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β-D-Glucose pentaacetate

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β-D-Glucose pentaacetate Basic information

Product Name:
β-D-Glucose pentaacetate
Synonyms:
  • Beta-Pentacetylglucose
  • PENTAACETYL-BETA-D-GLUCOSE
  • PENTA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE
  • PENTA-O-ACETYL-BETA-D-GLUCOPYRANOSE
  • 1,2,3,4,6-Penta-O-acetylhexopyranose
  • beta-D-Glucopyranosyl pentaacetate
  • Glucopyranose, pentaacetate, beta-D-
  • Pentaacetyl-beta-D-glucopyranose
CAS:
604-69-3
MF:
C16H22O11
MW:
390.34
EINECS:
210-074-8
Product Categories:
  • carbohydrate
  • Biochemistry
  • Glucose
  • O-Substituted Sugars
  • Sugars
  • Carbohydrates & Derivatives
  • Sugars, Carbohydrates & Glucosides
  • bc0001
Mol File:
604-69-3.mol
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β-D-Glucose pentaacetate Chemical Properties

Melting point:
130-132 °C
alpha 
5 º (c=1, CHCl3)
Boiling point:
435.58°C (rough estimate)
Density 
1,274 g/cm3
refractive index 
4.5 ° (C=5, CHCl3)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
chloroform: 0.1 g/mL, clear, colorless
form 
Crystalline Powder
color 
White to off-white
Odor
at 100.00?%. odorless
optical activity
[α]20/D +4.2°, c = 1 in chloroform
Water Solubility 
Soluble in chloroform and methanol. Insoluble in water.
BRN 
98851
InChIKey
LPTITAGPBXDDGR-XJGFBQBWSA-N
LogP
0.634 (est)
CAS DataBase Reference
604-69-3(CAS DataBase Reference)
NIST Chemistry Reference
Acetyl 2,3,4,6-tetra-o-acetyl-«beta»-D-glucopyranoside(604-69-3)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
21-36/38-46-62-63
Safety Statements 
24/25-53-36/37-26-25
WGK Germany 
3
HS Code 
29400090

MSDS

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β-D-Glucose pentaacetate Usage And Synthesis

Chemical Properties

white to beige powder

Uses

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.

Uses

beta-D-Glucose pentaacetate was reported to stimulate insulin release in rat pancreatic islets.

Definition

ChEBI: Beta-d-glucose pentaacetate is an organooxygen compound. It is functionally related to a hexacarboxylic acid.

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.]

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