5284-99-1

Basic information

• Product Name: Cyclohexyl beta-D-glucopyranoside
• Synonyms: Cyclohexyl beta-D-glucopyranoside
• CAS NO: 5284-99-1
• Molecular Formula: C₁₂H₂₂O₆
• Molecular Weight: 262.3
• Mol File: 5284-99-1.mol

Chemical Properties

• Boiling Point: 457.2°C at 760 mmHg
• Flash Point: 230.3°C
• Appearance: /
• Density: 1.34
• Vapor Pressure: 2.79E-10mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: Cyclohexyl beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexyl beta-D-glucopyranoside(5284-99-1)
• EPA Substance Registry System: Cyclohexyl beta-D-glucopyranoside(5284-99-1)

Safety Data

• Hazardous Substances Data: 5284-99-1(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
Cyclohexyl beta-D-glucopyranoside is used as a sweetening agent and flavor enhancer for its ability to impart a sweet taste and improve the overall flavor profile of products in this industry.
Used in Pharmaceutical Products:
In the pharmaceutical sector, Cyclohexyl beta-D-glucopyranoside serves as an emulsifier and stabilizer, contributing to the uniform dispersion of ingredients and maintaining the stability of formulations.
Used in Cosmetic Products:
Similarly, in cosmetics, Cyclohexyl beta-D-glucopyranoside is utilized as an emulsifier and stabilizer, ensuring the consistency and longevity of cosmetic products by preventing separation of components.
Used in Organic Synthesis:
Cyclohexyl beta-D-glucopyranoside is used as a protective group for hydroxyl groups in organic synthesis, playing a crucial role in shielding these groups during chemical reactions to prevent unwanted side reactions, thereby facilitating the synthesis of desired compounds.

InChI:InChI=1/C12H22O6/c13-6-8-9(14)10(15)11(16)12(18-8)17-7-4-2-1-3-5-7/h7-16H,1-6H2

Upstream product

• 50-99-7 D-glucose 
• 108-93-0 cyclohexanol 
• 1464-44-4 phenyl-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 5391-18-4 n-butyl β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 34272-03-2 propargyl β-D-glucopyranoside 
• 74352-37-7 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(pyridin-2-ylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 6605-39-6 cyclohexyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 89128-35-8 cyclohexyl-(O²,O³,O⁴-triacetyl-O⁶-trityl-β-D-glucopyranoside) 

Relevant articles and documents

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.

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.

Green glycosylation promoted by reusable biomass carbonaceous solid acid: An easy access to β-stereoselective terpene galactosides

An efficient green protocol has been developed for the atom economic glycosylation of unprotected, unactivated glycosyl donors and glycosylation of glycosyl trichloroacetimidates with the aid of reusable eco-friendly biomass carbonaceous solid acid as catalyst. The Royal Society of Chemistry.

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.

Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis

Straightforward glycosylation of various alcohols with unprotected and non-activated monosaccharides were performed under scandium triflate catalysis. Rate and yield of glycosylation were highly improved when using 1-butyl-3-methylimidazolium trifluoromethanesulfonate as a green solvent. This ionic liquid was allowed to be recycled at least three times without loss of activity. The possibility of drastically reducing the amounts of catalyst (down to 1 mol%) and aglycone (down to 1 equiv) when performing the reaction in ionic liquid opens new perspectives in O-glycosylation, as a direct coupling between an aglycone and free sugars.

Glycosylation using unprotected alkynyl donors

(Chemical Equation Presented) Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in ace

Novel reaction systems for the synthesis of O-glucosides by enzymatic reverse hydrolysis

Our studies are presented to replace alcohols as solvents in reverse hydrolytic reactions catalyzed by immobilized β-glucosidase to synthesize O-substituted β-D-glucopyranosides in preparative-scale. We found that 1,2-diacetoxyethane is a suitable solvent and O-alkyl or aryl β-D-glucosides were synthesized in moderate yields (after isolation 12-19%). In these reactions proportion of glucose and glucosyl acceptor hydroxy compounds was 1:20. We suggest that 1,2-diacetoxyethane can be useful not only for alcohols but for other glucosyl donor compounds unsuitable for the role of solvent (e.g., phenols) in the synthesis of O-β-D-glucosides by reverse hydrolysis.

Synthesis of detergent O-glucosides by reverse hydrolysis in alcohol- water biphasic systems using α- and β-glucosidases

The α- and β-glucosidases showed significant O-glycosylation activity with glucose as substrate and with different alcohols both as reaction partners and solvents in reverse hydrolytic processes. With native glucosidases upscaling resulted in low yields due to heterogeneity of reaction mixtures. Immobilization of the enzymes on a modified polyacrylamide-type bead support (Acrylex C-100) increased enzyme stability resulting in higher yields and permitted to perform glucosylations on a larger scale. From these experiments O-alkyl glucosides were isolated in moderate yields.

Enzyme-catalysed synthesis of alkyl β-D-Glucosides in organic media

The synthetic potential of Almond β-D-Glucosidase for the synthesis of alkyl glucosides was studied. The regio and stereoselectivity of the synthesis were analysed for the reverse hydrolysis and the transglucosylation methods in tert-butanol and acetonitrile media.

Preparation of New Terpenyl β-D-Glucopyranosides by a Modified Koenigs-Knorr Procedure.

Ten new hemi- and monoterpenyl β-D-glucopyranosides have been prepared by a modification of the Koenigs-Knorr procedure which utilises silver fluoroacetate as a soluble catalyst coupled with the introduction of a basic ion-exchange resin to effect the deacetylation step.Most of these compounds could not be obtained in acceptable yields using the classical procedure.