glucose pentaacetate

D-glucose pentaacetate

CAS: 3891-59-6 C16 H22 O11 MW: 390.34254000 odorless bitter

Identification

Nameglucose pentaacetate
IUPAC[(2R,3R,4S,5R)-1,2,4,5-tetraacetyloxy-6-oxohexan-3-yl] acetate
CAS Number3891-59-6
EINECS223-439-1
FDA UNII3040885R4N
Molecular FormulaC16 H22 O11
Molecular Weight390.34254000
Nikkaji NumberJ141.107A

Regulatory

DG SANTE Food Flavourings09.258 D-glucose pentaacetate
FEMA Number2524
FDANo longer provide for the use of these seven synthetic flavoring substances

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 110.00 to 115.00 °C. @ 760.00 mm Hg
Boiling Point 454.00 to 456.00 °C. @ 760.00 mm Hg
Flash Point 401.00 °F. TCC ( 205.00 °C. )
logP (o/w) 0.630
Soluble in alcohol
Insoluble in water

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesemulsion stabilisers

Organoleptic Properties

Taste Description at 100.00 ppm.

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 glucose pentaacetate usage levels up tonot for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU)0.061 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI)230000 (μg/person/day)
Threshold of Concern540 (μg/person/day)
Structure ClassII
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-
Dairy products, excluding products of category 02.0 (01.0)-
Fats and oils, and fat emulsions (type water-in-oil) (02.0)-
Edible ices, including sherbet and sorbet (03.0)-
Processed fruit (04.1)-
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2)-
Confectionery (05.0)-
Chewing gum (05.3)-
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0)-
Bakery wares (07.0)-
Meat and meat products, including poultry and game (08.0)1500.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0)-
Eggs and egg products (10.0)-
Sweeteners, including honey (11.0)-
Salts, spices, soups, sauces, salads, protein products, etc. (12.0)-
Foodstuffs intended for particular nutritional uses (13.0)-
Non-alcoholic ("soft") beverages, excl. dairy products (14.1)100.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2)-
Ready-to-eat savouries (15.0)-
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0)-

No supplier data available

Potential Uses

emulsion stabilisers

Natural Occurrence

not found in nature

Synonyms

glucose 2,3,4,5,6-pentaacetate D- glucose pentaacetate D- glucose, 2,3,4,5,6-pentaacetate glucosepentaacetate pentaacetyl-a-D-glucose pentaacetyl-alpha-D-glucose pentaacetyl-alpha-dextro-glucose [(2R,3R,4S,5R)-1,2,4,5- tetraacetyloxy-6-oxohexan-3-yl] acetate PubMed: Insulin release: the receptor hypothesis. PubMed: Deuterium-induced isotope effects on the 13C chemical shifts of α-D-glucose pentaacetate. PubMed: A simplified mass isotopomer approach to estimate gluconeogenesis rate in vivo using deuterium oxide. 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: Differentiation of extractive and synthetic salicin. The 2H aromatic pattern of natural 2-hydroxybenzyl alcohol. 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: Gluconeogenesis in isolated rat hepatocytes evaluated by gas chromatography/mass spectrometry using deuterated water. 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: Quantitation of positional isomers of deuterium-labeled glucose by gas chromatography/mass spectrometry. PubMed: Mass isotopomer pattern and precursor-product relationship. PubMed: Synthesis of L-gulose, L-galactose, and their acetylated aldehydo forms from 6-S-phenyl-6-thio-D-hexoses. PubMed: Esterase Activities of Fibrobacter succinogenes subsp. succinogenes S85. PubMed: Synthesis of certain nucleoside methylenediphosphonate sugars as potential inhibitors of glycosyltransferases. PubMed: Preparation of various glucose esters via lipase-catalyzed hydrolysis of glucose pentaacetate. PubMed: The X-ray crystal structure of DL-(1,3,5/2,4)-1,2,3,4-tetraacetoxy-5-(acetoxymethyl)cyclohexane. 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.