Record Information
Version1.0
Creation date2010-04-08 22:11:55 UTC
Update date2018-05-29 01:19:47 UTC
Primary IDFDB015553
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhloretin
DescriptionPhloretin is a dihydrochalcone, a type of natural phenols. It is the phloroglucin ester of paraoxyhydratropic acid. It can be found in apple tree leaves. Phloretin is a biomarker for the consumption of apples.
CAS Number60-82-2
Structure
Thumb
Synonyms
SynonymSource
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanoneChEBI
2,6-Dihydroxy-4-methoxyacetophenoneHMDB
4-O-MethylphloracetophenoneHMDB
DihydronaringeninHMDB
PhloretolHMDB
2',4,4',6'-Tetrahydroxydihydrochalconedb_source
Asebogenoldb_source
Phloretindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.23ALOGPS
logP3.9ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.96ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.71 m³·mol⁻¹ChemAxon
Polarizability27.75 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H14O5
IUPAC name3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
InChI IdentifierInChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2
InChI KeyVGEREEWJJVICBM-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1
Average Molecular Weight274.2687
Monoisotopic Molecular Weight274.084123558
Classification
Description belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone 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'-Hydroxy-dihydrochalcones
Alternative Parents
Substituents
  • 2'-hydroxy-dihydrochalcone
  • Cinnamylphenol
  • Alkyl-phenylketone
  • Acylphloroglucinol derivative
  • Butyrophenone
  • Benzenetriol
  • Phloroglucinol derivative
  • Phenylketone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 65.69%; H 5.14%; O 29.17%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 Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002f-0915000000-2cd118505cf4ff16b664View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002f-0915000000-2cd118505cf4ff16b664View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2920000000-ce9a5fce0e77c981b6d3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00r2-2207490000-670b5b16c28fb6b692e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-1900000000-b990d3eca878be81222bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-2900000000-4eb9bf83b7d70a97bd0bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0w2c-4900000000-77d3779ddd5455f0b9a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-004i-0090000000-a2a168a2f04c479df8edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-00dj-0090050000-15d417468db5c396463eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-0a4i-0900000000-bc6e2e1009d1b50ad9f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00xr-0690000000-e5774d71d08a1df83336View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-d051b74295a78047c5f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01b9-0900000000-6e6539df4cbbef8d26b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-01b9-0940000000-e06c676ae64bfbb5107bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-949e95a0767d512e3d04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0910000000-bb2134d05e29fff0bc78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0910000000-eb3ed13a8222a6f19622View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-826fa92be2be280f2e5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-0930000000-6abeede53ef1753e2613View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-a2ba5d714e72373837bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-8a18e7ae5b70f7a0683fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0930000000-66ecbda03ca96ea053b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3910000000-831048d96d049d47cd92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-826fa92be2be280f2e5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-0930000000-6abeede53ef1753e2613View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-a2ba5d714e72373837bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-8a18e7ae5b70f7a0683fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0930000000-66ecbda03ca96ea053b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3910000000-831048d96d049d47cd92View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID4624
ChEMBL IDCHEMBL45068
KEGG Compound IDC00774
Pubchem Compound ID4788
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID108
DrugBank IDDB07810
HMDB IDHMDB03306
CRC / DFC (Dictionary of Food Compounds) IDKDD94-S:KDD94-S
EAFUS ID3736
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDG50
Flavornet IDNot Available
GoodScent IDrw1274381
SuperScent IDNot Available
Wikipedia IDPhloretin
Phenol-Explorer Metabolite ID108
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
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.