Record Information
Version1.0
Creation date2010-04-08 22:12:30 UTC
Update date2019-11-26 03:13:28 UTC
Primary IDFDB016563
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLiquiritin rhamnoside
DescriptionLiquiritin rhamnoside, also known as 7,4'-dihydroxyflavanone, belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Liquiritin rhamnoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Liquiritin rhamnoside has been detected, but not quantified in, herbs and spices and tea. This could make liquiritin rhamnoside a potential biomarker for the consumption of these foods.
CAS Number31512-05-7
Structure
Thumb
Synonyms
SynonymSource
7,4'-DihydroxyflavanoneChEBI
4',7-DihydroxyflavanoneHMDB
5-DEOXYFLAVANONEHMDB
DFVHMDB
Liquiritigenin rhamnosylglucosidemanual
Liquiritin rhamnosidemanual
Rhamnoliquiritindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.79ALOGPS
logP2.49ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.79ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.31 m³·mol⁻¹ChemAxon
Polarizability26.41 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H12O4
IUPAC name7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2
InChI KeyFURUXTVZLHCCNA-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(C=C1)C1CC(=O)C2=C(O1)C=C(O)C=C2
Average Molecular Weight256.257
Monoisotopic Molecular Weight256.073558866
Classification
Description Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanones
Alternative Parents
Substituents
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavanone
  • Chromone
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.44%; H 5.71%; O 36.84%DFC
Melting PointMp 131°DFC
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-MS
TypeDescriptionSplash KeyView
GC-MSLiquiritigenin, non-derivatized, GC-MS Spectrumsplash10-002b-2933100000-ddf80ac4039ce216eb0eSpectrum
GC-MSLiquiritigenin, non-derivatized, GC-MS Spectrumsplash10-002b-1933100000-8647d225fcee75be2251Spectrum
GC-MSLiquiritigenin, non-derivatized, GC-MS Spectrumsplash10-004l-0910000000-63a750e75f49ab2a1ad8Spectrum
GC-MSLiquiritigenin, non-derivatized, GC-MS Spectrumsplash10-002b-2933100000-ddf80ac4039ce216eb0eSpectrum
GC-MSLiquiritigenin, non-derivatized, GC-MS Spectrumsplash10-002b-1933100000-8647d225fcee75be2251Spectrum
GC-MSLiquiritigenin, non-derivatized, GC-MS Spectrumsplash10-004l-0910000000-63a750e75f49ab2a1ad8Spectrum
Predicted GC-MSLiquiritigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06vr-1290000000-473372a9cbd8aa299c8cSpectrum
Predicted GC-MSLiquiritigenin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00b9-7639000000-bae8693dac55f48b7a98Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-0920000000-99358bcec35e8da3ac55Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0900000000-7c2a4142ad7ac925ab96Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000j-0970000000-57e6609f1e3db56fd859Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0920000000-99358bcec35e8da3ac55Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-1930000000-d1162e6450775d0179abSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-76d8588c0ed0a8f5ce31Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059i-0980000000-08a11004d141f30638f7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00y1-5910000000-e60e52225f16ed4919a7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-2325ae9643ac32fd23f9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1290000000-bd14bd382f234c971725Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-6930000000-2c9eaa5bfc05499d0bc4Spectrum
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 IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFK34-C:KRN66-D
EAFUS IDNot Available
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
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference