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alpha-dextro-pentaacetyl glucose

solvents/deluents for cosmetic, flavor and/or fragrance agents
2D:
3D:
CAS Number: 604-68-2
ECHA EC Number: 210-073-2
FDA UNII: 1CS424NS93
Category: solvents/deluents for cosmetic, flavor and/or fragrance agents
IUPAC Name: alpha-dextro-pentaacetyl glucose
InChI : InChI=1/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3
Std.InChI: InChI=1S/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3
InChIKey : LPTITAGPBXDDGR-UHFFFAOYAL
Std.InChIKey: LPTITAGPBXDDGR-UHFFFAOYSA-N
SMILES : CC(=O)OCC1C(C(C(C(O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
MDL: MFCD00064071
Molar Refractivity : 85.00 ± 0.4 cm3 (est)
Parachor : 779.0 ± 6.0 cm3 (est)
Index of Refraction : 1.482 ± 0.03 (est)
Surface Tension : 46.7 ± 5.0 dyne/cm (est)
Density : 1.30 ± 0.1 g/cm3 (est)
Polarizability : 33.69 ± 0.5 10-24cm3 (est)

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

Google Scholar:Search
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Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
FEMA Number:2524 alpha-D-glucose pentaacetate
FDA:No 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
ether
water, 1018 mg/L @ 25 °C (est)
Insoluble in:
water

Organoleptic Properties:

bitter citrus

Cosmetic Information:

CosIng:cosmetic data
Cosmetic Uses: emulsion stabilisers

Suppliers:

BOC Sciences
For experimental / research use only.
1,2,3,4,6-Penta-O-acetyl-a-D-glucopyranose
Carbosynth
For experimental / research use only.
1,2,3,4,6-Penta-O-acetyl-a-D-glucopyranose
Glentham Life Sciences
alpha-D-Glucose Pentaacetate
Penta International
a-GLUCOSE PENTAACETATE
Santa Cruz Biotechnology
For experimental / research use only.
a-D-Pentaacetyl Glucose
Sigma-Aldrich: Aldrich
For experimental / research use only.
a-D(+)-Glucose pentaacetate 99%
TCI AMERICA
For experimental / research use only.
Penta-O-acetyl-a-D-glucopyranose >97.0%(GC)

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

References:

[2,3,5-triacetyloxy-6-(acetyloxymethyl)oxan-4-yl] acetate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):79064
Pubchem (sid):135036643

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

Potential Blenders and core components :

None Found

Potential Uses:

FLbitters
emulsion stabilisers
FRgrapefruit

Occurrence (nature, food, other):

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

Articles:

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.
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