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Showing Compound Xanthoxylin (FDB000816)

Record Information
Version1.0
Creation date2010-04-08 22:04:43 UTC
Update date2020-02-24 19:10:15 UTC
Primary IDFDB000816
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthoxylin
DescriptionXanthoxylin, also known as brevifolin, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Xanthoxylin is a borneol and camphor tasting compound. Xanthoxylin has been detected, but not quantified in, several different foods, such as fats and oils, german camomiles (Matricaria recutita), herbs and spices, pomegranates (Punica granatum), and sweet oranges (Citrus sinensis). This could make xanthoxylin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Xanthoxylin.
CAS Number90-24-4
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
2-Hydroxy-4,6-dimethoxyacetophenoneMeSH
BrevifolinMeSH
XanthoxylineMeSH
1-(2-Hydroxy-4,6-dimethoxyphenyl)-ethanoneHMDB
1-(2-Hydroxy-4,6-dimethoxyphenyl)ethan-1-oneHMDB
1-(2-Hydroxy-4,6-dimethoxyphenyl)ethanoneHMDB
1-Acetyl-2-hydroxy-4,6-dimethoxybenzeneHMDB
2'-Hydroxy-4',6'-dimethoxy-acetophenoneHMDB
2'-Hydroxy-4',6'-dimethoxyacetophenoneHMDB
2,4-Di-O-methylphloroacetophenoneHMDB
2-Hydroxy-4, 6-dimethoxyacetophenoneHMDB
2-Hydroxyl-4,6-dimethoxy-acetophenoneHMDB
4, 6-Dimethoxy-2-hydroxyacetophenoneHMDB
4,6-Dimethoxy-2-hydroxyacetophenoneHMDB
6-MethoxypaeonolHMDB
Acetophenone der.HMDB
Acetophenone, 2'-hydroxy-4',6'-dimethoxy- (8ci)HMDB
Brevifolin (zanthoxylum)HMDB
Phloracetophenone dimethyl etherHMDB
Phloroacetophenone 2,4-dimethyl etherHMDB
2',4,-Dimethylpholoroacetophenonemanual
Acetophenone, 2'-hydroxy-4',6'-dimethoxy-biospider
Ethanone, 1-(2-hydroxy-4,6-dimethoxyphenyl)-biospider
Xanthoxylindb_source
Predicted Properties
PropertyValueSource
Water Solubility2.46 g/LALOGPS
logP1.69ALOGPS
logP1.56ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)10.13ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.37 m³·mol⁻¹ChemAxon
Polarizability19.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H12O4
IUPAC name1-(2-hydroxy-4,6-dimethoxyphenyl)ethan-1-one
InChI IdentifierInChI=1S/C10H12O4/c1-6(11)10-8(12)4-7(13-2)5-9(10)14-3/h4-5,12H,1-3H3
InChI KeyFBUBVLUPUDBFME-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(O)=C(C(C)=O)C(OC)=C1
Average Molecular Weight196.1999
Monoisotopic Molecular Weight196.073558872
Classification
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Methoxyphenol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Acetophenone
  • Phenoxy compound
  • Anisole
  • Benzoyl
  • Phenol ether
  • Aryl alkyl ketone
  • Methoxybenzene
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ether
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 61.22%; H 6.16%; O 32.62%DFC
Melting PointMp 85-88°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
GC-MSXanthoxylin, non-derivatized, GC-MS Spectrumsplash10-001i-2900000000-7f4577d7995fbddd577fSpectrum
GC-MSXanthoxylin, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-3cd64b53df7c93b840adSpectrum
GC-MSXanthoxylin, non-derivatized, GC-MS Spectrumsplash10-001i-2900000000-7f4577d7995fbddd577fSpectrum
GC-MSXanthoxylin, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-3cd64b53df7c93b840adSpectrum
Predicted GC-MSXanthoxylin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-2900000000-7f3dc4cd71234f173a0cSpectrum
Predicted GC-MSXanthoxylin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uk9-7490000000-7f3ba8e004b9854018cbSpectrum
Predicted GC-MSXanthoxylin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ik9-1497100000-bce3b5395532448137462017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0gba-3900000000-3016175ddc355d5ca94e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-01p9-0900000000-43bfa0bde3b4f442ecdc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-22166f1027bf3e06de042021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-568f7cd67cd1fc802fd42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0lk9-0900000000-5a2b415f82cac4381e392021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-a965b10d2d3aad048c6e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-0900000000-4f70cdfc7d4f2a990f842021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-db6a23774c46b4a953532016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-ef5b20a480a33ea141b92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-2900000000-2de8c0fec8d00685e7f72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-41dccc88b05c10fc01992016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-1900000000-942e591bf3dc0f2bb3512016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0592-6900000000-a42426d4ccaaf03e24ee2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-43e8b5890016d76975372021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0900000000-58ec00da7265801de99e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001u-9500000000-39958fd208cc560c3c1f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-3fa6590d885bd13074802021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-7338902de2bb9e7347142021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06ec-9400000000-59b2e65e6acc03f454ae2021-09-23View Spectrum
NMRNot Available
ChemSpider ID60021
ChEMBL IDCHEMBL450288
KEGG Compound IDC10726
Pubchem Compound ID66654
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29645
CRC / DFC (Dictionary of Food Compounds) IDBJH52-T:BJH53-U
EAFUS IDNot Available
Dr. Duke IDBREVIFOLIN|XANTHOXYLIN
BIGG IDNot Available
KNApSAcK IDC00002710
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1540351
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 feedantDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
borneol
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).