Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2020-02-24 19:11:10 UTC
Primary IDFDB002436
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFraxinol
Description6-hydroxy-5,7-dimethoxy-2H-chromen-2-one belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton. 6-hydroxy-5,7-dimethoxy-2H-chromen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-hydroxy-5,7-dimethoxy-2H-chromen-2-one has been detected, but not quantified in, sour cherries. This could make 6-hydroxy-5,7-dimethoxy-2H-chromen-2-one a potential biomarker for the consumption of these foods.
CAS Number486-28-2
Structure
Thumb
Synonyms
SynonymSource
2H-1-Benzopyran-2-one, 6-hydroxy-5,7-dimethoxy-biospider
5,7-Dimethoxy-6-hydroxycoumarinbiospider
6-Hydroxy-5,7-dimethoxy-2H-1-benzopyran-2-one, 9CIdb_source
6-Hydroxy-5,7-dimethoxycoumarindb_source
Fraxinoldb_source
Predicted Properties
PropertyValueSource
Water Solubility1.59 g/LALOGPS
logP1.76ALOGPS
logP1.16ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.46 m³·mol⁻¹ChemAxon
Polarizability21.07 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H10O5
IUPAC name6-hydroxy-5,7-dimethoxy-2H-chromen-2-one
InChI IdentifierInChI=1S/C11H10O5/c1-14-8-5-7-6(3-4-9(12)16-7)11(15-2)10(8)13/h3-5,13H,1-2H3
InChI KeyPBPNOAHYDPHKFH-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C(OC)=C2C=CC(=O)OC2=C1
Average Molecular Weight222.1941
Monoisotopic Molecular Weight222.05282343
Classification
Description Belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct ParentHydroxycoumarins
Alternative Parents
Substituents
  • Hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.46%; H 4.54%; O 36.00%DFC
Melting PointMp 171-172°DFC
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-MSFraxinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmi-4290000000-72301291d8e0294472f0Spectrum
Predicted GC-MSFraxinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-0920000000-a69a160ebf89eea47ff4Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-2781a207b8e331a9a420Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0190000000-ce414227d4ada5f67390Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cmi-1910000000-c9d4136367b4b2f1486bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-8c72c4b4e7068100bca5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0490000000-a97141842420807811f3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvj-1920000000-6c03639a9a3ff5c57b0bSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID3047739
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHFL42-W:CLT41-W
EAFUS IDNot Available
Dr. Duke IDFRAXINOL
BIGG IDNot Available
KNApSAcK IDC00019318
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 IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).