29781-80-4

Usage

Uses

1. Used in Pharmaceutical Industry:
N-OCTYL ALPHA-D-GLUCOPYRANOSIDE is used as an ACE inhibitor for its ability to inhibit the angiotensin-converting enzyme, which plays a crucial role in regulating blood pressure.
2. Used in Chemical Research:
N-OCTYL ALPHA-D-GLUCOPYRANOSIDE is used as a research compound for studying its chemical properties and potential applications in various fields, including drug development and material science.
3. Used in Cosmetics Industry:
N-OCTYL ALPHA-D-GLUCOPYRANOSIDE is used as an ingredient in the cosmetics industry, where it may serve as a skin conditioning agent or contribute to the formulation of various cosmetic products.
4. Used in Food Industry:
N-OCTYL ALPHA-D-GLUCOPYRANOSIDE may be used in the food industry as an additive or ingredient, potentially for its ability to enhance the texture or stability of certain products.

InChI:InChI=1/C14H28O6/c1-2-3-4-5-6-7-8-19-14-13(18)12(17)11(16)10(9-15)20-14/h10-18H,2-9H2,1H3/t10-,11-,12+,13-,14+/m1/s1

Upstream product

• 2280-44-6 D-Glucose 
• 111-87-5 octanol 
• 9004-34-6 cellulose 
• 5391-18-4 butyl-α-D-glucopyranoside 
• 75-36-5 acetyl chloride 
• 128299-96-7 n-octyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 71091-89-9 n-octyl triflate 
• 530-26-7 D-Mannose 
• 267890-72-2 n-octyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 50-99-7 D-glucose 

Downstream Products

• 124-07-2 Octanoic acid 
• 156967-55-4 1-O-octyl-α-D-glucopyranosiduronic acid 
• 492-62-6 alpha-D-glucopyranose 
• 111-87-5 octanol 
• 64-18-6 formic acid 
• 79-14-1 glycolic Acid 
• 488-16-4 D-erythronic acid 
• 80-69-3 tartronic acid 
• 147-73-9 meso-tartaric acid 
• 87-69-4 L-Tartaric acid 
• 526-95-4 gluconic acid 
• 87-73-0 D-glucaric acid 
• 144-62-7 oxalic acid 
• 695228-29-6 n-octyl 4,6-O-benzylidene-α-D-glucopyranoside 

Relevant academic research and scientific papers

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.

Glycosides and?amino acyl esters of?carbohydrates as?potent inhibitors of?angiotensin converting enzyme

About 12 glycosides prepared through amyloglucosidase catalysis and 23 amino acyl esters of carbohydrates prepared through lipase catalysis in organic solvents showed angiotensin converting enzyme (ACE) inhibition activity. Both amino acyl esters of carbohydrates and glycosides exhibited IC50 values for ACE inhibition in the 0.5?mM to 15.7?mM range. Eugenyl-d-glucoside (IC50: 0.5 ± 0.04?mM), l-isoleucyl-d-glucose (IC50: 0.7 ± 0.067?mM), vanillyl-d-sorbitol (IC50: 0.8 ± 0.09?mM), l-histidyl-d-fructose (IC50: 0.9 ± 0.087?mM), l-tryptophanyl-d-fructose (IC50: 0.9 ± 0.092?mM), octyl-d-glucoside (IC50: 1.0 ± 0.093?mM), vanillyl-d-mannoside (IC50: 1.0 ± 0.089?mM), l-valyl-d-mannitol (IC50: 1.0 ± 0.092?mM) and l-phenylalanyl-d-glucose (IC50: 1.0 ± 0.089?mM) were the compounds, which showed the best ACE inhibitory activities.

Estrogenicity of octyl glucoside synthesized by direct glucosidation as non-endocrine disruptive surfactant

The estrogenicity of octyl glucoside was studied with its preparation method using microporous zeolites. Its estrogenicity was estimated using E-assay method to confirm the possibility as nonendocrine disruptive surfactant. The octyl glucoside was synthesized from D-glucose with 1-octanol by direct glucosidation. The high conversion of D-glucose was obtained on H-FAU zeolite which has a mild acid strength. The conversion and yield were improved with increasing of acid site amount of the zeolite catalysts. The octyl glucopyranoside is more hydrophilic than nonylphenol and has a high wettability. The octyl glucosides represented extremely lower estrogenic cell proliferation compared with nonylphenol.

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.

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.

Protection-free synthesis of alkyl glycosides under hydrogenolytic conditions

A convenient protection-free synthetic route for the preparation of alkyl glycosides has been developed. The alcoholysis of one-step preparable glycosyl donors, 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) glycosides, under hydrogenolytic conditions gave the corresponding glycosides in good yields without the addition of any acid promoters. The method could be successfully applied to the glycosylation of an acidlabile oligosaccharide.

Straightforward glycosylation of alcohols and amino acids mediated by ionic liquid

Green glycosylation of functionalized alcohols and α-amino acids, using an ionic liquid as a recyclable solvent, was performed in one step directly from the unprotected monosaccharide under scandium triflate or ferric chloride catalysis. Pure α- and β-glycosides could be obtained after specific enzymatic hydrolysis.