Record Information
Creation date2010-04-08 22:04:39 UTC
Update date2019-11-26 02:55:09 UTC
Primary IDFDB000655
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLiquiritigenin
DescriptionLiquiritigenin 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. Thus, liquiritigenin is considered to be a flavonoid. Liquiritigenin is a bitter tasting compound. Liquiritigenin has been detected, but not quantified in, several different foods, such as nuts, winged beans (Psophocarpus tetragonolobus), brussel sprouts (Brassica oleracea var. gemmifera), green vegetables, and prairie turnips (Pediomelum esculentum). This could make liquiritigenin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Liquiritigenin.
CAS Number578-86-9
Predicted Properties
Water Solubility0.13 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H12O4
IUPAC name(2S)-7-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
Isomeric SMILESOC1=CC=C(C=C1)C1CC(=O)C2=C(O1)C=C(O)C=C2
Average Molecular Weight256.257
Monoisotopic Molecular Weight256.073558866
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
Sub ClassFlavans
Direct ParentFlavanones
Alternative Parents
  • 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.31%; H 4.72%; O 24.97%DFC
Melting PointMp 203-205°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -36.2 (c, 0.09 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
TypeDescriptionSplash KeyView
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06vr-1290000000-473372a9cbd8aa299c8cSpectrum
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014r-0900000000-8829ca13726fa5ef2894Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0090010000-4f0e0e7c69cd0563f154Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014r-0900000000-8829ca13726fa5ef2894Spectrum
MS/MSLC-MS/MS Spectrum - QIT 4V, positivesplash10-0a4i-0090000000-e0ef2b922828538142d6Spectrum
MS/MSLC-MS/MS Spectrum - QIT 15V, positivesplash10-01pa-0990000000-b55ccc74a2ff9f8ee58aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4r-0690000000-e4eb8456793483d7e47bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-000i-0910000000-1b26412c239d13150a16Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQQ , positivesplash10-0a4i-0090000000-5a6df4ef73b17801c15bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 17V, positivesplash10-0a4r-0390000000-030c074282d57f882ea6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 17V, positivesplash10-000j-0970000000-cc482ab502fe16da0b2cSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014r-0900000000-8829ca13726fa5ef2894Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-7e114a20c600b4c23218Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-00ac566b03c0d20a16bcSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014r-0900000000-37f3374e06351b592624Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-0910000000-afbe3e4c5fceeb057aacSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014i-1900000000-541af142929c530ffba1Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ap0-0970000000-5d4e47f2631f47124cc4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-93474b44c5d1cb8cb155Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0790000000-572e47bb5dd6e39a5083Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rj-5910000000-47c758a4f16f999867aaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-b48d7117a74eb8dea54dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0290000000-24d9ef16fb94c78f6cd9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-6930000000-82d8508c6ca9b5e8be2aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-74e7833e04a924835b1eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0790000000-f21efeafedd047dfaebdSpectrum
NMRNot Available
ChemSpider ID1818
ChEMBL IDNot Available
KEGG Compound IDC09762
Pubchem Compound ID1889
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB03601
CRC / DFC (Dictionary of Food Compounds) IDBFK34-C:BFK72-M
EAFUS IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000977
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLiquiritigenin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Biological Effects and Interactions
Health Effects / Bioactivities
anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
central nervous system active35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hemoglobin inducerDUKE
monoamine-oxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
  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
MSDSNot Available
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.