(TRIHYDROXY-PHENYL)-PROPAN-1-ONE (CHEM007729)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:29:37 UTC
Update Date2016-10-28 10:03:07 UTC
Accession NumberCHEM007729
Identification
Common Name(TRIHYDROXY-PHENYL)-PROPAN-1-ONE
ClassSmall Molecule
DescriptionPhloretin is a natural dihydrochalcone found in apples and many other fruits.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanoneChEBI
2,6-Dihydroxy-4-methoxyacetophenoneHMDB
4-O-MethylphloracetophenoneHMDB
DihydronaringeninHMDB
PhloretolHMDB
Chemical FormulaC15H14O5
Average Molecular Mass274.269 g/mol
Monoisotopic Mass274.084 g/mol
CAS Registry Number60-82-2
IUPAC Name3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
Traditional Namephloretin
SMILESOC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002f-0915000000-2cd118505cf4ff16b664Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002f-0915000000-2cd118505cf4ff16b664Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2920000000-ce9a5fce0e77c981b6d3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00r2-2207490000-670b5b16c28fb6b692e3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-1900000000-b990d3eca878be81222bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-2900000000-4eb9bf83b7d70a97bd0bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0w2c-4900000000-77d3779ddd5455f0b9a3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-004i-0090000000-a2a168a2f04c479df8edSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-00dj-0090050000-15d417468db5c396463eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-0a4i-0900000000-bc6e2e1009d1b50ad9f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00xr-0690000000-e5774d71d08a1df83336Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-d051b74295a78047c5f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01b9-0900000000-6e6539df4cbbef8d26b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-01b9-0940000000-e06c676ae64bfbb5107bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-949e95a0767d512e3d04Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0910000000-bb2134d05e29fff0bc78Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0910000000-eb3ed13a8222a6f19622Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-826fa92be2be280f2e5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-0930000000-6abeede53ef1753e2613Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-a2ba5d714e72373837bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-8a18e7ae5b70f7a0683fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0930000000-66ecbda03ca96ea053b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3910000000-831048d96d049d47cd92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-826fa92be2be280f2e5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-0930000000-6abeede53ef1753e2613Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-a2ba5d714e72373837bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-8a18e7ae5b70f7a0683fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0930000000-66ecbda03ca96ea053b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3910000000-831048d96d049d47cd92Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB07810
HMDB IDHMDB0003306
FooDB IDFDB015553
Phenol Explorer ID108
KNApSAcK IDC00007936
BiGG IDNot Available
BioCyc IDPHLORETIN
METLIN ID3405
PDB IDNot Available
Wikipedia LinkPhloretin
Chemspider ID4624
ChEBI ID17276
PubChem Compound ID4788
Kegg Compound IDC00774
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sharif NA, Crider JY, Davis TL: AL-3138 antagonizes FP prostanoid receptor-mediated inositol phosphates generation: comparison with some purported FP antagonists. J Pharm Pharmacol. 2000 Dec;52(12):1529-39.
2. Fan HT, Morishima S, Kida H, Okada Y: Phloretin differentially inhibits volume-sensitive and cyclic AMP-activated, but not Ca-activated, Cl(-) channels. Br J Pharmacol. 2001 Aug;133(7):1096-106.
3. Stangl V, Lorenz M, Ludwig A, Grimbo N, Guether C, Sanad W, Ziemer S, Martus P, Baumann G, Stangl K: The flavonoid phloretin suppresses stimulated expression of endothelial adhesion molecules and reduces activation of human platelets. J Nutr. 2005 Feb;135(2):172-8.
4. Rasmussen SE, Breinholt VM: Non-nutritive bioactive food constituents of plants: bioavailability of flavonoids. Int J Vitam Nutr Res. 2003 Mar;73(2):101-11.
5. Nielsen SE, Freese R, Kleemola P, Mutanen M: Flavonoids in human urine as biomarkers for intake of fruits and vegetables. Cancer Epidemiol Biomarkers Prev. 2002 May;11(5):459-66.
6. DuPont MS, Bennett RN, Mellon FA, Williamson G: Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans. J Nutr. 2002 Feb;132(2):172-5.
7. Ito H, Gonthier MP, Manach C, Morand C, Mennen L, Remesy C, Scalbert A: Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. Br J Nutr. 2005 Oct;94(4):500-9.
8. Zerbini G, Podesta F, Meregalli G, Deferrari G, Pontremoli R: Fibroblast Na+-Li+ countertransport rate is elevated in essential hypertension. J Hypertens. 2001 Jul;19(7):1263-9.
9. Park SY, Kim EJ, Shin HK, Kwon DY, Kim MS, Surh YJ, Park JH: Induction of apoptosis in HT-29 colon cancer cells by phloretin. J Med Food. 2007 Dec;10(4):581-6.
10. Tombola F, Morbiato L, Del Giudice G, Rappuoli R, Zoratti M, Papini E: The Helicobacter pylori VacA toxin is a urea permease that promotes urea diffusion across epithelia. J Clin Invest. 2001 Sep;108(6):929-37.
11. Pajor AM, Randolph KM, Kerner SA, Smith CD: Inhibitor binding in the human renal low- and high-affinity Na+/glucose cotransporters. J Pharmacol Exp Ther. 2008 Mar;324(3):985-91. Epub 2007 Dec 6.
12. Rezk BM, Haenen GR, van der Vijgh WJ, Bast A: The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids. Biochem Biophys Res Commun. 2002 Jul 5;295(1):9-13.
13. Pandey RP, Li TF, Kim EH, Yamaguchi T, Park YI, Kim JS, Sohng JK: Enzymatic synthesis of novel phloretin glucosides. Appl Environ Microbiol. 2013 Jun;79(11):3516-21. doi: 10.1128/AEM.00409-13. Epub 2013 Mar 29.
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=18767070
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23907072
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24487097
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=7126563