glucose pentaacetate
D-glucose pentaacetate
Identification
| Name | glucose pentaacetate |
| IUPAC | [(2R,3R,4S,5R)-1,2,4,5-tetraacetyloxy-6-oxohexan-3-yl] acetate |
| CAS Number | 3891-59-6 |
| EINECS | 223-439-1 |
| FDA UNII | 3040885R4N |
| Molecular Formula | C16 H22 O11 |
| Molecular Weight | 390.34254000 |
| Nikkaji Number | J141.107A |
Regulatory
| DG SANTE Food Flavourings | 09.258 D-glucose pentaacetate |
| FEMA Number | 2524 |
| FDA | No 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
| CosIng | cosmetic data |
| Cosmetic Uses | emulsion stabilisers |
Organoleptic Properties
| Taste Description | at 100.00 ppm. |
Safety Information
| 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 | solvents/deluents for flavor and/or fragrance agents |
| Recommendation for glucose pentaacetate usage levels up to | not 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 Concern | 540 (μg/person/day) |
| Structure Class | II |
| 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
Natural Occurrence
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.