Record Information
Version1.0
Creation date2010-04-08 22:04:30 UTC
Update date2019-11-26 02:54:36 UTC
Primary IDFDB000256
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFerulic acid 4-glucoside
DescriptionFerulic acid 4-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. Ferulic acid 4-glucoside is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Ferulic acid 4-glucoside can be found in a number of food items such as redcurrant, gooseberry, highbush blueberry, and blackcurrant, which makes ferulic acid 4-glucoside a potential biomarker for the consumption of these food products.
CAS Number537-98-4
Structure
Thumb
Synonyms
SynonymSource
Ferulate 4-glucosideGenerator
(2E)-3-[4-(beta-D-Glucopyranosyloxy)-3-methoxyphenyl]-2-propenoic acidPhytoBank
(2E)-3-[4-(β-D-Glucopyranosyloxy)-3-methoxyphenyl]-2-propenoic acidPhytoBank
(E)-Ferulic acid 4-O-beta-D-glucosidePhytoBank
(E)-Ferulic acid 4-O-β-D-glucosidePhytoBank
Ferulic acid 4-O-glucosidePhytoBank
Ferulic acid 4-O-beta-glucopyranosidePhytoBank
Ferulic acid 4-O-β-glucopyranosidePhytoBank
LavandosidePhytoBank
trans-4-O-beta-D-Glucopyranosylferulic acidPhytoBank
trans-4-O-β-D-Glucopyranosylferulic acidPhytoBank
trans-Ferulic acid 4-beta-D-glucosidePhytoBank
trans-Ferulic acid 4-β-D-glucosidePhytoBank
trans-Ferulic acid-4-beta-glucosidePhytoBank
trans-Ferulic acid-4-β-glucosidePhytoBank
trans-p-Feruloyl-beta-D-glucopyranosidePhytoBank
trans-p-Feruloyl-β-D-glucopyranosidePhytoBank
Ferulic acid 4-O-beta-D-glucopyranosidePhytoBank
Ferulic acid 4-O-β-D-glucopyranosidePhytoBank
Ferulic acid 4-glucosidemanual
Ferulic acid glucosidemanual
Predicted Properties
PropertyValueSource
Water Solubility4.91 g/LALOGPS
logP-0.29ALOGPS
logP-0.59ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.65 m³·mol⁻¹ChemAxon
Polarizability34.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H20O9
IUPAC name(2E)-3-(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C16H20O9/c1-23-10-6-8(3-5-12(18)19)2-4-9(10)24-16-15(22)14(21)13(20)11(7-17)25-16/h2-6,11,13-17,20-22H,7H2,1H3,(H,18,19)/b5-3+/t11-,13-,14+,15-,16-/m1/s1
InChI KeyIEMIRSXOYFWPFD-BJGSYIFTSA-N
Isomeric SMILESCOC1=CC(\C=C\C(O)=O)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Average Molecular Weight356.3246
Monoisotopic Molecular Weight356.110732238
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
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-054t-0916000000-ebc1cc4896fdc64a458cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0900000000-6a902dabbbf78442f23eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004s-1900000000-e4ad1acd6f4850f0bc2eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-1819000000-eba6f8f85bf8d5d53934Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-1911000000-77f2053078c1eb574d28Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-2900000000-2ff1d99e129350f50621Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID489
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDFERULIC-ACID-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.