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Showing Compound Tricin (FDB002440)

Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2025-11-18 22:37:29 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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3',5'-O-DimethyltricetinChEBI
5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-1-benzopyran-4-oneChEBI
TricinChEBI
Tricetin 3',5'-di-methyl etherKegg
5,7,4'-Trihydroxy-3',5'-dimethoxy-flavoneHMDB
5,7,4'-Trihydroxy-3',5'-dimethoxyflavoneHMDB
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
  • 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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTricin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0w30-0549000000-e14c5396fb64a68fefa1Spectrum
Predicted GC-MSTricin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0089-2190780000-31b199178d0def31abf9Spectrum
Predicted GC-MSTricin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-dfc714758de8cdbb00462016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0009000000-f817294bac54e99c1b102016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-2793000000-b83996240fd12d3a49232016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-b3200ffc7361a3de864b2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0019000000-6b23b340a1ad705fa57c2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lz9-1392000000-a9658144229a5cd4b2322016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-d315adca089d9b20a5b72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-5c0a50817e8fc7afe4ac2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-0592000000-d0ade450b1196d875ef72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-6e7c1f722f7f2751ab682021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0009000000-6e7c1f722f7f2751ab682021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0914000000-e8da5d0d054f7fedadb02021-09-24View Spectrum
NMRNot Available
ChemSpider ID4445019
ChEMBL IDCHEMBL454320
KEGG Compound IDC10193
Pubchem Compound ID5281702
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 IDTricin
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
AllelopathicBiochemicals that inhibit growth, survival, or reproduction in other organisms, with potential therapeutic applications in weed control, antimicrobial, and anticancer treatments, and key medical uses in developing novel pesticides, antibiotics, and chemotherapeutics.DUKE
Anti cariogenic52217 An agent that prevents tooth decay, reducing bacterial acid production and plaque formation. Its biological role is to inhibit the growth of cariogenic bacteria, and its therapeutic applications include preventing dental caries and managing tooth decay. Key medical uses include toothpaste, mouthwashes, and dental varnishes to maintain oral health.DUKE
Anti leukemic35610 An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
CatabolicA biological process that breaks down molecules, releasing energy used to fuel anabolic reactions. Therapeutically, catabolic agents are used to manage weight loss, treat metabolic disorders, and enhance athletic performance. Key medical uses includeDUKE
EstrogenicAn agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility.DUKE
HerbistatA topical herbal preparation with antimicrobial and anti-inflammatory properties, used to treat skin ailments such as cuts, bites, and infections, promoting wound healing and reducing the risk of infection.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Cyclooxygenase inhibitor35544 An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation.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).