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Phlorizin (FDB015554)

Record Information
Version1.0
Creation date2010-04-08 22:11:55 UTC
Update date2019-11-26 03:11:49 UTC
Primary IDFDB015554
Secondary Accession Numbers
  • FDB006826
Chemical Information
FooDB NamePhlorizin
DescriptionPhlorizin, also known as phlorizoside, belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Phlorizin is a bitter tasting compound. Phlorizin is found, on average, in the highest concentration within a few different foods, such as mexican oreganos (Lippia graveolens), european plums (Prunus domestica), and apples (Malus pumila) and in a lower concentration in pomegranates (Punica granatum) and apricots (Prunus armeniaca). Phlorizin has also been detected, but not quantified in, several different foods, such as tamarinds (Tamarindus indica), millets (Panicum miliaceum), figs (Ficus carica), black-eyed peas (Vigna unguiculata ssp. unguiculata), and roman camomiles (Chamaemelum nobile). This could make phlorizin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Phlorizin.
CAS Number60-81-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
logP0.44ALOGPS
logP0.98ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.87ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity105.85 m³·mol⁻¹ChemAxon
Polarizability42.36 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H24O10
IUPAC name1-(2,4-dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one
InChI IdentifierInChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
InChI KeyIOUVKUPGCMBWBT-QNDFHXLGSA-N
Isomeric SMILESOC[C@H]1O[C@@H](OC2=CC(O)=CC(O)=C2C(=O)CCC2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight436.4093
Monoisotopic Molecular Weight436.136946988
Classification
Description Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid o-glycoside
  • 2'-hydroxy-dihydrochalcone
  • Linear 1,3-diarylpropanoid
  • Cinnamylphenol
  • Phenolic glycoside
  • Alkyl-phenylketone
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Butyrophenone
  • Phenylketone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Resorcinol
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.80%; H 5.54%; O 36.66%DFC
Melting Point110.0 oC
Boiling PointNot Available
Experimental Water Solubility1 mg/mL at 22 oCMERCK INDEX (1996)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]18D -52.1 (EtOH aq.)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPhlororrhizin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gb9-5913400000-47cf252550936db167d6Spectrum
Predicted GC-MSPhlororrhizin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-4760119000-72f18a2449892aa53ec3Spectrum
Predicted GC-MSPhlororrhizin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0090000000-76b60140aba03098ef8d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0090000000-26c8a10836d524559b7a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0092000000-90a57e1f22eef000cfc22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0192000000-569b92df53d5414d6b9c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00or-0593000000-dd46ab71f853e528f8092017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0029500000-83a7b6481f9411db0c2a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014l-0029400000-1e2ddb25131a89de24732017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014l-0029400000-9b87e9e9e7047311fe432017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014l-0129300000-85b4094b3a111acabac52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0019700000-17beed8e63a40dbe0fad2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0019700000-e6f57c85d791f73ddac42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0019800000-04f42cab2c73ebc8bfdd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0019700000-83eac943753547575e742017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0193100000-60d4307e81921a8848812017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0193100000-4ef83973bcb1d290871b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090100000-a7a243468c02717395712021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-36c0b1e835cbef4b2ba62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0092000000-3e89a8c85f5d700f5b872021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090200000-410af542557a682770cc2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00p0-0290600000-83064b80a026d781f15a2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pdi-0980000000-825463dfd002813e90b32016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-1930000000-d13d22201525f5a889b72016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-1361900000-f4ac825585d69e78246e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1591100000-4099114d9b7e981d8ed02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xu-4790000000-c222fbd317f639c6ecf72016-08-03View Spectrum
NMRNot Available
ChemSpider ID16498836
ChEMBL IDCHEMBL245067
KEGG Compound IDC01604
Pubchem Compound ID6072
Pubchem Substance IDNot Available
ChEBI ID8113
Phenol-Explorer ID109
DrugBank IDNot Available
HMDB IDHMDB36634
CRC / DFC (Dictionary of Food Compounds) IDKDD94-S:KDD95-T
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000990
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPhloridzin
Phenol-Explorer Metabolite IDNot Available
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
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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.