Cryptoxanthin 5,6:5',8'-diepoxide (CHEM024533)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:46:08 UTC
Update Date2016-11-09 01:17:54 UTC
Accession NumberCHEM024533
Identification
Common NameCryptoxanthin 5,6:5',8'-diepoxide
ClassSmall Molecule
DescriptionCryptoxanthin 5,6:5',8'-diepoxide is found in citrus. Cryptoxanthin 5,6:5',8'-diepoxide is isolated from juice of Shamouti orange (Citrus sinensis) and mature fruit of peach (Prunus persica
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-caroten-3-olHMDB
Chemical FormulaC40H56O3
Average Molecular Mass584.871 g/mol
Monoisotopic Mass584.423 g/mol
CAS Registry Number55965-22-5
IUPAC Name6-[(1E,3E,5E,7E,9E,11E,13E,15E)-16-(4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-yl)-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
Traditional Name6-[(1E,3E,5E,7E,9E,11E,13E,15E)-16-(4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
SMILESC\C(\C=C\C=C(/C)\C=C\C12OC1(C)CC(O)CC2(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)C1OC2(C)CCCC(C)(C)C2=C1
InChI IdentifierInChI=1S/C40H56O3/c1-29(18-13-19-31(3)22-25-40-37(7,8)27-33(41)28-39(40,10)43-40)16-11-12-17-30(2)20-14-21-32(4)34-26-35-36(5,6)23-15-24-38(35,9)42-34/h11-14,16-22,25-26,33-34,41H,15,23-24,27-28H2,1-10H3/b12-11+,18-13+,20-14+,25-22+,29-16+,30-17+,31-19+,32-21+
InChI KeyRXRDUVZIGPRFRB-YLFACGADSA-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
  • Benzofuran
  • Oxepane
  • Cyclic alcohol
  • Dihydrofuran
  • Secondary alcohol
  • Dialkyl ether
  • Oxacycle
  • Oxirane
  • Ether
  • Organoheterocyclic compound
  • 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 Solubility0.00037 g/LALOGPS
logP9.12ALOGPS
logP8.45ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)15.14ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.99 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity190.58 m³·mol⁻¹ChemAxon
Polarizability73.31 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, Positivesplash10-014i-4400190000-f092fd17fd36bafddf34Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-2700009000-47ee2e8e0549223efd95Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Cryptoxanthin 5,6:5',8'-diepoxide,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0333390000-a67e888097e64418a7f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066s-0496120000-17dcf9cc24ac3f9626f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0540-9874100000-9506584a878f52982dceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0100190000-e921147617dec4f8d541Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-0400090000-b0a3c01c8b5aeca545a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00li-2900680000-692e03d77eb6613c5754Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0021190000-fedeb48211b8fb44439eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-1042290000-98becea7d9b1ba67c3f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0932000000-7cc08f40676711bb5046Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0400090000-890eb444dbc12dd1a354Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0212290000-9f6d0d550e31fc4a5c69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001s-0466090000-a8321336c62ea0f1f682Spectrum
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 IDHMDB0030537
FooDB IDFDB002410
Phenol Explorer IDNot Available
KNApSAcK IDC00054521
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013223
ChEBI IDNot Available
PubChem Compound ID131751047
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