beta-dextro-pentaacetyl glucose
1,2,3,4,6-penta-O-acetyl-b-D-glucopyranose
Identification
| Name | beta-dextro-pentaacetyl glucose |
| IUPAC | [(2R,3R,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]methyl acetate |
| CAS Number | 604-69-3 |
| EINECS | 210-074-8 |
| FDA UNII | V833P95COC |
| Molecular Formula | C16 H22 O11 |
| Molecular Weight | 390.34254000 |
| MDL Number | MFCD00006597 |
| Beilstein | 0098851 |
| XlogP3 | 0.60 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 130.00 to 134.00 °C. @ 760.00 mm Hg |
| Boiling Point | 434.00 to 435.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 370.00 °F. TCC ( 188.10 °C. ) (est) |
| logP (o/w) | 0.634 (est) |
| Soluble in | alcohol |
Organoleptic Properties
| Odor Strength | none |
| Odor Description | at 100.00 %. |
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | information only not used for fragrances or flavors |
| Recommendation for beta-dextro-pentaacetyl glucose usage levels up to | not for fragrance use. |
| Recommendation for beta-dextro-pentaacetyl glucose flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
beta-d-
glucopyranose, pentaacetate
β-D-
glucopyranose, pentaacetate
beta-D-
glucose pentaacetate
beta-dextro-
glucose pentaacetate
1,2,3,4,6-
penta-O-acetyl-b-D-glucopyranose
beta-D-
pentaacetyl glucose
[(2R,3R,5R,6S)-3,4,5,6-
tetraacetyloxyoxan-2-yl]methyl acetate
PubMed:
Insulin release: the receptor hypothesis.
PubMed:
Deuterium-induced isotope effects on the 13C chemical shifts of α-D-glucose pentaacetate.
PubMed:
Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones.
PubMed:
Sugar acetates as CO2-philes: molecular interactions and structure aspects from absorption measurement using quartz crystal microbalance.
PubMed:
A simple preparation of 2,3,4,6-tetra-o-acyl-gluco-, galacto- and mannopyranoses and relevant theoretical study.
PubMed:
Preparation of nucleoside-carbohydrate phosphodiester prodrug analogues by chemoenzymatic procedure.
PubMed:
Directed assembly of sub-nanometer thin organic materials with programmed-size nanopores.
PubMed:
Measurement of gluconeogenesis using glucose fragments and mass spectrometry after ingestion of deuterium oxide.
PubMed:
Characterization of a new rhamnogalacturonan acetyl esterase from Bacillus halodurans C-125 with a new putative carbohydrate binding domain.
PubMed:
YesT: a new rhamnogalacturonan acetyl esterase from Bacillus subtilis.
PubMed:
Examination of glass transitions in CO(2)-processed, peracetylated sugars using sum frequency generation spectroscopy.
PubMed:
Mirror-image carbohydrates: synthesis of the unnatural enantiomer of a blood group trisaccharide.
PubMed:
Monosaccharide esters: new tools in biomedicine.
PubMed:
Monosaccharide esters: clinically relevant?
PubMed:
Synthesis of 2-thiohydantoins and their S-glucosylated derivatives as potential antiviral and antitumor agents.
PubMed:
Synthesis and antiperoxidant activity of new phenolic O-glycosides.
PubMed:
Metabolism of alpha-D-[1,2-13C]glucose pentaacetate and alpha-D-glucose penta[2-13C]acetate in rat hepatocytes.
PubMed:
Activation of glycogen synthase a in hepatocytes exposed to alpha-D-glucose pentaacetate.
PubMed:
Stimulation of insulin synthesis and release by alpha-D-glucose pentaacetate in pancreatic islets from human subjects.
PubMed:
Metabolism of D-[1,2-13C]glucose and alpha-D-[1,2-13C]glucose pentaacetate in tumoral pancreatic islet cells.
PubMed:
Metabolism of d-glucose and its pentaacetate ester in muscles and pancreatic islets of GLUT4 null mice.
PubMed:
Effect of D-mannoheptulose upon the cationic and secretory responses to alpha-D-glucose pentaacetate in perifused rat pancreatic islets.
PubMed:
Differences in the time course of the metabolic response of B and non-B pancreatic islet cells to D-glucose and metabolized or non-metabolized hexose esters.
