alpha-dextro-pentaacetyl glucose

alpha-D-glucose pentaacetate

CAS: 604-68-2 C16 H22 O11 MW: 390.34254000 odorless bitter

Identification

Namealpha-dextro-pentaacetyl glucose
IUPAC[2,3,5-triacetyloxy-6-(acetyloxymethyl)oxan-4-yl] acetate
CAS Number604-68-2
EINECS210-073-2
FDA UNII1CS424NS93
Molecular FormulaC16 H22 O11
Molecular Weight390.34254000
MDL NumberMFCD00064071
Beilstein0098852
XlogP30.60 (est)

Regulatory

FEMA Number2524
FDANo longer provide for the use of these seven synthetic flavoring substances

Physical Properties

Appearance white crystals (est)
Assay 99.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 110.00 to 115.00 °C. @ 760.00 mm Hg
Boiling Point 433.00 to 434.00 °C. @ 760.00 mm Hg
Flash Point 370.00 °F. TCC ( 187.78 °C. )
logP (o/w) 0.630
Soluble in alcohol
Insoluble in water

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesemulsion stabilisers

Organoleptic Properties

Odor Strength none
Odor Description at 100.00 %.
Taste Description at 100.00 ppm.

Safety Information

Preferred SDSView
European informationMost important hazard(s):
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 cosmetic, flavor and/or fragrance agents
Recommendation for alpha-dextro-pentaacetyl glucose usage levels up tonot for fragrance use.
baked goods-
beverages(nonalcoholic)-
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices-
gelatins / puddings-
granulated sugar-
gravies-
hard candy-
imitation dairy-
instant coffee / tea-
jams / jellies-
meat products-
milk products-
nut products-
other grains-
poultry-
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors-
snack foods-
soft candy-
soups-
sugar substitutes-
sweet sauces-

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Potential Uses

FL bitters emulsion stabilisers FR grapefruit

Natural Occurrence

not found in nature

Synonyms

(2S,3R,4S,5R,6R)-6-( acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate alpha-D- glucopyranose pentaacetate alpha-dextro- glucopyranose pentaacetate alpha-D- glucose pentaacetate alpha-dextro- glucose pentaacetate hexopyranose, pentaacetate 1,2,3,4,6- penta-O-acetyl-a-D-galactopyranose 1,2,3,4,6- penta-O-acetyl-a-D-glucopyranose 1,2,3,4,6- penta-O-acetyl-a-D-mannopyranose 1,2,3,4,6- penta-O-acetylhexopyranose alpha-D- pentaacetyl glucose alpha-dextro- pentaacetyl glucose 1,2,3,4,6- pentaacetyl-alpha-dextro-glucose alpha- pentaacetyl-D-glucose alpha- pentaacetyl-dextro-glucose [3,4,5,6- tetrakis(acetyloxy)tetrahydro-2H-pyran-2-yl]methyl acetate 3,4,5- triacetyloxy-6-(acetyloxymethyl)-2H-3,4,5,6-tetrahydropyran-2-yl acetate [2,3,5- triacetyloxy-6-(acetyloxymethyl)oxan-4-yl] 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.