Record Information
Version1.0
Creation date2010-04-08 22:12:44 UTC
Update date2019-11-26 03:13:59 UTC
Primary IDFDB016939
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one
Description(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one 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. Based on a literature review a small amount of articles have been published on (3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one.
CAS Number256505-53-0
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.00076 g/LALOGPS
logP7.38ALOGPS
logP7.44ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)8.88ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity195.39 m³·mol⁻¹ChemAxon
Polarizability75.43 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC40H56O5
IUPAC name(2Z,4E,6E,8E,10E,12E,14E,16E,18E)-3-hydroxy-1-(3-hydroxy-1,2,2-trimethylcyclopentyl)-19-{2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl}-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
InChI IdentifierInChI=1S/C40H56O5/c1-28(17-13-18-30(3)21-24-40-36(5,6)26-32(45-40)27-39(40,10)44)15-11-12-16-29(2)19-14-20-31(4)33(41)25-35(43)38(9)23-22-34(42)37(38,7)8/h11-21,24-25,32,34,41-42,44H,22-23,26-27H2,1-10H3/b12-11+,17-13+,19-14+,24-21+,28-15+,29-16+,30-18+,31-20+,33-25-
InChI KeyJBFAUTAUPAPLMY-UQDXBYLISA-N
Isomeric 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(/O)=C/C(=O)C1(C)CCC(O)C1(C)C
Average Molecular Weight616.8696
Monoisotopic Molecular Weight616.412774902
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
  • Cyclopentanol
  • Monosaccharide
  • Acryloyl-group
  • Cyclic alcohol
  • Enone
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Tetrahydrofuran
  • Tertiary alcohol
  • Ketone
  • Secondary alcohol
  • Dialkyl ether
  • Enol
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pb9-7100294000-70b2c68b664763cace64Spectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-7100049000-2c6595df0e1bea6c74dcSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, "(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0521942000-06a440d53a07f0e8f10a2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-3642930000-1c1db9100109609353de2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-3960100000-cb602f77717137c9f4d82016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0500539000-decbf06136b865825d5c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0800933000-f439dc3a0f87fd1efc0e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1009-1900240000-02c218983e61abc2d7f12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0710009000-284ccdd7f575875a47132021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0605934000-29bbc3bcd234348c9ca82021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6539551000-dded066ce27a07be07ae2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1204097000-3a885104aa0f8a6215572021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-3329220000-e25d6418a9339959f3632021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00p0-5497300000-430f0c5c73b5660841762021-09-25View 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 IDHMDB37795
CRC / DFC (Dictionary of Food Compounds) IDKVG04-C:KVL24-H
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
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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