Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2015-07-20 22:51:25 UTC
Primary IDFDB012529
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2,3,4,5,6-Penta-O-acetyl-D-glucose
Description2,3,4,5,6-Penta-O-acetyl-D-glucose, also known as b-D-glucopyranose pentaacetic acid or D-glucose pentaacetate, belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. 2,3,4,5,6-Penta-O-acetyl-D-glucose is possibly neutral. 2,3,4,5,6-Penta-O-acetyl-D-glucose is a bitter tasting compound.
CAS Number3891-59-6
Structure
Thumb
Synonyms
SynonymSource
Beta-D-Glucopyranose pentaacetateHMDB
b-D-Glucopyranose pentaacetateHMDB
b-D-Glucopyranose pentaacetic acidHMDB
beta-D-Glucopyranose pentaacetic acidHMDB
Β-D-glucopyranose pentaacetateHMDB
Β-D-glucopyranose pentaacetic acidHMDB
D-Glucose pentaacetateHMDB
D-Glucose, 2,3,4,5,6-pentaacetateHMDB
FEMA 2524HMDB
Glucose 2,3,4,5,6-pentaacetateHMDB
Glucose pentaacetateHMDB
[(2R,3R,4S,5R,6S)-3,4,5,6-Tetrakis(acetyloxy)oxan-2-yl]methyl acetic acidGenerator
1,2,3,4,6-Penta-O-acetyl-alpha-D-glucopyranosideMeSH
beta-D-Glucose pentaacetateMeSH
Glucose pentaacetate, (D)-isomerMeSH
Glucose pentaacetate, (alpha-D)-isomerMeSH
Glucose pentaacetate, (beta-(D))-isomerMeSH
Penta-O-acetyl-alpha-D-glucopyranoseMeSH
Penta-O-acetylglucopyranoseMeSH
2,3,4,5,6-Penta-O-acetyl-D-glucosedb_source
Predicted Properties
PropertyValueSource
Water Solubility6.62 g/LALOGPS
logP0.53ALOGPS
logS-1.8ALOGPS
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Chemical FormulaC16H22O11
IUPAC name
InChI IdentifierInChI=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/t12-,13-,14+,15-,16-/m1/s1
InChI KeyLPTITAGPBXDDGR-IBEHDNSVSA-N
Isomeric SMILESCC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
Average Molecular Weight390.3393
Monoisotopic Molecular Weight390.116211546
Classification
Description belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassPentacarboxylic acids and derivatives
Direct ParentPentacarboxylic acids and derivatives
Alternative Parents
Substituents
  • Pentacarboxylic acid or derivatives
  • Oxane
  • Monosaccharide
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 49.23%; H 5.68%; O 45.09%DFC
Melting PointMp 135° (b-anomer)DFC
Boiling PointNot Available
Experimental Water Solubility1.5 mg/mL at 18 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP0.63POMONA (1987)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +4.4 (c, 1 in CHCl3) (b-anomer)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0k97-5930000000-e21c830a522243fe6a57JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0k97-5930000000-e21c830a522243fe6a57JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1139000000-3ad29b7ec1ee51f6ccccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001s-1049000000-735fd11b19acc0cfec1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053i-1169000000-9de811ff6439bdded06aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-5192000000-6ef079e665faaf42b941JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052k-6019000000-421048e865237bb9f853JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9223000000-5f54ba2bb711fac1cedbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9120000000-78e14e14341a24df674fJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID92972
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34223
CRC / DFC (Dictionary of Food Compounds) IDHHS40-R:HHS41-S
EAFUS ID1503
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference