Record Information
Version1.0
Creation date2010-04-08 22:05:20 UTC
Update date2018-05-28 22:40:08 UTC
Primary IDFDB002339
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-(4-Hydroxyphenyl)-2-butanone O-[6-galloylglucoside]
DescriptionIsolated from rhubarb. 4-(4-Hydroxyphenyl)-2-butanone O-[6-galloylglucoside] is found in green vegetables and garden rhubarb.
CAS Number59282-56-3
Structure
Thumb
Synonyms
SynonymSource
{3,4,5-trihydroxy-6-[4-(3-oxobutyl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoic acidGenerator
4-(4-Hydroxyphenyl)-2-butanone O-[3,4,5-trihydroxybenzoyl-(->6)-b-D-glucopyranoside]manual
4-(4-Hydroxyphenyl)-2-butanone O-[3,4,5-trihydroxybenzoyl-(->6)-b-D-glucoside]manual
4-(4-Hydroxyphenyl)-2-butanone O-[6-galloylglucoside]manual
4-(4-Hydroxyphenyl)-2-butanone O-[galloyl-(->6)-b-D-glucoside]manual
Lindleyindb_source
Rheosmine O-[6-galloylglucoside]manual
Predicted Properties
PropertyValueSource
Water Solubility0.58 g/LALOGPS
logP1.22ALOGPS
logP1.4ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)8.11ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area183.21 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity115.41 m³·mol⁻¹ChemAxon
Polarizability47.23 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC23H26O11
IUPAC name{3,4,5-trihydroxy-6-[4-(3-oxobutyl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C23H26O11/c1-11(24)2-3-12-4-6-14(7-5-12)33-23-21(30)20(29)19(28)17(34-23)10-32-22(31)13-8-15(25)18(27)16(26)9-13/h4-9,17,19-21,23,25-30H,2-3,10H2,1H3
InChI KeyBJYRNIFAMMOVGW-UHFFFAOYSA-N
Isomeric SMILESCC(=O)CCC1=CC=C(OC2OC(COC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)C(O)C2O)C=C1
Average Molecular Weight478.4459
Monoisotopic Molecular Weight478.147511674
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
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • O-glycosyl compound
  • Benzoate ester
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Phenoxy compound
  • Phenol ether
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Benzenoid
  • Ketone
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.74%; H 5.48%; O 36.78%DFC
Melting PointMp 210-211° (206-207°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -18.6 (c, 0.8 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID26502074
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID14345581
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30470
CRC / DFC (Dictionary of Food Compounds) IDGZX39-H:CKL75-O
EAFUS IDNot Available
Dr. Duke IDLINDLEYIN
BIGG IDNot Available
KNApSAcK IDC00037422
HET 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 / Bioactivities
DescriptorIDDefinitionReference
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
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).