Xanthorrhizol (CHEM031576)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:45:18 UTC
Update Date2016-11-09 01:19:17 UTC
Accession NumberCHEM031576
Identification
Common NameXanthorrhizol
ClassSmall Molecule
DescriptionXanthorrhizol is found in beverages. Xanthorrhizol is a constituent of rhizomes of Curcuma xanthorrhiza (Java turmeric)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-5-(1,5-Dimethyl-4-hexenyl)-2-methylphenolHMDB
(R)-(-)-XanthorrhizolHMDB
(R)-5-(1,5-Dimethyl-4-hexenyl)-O-cresolHMDB
(R)-5-(1-5-Dimethyl-4-hexenyl)-2-methylphenolHMDB
5-(1,5-Dimethyl-4-hexenyl)-(-)-O-cresolHMDB
5-(1,5-Dimethyl-4-hexenyl)-2-methyl-(-)-phenolHMDB
5-(1,5-Dimethyl-4-hexenyl)-2-methylphenolHMDB
5-(1,5-Dimethyl-4-hexenyl)-2-methylphenol, 9ciHMDB
5-[(1R)-1,5-Dimethyl-4-hexenyl]-2-methyl-phenolHMDB
Chemical FormulaC15H22O
Average Molecular Mass218.335 g/mol
Monoisotopic Mass218.167 g/mol
CAS Registry Number30199-26-9
IUPAC Name2-methyl-5-(6-methylhept-5-en-2-yl)phenol
Traditional Name2-methyl-5-(6-methylhept-5-en-2-yl)phenol
SMILESCC(CCC=C(C)C)C1=CC(O)=C(C)C=C1
InChI IdentifierInChI=1S/C15H22O/c1-11(2)6-5-7-12(3)14-9-8-13(4)15(16)10-14/h6,8-10,12,16H,5,7H2,1-4H3
InChI KeyFKWGCEDRLNNZOZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Bisabolane sesquiterpenoid
  • Sesquiterpenoid
  • P-cymene
  • O-cresol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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 Solubility0.029 g/LALOGPS
logP5.64ALOGPS
logP5.09ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)10.42ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.07 m³·mol⁻¹ChemAxon
Polarizability27.06 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-5910000000-bbbc808402d4ed1b9d87Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05di-9380000000-5efc594d791232cfba9eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1490000000-7b7917bbd2d076a6a1bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3930000000-f36e65d14851d985f07cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldi-9500000000-5dae3bd921c5b051d077Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-e9ece6fa864d7f85bd6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0190000000-825f4354c46942faba2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgr-2920000000-ed263b9c3352ae00c36fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-868e2fb00a2cfbf6c529Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0690000000-832a55e37cc53c279022Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-9c4703d7c228cc18545cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9500000000-6361694e7914d5c8167bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ox-9200000000-ded2bd26eb1ced7c2c22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-92500c706afd0d6d2d87Spectrum
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 IDNot Available
HMDB IDHMDB0038195
FooDB IDFDB017434
Phenol Explorer IDNot Available
KNApSAcK IDC00011622
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID453998
ChEBI IDNot Available
PubChem Compound ID520468
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Mustaffa F, Indurkar J, Ismail S, Shah M, Mansor SM: An antimicrobial compound isolated from Cinnamomum iners leaves with activity against methicillin-resistant Staphylococcus aureus. Molecules. 2011 Apr 8;16(4):3037-47. doi: 10.3390/molecules16043037.
2. Handayani T, Sakinah S, Nallappan M, Pihie AH: Regulation of p53-, Bcl-2- and caspase-dependent signaling pathway in xanthorrhizol-induced apoptosis of HepG2 hepatoma cells. Anticancer Res. 2007 Mar-Apr;27(2):965-71.
3. Lee LY, Shim JS, Rukayadi Y, Hwang JK: Antibacterial activity of xanthorrhizol isolated from Curcuma xanthorrhiza Roxb. against foodborne pathogens. J Food Prot. 2008 Sep;71(9):1926-30.
4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
8. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
9. The lipid handbook with CD-ROM