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alpha-dextro-pentaacetyl glucose

Chemical Structure

General Material Information

Preferred name alpha-dextro-pentaacetyl glucose
Trivial Name Penta-O-acetyl-α-D-glucopyranose
Short Description alpha-D-glucose pentaacetate
Formula C16 H22 O11
CAS Number 604-68-2
FEMA Number 2524
ECHA Number 210-073-2
FDA UNII 1CS424NS93
Beilstein Number 0098852
MDL MFCD00064071
Bio Activity Summary External link
NMR Predictor External link
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
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
  • [2,3,5-triacetyloxy-6-(acetyloxymethyl)oxan-4-yl] acetate
  • α-D-Glucopyranose, 1,2,3,4,6-pentaacetate
  • Glucopyranose, pentaacetate, α-D-
  • α-D-Glucopyranose, pentaacetate
  • α-D-Glucose pentaacetate
  • 1,2,3,4,6-Penta-O-acetyl-α-D-glucopyranose
  • Pentaacetyl-α-D-glucose
  • α-D-Glucopyranosyl pentaacetate
  • Pentaacetyl-α-D-glucopyranose
  • Penta-O-acetyl-α-D-glucopyranose
  • NSC 119335
  • NSC 9290
  • 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl acetate
  • 1,2,3,4,6-Tetra-O-acetyl-α-D-glucopyranoside

