glucose pentaacetate
D-glucose pentaacetate
 
Notes:
Flavouring agent
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CAS Number: 3891-59-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 223-439-1
FDA UNII: 3040885R4N
Nikkaji Web: J141.107A
XlogP3-AA: -0.60 (est)
Molecular Weight: 390.34254000
Formula: C16 H22 O11
NMR Predictor: Predict (works with chrome or firefox)
EFSA/JECFA Comments: The CASrn referes to the D-Glucose pentaacetate. Industry informs that the 95 % assay minimum covers the complete acetylated D-glucose (Dglucose pentaacetate).
Category: solvents/deluents for flavor and/or fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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DG SANTE Food Flavourings: 09.258  D-glucose pentaacetate
FEMA Number: 2524 glucose pentaacetate
FDA:No longer provide for the use of these seven synthetic flavoring substances
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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
 water, 1500 mg/L @ 18C (exp)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor Type: odorless
 
 
 
Flavor Type: bitter
 
 bitter  citrus  
Taste Description:
at 100.00 ppm.  
Bitters-like, with a citrus tonic flavor
Mosciano, Gerard P&F 16, No. 1, 31, (1991)
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: emulsion stabilisers
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Suppliers:
Carbosynth
For experimental / research use only.
1,2,3,4,6-Penta-O-acetyl-D-glucopyranose
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Safety Information:
 
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
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Safety in Use Information:
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
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: --
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
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): --
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): 1500.000001500.00000
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): 100.00000100.00000
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): --
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Safety References:
European Food Safety Athority(efsa): Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
European Food Safety Authority (EFSA) reference(s):
Scientific Opinion on Flavouring Group Evaluation 308 (FGE.308): Glucose Pentaacetate and Sucrose Octaacetate
View page or View pdf
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 3891-59-6
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 92972
National Institute of Allergy and Infectious Diseases: Data
 [(2R,3R,4S,5R)-1,2,4,5-tetraacetyloxy-6-oxohexan-3-yl] acetate
Chemidplus: 0003891596
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References:
 [(2R,3R,4S,5R)-1,2,4,5-tetraacetyloxy-6-oxohexan-3-yl] acetate
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 3891-59-6
Pubchem (cid): 92972
Pubchem (sid): 135050565
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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
HMDB (The Human Metabolome Database): HMDB34223
FooDB: FDB012529
FDA Listing of Food Additive Status: View
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
 emulsion stabilisers 
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Occurrence (nature, food, other): note
 not found in nature
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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
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Articles:
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.
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