Record Information
Version1.0
Creation date2010-04-08 22:06:49 UTC
Update date2020-02-24 19:11:07 UTC
Primary IDFDB005736
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePectolinarigenin
DescriptionPectolinarigenin, also known as 5,7-dihydroxy-4',6-dimethoxyflavone or 4'-methylcapillarisin, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, pectolinarigenin is considered to be a flavonoid lipid molecule. Pectolinarigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pectolinarigenin can be found in sunflower and tarragon, which makes pectolinarigenin a potential biomarker for the consumption of these food products. Pectolinarigenin is a Cirsium isolate with anti-inflammatory activity and belongs to the flavones .
CAS Number520-12-7
Structure
Thumb
Synonyms
SynonymSource
4'-MethylcapillarisinChEBI
5,7-Dihydroxy-4',6-dimethoxyflavoneChEBI
Scutellarein-6,4'-dimethyl etherChEBI
5,7-Dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-onePhytoBank
4'-O-MethylcapillarisinPhytoBank
4’-O-MethylcapillarisinPhytoBank
5,7-Dihydroxy-4’,6-dimethoxyflavonePhytoBank
5,7-Dihydroxy-6,4'-dimethoxyflavonePhytoBank
5,7-Dihydroxy-6,4’-dimethoxyflavonePhytoBank
6,4'-Di-O-methylscutellareinPhytoBank
6,4’-Di-O-methylscutellareinPhytoBank
6-Methoxy-4'-O-methylapigeninPhytoBank
6-Methoxy-4’-O-methylapigeninPhytoBank
6-MethoxyacacetinPhytoBank
6-Methoxyapigenin 4'-methyl etherPhytoBank
6-Methoxyapigenin 4’-methyl etherPhytoBank
Capillarisin 4'-methyl etherPhytoBank
Capillarisin 4’-methyl etherPhytoBank
HortensinPhytoBank
PectolarigeninPhytoBank
PectolinangeninPhytoBank
PectolinargeninPhytoBank
PectolinaringeninPhytoBank
PectolinariogeninPhytoBank
Scutellarein 4',6-dimethyl etherPhytoBank
Scutellarein 4’,6-dimethyl etherPhytoBank
Scutellarein 6,4'-dimethyl etherPhytoBank
Scutellarein 6,4’-dimethyl etherPhytoBank
5, 7-Dihydroxy-4',6-dimethoxyflavonebiospider
5,7-Dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4-benzopyronebiospider
5,7-Dihydroxy-6, 4'-dimethoxyflavonebiospider
Flavone, 5,7-dihydroxy-4',6-dimethoxy-biospider
Flavone, 5,7-dihydroxy-4',6-dimethoxy- (8CI)biospider
Pectolinarigeninbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.043 g/LALOGPS
logP3.27ALOGPS
logP2.69ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.1ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.86 m³·mol⁻¹ChemAxon
Polarizability31.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H14O6
IUPAC name5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C17H14O6/c1-21-10-5-3-9(4-6-10)13-7-11(18)15-14(23-13)8-12(19)17(22-2)16(15)20/h3-8,19-20H,1-2H3
InChI KeyGPQLHGCIAUEJQK-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C(OC)=C2O
Average Molecular Weight314.2895
Monoisotopic Molecular Weight314.07903818
Classification
Description Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent6-O-methylated flavonoids
Alternative Parents
Substituents
  • 4p-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavone
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Anisole
  • Phenol ether
  • Phenoxy compound
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point221 oC
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
Predicted GC-MSPectolinarigenin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00r6-2418900000-df95f0e61458decca87fSpectrum
Predicted GC-MSPectolinarigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03ys-0791000000-836fecbd17351b108f80Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-920c2c245a2edf3b26faSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0019000000-cb56dc60015d3d4f40fdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015i-1690000000-15801b75750bca804042Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-23323343b3c8ca9eeb0bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0039000000-4c6fca08a28fa74cfb5eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-2790000000-2eb4853f161600213d16Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5320438
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDPECTOLINARIGENIN
BIGG IDNot Available
KNApSAcK IDC00003838
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
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.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).