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Showing Compound Butein (FDB000082)

Record Information
Version1.0
Creation date2010-04-08 22:04:26 UTC
Update date2019-11-26 02:54:31 UTC
Primary IDFDB000082
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameButein
DescriptionButein, also known as 2',3,4,4'-tetrahydroxychalcone, is a member of the class of compounds known as 2'-hydroxychalcones. 2'-hydroxychalcones are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, butein is considered to be a flavonoid lipid molecule. Butein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Butein is a bitter tasting compound found in broad bean, which makes butein a potential biomarker for the consumption of this food product. Butein is a chalcone of the chalconoids. It can be found in Toxicodendron vernicifluum (or formerly Rhus verniciflua), Dahlia, Butea (Butea monosperma) and Coreopsis It has antioxidative, aldose reductase and advanced glycation endproducts inhibitory effects. It is also a sirtuin-activating compound, a chemical compound having an effect on sirtuins, a group of enzymes that use NAD+ to remove acetyl groups from proteins. It turned out that buteins possess a high ability to inhibit aromatase process in the human body, for this reason, the use of these compounds in the treatment of breast cancer on the estrogen ground has been taken into account. The first attempts of sport pro-hormone supplementation with the use of buteins took place in Poland .
CAS Number487-52-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(e)-2',3,4,4'-TerahydroxychalconeChEBI
2',3,4,4'-TetrahydroxychalconeChEBI
3,4,2',4'-TetrahydroxychalconeChEBI
2',4',3,4-TetrahydroxychalconeMeSH
2',3,4,4'-Tetrahydrochalconebiospider
3-(3,4-Dihydroxy-phenyl)-1-(2,4-dihydroxy-phenyl)-propenonebiospider
Acrylophenone, 2',4'-dihydroxy-3-(3,4-dihydroxyphenyl)-biospider
Chalcone, 2',3,4,4'-tetrahydroxy- (7CI,8CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility0.074 g/LALOGPS
logP2.61ALOGPS
logP3.33ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.11ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.8 m³·mol⁻¹ChemAxon
Polarizability27.48 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H12O5
IUPAC name(2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
InChI IdentifierInChI=1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+
InChI KeyAYMYWHCQALZEGT-ORCRQEGFSA-N
Isomeric SMILES[H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)C1=C(O)C=C(O)C=C1
Average Molecular Weight272.2528
Monoisotopic Molecular Weight272.068473494
Classification
Description Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent2'-Hydroxychalcones
Alternative Parents
Substituents
  • 2'-hydroxychalcone
  • Cinnamylphenol
  • Hydroxycinnamic acid or derivatives
  • Benzoyl
  • Catechol
  • Aryl ketone
  • Styrene
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Acryloyl-group
  • Enone
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
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-MSButein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-1970000000-3b861b49974b46be5baeSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 19V, positivesplash10-0bt9-0690000000-cc1d721b42a1f299b3712020-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 19V, positivesplash10-08fr-0970000000-0e10aa91e1e766b9e07f2020-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0290000000-68a29b4caa455b22fb0e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ki-0950000000-91b48c62184834f21b292016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-4910000000-58de60c33d5b9886c4172016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-4ecb6a02be282b901c912016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0590000000-978cd7bc59526c9eb0272016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4920000000-0f64f8b79c9b90acdaeb2016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08578
Pubchem Compound ID5281222
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID104
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDBUTEIN
BIGG IDNot Available
KNApSAcK IDC00006941
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 ID104
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti inflammatory35472 A substance that reduces or suppresses inflammation.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
oxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pigment26130 An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.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— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).