Cryptoxanthin diepoxide (CHEM023519)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:06:50 UTC
Update Date2016-11-09 01:17:43 UTC
Accession NumberCHEM023519
Identification
Common NameCryptoxanthin diepoxide
ClassSmall Molecule
DescriptionCryptoxanthin diepoxide is found in fruits. Cryptoxanthin diepoxide is isolated from Eriobotrya japonica (loquat) fruit and Prunus persica fruit (peach mesocarp during ripening
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5,5',6,6'-Diepoxy-5,5',6,6'-tetrahydro-b,b-caroten-3-ol, 9ciHMDB
5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta-caroten-3-olHMDB
Chemical FormulaC40H56O3
Average Molecular Mass584.871 g/mol
Monoisotopic Mass584.423 g/mol
CAS Registry Number2086-87-5
IUPAC Name1,5,5-trimethyl-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-7-oxabicyclo[4.1.0]heptan-3-ol
Traditional Name1,5,5-trimethyl-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-7-oxabicyclo[4.1.0]heptan-3-ol
SMILESC\C(\C=C\C=C(/C)\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C
InChI IdentifierInChI=1S/C40H56O3/c1-30(18-13-20-32(3)22-26-39-35(5,6)24-15-25-37(39,9)42-39)16-11-12-17-31(2)19-14-21-33(4)23-27-40-36(7,8)28-34(41)29-38(40,10)43-40/h11-14,16-23,26-27,34,41H,15,24-25,28-29H2,1-10H3/b12-11+,18-13+,19-14+,26-22+,27-23+,30-16+,31-17+,32-20+,33-21+
InChI KeyONQKWANDXQNLEJ-CGYYJCQDSA-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
  • Oxepane
  • Cyclic alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • 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 Solubility0.00029 g/LALOGPS
logP9.02ALOGPS
logP8.72ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)15.14ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.29 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity190.7 m³·mol⁻¹ChemAxon
Polarizability73.96 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-6000190000-3cb67b5fdc305d66fa8bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-6200019000-ad65a0b5c2e67dcc7e7dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Cryptoxanthin 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, Positivesplash10-014i-0232690000-a4b91e5a36320835b32aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07vj-1396330000-f38238d5ab4c94769d3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0900-6493100000-c5f607e7bfe092d63821Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0100090000-2725ed72f7be2b893824Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-0100090000-45bc073eff602eebcaf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-4900580000-ae9073fac62e35e84334Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0200090000-d1e086cd75fc2754e8adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0203290000-541af23bbc514ebf6872Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-0449180000-ee5733fe7977d872a37bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0011090000-44122ce316cefce3e739Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0122190000-56eed5767f7676db88a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdi-4739260000-8ec92c4f35ed291b923dSpectrum
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 IDHMDB0029896
FooDB IDFDB001139
Phenol Explorer IDNot Available
KNApSAcK IDC00022953
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013097
ChEBI IDNot Available
PubChem Compound ID14558488
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