29781-81-5

Usage

Uses

Used in Personal Care Industry:
N-Decyl A-D-Glucopyranoside is used as a surfactant in the formulation of shampoos, body washes, and other personal care products for its excellent foaming and cleaning properties. It is mild and non-irritating to the skin, making it suitable for use in products designed for sensitive skin.
Used in Household Products Industry:
N-Decyl A-D-Glucopyranoside is used as a surfactant in the production of household cleaners for its effective cleaning properties. Its biodegradability and environmental friendliness make it a preferred choice for formulators in this industry.

InChI:InChI=1/C16H32O6/c1-2-3-4-5-6-7-8-9-10-21-16-15(20)14(19)13(18)12(11-17)22-16/h12-20H,2-11H2,1H3/t12-,13-,14+,15-,16+/m1/s1

Upstream product

• 103168-14-5 Decyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 112-30-1 1-Decanol 
• 2816-24-2 o-nitrophenyl D-galactopyranoside 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 25878-60-8 D-galactose pentaacetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 440652-81-3 isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 120001-60-7 decyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 161344-76-9 Decyl 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranoside 
• 31387-97-0 n-butyl D-glucoside 
• 83-87-4 D-glucose pentaacetate 
• 604-69-3 β-D-glucose pentaacetate 

Relevant academic research and scientific papers

Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics

A series of 19 synthetic alkyl and thioalkyl glycosides derived from D-mannose, D-glucose and D-galactose and having C10–C16 aglycone were investigated for cytotoxic activity against 7 human cancer and 2 non-tumor cell lines as well as for antimicrobial potential on 12 bacterial and yeast strains. The most potent compounds were found to be tetradecyl and hexadecyl β-D-galactopyranosides (18, 19), which showed the best cytotoxicity and therapeutic index against CCRF-CEM cancer cell line. Similar cytotoxic activity showed hexadecyl α-D-mannopyranoside (5) but it also inhibited non-tumor cell lines. Because these two galactosides (18, 19) were inactive against all tested bacteria and yeast strains, they could be a target-specific for eukaryotic cells. On the other hand, β-D-glucopyranosides with tetradecyl (11) and hexadecyl (12) aglycone inhibited only Gram-positive bacterial strain Enterococcus faecalis. The studied glycosides induce changes in the lipid bilayer thickness and lateral phase separation at high concentration, as derived from SAXS experiments on POPC model membranes. In general, glucosides and galactosides exhibit more specific properties. Those with longer aglycone show high cytotoxicity and therefore, they are more promising candidates for cancer cell line targeted inhibition.

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.

Micellar effect on the direct Fischer synthesis of alkyl glucosides

This manuscript presents results from the investigation on the synthesis of alkyl glucosides by the novel, very efficient and environmentally friendly protocol of the Fischer-type synthesis from unprotected glucose and aliphatic alcohols. The use of the dual functionality catalysts (surfactant?+?acid catalyst) and micellar reaction system are the main novelty of described method. It has been found, that in developed method of synthesis the reaction of unprotected glucose with aliphatic alcohols carried out with significantly different route, than the normal (classical) route and leads to alkyl glucopyranoside derivatives with high yields. In progress analyses by DLS, HPLC and GC/MS confirm the general postulated pathway of developed method.

Synthesis and Properties of Alkyl β-d-Galactopyranoside

A series of alkyl β-d-galactopyranosides were prepared by the trichloroacetimidate method with d-galactose and alcohols with different chain lengths as raw materials. Their solubility, surface tension, emulsification, foaming, wettability, thermotropic liquid crystalline properties, and thermal stability were investigated. Alkyl β-d-galactopyranosides are soluble in water and ethanol, and the solubility decreases with increasing alkyl chain length. Decyl β-d-galactopyranoside was insoluble in water, but soluble in ethanol. Dissolution of alkyl β-d-galactopyranoside in water is an endothermic process with dissolution enthalpies greater than zero. Nonyl β-d-galactopyranoside had an excellent emulsifying?property, better foaming ability and the best foam stability. The CMC values of alkyl β-d-galactopyranosides decrease with increasing of alkyl chain length. Alkyl β-d-galactopyranosides are thermally stable up to 270?°C. Alkyl β-d-galactopyranosides show the distinctive optical texture of a thermotropic liquid crystal smectic A type phase. Decyl β-d-galactopyranoside showed the strongest wettability.

Protecting-group-free O-glysosidation using p-toluenesulfonohydrazide and glycosyl chloride donors

A range of N′-glycosylsulfonohydrazides (GSHs) display good reactivity but poor stereoselectivity in protecting-group-free O-glycosidations when a moderate excess of the model acceptor n-decanol is employed. This stable, readily-accessed class of donor may be more tractable for the glycosylation of non-volatile acceptors than Fischer's glycosidation conditions. It is possible to generate unprotected glycosyl chlorides from GSHs in situ. In an effort to find conditions to improve glycosidation stereoselectivity, methanolysis of unprotected glucosyl chloride under halide-ion exchange conditions was examined. Relative to its tetra-O-benzyl analogue, this donor displays moderate, inverted stereoselectivity and a significantly faster reaction rate.

The anomeric mixture of some O-galactolipid derivatives is more toxic against cancer cells than either anomer alone

The anomeric mixture of a series of O-galactolipid derivatives is revealed to be more toxic against several cancer cell lines than their either single component with the pure α- or β-configuration. This interesting phenomenon has been confirmed on pairs of synthesized O-galactosyl anomers bearing length-varied alkyl chains at the lipid end. Furthermore, the most potent mixture was determined inoffensive to a normal cell line tested.

Current perspectives on microwave-enhanced reactions of monosaccharides promoted by heterogeneous catalysts

Involvement of heterogeneous catalysts as promoters of carbohydrate conversions, in synergy with microwaves as the heating source, is reported. This paper deals with the application of ion-exchange resins, zeolites, clays and metal oxides as convenient mediators for key transformations of carbohydrates. A special emphasis is placed on the use of (doped) mineral supports, in solventless conditions, as clean promoters in combination with microwave dielectric heating.

Synthesis, surface activities and antimicrobial properties of n-alkyl - glucosides and maltosides

THIS WORK was designed to synthesize n-alkyl α-D- glucopyranosides and α-D-maltopyranosides with alkyl chains having from 8 to 18 carbon atoms in acid catalyst under different conditions. Stearyl alcohol was reacted with glucose and the parameters affecting the yield of stearyl glucoside were tested in an attempt to optimize the reaction conditions leading to maximum glucoside production, e.g. effect of temperature, time, solvent and type of acid catalyst. A large group of fatty glucosides and maltosides were prepared and their surface properties were evaluated such as surface tension (γ), interfacial tension (γI), critical micelle concentration (CMC), occupation area of molecule (A), lime soap dispersion (LSD), foaming, wetting, emulsification, dishwashing powers and the efficiency of these surfactants to be used as foam boosters. Furthermore, the antimicrobial activities of these compounds were also evaluated.

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 III - Synthesis of alkyl D-galactopyranosides in the presence of tin(IV) chloride as a Lewis acid catalyst

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