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Showing Compound 3',4',5,7-Tetrahydroxyflavanone (FDB011936)

Record Information
Version1.0
Creation date2010-04-08 22:09:54 UTC
Update date2019-11-26 03:05:47 UTC
Primary IDFDB011936
Secondary Accession Numbers
  • FDB000688
Chemical Information
FooDB Name3',4',5,7-Tetrahydroxyflavanone
DescriptionEriodictyol, also known as 573'5'-tetrahydroxyflavanone, 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. Eriodictyol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Eriodictyol can be found in a number of food items such as rowal, grape, cardamom, and lemon balm, which makes eriodictyol a potential biomarker for the consumption of these food products. Eriodictyol is a bitter-masking flavanone, a flavonoid extracted from yerba santa (Eriodictyon californicum), a plant native to North America. Eriodictyol is one of the four flavanones identified in this plant as having taste-modifying properties, the other three being homoeriodictyol, its sodium salt, and sterubin .
CAS Number4049-38-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(S)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4-benzopyroneChEBI
(S)-EriodictyolChEBI
EriodictiolChEBI
(+)-EriodictyolHMDB
(2S)-EriodictyolHMDB
(S)-2,3-DihydroluteolinHMDB
(S)-3',4',5,7-TetrahydroxyflavanoneHMDB
(S)-3’,4’,5,7-TetrahydroxyflavanoneHMDB
3',4',5,7-TetrahydroxyflavanoneHMDB
3’,4’,5,7-TetrahydroxyflavanoneHMDB
(2S)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-oneHMDB
(2S)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydrochromen-4-oneHMDB
HuazhongilexoneHMDB
2-(3,4-Dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.37 g/LALOGPS
logP2.15ALOGPS
logP2.53ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.85ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.27 m³·mol⁻¹ChemAxon
Polarizability27.33 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H12O6
IUPAC name(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C15H12O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-5,13,16-19H,6H2
InChI KeySBHXYTNGIZCORC-UHFFFAOYSA-N
Isomeric SMILESOC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC(O)=C(O)C=C1
Average Molecular Weight288.255
Monoisotopic Molecular Weight288.063388106
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
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Catechol
  • Aryl ketone
  • Aryl alkyl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.50%; H 4.20%; O 33.30%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 DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS, 5 TMS, GC-MS Spectrumsplash10-00o3-2964120000-760c54cbe3d97e214b89Spectrum
GC-MS, 1 MEOX; 4 TMS, GC-MS Spectrumsplash10-05i4-3982160000-16d59df001928b3a3494Spectrum
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06y9-0690000000-250ba7bd6576410f8734Spectrum
Predicted GC-MS, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0imi-2530190000-6bcd43fd8b42301ed166Spectrum
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-778b9cb4a7b875c6bbec2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-052r-0090000000-9178a74a6239d2ef38822017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-052r-0290000000-287f5fa660d816283c292017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0019-0090000000-cb3df3f82944d76bf2242017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0019-0090000000-cb3df3f82944d76bf2242017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0019-0090000000-cb3df3f82944d76bf2242017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-778b9cb4a7b875c6bbec2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-052r-0090000000-9178a74a6239d2ef38822017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-052r-0290000000-287f5fa660d816283c292017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0019-0090000000-cb3df3f82944d76bf2242017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-772ca2fc672ef9668bfa2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0920000000-4bc67dc66facd1fa75e52017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f79-0910000000-c48ad5f3958e9c41f5de2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0970000000-cb17dd84eda67cc9d6a42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0900000000-5c65882b59856d787f672017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0910000000-85200d3bfe0ef9f8c6cf2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f79-0900000000-8aa62dd381d8e70390e12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-1900000000-c83d3fbbf98b1c8e768d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f79-0950000000-70ad9d5c48c3fd3ab1fe2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0390000000-0dc39ca84a3e57cc45532016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0980000000-1ccfe66899ea0c7d03a32016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fa9-4900000000-df7958810e2c565408772016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0190000000-a7838f78d4cef436da5f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0390000000-adb9e4c67817a09b2fd02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0apr-5940000000-9fb4bafc0204f514e65f2016-08-03View Spectrum
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) IDHBX33-A:HBX33-A
EAFUS IDNot Available
Dr. Duke IDERIODICTYOL
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
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti feedantDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti peroxidantDUKE
aphidifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
juvabionalDUKE
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
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).