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

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 
• 3458-28-4 D-Mannose 
• 530-26-7 D-Mannose 
• 5019-25-0 methyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 563-63-3 silver(I) acetate 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 71-43-2 benzene 
• 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 
• 99337-73-2 1,2,3,6-tetra-O-acetyl-4-O-trityl-β-D-glucopyranose 
• 127066-72-2 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranosyl-1-deoxy-1-thiocyanate 
• 130052-60-7 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl thiocyanate 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 

Downstream Products

• 13242-51-8 1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside 
• 125354-48-5 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 37797-55-0 1-O-phenyl-2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 14227-52-2 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl chloride 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 13242-53-0 acetobromomannose 
• 6087-47-4 O³,O⁴,O⁶-triacetyl-O²-trichloroacetyl-β-D-mannopyranosyl chloride 
• 74590-42-4 o-cyanophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 28619-26-3 p-cresyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 134698-99-0 phenylethyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 134698-98-9 p-phenylphenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 

Relevant articles and documents

Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents

In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.

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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.

A Sweet H2S/H2O2Dual Release System and Specific Protein S-Persulfidation Mediated by Thioglucose/Glucose Oxidase

H2S and H2O2 are two redox regulating molecules that play important roles in many physiological and pathological processes. While each of them has distinct biosynthetic pathways and signaling mechanisms, the crosstalk between these two species is also known to cause critical biological responses such as protein S-persulfidation. So far, many chemical tools for the studies of H2S and H2O2 have been developed, such as the donors and sensors for H2S and H2O2. However, these tools are normally targeting single species (e.g., only H2S or only H2O2). As such, the crosstalk and synergetic effects between H2S and H2O2 have hardly been studied with those tools. In this work, we report a unique H2S/H2O2 dual donor system by employing 1-thio-β-d-glucose and glucose oxidase (GOx) as the substrates. This enzymatic system can simultaneously produce H2S and H2O2 in a slow and controllable fashion, without generating any bio-unfriendly byproducts. This system was demonstrated to cause efficient S-persulfidation on proteins. In addition, we expanded the system to thiolactose and thioglucose-disulfide; therefore, additional factors (β-galactosidase and cellular reductants) could be introduced to further control the release of H2S/H2O2. This dual release system should be useful for future research on H2S and H2O2.

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An alternative approach for the synthesis of sulfoquinovosyldiacylglycerol

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Mannose-modified azide exosome and application thereof

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