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dextro-glucose pentaacetate
1,2,3,4,6-pentaacetyl-D-glucose

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Name:[(2R,3R,4S,5R)-2,3,4,5-tetraacetyloxy-6-oxohexyl] acetate
CAS Number: 83-87-4Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J885.970A
XlogP3:0.60 (est)
Molecular Weight:390.34254000
Formula:C16 H22 O11
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:solvents/deluents for flavor and/or fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
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PubMed:Search
NCBI:Search
FDA Mainterm (SATF):83-87-4 ; GLUCOSE PENTAACETATE
FDA Regulation:
FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION
Subpart F--Flavoring Agents and Related Substances
Sec. 172.515 Synthetic flavoring substances and adjuvants.
 
Physical Properties:
Food Chemicals Codex Listed: No
Boiling Point: 472.02 °C. @ 760.00 mm Hg (est)
Flash Point: 401.00 °F. TCC ( 205.20 °C. ) (est)
logP (o/w): 0.170 (est)
Soluble in:
 water, 1018 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
1,2,3,4,6-Penta-O-acetyl-D-glucopyranose
Santa Cruz Biotechnology
For experimental / research use only.
a,β-D-Glucose Pentaacetate
 
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
 
Safety in Use Information:
Category:
solvents/deluents for flavor and/or fragrance agents
Recommendation for dextro-glucose pentaacetate usage levels up to:
 not for fragrance use.
 
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10293747
National Institute of Allergy and Infectious Diseases:Data
[(2R,3R,4S,5R)-2,3,4,5-tetraacetyloxy-6-oxohexyl] acetate
Chemidplus:0003891596
 
References:
 [(2R,3R,4S,5R)-2,3,4,5-tetraacetyloxy-6-oxohexyl] acetate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):10293747
Pubchem (sid):135050565
 
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 Substances Added to Food (formerly EAFUS):View
HMDB (The Human Metabolome Database):Search
FDA Listing of Food Additive Status:View
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
peracetyl glucose
D-glucose pentaacetate
1,2,3,4,6-pentaacetyl-D-glucose
1,2,3,4,6-pentaacetyl-dextro-glucose
[(2R,3R,4S,5R)-2,3,4,5-tetraacetyloxy-6-oxohexyl] acetate
 

Articles:

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: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:Synthesis of 2-thiohydantoins and their S-glucosylated derivatives as potential antiviral and antitumor agents.
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: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 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:Insulinotropic action of the polyacetate esters of two non-nutrient monosaccharides in normal and diabetic rats.
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:Preparation of various glucose esters via lipase-catalyzed hydrolysis of 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.
 
Notes:
None found
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