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(3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol (FDB023128)

Record Information
Version1.0
Creation date2011-09-21 00:25:05 UTC
Update date2015-07-21 06:57:31 UTC
Primary IDFDB023128
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol
Description(3R,3'R,15-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 Number60046-54-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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
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-0000490000-61514ff28dff7d7222e12020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QIT 1V, positivesplash10-0udi-0000290000-09f7ca5714961ff8f77e2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-00or-0930100000-c29159f503dad4260c042020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00or-0960430000-8996d3474c2f84178dd02020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-0aba-0930000000-8b9aa98251b44f2236fa2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-014i-0930030000-987a65a5fdcee38163382020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-b50e7afd480c604277302021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950320000-82e2fd12101c0f8a5aa32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950420000-376dfbe507c212fad75c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0930030000-7a03386b81c0af2daaae2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-63535133943f458f56192021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0930030000-18da3552a389eec494702021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950420000-97b603fc0db5c5d1268c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-a5be07cc9aa560c7ad052021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-247f26afe81a420dd3292021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950320000-a6da820e1ac88487b3542021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0111190000-a3e4a4d0d67ea298da492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frt-0649330000-191e0ac14dcad154b4b32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-0449130000-5644e7cc2bbfa6ef09f02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-8f8c6909e2b7e1022ce92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-421f46802deab60d756d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-0553390000-883720ed84543eb475e22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001090000-762864ffd0f72009c6882021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0104290000-79f130816293d1629a5c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003b-0229210000-8aa487c6a883739666a22021-09-22View Spectrum
NMRNot Available
ChemSpider ID30776559
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477766
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03240
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