604-69-3

Basic information

• Product Name: beta-D-Glucose pentaacetate
• Synonyms: Beta-Pentacetylglucose;b-D-GLUCOSE PENTACETATE;Penta-O-acetyl-beta-D-glucopyranose Pentaacetyl-beta-D-glucose 1,2,5,6-Di-O-isopropylidene-D- Mannitol 1,2:5,6-Bis-o-(1-Methylethylidene)-D-Mannitol 1,2-Bis(2,2-Dimethyl-1,3-Dioxolan-4-yl)-1,2-Ethanediol 1,2,3,4,6-Penta-O;beta-D-Glucose Pentaacetate,99%d.e.;-D-Glucose pentaacetate for synthesis;PENTAACETYL-BETA-D-GLUCOSE;PENTA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE;PENTA-O-ACETYL-BETA-D-GLUCOPYRANOSE
• CAS NO: 604-69-3
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34
• EINECS: 210-074-8
• Product Categories: Sugars, Carbohydrates & Glucosides;Biochemistry;Glucose;O-Substituted Sugars;Sugars;Carbohydrates & Derivatives;carbohydrate
• Mol File: 604-69-3.mol
• Article Data: 312

Chemical Properties

• Melting Point: 130-132 °C
• Boiling Point: 435.58°C (rough estimate)
• Flash Point: 188.1 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1,274 g/cm3
• Vapor Pressure: 9.23E-08mmHg at 25°C
• Refractive Index: 4.5 ° (C=5, CHCl3)
• Storage Temp.: 2-8°C
• Solubility: chloroform: 0.1 g/mL, clear, colorless
• Water Solubility: Soluble in chloroform and methanol. Insoluble in water.
• BRN: 98851
• CAS DataBase Reference: beta-D-Glucose pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: beta-D-Glucose pentaacetate(604-69-3)
• EPA Substance Registry System: beta-D-Glucose pentaacetate(604-69-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 21-36/38-46-62-63
• Safety Statements: 24/25-53-36/37-26-25
• WGK Germany: 3
• Hazardous Substances Data: 604-69-3(Hazardous Substances Data)

Usage

Chemical Properties

white to beige powder

Uses

Different sources of media describe the Uses of 604-69-3 differently. You can refer to the following data:
1. beta-D-Glucose pentaacetate was reported to stimulate insulin release in rat pancreatic islets.
2. β-D-Glucose Pentaacetate is used in biochemical reaction and also used as an active pharmaceutical intermediate. Further, it is used to stimulate insulin release in rat pancreatic islets.

Purification Methods

Crystallise the pentaacetate from MeOH or EtOH. It is best purified by recrystallising 160g from 1L of hot 95% EtOH (charcoal) and filtering hot. It is important that as soon as the temperature of the filtrate cools to ~20o it is filtered off. Note that some -D-isomer will crystallise out if a prolonged crystallisation period is allowed. Further crystallisation in this manner and drying in a vacuum over CaCl2 will give pure -D-anomer which has m 132o, [] D 20 + 4o (c 5, CHCl3). [Wolfrom & Thompson Methods in Carbohydrate Chemistry II 212 1963, Academic Press, Krahl & Cori Biochemical Preparations 1 33 1955, Beilstein 17/7 V 319.]

InChI:InChI=1/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15-,16-/m1/s1

Upstream product

• 7322-31-8 β-D-mannose 
• 108-24-7 acetic anhydride 
• 530-26-7 D-Mannose 
• 75474-03-2 p-nitrobenzoic acetic anhydride 
• 81342-44-1 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 64-19-7 acetic acid 
• 17460-45-6 tetra-acetyl glucosamine 
• 67-56-1 methanol 
• 2280-44-6 D-Glucose 
• 56180-94-0 acarbose 
• 1013648-93-5 C₂₈H₄₇NO₁₈ 
• 10257-28-0 D-Galactose 
• 3458-28-4 D-Mannose 
• 7296-15-3 alpha-D-mannopyranoside 

