140147-38-2

Basic information

• Product Name: Octylb-D-mannopyranoside
• Synonyms: Octyl beta-D-mannopyranoside;1-O-Octyl-β-D-Mannopyranoside
• CAS NO: 140147-38-2
• Molecular Formula: C₁₄H₂₈O₆
• Molecular Weight: 292.369
• Product Categories: Carbohydrates & Derivatives
• Mol File: 140147-38-2.mol

Chemical Properties

• Melting Point: 80-82°C
• Appearance: /
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Octylb-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Octylb-D-mannopyranoside(140147-38-2)
• EPA Substance Registry System: Octylb-D-mannopyranoside(140147-38-2)

Safety Data

• Hazardous Substances Data: 140147-38-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Octyl β-D-Mannopyranoside is used as an intermediate in the synthesis of various organic compounds. Its application is primarily due to its unique structure, which can be manipulated to create a range of different molecules with specific properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Octyl β-D-Mannopyranoside is used as a building block for the development of new drugs. Its unique structure allows it to be incorporated into drug molecules, potentially enhancing their efficacy and selectivity.
Used in Chemical Research:
Octyl β-D-Mannopyranoside is also used in chemical research as a model compound for studying the properties and behavior of similar sugar-based molecules. This can help researchers better understand the interactions between these molecules and their biological targets.
Used in Material Science:
In the field of material science, Octyl β-D-Mannopyranoside can be used to develop new materials with specific properties. Its unique structure can be used to create materials with tailored characteristics, such as improved solubility or enhanced stability.
Overall, Octyl β-D-Mannopyranoside is a versatile compound with a wide range of applications across different industries. Its unique structure and properties make it a valuable tool in organic synthesis, pharmaceutical development, chemical research, and material science.

Upstream product

• 71091-89-9 n-octyl triflate 
• 128299-96-7 n-octyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 111-87-5 octanol 
• 267890-72-2 n-octyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 

Downstream Products

• 1173893-91-8 C₃₃H₄₂O₆ 
• 141936-72-3 Octyl endo-2,3:4,5-di-O-benzylidene-β-D-mannopyranoside 
• 141936-71-2 Octyl exo-2,3:4,6-di-O-benzylidene-β-D-mannopyranoside 

Relevant articles and documents

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.

Polyvinyl trisulfonate ethylamine based solid acid catalyst for the efficient glycosylation of sugars under solvent free conditions

Heterogeneous Bronsted solid acid catalysts have the potential to decrease the environmental impact related to chemical production. Herein, we have synthesized polyvinyl bound trisulfonate ethylamine chloride (PV-THEAC) and polyvinyl bound disulfonate ethylamine (PV-DSEA) as Bronsted solid acid catalysts which exhibited effective catalytic activity for acid catalyzed glycosylation reactions with sugar derivatives. In particular, 0.3 equiv. of the PV-THEAC catalyst was found to be the most efficient and a reusable catalyst for glycosylation reactions. A high density of the trisulfonic group (-OSO3H) contributed to the excellent catalytic activity during glycosylation. Moreover, glycosylation reactions with d-mannose, d-xylose and d-glucose have been studied with alcohol. Remarkable acceleration of the glycosylation reaction using a glycosyltrichloroacetimidate donor was obtained with the selective production of β-glycoside.

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.

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.

POLYMER STABILIZER

A polymer stabilizer comprising the following alkoxy compound: the alkoxy compound: a compound obtained by alkoxylating at least one hydroxyl group contained in a compound of the following formula (1) containing one formyl group or carbonyl group and (n?1) hydroxyl groups in the molecule with an alkyl group having 1 to 12 carbon atoms: [in-line-formulae]CnH2nOn??(1)[/in-line-formulae] (wherein, n represents an integer of 3 or more).

A simple polar deacetylated caloporoside derivative is a positive modulator of the GABA(A) chloride channel complex in cortical mammalian neurones

Synthesis of octyl-O-β-D-mannopyranoside, a caloporoside analogue was achieved by the activation of 2,3,4,6-tetra-O-benzyl-1-O-1',3'2'-dioxaphosphacy clohexane-α,β-D-mannopyranosyl-2-oxide with TMSOTf (Trimethyl silyl triflate) and subsequent debenzylation. At 100 μM the molecule significantly and reversibly increased the magnitude of GABA(A) currents evoked in cultured rat pyramidal neurones whilst concomitantly reducing the incidence of spontaneous synaptic activity. These results contradict earlier proposals that such molecules bind to the TBPS (tert-Butylbicyclophosphorothionate) site to block the chloride channel. (C) 2000 Elsevier Science Ltd. All rights reserved.