Record Information
Version1.0
Creation date2010-04-08 22:05:30 UTC
Update date2019-11-26 02:57:55 UTC
Primary IDFDB002758
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePinocembrin
Description(s)-pinocembrin, also known as 5,7-dihydroxyflavanone or dihydrochrysin, is a member of the class of 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 (s)-pinocembrin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (s)-pinocembrin is a bitter tasting compound found in mexican oregano and tarragon, which makes (s)-pinocembrin a potential biomarker for the consumption of these food products.
CAS Number68745-38-0
Structure
Thumb
Synonyms
SynonymSource
(S)-5,7-DihydroxyflavanoneHMDB
5,7-DihydroxyflavanoneHMDB
DihydrochrysinHMDB
Galangin flavanoneHMDB
Pinocembrin (6ci)HMDB
PinocembrinMeSH, HMDB
PinocembrineMeSH, HMDB
(+)-PinocoembrinMeSH
2,3-Dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP2.85ALOGPS
logP3.14ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.87ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.31 m³·mol⁻¹ChemAxon
Polarizability26.27 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H12O4
IUPAC name5,7-dihydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2
InChI KeyURFCJEUYXNAHFI-UHFFFAOYSA-N
Isomeric SMILESOC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC=CC=C1
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
  • Flavanone
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Aryl ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.31%; H 4.72%; O 24.97%DFC
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 Data325 () (MeOH/NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPinocembrin, non-derivatized, GC-MS Spectrumsplash10-0zi0-4940000000-e82938be666b8efbd57dSpectrum
GC-MSPinocembrin, non-derivatized, GC-MS Spectrumsplash10-0zi0-4940000000-e82938be666b8efbd57dSpectrum
Predicted GC-MSPinocembrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kdr-2390000000-e5b2a24d0f85221b06d5Spectrum
Predicted GC-MSPinocembrin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-024i-7359000000-bbe602140f5eb8e64c35Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-0980000000-1e2fb974e66fdf1905deSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0090000000-e7a2d42e43fa0b871d58Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0490000000-db48745a3d543c14c6fcSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0pi0-0900000000-31c7469fd05b2dfa0d26Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0590000000-a0bd5e67864cbcce0ef1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0490000000-e3e0fd288f81b7d8a9f6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-bb65e58e45d6926a4d0eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-405d5e70eb1870fb79b7Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0890000000-53a90fbc9a29bf0adf0aSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0900000000-20e5dc727e70bdfb32adSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0920000000-51d135533a4a8f649cbaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-b164f424f75fa66b547aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbi-0970000000-077fc628bf2155480d1eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-3900000000-cfbae6b4977762472890Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-cc887329ec72033da059Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1390000000-73b4983f6ed53a910578Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-5910000000-d0b4a2815a601b641cdbSpectrum
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) IDCNM52-F:CNM52-F
EAFUS IDNot Available
Dr. Duke IDPINOCEMBRIN
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 / Bioactivities
DescriptorIDDefinitionReference
anestheticDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
artemicideDUKE
candidicideDUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
fungicide24127 A substance used to destroy fungal pests.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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  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
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).