Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2020-02-24 19:10:33 UTC
Primary IDFDB002579
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChrysoeriol
DescriptionChrysoeriol, also known as scoparol, 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. Thus, chrysoeriol is considered to be a flavonoid lipid molecule. Chrysoeriol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Chrysoeriol is a bitter tasting compound. Chrysoeriol has been detected, but not quantified in, several different foods, such as ryes, common sages, german camomiles, corns, and annual wild rices. This could make chrysoeriol a potential biomarker for the consumption of these foods.
CAS Number491-71-4
Structure
Thumb
Synonyms
SynonymSource
3'-MethoxyapigeninChEBI
3'-O-MethylluteolinChEBI
5,7,4'-Trihydroxy-3'-methoxyflavoneChEBI
5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyroneChEBI
5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-oneChEBI
ChryseriolChEBI
ChrysoeriolChEBI
Luteolin 3'-methyl etherChEBI
2-(5-Methoxy,4-hydroxyphenyl)5,7-dihydroxy-benzpyran-4-oneHMDB
3'-Methoxy-4',5,7-trihydroxyflavoneHMDB
3'-O-MethyluteolinHMDB
4',5,7-Trihydroxy-3'-methoxy-flavoneHMDB
5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one, 9ciHMDB
ScoparolHMDB
8-ChrysoeriolMeSH
3’-Methoxy-4’,5,7-trihydroxyflavoneHMDB
3’-MethoxyapigeninHMDB
3’-O-MethylluteolinHMDB
5,7,4’-Trihydroxy-3’-methoxyflavoneHMDB
ChrysoriolHMDB
Luteolin 3’-methyl etherHMDB
2-(5-methoxy,4-hydroxyphenyl)5,7-dihydroxy-benzpyran-4-onebiospider
5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
Flavone, 4',5,7-trihydroxy-3'-methoxy-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP3.07ALOGPS
logP2.55ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.58ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.38 m³·mol⁻¹ChemAxon
Polarizability29.74 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H12O6
IUPAC name5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C16H12O6/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/h2-7,17-19H,1H3
InChI KeySCZVLDHREVKTSH-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1
Average Molecular Weight300.2629
Monoisotopic Molecular Weight300.063388116
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
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.00%; H 4.03%; O 31.97%DFC
Melting PointMp 330-331°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data347 () (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0khi-0592000000-6ea6e2a1a8294d4ab051Spectrum
Predicted GC-MSChrysoeriol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zn9-0591000000-7220607989921b5eb2cfSpectrum
Predicted GC-MSChrysoeriol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ukc-2190860000-4372f124a3dd76bf7eeeSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udj-0159000000-3b5e183acbd84887fe16Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udj-0159000000-3b5e183acbd84887fe16Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0a59-0190000000-e41a7a0b369e042fae34Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-057i-0590000000-9bcbe16e3cceb12dd431Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-057i-0590000000-9bcbe16e3cceb12dd431Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0091010000-c79a20e1046701a4b60aSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001j-0090000000-10b8cb8801e211ef50f3Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0a59-0190000000-e41a7a0b369e042fae34Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-057i-0590000000-9bcbe16e3cceb12dd431Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0091000000-bcccd2fe60d84477404fSpectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-001i-0090000000-949568b80cb16a148dbcSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-0390000000-05ee89ba1f8ae9db73ccSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0090000000-1784fb1bc26ba2970df0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0090000000-8a5f685e7c770df2fae8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a59-0690000000-f42c517370ac99fa2b5fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001j-0090000000-10b8cb8801e211ef50f3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a59-0190000000-e41a7a0b369e042fae34Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-057i-0590000000-9bcbe16e3cceb12dd431Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-af2dad55a1de3a0bb83bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-092a839c4ea4b680b7ebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0029000000-cbb434b2646e02f29d56Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2590000000-ff4ac1c0435d02e5a2a4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-1080ec21704ad22b1e2dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-7da56dabd16c2e5c217aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v0u-1390000000-a28554e987b0184da54fSpectrum
NMR
TypeDescriptionView
ChemSpider ID4444263
ChEMBL IDCHEMBL214321
KEGG Compound IDC04293
Pubchem Compound ID5280666
Pubchem Substance IDNot Available
ChEBI ID16514
Phenol-Explorer ID282
DrugBank IDNot Available
HMDB IDHMDB30667
CRC / DFC (Dictionary of Food Compounds) IDCML88-I:CML88-I
EAFUS IDNot Available
Dr. Duke IDCHRYSOERIOL
BIGG IDNot Available
KNApSAcK IDC00001029
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
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti complementaryDUKE
anti mutagenicDUKE
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 rhinoviral22587 A substance that destroys or inhibits replication of viruses.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).