beta-dextro-pentaacetyl glucose

1,2,3,4,6-penta-O-acetyl-b-D-glucopyranose

CAS: 604-69-3 C16 H22 O11 MW: 390.34254000

Identification

Namebeta-dextro-pentaacetyl glucose
IUPAC[(2R,3R,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]methyl acetate
CAS Number604-69-3
EINECS210-074-8
FDA UNIIV833P95COC
Molecular FormulaC16 H22 O11
Molecular Weight390.34254000
MDL NumberMFCD00006597
Beilstein0098851
XlogP30.60 (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 SDSView
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

Categoryinformation only not used for fragrances or flavors
Recommendation for beta-dextro-pentaacetyl glucose usage levels up tonot for fragrance use.
Recommendation for beta-dextro-pentaacetyl glucose flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

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.