Record Information
Version1.0
Creation date2011-09-21 00:19:48 UTC
Update date2015-07-21 06:57:22 UTC
Primary IDFDB022800
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3'-Hydroxy-epsilon,epsilon-caroten-3-one
Description3'-hydroxy-Caroten-3-one is a carotenoid found in human fluids. Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds and crustacea. Animals are unable to synthesise carotenoids de novo, and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important. (PMID: 1416048, 15003396) [HMDB]
CAS Number140460-59-9
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.00069 g/LALOGPS
logP8.4ALOGPS
logP9.16ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.22ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity194.28 m³·mol⁻¹ChemAxon
Polarizability72.46 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC40H54O2
IUPAC name4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one
InChI IdentifierInChI=1S/C40H54O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-26,35,37-38,41H,27-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+
InChI KeyOTHWKRBAHPOBSP-DKLMTRRASA-N
Isomeric SMILESC\C(\C=C\C=C(/C)\C=C\C1C(C)=CC(O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1C(C)=CC(=O)CC1(C)C
Average Molecular Weight566.8556
Monoisotopic Molecular Weight566.412380972
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
  • Cyclohexenone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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-MS3'-Hydroxy-epsilon,epsilon-caroten-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uds-3100190000-ae79030407954c20efbbSpectrum
Predicted GC-MS3'-Hydroxy-epsilon,epsilon-caroten-3-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-2000029000-1724b72b54f0a0265adcSpectrum
Predicted GC-MS3'-Hydroxy-epsilon,epsilon-caroten-3-one, "3'-Hydroxy-e,e-caroten-3-one,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3'-Hydroxy-epsilon,epsilon-caroten-3-one, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3'-Hydroxy-epsilon,epsilon-caroten-3-one, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3'-Hydroxy-epsilon,epsilon-caroten-3-one, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0211290000-6c8c2ef385da7bfc53042017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0954610000-6d45cfe85a5fbda34f2f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c11-5498740000-c86d669a809b693948b62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-242a96fa86c49ca4da5b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-81bb2029832dac6acaf22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0412690000-b30d6768c5d3f0884ef12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01rb-0241930000-d4f1259d132530bf20c62021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000m-0113910000-b6a3cbb923da373b495d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p2-0179400000-cdffbe85fcce729b424b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0202090000-08b0f9080377abbe81492021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014s-0415490000-3eeb135608330987b3342021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-0419200000-880299cdb4af7de054b42021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID14409079
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02020
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
Processing...
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