15,15'-dihydroxy-β-carotene (CHEM041854)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:43:29 UTC
Update Date2016-11-09 01:22:33 UTC
Accession NumberCHEM041854
Identification
Common Name15,15'-dihydroxy-β-carotene
ClassSmall Molecule
DescriptionA carotenol obtained by formal dihydroxylation across the 15,15'-double bond of beta-carotene.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC40H58O2
Average Molecular Mass570.887 g/mol
Monoisotopic Mass570.444 g/mol
CAS Registry NumberNot Available
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
Traditional 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
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
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053i-0090040000-a1d23d6ce14e070e4a46Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-056r-4035009000-b3b1d3f80fc236d9f252Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("15,15'-Dihydroxy-beta-carotene,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0442390000-76834980e77992eb05bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-0975520000-02f573d03b01b694b72eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-1973520000-61617d3d49f54dac793dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0011090000-501e1b74c7642f994ceeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-0092030000-2ac1302ce27833de27fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-0190010000-81b56555c2fbde269f38Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060340
FooDB IDFDB030264
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-14387
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID67228
PubChem Compound ID70678891
Kegg Compound IDC20332
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. The lipid handbook with CD-ROM