Cycloviolaxanthin (CHEM031498)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:41:52 UTC
Update Date2016-11-09 01:19:16 UTC
Accession NumberCHEM031498
Identification
Common NameCycloviolaxanthin
ClassSmall Molecule
DescriptionCycloviolaxanthin is found in herbs and spices. Cycloviolaxanthin is isolated from red paprika Capsicum annuum var. longum nigrum.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3S,3's,5R,5'r,6R,6'r)-3,6:3',6'-Diepoxy-5,5',6,6'-tetrahydro-5,5'-dihydroxy-beta,beta-caroteneHMDB
3,6:3',6'-Diepoxy-5,5',6,6'-tetrahydro-b,b-carotene-5,5'-diolHMDB
CycloviolaxanthinMeSH
Chemical FormulaC40H56O4
Average Molecular Mass600.870 g/mol
Monoisotopic Mass600.418 g/mol
CAS Registry Number136624-30-1
IUPAC Name1-[(1E,3Z,5E,7Z,9E,11E,13Z,15E,17E)-18-{2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl}-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-2-ol
Traditional Name1-[(1E,3Z,5E,7Z,9E,11E,13Z,15E,17E)-18-{2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl}-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-2-ol
SMILESC/C(/C=C/C=C(/C)\C=C\C12OC(CC1(C)C)CC2(C)O)=C/C=C/C=C(\C)/C=C\C=C(/C)\C=C\C12OC(CC1(C)C)CC2(C)O
InChI IdentifierInChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(43-39)27-37(39,9)41)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(44-40)28-38(40,10)42/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13-,18-14+,23-21+,24-22+,29-15+,30-16-,31-19+,32-20-
InChI KeyRZEVGLVRLUDYEA-GGFCQLCOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Monosaccharide
  • Tetrahydrofuran
  • Tertiary alcohol
  • Cyclic 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 Solubility0.00036 g/LALOGPS
logP8.11ALOGPS
logP7.26ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)13.41ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity192.33 m³·mol⁻¹ChemAxon
Polarizability70.41 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, Positivesplash10-0a4r-4000090000-6320325d90a5971be24bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-5000029000-5d6d412890e035c256efSpectrum
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 ("Cycloviolaxanthin,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0043529000-fa077a6d0f79fff2a511Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0398511000-eeba61211a6ee56ad3bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bta-4692200000-7fe29802cd7a28aad826Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-fef2967608d2e0e71930Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0100090000-7af631361e413241d05aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-2900030000-6469e8a3d41166640f18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2111049000-328eb4de62acb99c9880Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9312281000-c07810a56a13025312b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0041-1963300000-56551e5281e6c4d3e836Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0100090000-139dee97c51023e40bb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-1104490000-8d0da44f4bbfc0f3efd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-6119150000-578c5337b724c81d4ce8Spectrum
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 IDHMDB0038106
FooDB IDFDB017330
Phenol Explorer IDNot Available
KNApSAcK IDC00022955
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014506
ChEBI IDNot Available
PubChem Compound ID131752303
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. 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.
3. 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.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM