604-68-2

Basic information

• Product Name: Glucose pentaacetate
• Synonyms: Glucopyranose, pentaacetate, alpha-D-;1,2,3,4,6-PENTA-O-ACETYL-A-D-GLUCOPYRANOSE;1,2,3,4,6-PENTA-O-ACETYL-A-GLUCOPYRANOSE;1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-GLUCOPYRANOSE;1,2,3,4,6-PENTA-O-ACETYL-ALPHA-GLUCOPYRANOSE;1,2,3,4,6-PENTAACETYL-ALPHA-D-GLUCOSE;ALPHA-D-GLUCOPYRANOSE-PENTAACETATE;ALPHA-GLUCOSE PENTAACETATE
• CAS NO: 604-68-2
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34
• EINECS: 210-073-2
• Product Categories: chiral;Biochemistry;Glucose;O-Substituted Sugars;Sugars;Dextrins、Sugar & Carbohydrates;Carbohydrates & Derivatives
• Mol File: 604-68-2.mol
• Article Data: 316

Chemical Properties

• Melting Point: 111-113 °C
• Boiling Point: 435.58°C (rough estimate)
• Flash Point: 188.1 °C
• Appearance: White to off-white/Powder
• Density: 1.3984 (rough estimate)
• Vapor Pressure: 0-0Pa at 20-50℃
• Refractive Index: 105.5 ° (C=1.5, MeOH)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: chloroform: 0.1 g/mL, clear, colorless
• Water Solubility: < 5 G/L (25℃)
• BRN: 98852
• CAS DataBase Reference: Glucose pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Glucose pentaacetate(604-68-2)
• EPA Substance Registry System: Glucose pentaacetate(604-68-2)

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
• TSCA: Yes
• Hazardous Substances Data: 604-68-2(Hazardous Substances Data)

Usage

Description

Glucose pentaacetate is a white to light yellow crystalline powder that is a derivative of glucose, with five acetate groups attached to its hydroxyl groups. This modification of glucose provides it with unique chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
Glucose pentaacetate is used as a pharmaceutical agent for its ability to stimulate insulin release in rat pancreatic islets. Specifically, the α-D-glucose pentaacetate isomer has been found to cause an immediate increase in insulin output, which can be beneficial for the treatment and management of diabetes.
Additionally, the β-anomer of D-glucose pentaacetate initially transiently inhibits insulin release, followed by a secondary rise in the secretory rate. This dual action could potentially be utilized in the development of novel therapies for diabetes, where precise control of insulin release is crucial.
Used in Chemical Research:
As a modified form of glucose, glucose pentaacetate can be used in chemical research for studying the effects of structural modifications on the properties and reactivity of carbohydrates. This can lead to the development of new compounds and materials with specific applications in various industries.
Used in Drug Delivery Systems:
Similar to gallotannin, glucose pentaacetate could potentially be employed in the development of drug delivery systems. Its unique chemical properties may allow for the design of novel carriers or enhancers for the delivery of therapeutic agents, improving their bioavailability and efficacy.

Purification Methods

Crystallise it from MeOH, EtOH or three recrystallisations from 95% EtOH. [Wolfrom & Thompson Methods in Carbohydrate Chemistry II 212 1963, Academic Press, Beilstein 17/7 V 318.]

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 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 
• 64-19-7 acetic acid 
• 17460-45-6 tetra-acetyl glucosamine 
• 604-69-3 β-D-glucose pentaacetate 
• 7726-95-6 bromine 
• 23661-29-2 phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-glucopyranoside 
• 56180-94-0 acarbose 
• 1013648-93-5 C₂₈H₄₇NO₁₈ 
• 10257-28-0 D-Galactose 
• 7296-15-3 alpha-D-mannopyranoside 

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

PROCESS OF SYNTHESIS OF β-6'SULFOQUINOVOSYL DIACYLGLYCEROLS

The present invention relates to a synthesis process of β-6-sulfoquinovosyl-diacylglycerols. In particular, said process is for the synthesis of the compounds 1,2-O-distearoyl-3-O-(β- sulfoquinovosyl)-R/S-glycerol, 1,2-O-distearoyl-3-O-(β-sulfoquinovosyl)-R-glycerol or 1,2- O-distearoyl-3-O-(β-sulfoquinovosyl)-S-glycerol, named respectively Sulfavant A, Sulfavant R and Sulfavant S.

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.

CuAAC mediated synthesis of cyclen cored glycodendrimers of high sugar tethers at low generation

Glycodendrimers are receiving considerable attention to mimic a number of imperative features of cell surface glycoconjugate and acquired excellent relevance to a wide domain of investigations including medicine, pharmaceutics, catalysis, nanotechnology, carbohydrate-protein interaction, and moreover in drug delivery systems. Toward this end, an expeditious, modular, and regioselective triazole-forming CuAAC click approach along with double stage convergent synthetic method was chosen to develop a variety of novel chlorine-containing cyclen cored glycodendrimers of high sugar tethers at low generation of promising therapeutic potential. We developed a novel chlorine-containing hypercore unit with 12 alkynyl functionality originated from cyclen scaffold which was confirmed by its single crystal X-ray data analysis. Further, the modular CuAAC technique was utilized to produce a variety of novel 12–sugar coated (G0) glycodendrimers 12-15 adorn with β-Glc-, β-Man-, β-Gal-, β-Lac, along with 36-galactose coated (G1) glycodendrimer 18 in good-to-high yield. The structures of the developed glycodendrimer architectures have been well elucidated by extensive spectral analysis including NMR (1H & 13CNMR), HRMS, MALDI-TOF MS, UV–Vis, IR, and SEC (Size Exclusion Chromatogram) data.