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
• Article Data: 13

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

General Description

Cyclohexyl beta-D-glucopyranoside is a chemical compound derived from the sugar glucose. It is a colorless, odorless solid that is soluble in water. This particular compound is often used in the flavor and fragrance industry, particularly as a sweetening agent and flavor enhancer. It is also utilized in pharmaceutical and cosmetic products as an emulsifier and stabilizer. Furthermore, cyclohexyl beta-D-glucopyranoside is commonly used in organic synthesis as a protective group for hydroxyl groups in various chemical reactions. Overall, this compound plays a significant role in various industries due to its sweetening, stabilizing, and emulsifying properties.

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 
• 6605-39-6 cyclohexyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 2280-44-6 D-Glucose 
• 5391-18-4 n-butyl β-D-glucopyranoside 
• 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 

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.

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.

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.