Record Information
Version1.0
Creation date2015-05-07 18:55:23 UTC
Update date2019-11-26 03:21:40 UTC
Primary IDFDB030264
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name15,15'-dihydroxy-β-carotene
Description15,15'-dihydroxy-beta-carotene, also known as retinal-pinacol or 15,15'-dihydro-15,15'-dihydroxy-b,b-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. 15,15'-dihydroxy-beta-carotene is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 15,15'-dihydroxy-beta-carotene can be found in a number of food items such as white lupine, breadfruit, brussel sprouts, and black salsify, which makes 15,15'-dihydroxy-beta-carotene a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
15,15'-Dihydro-15,15'-dihydroxy-beta,beta-caroteneChEBI
Retinal-pinacolChEBI
15,15'-Dihydro-15,15'-dihydroxy-b,b-caroteneGenerator
15,15'-Dihydro-15,15'-dihydroxy-β,β-caroteneGenerator
15,15'-Dihydroxy-b-caroteneGenerator
15,15'-Dihydroxy-β-caroteneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.00057 g/LALOGPS
logP8.1ALOGPS
logP9.34ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)13.46ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity193.22 m³·mol⁻¹ChemAxon
Polarizability73.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC40H58O2
IUPAC name(1E,3E,5E,7E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-1,18-bis(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,11,13,15,17-octaene-9,10-diol
InChI IdentifierInChI=1S/C40H58O2/c1-29(21-23-35-33(5)19-13-25-39(35,7)8)15-11-17-31(3)27-37(41)38(42)28-32(4)18-12-16-30(2)22-24-36-34(6)20-14-26-40(36,9)10/h11-12,15-18,21-24,27-28,37-38,41-42H,13-14,19-20,25-26H2,1-10H3/b17-11+,18-12+,23-21+,24-22+,29-15+,30-16+,31-27+,32-28+
InChI KeyLAMXZCLZRAUDED-WDJSDFAOSA-N
Isomeric SMILESC\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)C(O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
Average Molecular Weight570.8873
Monoisotopic Molecular Weight570.4436811
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
  • Retinoid skeleton
  • Fatty alcohol
  • Fatty acyl
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS15,15'-dihydroxy-β-carotene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053i-0090040000-a1d23d6ce14e070e4a46Spectrum
Predicted GC-MS15,15'-dihydroxy-β-carotene, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056r-4035009000-b3b1d3f80fc236d9f252Spectrum
Predicted GC-MS15,15'-dihydroxy-β-carotene, "15,15'-Dihydroxy-beta-carotene,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS15,15'-dihydroxy-β-carotene, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS15,15'-dihydroxy-β-carotene, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS15,15'-dihydroxy-β-carotene, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0442390000-76834980e77992eb05bcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-0975520000-02f573d03b01b694b72eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-1973520000-61617d3d49f54dac793dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0011090000-501e1b74c7642f994ceeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-0092030000-2ac1302ce27833de27fdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-0190010000-81b56555c2fbde269f38Spectrum
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 IDNot Available
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