Record Information
Version1.0
Creation date2010-04-08 22:10:00 UTC
Update date2019-11-26 03:06:15 UTC
Primary IDFDB012133
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthoxyletin
DescriptionXanthoxyletin belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. Xanthoxyletin is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Xanthoxyletin has also been detected, but not quantified in, a few different foods, such as herbs and spices, lemons (Citrus limon), and mandarin orange (clementine, tangerine). This could make xanthoxyletin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Xanthoxyletin.
CAS Number84-99-1
Structure
Thumb
Synonyms
SynonymSource
5-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one,9ciHMDB
5-Methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-oneHMDB
Xanthoxylin NHMDB
XanthoxyloinHMDB
XanthoxyletinMeSH
5-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one,9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP3.05ALOGPS
logP2.53ChemAxon
logS-4.1ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.41 m³·mol⁻¹ChemAxon
Polarizability26.9 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H14O4
IUPAC name5-methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one
InChI IdentifierInChI=1S/C15H14O4/c1-15(2)7-6-10-12(19-15)8-11-9(14(10)17-3)4-5-13(16)18-11/h4-8H,1-3H3
InChI KeyJSJIIHRNDMLJGK-UHFFFAOYSA-N
Isomeric SMILESCOC1=C2C=CC(=O)OC2=CC2=C1C=CC(C)(C)O2
Average Molecular Weight258.2693
Monoisotopic Molecular Weight258.089208936
Classification
Description Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassPyranocoumarins
Direct ParentLinear pyranocoumarins
Alternative Parents
Substituents
  • Linear pyranocoumarin
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.76%; H 5.46%; O 24.78%DFC
Melting PointMp 133°DFC
Boiling PointNot Available
Experimental Water Solubilitycold water]
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-MSXanthoxyletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-07ef-1190000000-78b72a1e70ea0b853cccSpectrum
Predicted GC-MSXanthoxyletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0uei-0940000000-f1e9eeeb83d8740504fcSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0890000000-3a18d9c240e9f3626355Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-0290000000-1de65956796614ac099eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-aa6d574f073513b5a829Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-6c6860209ee19099b43cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi0-4890000000-1ab1343a5be832f0b76eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-573b07a2c6c0cb5cbcd5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090000000-fb78f7d59b6f70625682Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ow-0980000000-b3f729731c4334112db9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-5899da0eda98839d58adSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-2cf3ccdcea338c77fa5aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-1290000000-6d0938937a8c48a429edSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-c2a50a42dfada53572a9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-0090000000-bb952c86674434372dddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02ti-0290000000-4afb4baf58c4f7b7019aSpectrum
NMRNot Available
ChemSpider ID59919
ChEMBL IDCHEMBL501358
KEGG Compound IDNot Available
Pubchem Compound ID66548
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33931
CRC / DFC (Dictionary of Food Compounds) IDHDM83-A:HDM83-A
EAFUS IDNot Available
Dr. Duke IDXANTHOXYLETIN
BIGG IDNot Available
KNApSAcK IDC00032520
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
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.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).