Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2018-05-29 00:35:10 UTC
Primary IDFDB002440
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTricin
Description5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one, also known as 3',5'-O-dimethyltricetin or 5,7,4'-trihydroxy-3',5'-dimethoxy-flavone, 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. Thus, 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one can be synthesized from tricetin. 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one is also a parent compound for other transformation products, including but not limited to, tricin 7-O-glucoside, 4'-O-beta-glucosyl-7-O-(6-O-sinapoylglucosyl)tricin, and tricin 7-O-(6''-O-malonyl)-beta-D-glucopyranoside. 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one can be found in barley, common wheat, oat, and rice, which makes 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one a potential biomarker for the consumption of these food products.
CAS Number520-32-1
Structure
Thumb
Synonyms
SynonymSource
3',5'-O-DimethyltricetinChEBI
5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-1-benzopyran-4-oneChEBI
5,7,4'-Trihydroxy-3',5'-dimethoxy-flavoneMeSH
5,7,4'-Trihydroxy-3',5'-dimethoxyflavoneMeSH
5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
Phelipeonedb_source
Phoelipeonedb_source
Tricetin 3',5'-dimethyl etherdb_source
Tricindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP3.05ALOGPS
logP2.39ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.57ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity85.84 m³·mol⁻¹ChemAxon
Polarizability32.75 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC17H14O7
IUPAC name5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C17H14O7/c1-22-14-3-8(4-15(23-2)17(14)21)12-7-11(20)16-10(19)5-9(18)6-13(16)24-12/h3-7,18-19,21H,1-2H3
InChI KeyHRGUSFBJBOKSML-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(=CC(OC)=C1O)C1=CC(=O)C2=C(O)C=C(O)C=C2O1
Average Molecular Weight330.2889
Monoisotopic Molecular Weight330.073952802
Classification
DescriptionThis compound 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
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 61.82%; H 4.27%; O 33.91%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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w30-0549000000-e14c5396fb64a68fefa1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0089-2190780000-31b199178d0def31abf9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-dfc714758de8cdbb0046JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0009000000-f817294bac54e99c1b10JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-2793000000-b83996240fd12d3a4923JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-b3200ffc7361a3de864bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0019000000-6b23b340a1ad705fa57cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lz9-1392000000-a9658144229a5cd4b232JSpectraViewer
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) IDCLT97-R:CLT97-R
EAFUS IDNot Available
Dr. Duke IDTRICIN
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
allelopathicDUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.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
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
catabolicDUKE
estrogenicDUKE
herbistatDUKE
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
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.CHEBI
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).