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Phloretin (FDB015553)

Record Information
Version1.0
Creation date2010-04-08 22:11:55 UTC
Update date2019-11-26 03:11:49 UTC
Primary IDFDB015553
Secondary Accession Numbers
  • FDB016581
Chemical Information
FooDB NamePhloretin
DescriptionPhloretin, also known as dihydronaringenin or phloretol, 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. Thus, phloretin is considered to be a flavonoid lipid molecule. Phloretin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Phloretin is an odorless tasting compound. Phloretin is found, on average, in the highest concentration within apples. Phloretin has also been detected, but not quantified in, several different foods, such as sweet rowanberries, chinese broccoli, common salsifies, wild carrots, and saskatoon berries. This could make phloretin a potential biomarker for the consumption of these foods.
CAS Number60-82-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Foods

Fruits and vegetables:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPhloretin, non-derivatized, GC-MS Spectrumsplash10-002f-0915000000-2cd118505cf4ff16b664Spectrum
GC-MSPhloretin, non-derivatized, GC-MS Spectrumsplash10-002f-0915000000-2cd118505cf4ff16b664Spectrum
Predicted GC-MSPhloretin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-2920000000-ce9a5fce0e77c981b6d3Spectrum
Predicted GC-MSPhloretin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00r2-2207490000-670b5b16c28fb6b692e3Spectrum
Predicted GC-MSPhloretin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-1900000000-b990d3eca878be81222b2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-2900000000-4eb9bf83b7d70a97bd0b2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0w2c-4900000000-77d3779ddd5455f0b9a32012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-004i-0090000000-a2a168a2f04c479df8ed2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-00dj-0090050000-15d417468db5c396463e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-0a4i-0900000000-bc6e2e1009d1b50ad9f72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00xr-0690000000-e5774d71d08a1df833362017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-d051b74295a78047c5f02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01b9-0900000000-6e6539df4cbbef8d26b32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-01b9-0940000000-e06c676ae64bfbb5107b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-949e95a0767d512e3d042017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0910000000-bb2134d05e29fff0bc782017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0910000000-eb3ed13a8222a6f196222017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-826fa92be2be280f2e5e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-0930000000-6abeede53ef1753e26132015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-a2ba5d714e72373837bb2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-8a18e7ae5b70f7a0683f2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0930000000-66ecbda03ca96ea053b32015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3910000000-831048d96d049d47cd922015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-826fa92be2be280f2e5e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-0930000000-6abeede53ef1753e26132015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-a2ba5d714e72373837bb2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-8a18e7ae5b70f7a0683f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0930000000-66ecbda03ca96ea053b32015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3910000000-831048d96d049d47cd922015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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.