Downstream Products

• 25712-94-1 homoarbutin 
• 30361-03-6 (2,4,6-triiodo-phenyl)-(tetra-O-acetyl-α-D-glucopyranoside) 
• 30361-03-6 (2,4,6-triiodo-phenyl)-(tetra-O-acetyl-β-D-glucopyranoside) 
• 380153-99-1 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylbenzoate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 2887-07-2 4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 14581-83-0 helicin acetate 
• 91364-06-6 ortho-hydroxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 898283-47-1 1,2-Bis-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzene 
• 51482-43-0 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)vanillin 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 17042-34-1 3-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 5346-66-7 2-methylphenyl-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside 
• 32742-28-2 2-methylphenyl-tetra-O-acetyl-α-D-glucopyranoside 

Relevant articles and documents

Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity

Tacrine is a known Acetylcholinesterase (AChE) inhibitors having hepatotoxicity as main liability associated with it. The present study aims to reduce its hepatotoxicity by synthesizing tacrine linked triazole glycoconjugates via Huisgen's [3 + 2] cycloaddition of anomeric azides and terminal acetylenes derived from tacrine. A series of triazole based glycoconjugates containing both acetylated (A-1 to A-7) and free sugar hydroxyl groups (A-8 to A-14) at the amino position of tacrine were synthesized in good yield taking aid from molecular docking studies and evaluated for their in vitro AChE inhibition activity as well as hepatotoxicity. All the hybrids were found to be non-toxic on HePG2 cell line at 200 μM (100 % cell viability) as compared to tacrine (35 % cell viability) after 24 h of incubation period. Enzyme kinetic studies carried out for one of the potent hybrids in the series A-1 (IC50 0.4 μM) revealed its mixed inhibition approach. Thus, compound A-1 can be used as principle template to further explore the mechanism of action of different targets involved in Alzheimer's disease (AD) which stands as an adequate chemical probe to be launched in an AD drug discovery program.

Selectivity of 1-O-Propargyl-D-Mannose Preparations

Thanks to their ability to bind to specific biological receptors, mannosylated structures are examined in biomedical applications. One of the most common ways of linking a functional moiety to a structure is to use an azide-alkyne click reaction. Therefore, it is necessary to prepare and isolate a propargylated mannose derivative of high purity to maintain its bioactivity. Three known preparations of propargyl-α-mannopyranoside were revisited, and products were analysed by NMR spectroscopy. The preparations were shown to yield by-products that have not been described in the literature yet. Our experiments showed that one-step procedures could not provide pure propargyl-α-mannopyranoside, while a three-step procedure yielded the desired compound of high purity.

Preparation and formulation optimization of methotrexate-loaded human serum albumin nanoparticles modified by mannose

Background: Methotrexate (MTX) is the representative drug among the dis-ease-modifying anti-rheumatic drugs. However, the conventional treatment with MTX showed many limitations and side effects. Objective: To strengthen the targeting ability and circulation time of MTX in the treatment of rheumatoid arthritis, the present study focused on developing a novel drug delivery system of methotrexate-loaded human serum albumin nanoparticles (MTX-NPs) modified by mannose, which are referred to as MTX-M-NPs. Methods: Firstly, mannose-derived carboxylic acid was synthesized and further modified on the surface of MTX-NPs to prepare MTX-M-NPs. The formulation of nanoparticles was optimized by the method of central composite design (CCD), with the drug lipid ra-tio, oil-aqueous ratio, and cholesterol or lecithin weight as the independent variables. The average particle size and encapsulation efficiency were the response variables. The response of different formulations was calculated, and the response surface diagram, con-tour diagram, and mathematical equation were used to relate the dependent and independent variables to predict the optimal formula ratio. The uptake of MTX-M-NPs by neu-trophils was studied through confocal laser detection. Further, MTX-M-NPs were subject-ed to assessment of the pharmacokinetics profile after intravenous injection with Sprague-Dawley rats. Results: This targeting drug delivery system was successfully developed. Results from Nuclear Magnetic Resonance and Fourier Transform Infrared Spectroscopy analysis can verify the successful preparation of this drug delivery system. Based on the optimized for-mula, MTX-M-NPs were prepared with a particle size of 188.17 ± 1.71 nm and an encapsulation rate of 95.55 ± 0.33%. MTX-M-NPs displayed significantly higher cellular uptake than MTX-NPs. The pharmacokinetic results showed that MTX-M-NPs could pro-long the in vivo circulation time of MTX. Conclusion: This targeting drug delivery system laid a promising foundation for the treatment of RA.