides.

ALKENYL GLYCOSIDES AND THEIR PREPARATION

An alkenyl glycoside is prepared by reacting a metathesis-derived unsaturated fatty alcohol containing 10 to 30 carbon atoms with either (1) a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide, or (2) a hydrocarbyl glycoside produced by reacting an alcohol containing up to 6 carbon atoms with a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide. Each of these reactions is performed in the presence of an acid catalyst and under conditions sufficient to form the alkenyl glycoside or hydrocarbyl glycoside. The preferred alkenyl glycosides are 9-decen-1-yl glycoside; 9-dodecen-1-yl glycoside; 9-tridecen-1-yl glycoside; 9-pentadecen-1-yl glycoside; 9-octadecen-yl glycoside; or 9-octadecen-1,18-diyl glycoside.

Glycosylation mediated - BAIL in aqueous solution

The use of Br?nsted acid ionic liquid (BAIL) as a catalyst for the activation of unreactive and unprotected glycosyl donors has been demonstrated for the first time in aqueous solution.

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.