PubMed:
Effects of extracellular pH upon the insulinotropic action of alpha-D-glucose pentaacetate.
PubMed:
Isomeric and anomeric specificity of the metabolic and secretory response of rat pancreatic islets to glucose pentaacetate.
PubMed:
Regioselective hydrolysis of peracetylated alpha-D-glycopyranose catalyzed by immobilized lipases in aqueous medium. A facile preparation of useful intermediates for oligosaccharide synthesis.
PubMed:
Insulinotropic action of monosaccharide esters: therapeutic perspectives.
PubMed:
Opposite effects of D-glucose pentaacetate and D-galactose pentaacetate anomers on insulin release evoked by succinic acid dimethyl ester in rat pancreatic islets.
PubMed:
Effects of alpha-D- and beta-L-glucose pentaacetate on effluent radioactivity from pancreatic islets labelled with [(32)P]phosphate and myo-[2-(3)H]inositol.
PubMed:
Effects of artificial sweeteners on insulin release and cationic fluxes in rat pancreatic islets.
PubMed:
Effects of hexose pentaacetates on electrical activity and cytosolic Ca2+ in mouse pancreatic islets.
PubMed:
Failure of streptozotocin tetraacetate to undergo extensive hydrolysis and to inhibit D-glucose metabolism and insulinotropic action in rat pancreatic islets.
PubMed:
The riddle of L-glucose pentaacetate insulinotropic action (review).
PubMed:
Insulinotropic action of the polyacetate esters of two non-nutrient monosaccharides in normal and diabetic rats.
PubMed:
Insulinotropic action of beta-L-glucose pentaacetate.
PubMed:
Monosaccharide esters: new tools in biomedical research.
PubMed:
Hydrolysis of hexose pentaacetate esters in rat pancreatic islets.
PubMed:
Dual mode of action of glucose pentaacetates on hormonal secretion from the isolated perfused rat pancreas.
PubMed:
Comparison of the effects of D-mannoheptulose and its hexaacetate ester on D-glucose metabolism and insulinotropic action in rat pancreatic islets.
PubMed:
Insulinotropic action of alpha-D-glucose pentaacetate: metabolic aspects.
PubMed:
Stimulation by hexose esters of lactate production by rat erythrocytes: insensitivity to 3-O-methyl-D-glucose and inhibition by 2-deoxy-D-glucose and its tetraacetic ester.
PubMed:
Resistance of the insulinotropic action of alpha-D-glucose and beta-L-glucose pentaacetates to cholera and pertussis toxins.
PubMed:
Synergistic insulinotropic action of succinate, acetate, and glucose esters in islets from normal and diabetic rats.
PubMed:
Insulinotropic action of the polyacetate esters of metabolized and non-metabolized monosaccharides in pancreatic islets from normal and diabetic rats.
PubMed:
Bitter taste of monosaccharide pentaacetate esters.
PubMed:
Insulinotropic action of alpha-D-glucose pentaacetate: functional aspects.
PubMed:
Stimulation of insulin release by alpha-D-glucose pentaacetate.
PubMed:
SW.B6-Soa(b) nontaster congenic strains completed and a sucrose octaacetate congenic quartet tested with other bitters.
PubMed:
Mass isotopomer pattern and precursor-product relationship.
PubMed:
Esterase Activities of Fibrobacter succinogenes subsp. succinogenes S85.
PubMed:
Preparation of various glucose esters via lipase-catalyzed hydrolysis of glucose pentaacetate.
PubMed:
Rapid and specific isolation of radioactive glucose from biological samples.
PubMed:
Utilization of propionic acid by the L4 and adult stages of Cooperia punctata (Nematoda: Trichostrongylidae) grown in vitro.
PubMed:
Rapid determination of (carbon-14) glucose specific radioactivity for in vivo glucose kinetics.
PubMed:
DETERMINATION OF THE SPECIFIC ACTIVITY OF LABELED BLOOD GLUCOSE BY LIQUID SCINTILLATION USING GLUCOSE PENTAACETATE.
PubMed:
The suitability of beta-D-glucose pentaacetate for food use. I. The subscute toxicity of beta-D-glucose pentaacete.
PubMed:
The suitability of beta-D-glucose pentaacetate for food use. II. Studies on the absorption and metabolism.
PubMed:
Action of the Grignard reagent on beta-d-glucose pentaacetate.