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Showing Compound Homoeriodictyol (FDB016549)

Record Information
Version1.0
Creation date2010-04-08 22:12:30 UTC
Update date2020-02-24 19:11:07 UTC
Primary IDFDB016549
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHomoeriodictyol
DescriptionHomoeriodictyol is a member of the class of compounds known as 3'-o-methylated flavonoids. 3'-o-methylated flavonoids are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone. Homoeriodictyol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Homoeriodictyol can be found in coriander, which makes homoeriodictyol a potential biomarker for the consumption of this food product. Homoeriodictyol (3`-methoxy-4`,5,7-trihydroxyflavanone) is one of the 4 flavanones identified by Symrise in this plant eliciting taste-modifying property: homoeriodictyol sodium salt, eriodictyol and sterubin. Homoeriodictyol Sodium salt elicited the most potent bitter-masking activity by reducing from 10 to 40% the bitterness of salicin, amarogentin, paracetamol and quinine. However no bitter-masking activity was detected with bitter linoleic acid emulsions. According to Symrise's scientists homoeriodictyol sodium salt seems to be a taste-modifier with large potential in food applications and pharmaceuticals .
CAS Number446-71-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-homoeriodictyolbiospider
4',5,7-Trihydroxy-3'-methoxyflavanonedb_source
5,7,4'-Trihydroxy-3'-methoxyflavanonebiospider
Eriodictyol 3'-methyl etherbiospider
Eriodictyononedb_source
Homoeriodictyoldb_source
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.53ALOGPS
logP2.68ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.86ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.75 m³·mol⁻¹ChemAxon
Polarizability30.18 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H14O6
IUPAC name5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C16H14O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-6,13,17-19H,7H2,1H3
InChI KeyFTODBIPDTXRIGS-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1
Average Molecular Weight302.2788
Monoisotopic Molecular Weight302.07903818
Classification
Description Belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent3'-O-methylated flavonoids
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
  • Flavanone
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • Chromone
  • Chromane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Methoxybenzene
  • Aryl alkyl ketone
  • Anisole
  • Phenol ether
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 63.57%; H 4.67%; O 31.76%DFC
Melting PointMp 224°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -28.2 (EtOH)DFC
Spectroscopic UV Data320 () (MeOH/NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSHomoeriodictyol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udj-3860980000-8fac7c053d9a3fd38b92Spectrum
Predicted GC-MSHomoeriodictyol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-0891000000-de66d9997441a704bfbbSpectrum
Predicted GC-MSHomoeriodictyol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomoeriodictyol, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0901000000-0c03d0debde409d732712021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0309000000-1e75667c419401d431682021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0329000000-5399ec0a04197add7b5b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-0911000000-683031426af2b0b207db2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-053r-4900000000-e6ae1ba2ec48b134d7442021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0910000000-97254ecbd73f0695e0b22021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0329000000-2e448e392dd30f2896b62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0944000000-06473a1b9b10bd356e4d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-2900000000-94ddc69e26fd02fbdd162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0109000000-4b13f87245d8593ec8372016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0569000000-a139ca899655d2d70dab2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-3940000000-75faf654e55300c262ff2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-b74362932d87e15c9ce22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0309000000-4c59007c75c7cf8e58062021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-41d817369fa137077c1b2021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09756
Pubchem Compound ID73635
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:KRN04-J
EAFUS IDNot Available
Dr. Duke IDHOMOERIODICTYOL
BIGG IDNot Available
KNApSAcK IDC00000969
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 ID795
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti feedantDUKE
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
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).