Record Information
Version1.0
Creation date2011-03-17 23:25:12 UTC
Update date2019-11-26 03:20:37 UTC
Primary IDFDB021634
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxybenzoic acid glucoside
Description4-hydroxybenzoic acid glucoside is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 4-hydroxybenzoic acid glucoside is soluble (in water) and a weakly acidic compound (based on its pKa). 4-hydroxybenzoic acid glucoside can be found in a number of food items such as highbush blueberry, jostaberry, caraway, and carrot, which makes 4-hydroxybenzoic acid glucoside a potential biomarker for the consumption of these food products.
CAS Number15397-25-8
Structure
Thumb
Synonyms
SynonymSource
4-Hydroxybenzoate glucosideGenerator
4-Glucosyloxybenzoic aciddb_source
4-Hydroxybenzoic acid glucosidemanual
Predicted Properties
PropertyValueSource
Water Solubility15.2 g/LALOGPS
logP-0.99ALOGPS
logP-0.94ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4.32ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.44 m³·mol⁻¹ChemAxon
Polarizability28.36 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC13H16O8
IUPAC name4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid
InChI IdentifierInChI=1S/C13H16O8/c14-5-8-9(15)10(16)11(17)13(21-8)20-7-3-1-6(2-4-7)12(18)19/h1-4,8-11,13-17H,5H2,(H,18,19)
InChI KeyXSSDYIMYZONMBL-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=CC=C(C=C2)C(O)=O)C(O)C(O)C1O
Average Molecular Weight300.263
Monoisotopic Molecular Weight300.084517475
Classification
Description belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Benzoic acid or derivatives
  • Benzoic acid
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Sugar acid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Acetal
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical statesolid
Physical DescriptionNeedles (H2O)DFC
Mass CompositionC 52.00%; H 5.37%; O 42.63%DFC
Melting PointMp 117-143?.; Mp 211-212?DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]21D -81.4 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06sr-9660000000-bb13132c9068081a8b65JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f80-0973000000-bac0c166e1731676079aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-1910000000-ffcce3da7c134e2d430eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-5900000000-4cf503b4034676fb3986JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-1690000000-48fa2d9eaf836a930295JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-4950000000-62dd8d09ed1e301c4df9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9600000000-6f04d9548d6d280ea0a9JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID433
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDFBS67-S:FCR15-D
EAFUS IDNot Available
Dr. Duke IDBENZOIC-ACID-4-O-BETA-D-GLUCOSIDE
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
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.