38954-67-5

Usage

Uses

Used in Biochemistry and Molecular Biology Research:
1-O-Octyl-beta-D-glucopyranoside 2,3,4,6-tetraacetate is used as a solubilizing agent for membrane proteins and lipids, facilitating their study and analysis. Its increased lipophilicity and solubility, due to the acetyl groups, make it particularly effective in stabilizing these biological molecules during purification and crystallization processes.
Used in Membrane Protein Purification:
In the field of protein purification, 1-O-Octyl-beta-D-glucopyranoside 2,3,4,6-tetraacetate is used as a detergent to solubilize membrane proteins, which are otherwise difficult to isolate due to their hydrophobic nature. This allows for the efficient extraction and subsequent study of these proteins.
Used in Crystallization of Membrane Proteins:
For structural biology, 1-O-Octyl-beta-D-glucopyranoside 2,3,4,6-tetraacetate is utilized as a component in crystallization cocktails to aid in the formation of well-ordered protein crystals. These crystals are essential for determining the three-dimensional structure of membrane proteins using techniques such as X-ray crystallography.
Used in Detergent Formulation:
In the detergent industry, 1-O-Octyl-beta-D-glucopyranoside 2,3,4,6-tetraacetate is used as a component in the formulation of non-ionic surfactants. Its properties contribute to the development of effective cleaning agents that can dissolve a wide range of substances, including lipids and proteins, without causing damage to sensitive materials.

InChI:InChI=1/C22H36O10/c1-6-7-8-9-10-11-12-27-22-21(31-17(5)26)20(30-16(4)25)19(29-15(3)24)18(32-22)13-28-14(2)23/h18-22H,6-13H2,1-5H3/t18-,19-,20+,21-,22-/m1/s1

Upstream product

• 111-87-5 octanol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 934-87-2 S-phenyl thioacetate 
• 108-24-7 acetic anhydride 
• 29836-26-8 n-octyl β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 83-87-4 D-glucose pentaacetate 
• 2280-44-6 D-Glucose 
• 41444-50-2 n-octyl glucopyranoside 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 1420786-79-3 per-O-acetyl-D-glucopyranosyl-o-(phenylethynyl)benzoate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 188778-83-8 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(8-hydroxy-octyloxy)-tetrahydro-pyran-4-yl ester 
• 724771-77-1 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(8-iodo-octyloxy)-tetrahydro-pyran-4-yl ester 

Downstream Products

• 102935-48-8 octyl (2,3,4,6-tetra-O-acetyl)-α-D-glucopyranoside 
• 29836-26-8 n-octyl β-D-glucopyranoside 
• 724771-79-3 octyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranoside 
• 724771-78-2 (2R,3R,4S,5S,6R)-2-Octyloxy-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol 

Relevant academic research and scientific papers

N-Octyl (Thio)glycosides as Potential Cryoprotectants: Glass Transition Behaviour, Membrane Permeability, and Ice Recrystallization Inhibition Studies

A series of eight n-octyl (thio)glycosides (1α, β-4α, β) with d-glucose or d-galactose-configured head groups and varying anomeric configuration were synthesized and evaluated for glass transition behaviour, membrane permeability, and ice recrystallization inhibition (IRI) activity. Of these, n-octyl β-d-glucopyranoside (2β) exhibited a high glass transition temperatures (Tg), both as a neat sample and 20 wt-% aqueous solution. Membrane permeability studies of this compound revealed cellular uptake to concentrations relevant to the inhibition of intracellular ice formation, thus presenting a promising lead candidate for further biophysical and cryopreservation studies. Compounds were also evaluated as ice recrystallization inhibitors; however, no detectable activity was observed for the newly tested compounds.

Synthesis, PASS predication, in vitro antimicrobial evaluation and pharmacokinetic study of novel n-octyl glucopyranoside esters

Octyl β-D-glucopyranoside (OBG), prepared from D-glucose and octan-1-ol employing MW method, was subjected to direct dimolar valeroylation in pyridine at room temperature (25 °C) with valeroyl chloride. This mainly furnished the corresponding 3,6-di-O-valeroate in 57% yield indicating the regioselectivity at C-6 and C-3 positions. For structural elucidation and to get newer glucopyranosides of potential antimicrobial 3,6-di-O-valeroate was further converted into four novel 2,4-di-O-acyl esters reasonably in good yields. Per-O-acetate and per-O-benzoate of OBG were also prepared for SAR study. PASS predication and in vitro antimicrobial studies established them as better antifungal agent than that of antibacterial. SAR study along with AdmetSAR and SwissADME suggested that incorporation of alkanoyl and aromatic ester groups on octyl glucopyranoside core increase antimicrobial potentiality in very low concentration (10 μgmL?1). Molecular docking revealed that novel 2,4-di-O-tosyl ester and 2,3,4,6-tetra-O-benzoyl ester may act as competitive inhibitors of lanosterol 14-alpha demethylase.

