Auroxanthin (CHEM030530)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:57:41 UTC
Update Date2016-11-09 01:19:05 UTC
Accession NumberCHEM030530
Identification
Common NameAuroxanthin
ClassSmall Molecule
DescriptionAuroxanthin is found in pepper (c. annuum). Auroxanthin is isolated from Viola tricolor, Lonicera japonica, Delonix regia and other plants.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5,8:5',8'-Diepoxy-5,5',8,8'-tetrahydro-b,b-carotene-3,3'-diolHMDB
Chemical FormulaC40H56O4
Average Molecular Mass600.870 g/mol
Monoisotopic Mass600.418 g/mol
CAS Registry Number27785-15-5
IUPAC Name2-[(2Z,4E,6E,8Z,10E,12Z,14Z)-15-(6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-yl)-6,11-dimethylhexadeca-2,4,6,8,10,12,14-heptaen-2-yl]-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-6-ol
Traditional Name2-[(2Z,4E,6E,8Z,10E,12Z,14Z)-15-(6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)-6,11-dimethylhexadeca-2,4,6,8,10,12,14-heptaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol
SMILESC\C(\C=C\C=C(\C)C1OC2(C)CC(O)CC(C)(C)C2=C1)=C/C=C\C=C(/C)\C=C/C=C(/C)C1OC2(C)CC(O)CC(C)(C)C2=C1
InChI IdentifierInChI=1S/C40H56O4/c1-27(17-13-19-29(3)33-21-35-37(5,6)23-31(41)25-39(35,9)43-33)15-11-12-16-28(2)18-14-20-30(4)34-22-36-38(7,8)24-32(42)26-40(36,10)44-34/h11-22,31-34,41-42H,23-26H2,1-10H3/b12-11-,17-13-,18-14+,27-15+,28-16+,29-19-,30-20-
InChI KeyYLUSVJDFTAATNS-CDQXKQFZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetraterpenoids. These are terpenoid molecules containing 10 consecutively linked isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentTetraterpenoids
Alternative Parents
Substituents
  • Tetraterpenoid
  • Benzofuran
  • Dihydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility0.00072 g/LALOGPS
logP8.13ALOGPS
logP6.72ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)14.83ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity192.08 m³·mol⁻¹ChemAxon
Polarizability71.14 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1500190000-643ec46632ae7ad894fbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-3310029000-ec3e0e0503b8ce2c686eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Auroxanthin,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0243097000-e06ed5f745b95399b76eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ff0-0569021000-9e7246091ce74ff6cdf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0r09-2968300000-398ef9f22517f2bebdeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-c2d4610ebb745009b984Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0200090000-83eb37c0c70b6e59b887Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ls-0821790000-e99e0d0a1636914afe51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0312297000-e8ea6df004d475fdde80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3032390000-5a19773eea6f8968044fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ns-0924320000-05929028c40c7a6de857Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-6b122a25d7104882894cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0001090000-a5bd307d6627faa29ef2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-0174290000-3858b5204cc76f91b659Spectrum
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 IDHMDB0036876
FooDB IDFDB015834
Phenol Explorer IDNot Available
KNApSAcK IDC00054689
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014289
ChEBI IDNot Available
PubChem Compound ID131752074
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Crupi P, Milella RA, Antonacci D: Simultaneous HPLC-DAD-MS (ESI+) determination of structural and geometrical isomers of carotenoids in mature grapes. J Mass Spectrom. 2010 Sep;45(9):971-80. doi: 10.1002/jms.1794.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. 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.
4. 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.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
7. The lipid handbook with CD-ROM