dextro-glucose pentaacetate

1,2,3,4,6-pentaacetyl-D-glucose

CAS: 83-87-4 C16 H22 O11 MW: 390.34254000

Identification

Namedextro-glucose pentaacetate
IUPAC[(2R,3R,4S,5R)-2,3,4,5-tetraacetyloxy-6-oxohexyl] acetate
CAS Number83-87-4
FDA UNIISearch
Molecular FormulaC16 H22 O11
Molecular Weight390.34254000
Nikkaji NumberJ885.970A
XlogP30.60 (est)

Regulatory

FDA Mainterm (SATF)83-87-4 ; GLUCOSE PENTAACETATE
FDA RegulationFDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION

Physical Properties

Food Chemicals Codex Listed No
Boiling Point 472.02 °C. @ 760.00 mm Hg (est)
Flash Point 401.00 °F. TCC ( 205.20 °C. ) (est)
logP (o/w) 0.170 (est)
Soluble in water, 1018 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorysolvents/deluents for flavor and/or fragrance agents
Recommendation for dextro-glucose pentaacetate usage levels up tonot for fragrance use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

Synonyms

per acetyl glucose D- glucose pentaacetate 1,2,3,4,6- pentaacetyl-D-glucose 1,2,3,4,6- pentaacetyl-dextro-glucose [(2R,3R,4S,5R)-2,3,4,5- tetraacetyloxy-6-oxohexyl] acetate 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: 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: Synthesis of 2-thiohydantoins and their S-glucosylated derivatives as potential antiviral and antitumor agents. 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: 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 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: Insulinotropic action of the polyacetate esters of two non-nutrient monosaccharides in normal and diabetic rats. 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: Preparation of various glucose esters via lipase-catalyzed hydrolysis of 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.