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.

Exploring the meaning of sugar configuration in a supramolecular environment: Comparison of six octyl glycoside micelles by ITC and NMR spectroscopy

A series of octyl α- and β-glycosides of the manno- galacto- and gluco-series were synthesized and employed in formation of homo- and hetero-micelles in water. Critical micelle concentrations (cmc), thermodynamic quantities of demicellation and, to some extent, the hydrodynamic radii of glycomicelles were determined by isothermal titration calorimetry (ITC) and diffusion NMR studies. The goal of this work was to determine the significance of anomeric configuration as well as of epimerisation at the sugar ring for supramolecular features of the respective glycoside. A new projection of glycoside structures is proposed to facilitate interpretation of structure-property relationships in this regard. This journal is the Partner Organisations 2014.

Solvent-free mechanochemical glycosylation in ball mill

Starting from acetobromosugars and an alcohol (alkyl/substituted alkyl/akenyl/alkynyl/glyceryl/cyclohexyl/steryl) various O-glycosides have been prepared mechanochemically under solvent-free conditions employing a planetary ball mill in the presence of metal carbonates (environmentally benign or otherwise) as promoters. The method was proven to be mild and efficient and applicable on preparative scale for the synthesis of various mono- and disaccharide glycosides. 4-Pentenyl glycoside so produced could, in four successive reactions in the same pot, be converted in high isolated yields into triazole-substituted pentyl glycoside that can find application in the area of medicinal chemistry.

Use of iodine for efficient and chemoselective glycosylation with glycosyl ortho-alkynylbenzoates as donor in presence of thioglycosides

A novel and high yielding glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors and iodine as promoter is described. The donors are stable and can be chemoselectively activated in the presence of thioethyl and thiophenyl glycosides. The application of this methodology in one-pot consecutive glycosylation reaction is described.

Efficient glycosylation of unprotected sugars using sulfamic acid: A mild eco-friendly catalyst

Sulfamic acid, a mild and environmentally benign catalyst has been successfully used in the Fischer glycosylation of unprotected sugars for the preparation alkyl glycosides. A diverse range of aliphatic alcohols have been used to prepare a series of alkyl glycosides in good to excellent yield.

Microwave-assisted synthesis of long-chain alkyl glucopyranosides

Long-chain (C6 to C16) alkyl glucopyranosides have been synthesized using microwave irradiation. Yields and anomeric ratios can be controlled under precise and short irradiation times (few min). Comparison with classical heating showed a better efficiency of microwaves.

Synthesis of sugar-based chelating surfactants for metal removal from wastewater

Four chelating surfactants were synthesized in a few steps from octyl d-glucosides. Their main interfacial properties were determined, and their flotation properties were evaluated on a laboratory scale using Fe(III) as a model contaminant metal. The performance on metal extraction was mainly dependent on the complexing functional group, but the surfactant efficiency was also important.

Zeolite-catalyzed Helferich-type glycosylation of long-chain alcohols. Synthesis of acetylated alkyl 1,2-trans glycopyranosides and alkyl 1,2-cis C2-hydroxy-glycopyranosides

Zeolite-catalyzed glycosylation of long-chain alcohols, using the inexpensive and readily available peracetylated β-d-gluco- and galactopyranoses as glycosyl donors under solvent free conditions, has been explored for the first time. Among the various forms (H-, Na-, Fe- and Zn) of β zeolite examined as catalysts in the reaction of 1,2,3,4,6-penta-O-acetyl-β-d-galactopyranose with cetyl alcohol, Fe-β zeolite gave the maximum yield of 63% of cetyl 2,3,4,6-tetra-O-acetyl-β-d-galactopyranoside and cetyl 3,4,6-tri-O-acetyl-α-d-galactopyranoside. Fe-β Zeolite-catalyzed glycosylation was found to be general affording the title compounds in each case in a moderate yield, but with a good stereoselectivity. The yield of synthetically valuable acetylated long-chain alkyl 1,2-cis C2-hydroxy-glycopyranosides obtained in the present single-step procedure is considerably higher than that of the previously reported multi-step method employing the Stork silicon tether approach.