Record Information
Version1.0
Creation date2011-09-21 00:24:53 UTC
Update date2015-07-21 06:57:31 UTC
Primary IDFDB023113
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(3R,3'R,9-cis)-beta,beta-Carotene-3,3'-diol
Description(3R,3'R,9-cis)-Carotene-3,3'-diol 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 Number60497-64-5
Structure
Thumb
Synonyms
SynonymSource
(3R,3'r)-Dihydroxy-beta,beta-caroteneChEBI
all-trans-beta-Carotene-3,3'-diolChEBI
all-trans-ZeaxanthinChEBI
AnchovyxanthinChEBI
beta,beta-Carotene-3,3'-diolChEBI
(3R,3'r)-beta,beta-Carotene-3,3'-diolKegg
(3R,3'r)-Dihydroxy-b,b-caroteneGenerator
(3R,3'r)-Dihydroxy-β,β-caroteneGenerator
all-trans-b-Carotene-3,3'-diolGenerator
all-trans-Β-carotene-3,3'-diolGenerator
b,b-Carotene-3,3'-diolGenerator
Β,β-carotene-3,3'-diolGenerator
(3R,3'r)-b,b-Carotene-3,3'-diolGenerator
(3R,3'r)-Β,β-carotene-3,3'-diolGenerator
3R,3'r ZeaxanthinMeSH
3R,3'r-ZeaxanthinMeSH
Beta Carotene 3,3' diolMeSH
ZeaxanthinsMeSH
beta-Carotene-3,3'-diolMeSH
(3R,3'r)-ZeaxanthinHMDB
all-trans-AnchovyxanthinHMDB
Xanthophyll 3HMDB
ZeaxantholHMDB
(3R,3'R)-Dihydroxy-beta-caroteneHMDB
(3R,3'R)-Dihydroxy-β-caroteneHMDB
(3R,3'R)-ZeaxanthinHMDB
(3R,3’R)-Dihydroxy-β-caroteneHMDB
(3R,3’R)-ZeaxanthinHMDB
(3R,3’R)-β,β-Carotene-3,3’-diolHMDB
all-E-ZeaxanthinHMDB
all-trans-3R,3'R-ZeaxanthinHMDB
all-trans-3R,3’R-ZeaxanthinHMDB
(3R,3'R,9-cis)-b,b-Carotene-3,3'-diolhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00065 g/LALOGPS
logP8.3ALOGPS
logP8.35ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.91ChemAxon
pKa (Strongest Basic)-0.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity194.95 m³·mol⁻¹ChemAxon
Polarizability73.47 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC40H56O2
IUPAC name(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol
InChI IdentifierInChI=1S/C40H56O2/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/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m1/s1
InChI KeyJKQXZKUSFCKOGQ-QAYBQHTQSA-N
Isomeric SMILESC\C(\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C
Average Molecular Weight568.886
Monoisotopic Molecular Weight568.428031043
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
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
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-MS(3R,3'R,13-cis)-beta,beta-Carotene-3,3'-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-2000190000-2cc8481518a353268253Spectrum
Predicted GC-MS(3R,3'R,13-cis)-beta,beta-Carotene-3,3'-diol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-3000049000-45b1b78e4b208f89e457Spectrum
Predicted GC-MS(3R,3'R,13-cis)-beta,beta-Carotene-3,3'-diol, "Zeaxanthin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3R,3'R,13-cis)-beta,beta-Carotene-3,3'-diol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3R,3'R,13-cis)-beta,beta-Carotene-3,3'-diol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3R,3'R,13-cis)-beta,beta-Carotene-3,3'-diol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QIT 20V, positivesplash10-0xsi-0000490000-61514ff28dff7d7222e1Spectrum
MS/MSLC-MS/MS Spectrum - QIT 1V, positivesplash10-0udi-0000290000-09f7ca5714961ff8f77eSpectrum
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-00or-0930100000-c29159f503dad4260c04Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00or-0960430000-8996d3474c2f84178dd0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-0aba-0930000000-8b9aa98251b44f2236faSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-014i-0930030000-987a65a5fdcee3816338Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-b50e7afd480c60427730Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950320000-82e2fd12101c0f8a5aa3Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950420000-376dfbe507c212fad75cSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0930030000-7a03386b81c0af2daaaeSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-63535133943f458f5619Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0930030000-18da3552a389eec49470Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950420000-97b603fc0db5c5d1268cSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-a5be07cc9aa560c7ad05Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-247f26afe81a420dd329Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950320000-a6da820e1ac88487b354Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0111190000-a3e4a4d0d67ea298da49Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frt-0649330000-191e0ac14dcad154b4b3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-0449130000-5644e7cc2bbfa6ef09f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-8f8c6909e2b7e1022ce9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-421f46802deab60d756dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-0553390000-883720ed84543eb475e2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001090000-762864ffd0f72009c688Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0104290000-79f130816293d1629a5cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003b-0229210000-8aa487c6a883739666a2Spectrum
NMRNot Available
ChemSpider ID10390741
ChEMBL IDCHEMBL1357855
KEGG Compound IDNot Available
Pubchem Compound ID21769059
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03146
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