Record Information
Version1.0
Creation date2010-04-08 22:05:00 UTC
Update date2019-11-26 02:56:34 UTC
Primary IDFDB001533
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namebeta-Carotene 5,6-epoxide
DescriptionBeta-carotene 5,6-epoxide, also known as 5,6-epoxy-beta,beta-carotene, 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. Thus, beta-carotene 5,6-epoxide is considered to be an isoprenoid lipid molecule. Beta-carotene 5,6-epoxide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Beta-carotene 5,6-epoxide can be found in a number of food items such as mango, apple, sweet orange, and papaya, which makes beta-carotene 5,6-epoxide a potential biomarker for the consumption of these food products.
CAS Number1923-89-3
Structure
Thumb
Synonyms
SynonymSource
5,6-Epoxy-beta,beta-caroteneChEBI
5,6-Epoxy-b,b-caroteneGenerator
5,6-Epoxy-β,β-caroteneGenerator
b-Carotene 5,6-epoxideGenerator
β-carotene 5,6-epoxideGenerator
5,6-epoxy-5,6-dihydro-beta,beta-carotenebiospider
5,6-epoxy-beta-Carotenebiospider
5,6-epoxy-beta,beta-carotenebiospider
beta,beta-Carotene, 5,6-epoxy-5,6-dihydro-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.00025 g/LALOGPS
logP9.83ALOGPS
logP10.65ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity190.34 m³·mol⁻¹ChemAxon
Polarizability72.36 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC40H56O
IUPAC name2,2,6-trimethyl-1-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-7-oxabicyclo[4.1.0]heptane
InChI IdentifierInChI=1S/C40H56O/c1-31(19-13-21-33(3)24-25-36-35(5)23-15-27-37(36,6)7)17-11-12-18-32(2)20-14-22-34(4)26-30-40-38(8,9)28-16-29-39(40,10)41-40/h11-14,17-22,24-26,30H,15-16,23,27-29H2,1-10H3/b12-11+,19-13+,20-14+,25-24+,30-26+,31-17+,32-18+,33-21+,34-22+
InChI KeyRVCRIPILOFSMFG-WWSVUWEKSA-N
Isomeric SMILES[H]/C(=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])C12OC1(C)CCCC2(C)C)/C(/[H])=C(\C)/C(/[H])=C(\[H])/C(/[H])=C(\C)/C(/[H])=C(\[H])C1=C(C)CCCC1(C)C
Average Molecular Weight552.887
Monoisotopic Molecular Weight552.433116423
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
  • Oxepane
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
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
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0657690000-275589ed1b8d45c0b395JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ds-0698310000-7b5fa72f456a72069225JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03y0-5796100000-c5eb8a3692d1462afcbaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-283b1491bec27732b724JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0100090000-d9e7e740fc44389aaddfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2902250000-881390a05d64ca985d5dJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08587
Pubchem Compound ID5281231
Pubchem Substance IDNot Available
ChEBI ID27793
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDBETA-CAROTENE-5,6-EPOXIDE
BIGG IDNot Available
KNApSAcK IDC00003767
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.