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Literature & References

[2,3,5-triacetyloxy-6-(acetyloxymethyl)oxan-4-yl] acetate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):79064
Pubchem (sid):135036643
Publications by PubMed
Insulin release: the receptor hypothesis.
Deuterium-induced isotope effects on the 13C chemical shifts of α-D-glucose pentaacetate.
Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones.
Sugar acetates as CO2-philes: molecular interactions and structure aspects from absorption measurement using quartz crystal microbalance.
A simple preparation of 2,3,4,6-tetra-o-acyl-gluco-, galacto- and mannopyranoses and relevant theoretical study.
Preparation of nucleoside-carbohydrate phosphodiester prodrug analogues by chemoenzymatic procedure.
Directed assembly of sub-nanometer thin organic materials with programmed-size nanopores.
Measurement of gluconeogenesis using glucose fragments and mass spectrometry after ingestion of deuterium oxide.
Characterization of a new rhamnogalacturonan acetyl esterase from Bacillus halodurans C-125 with a new putative carbohydrate binding domain.
YesT: a new rhamnogalacturonan acetyl esterase from Bacillus subtilis.
Examination of glass transitions in CO(2)-processed, peracetylated sugars using sum frequency generation spectroscopy.
Mirror-image carbohydrates: synthesis of the unnatural enantiomer of a blood group trisaccharide.
Monosaccharide esters: new tools in biomedicine.
Monosaccharide esters: clinically relevant?
Synthesis of 2-thiohydantoins and their S-glucosylated derivatives as potential antiviral and antitumor agents.
Synthesis and antiperoxidant activity of new phenolic O-glycosides.
Metabolism of alpha-D-[1,2-13C]glucose pentaacetate and alpha-D-glucose penta[2-13C]acetate in rat hepatocytes.
Activation of glycogen synthase a in hepatocytes exposed to alpha-D-glucose pentaacetate.
Stimulation of insulin synthesis and release by alpha-D-glucose pentaacetate in pancreatic islets from human subjects.
Metabolism of D-[1,2-13C]glucose and alpha-D-[1,2-13C]glucose pentaacetate in tumoral pancreatic islet cells.
Metabolism of d-glucose and its pentaacetate ester in muscles and pancreatic islets of GLUT4 null mice.
Effect of D-mannoheptulose upon the cationic and secretory responses to alpha-D-glucose pentaacetate in perifused rat pancreatic islets.
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.
Effects of extracellular pH upon the insulinotropic action of alpha-D-glucose pentaacetate.
Isomeric and anomeric specificity of the metabolic and secretory response of rat pancreatic islets to glucose pentaacetate.
Regioselective hydrolysis of peracetylated alpha-D-glycopyranose catalyzed by immobilized lipases in aqueous medium. A facile preparation of useful intermediates for oligosaccharide synthesis.
Insulinotropic action of monosaccharide esters: therapeutic perspectives.
Opposite effects of D-glucose pentaacetate and D-galactose pentaacetate anomers on insulin release evoked by succinic acid dimethyl ester in rat pancreatic islets.
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.
Effects of artificial sweeteners on insulin release and cationic fluxes in rat pancreatic islets.
Effects of hexose pentaacetates on electrical activity and cytosolic Ca2+ in mouse pancreatic islets.
Failure of streptozotocin tetraacetate to undergo extensive hydrolysis and to inhibit D-glucose metabolism and insulinotropic action in rat pancreatic islets.
The riddle of L-glucose pentaacetate insulinotropic action (review).
Insulinotropic action of the polyacetate esters of two non-nutrient monosaccharides in normal and diabetic rats.
Insulinotropic action of beta-L-glucose pentaacetate.
Monosaccharide esters: new tools in biomedical research.
Hydrolysis of hexose pentaacetate esters in rat pancreatic islets.
Dual mode of action of glucose pentaacetates on hormonal secretion from the isolated perfused rat pancreas.
Comparison of the effects of D-mannoheptulose and its hexaacetate ester on D-glucose metabolism and insulinotropic action in rat pancreatic islets.
Insulinotropic action of alpha-D-glucose pentaacetate: metabolic aspects.
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.
Resistance of the insulinotropic action of alpha-D-glucose and beta-L-glucose pentaacetates to cholera and pertussis toxins.
Synergistic insulinotropic action of succinate, acetate, and glucose esters in islets from normal and diabetic rats.
Insulinotropic action of the polyacetate esters of metabolized and non-metabolized monosaccharides in pancreatic islets from normal and diabetic rats.
Bitter taste of monosaccharide pentaacetate esters.
Insulinotropic action of alpha-D-glucose pentaacetate: functional aspects.
Stimulation of insulin release by alpha-D-glucose pentaacetate.
SW.B6-Soa(b) nontaster congenic strains completed and a sucrose octaacetate congenic quartet tested with other bitters.
Mass isotopomer pattern and precursor-product relationship.
Esterase Activities of Fibrobacter succinogenes subsp. succinogenes S85.
Preparation of various glucose esters via lipase-catalyzed hydrolysis of glucose pentaacetate.
Rapid and specific isolation of radioactive glucose from biological samples.
Utilization of propionic acid by the L4 and adult stages of Cooperia punctata (Nematoda: Trichostrongylidae) grown in vitro.
Rapid determination of (carbon-14) glucose specific radioactivity for in vivo glucose kinetics.
DETERMINATION OF THE SPECIFIC ACTIVITY OF LABELED BLOOD GLUCOSE BY LIQUID SCINTILLATION USING GLUCOSE PENTAACETATE.
The suitability of beta-D-glucose pentaacetate for food use. I. The subscute toxicity of beta-D-glucose pentaacete.
The suitability of beta-D-glucose pentaacetate for food use. II. Studies on the absorption and metabolism.
Action of the Grignard reagent on beta-d-glucose pentaacetate.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Indirect Additives used in Food Contact Substances:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2915.39.9050
FDA Listing of Food Additive Status:View
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 390.34252929688
Melting Point 110 to 115°C @ 760 mm Hg
Boiling Point 433 to 434°C @ 760 mm Hg
Flash Point TCC Value 187.78 °C TCC
logP (o/w) 0.63
Solubility
alcohol Yes
ether Yes
water, 1018 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Odorless
Odor strength none
General comment At 100.00 %. odorless
Flavor Type: Bitter
bitter, citrus
Mosciano, Gerard P&F 16, No. 1, 31, (1991) At 100.00 ppm. Bitters-like, with a citrus tonic flavor

Potential Uses

Applications
Odor purposes Grapefruit
Flavoring purposes Bitters
Other purposes Emulsion stabilisers
Cosmetic purposes Emulsion stabilisers

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
solvents/deluents for cosmetic, flavor and/or fragrance agents
Recommendation for alpha-dextro-pentaacetyl glucose usage levels up to:
not for fragrance use.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -1500.00000
beverages(nonalcoholic): -100.00000
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: --

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):604-68-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :79064
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
[2,3,5-triacetyloxy-6-(acetyloxymethyl)oxan-4-yl] acetate
Chemidplus:0000604682