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β-carotene 15,15' epoxide (FDB031284)

Record Information
Version1.0
Creation date2015-05-07 21:30:21 UTC
Update date2019-11-26 03:22:14 UTC
Primary IDFDB031284
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameβ-carotene 15,15' epoxide
DescriptionBeta-carotene-15,15'-epoxide, also known as 15,15'-epoxy-beta,beta-carotene or 15-ebbct, is a member of the class of compounds known as xanthophylls. Xanthophylls 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. Beta-carotene-15,15'-epoxide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Beta-carotene-15,15'-epoxide can be found in a number of food items such as ginseng, pepper (c. frutescens), leek, and strawberry, which makes beta-carotene-15,15'-epoxide a potential biomarker for the consumption of these food products.
CAS Number132541-62-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00045 g/LALOGPS
logP9.11ALOGPS
logP10.5ChemAxon
logS-6.1ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity189.71 m³·mol⁻¹ChemAxon
Polarizability72.78 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC40H56O
IUPAC name2,3-bis[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]oxirane
InChI IdentifierInChI=1S/C40H56O/c1-29(21-23-35-33(5)19-13-25-39(35,7)8)15-11-17-31(3)27-37-38(41-37)28-32(4)18-12-16-30(2)22-24-36-34(6)20-14-26-40(36,9)10/h11-12,15-18,21-24,27-28,37-38H,13-14,19-20,25-26H2,1-10H3/b17-11+,18-12+,23-21+,24-22+,29-15+,30-16+,31-27+,32-28+
InChI KeyAULCUSCIZQQSMU-WDJSDFAOSA-N
Isomeric SMILESC\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C1OC1\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
Average Molecular Weight552.872
Monoisotopic Molecular Weight552.433116414
Classification
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
  • Retinoid skeleton
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSβ-carotene 15,15' epoxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kr-3190180000-18fa5fe375427a90ed93Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0443390000-b86b444d8de208d46aaa2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02aa-0984620000-2682c6f17feedeb9332d2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-029i-3894710000-ef12554b6332cee19bed2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0010090000-fec996a718d809f6d4f82017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1050090000-bcba82082e0652fa9ae12017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-1192020000-eea6310dad0468f80d932017-10-06View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference