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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:54:54 UTC
Update Date2022-03-07 03:17:43 UTC
HMDB IDHMDB0060340
Secondary Accession Numbers
  • HMDB60340
Metabolite Identification
Common Name15,15'-Dihydroxy-beta-carotene
Description15,15'-Dihydroxy-beta-carotene, also known as retinal-pinacol, 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. 15,15'-Dihydroxy-beta-carotene is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866047
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 Weight570.8873
Monoisotopic Molecular Weight570.4436811
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
CAS Registry NumberNot Available
SMILES
C\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 Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+248.61931661259
DarkChem[M-H]-242.96731661259
DeepCCS[M+H]+263.96930932474
DeepCCS[M-H]-262.14430932474
DeepCCS[M-2H]-295.38630932474
DeepCCS[M+Na]+269.57530932474
AllCCS[M+H]+257.732859911
AllCCS[M+H-H2O]+256.032859911
AllCCS[M+NH4]+259.232859911
AllCCS[M+Na]+259.732859911
AllCCS[M-H]-235.832859911
AllCCS[M+Na-2H]-240.032859911
AllCCS[M+HCOO]-244.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
15,15'-Dihydroxy-beta-caroteneC\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)C5416.6Standard polar33892256
15,15'-Dihydroxy-beta-caroteneC\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)C4512.4Standard non polar33892256
15,15'-Dihydroxy-beta-caroteneC\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)C4503.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
15,15'-Dihydroxy-beta-carotene,1TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(O)C(/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)CCCC2(C)C)O[Si](C)(C)C)C(C)(C)CCC14525.9Semi standard non polar33892256
15,15'-Dihydroxy-beta-carotene,2TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(O[Si](C)(C)C)C(/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)CCCC2(C)C)O[Si](C)(C)C)C(C)(C)CCC14512.2Semi standard non polar33892256
15,15'-Dihydroxy-beta-carotene,1TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(O)C(/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)CCCC2(C)C)O[Si](C)(C)C(C)(C)C)C(C)(C)CCC14735.3Semi standard non polar33892256
15,15'-Dihydroxy-beta-carotene,2TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(O[Si](C)(C)C(C)(C)C)C(/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)CCCC2(C)C)O[Si](C)(C)C(C)(C)C)C(C)(C)CCC14959.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 15,15'-Dihydroxy-beta-carotene GC-MS (Non-derivatized) - 70eV, Positivesplash10-053i-0090040000-a1d23d6ce14e070e4a462017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15,15'-Dihydroxy-beta-carotene GC-MS (1 TMS) - 70eV, Positivesplash10-056r-4035009000-b3b1d3f80fc236d9f2522017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15,15'-Dihydroxy-beta-carotene GC-MS ("15,15'-Dihydroxy-beta-carotene,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15,15'-Dihydroxy-beta-carotene GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15,15'-Dihydroxy-beta-carotene GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15,15'-Dihydroxy-beta-carotene GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15,15'-Dihydroxy-beta-carotene 10V, Positive-QTOFsplash10-00di-0442390000-76834980e77992eb05bc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15,15'-Dihydroxy-beta-carotene 20V, Positive-QTOFsplash10-001r-0975520000-02f573d03b01b694b72e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15,15'-Dihydroxy-beta-carotene 40V, Positive-QTOFsplash10-0019-1973520000-61617d3d49f54dac793d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15,15'-Dihydroxy-beta-carotene 10V, Negative-QTOFsplash10-014i-0011090000-501e1b74c7642f994cee2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15,15'-Dihydroxy-beta-carotene 20V, Negative-QTOFsplash10-0aor-0092030000-2ac1302ce27833de27fd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15,15'-Dihydroxy-beta-carotene 40V, Negative-QTOFsplash10-0a4r-0190010000-81b56555c2fbde269f382017-10-06Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030264
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC20332
BioCyc IDCPD-14387
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound70678891
PDB IDNot Available
ChEBI ID67228
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Symmetrically cleaves beta-carotene into two molecules of retinal. The reaction proceeds in three stages, epoxidation of the 15,15'-double bond, hydration of the double bond leading to ring opening, and oxidative cleavage of the diol formed.
Gene Name:
BCMO1
Uniprot ID:
Q9HAY6
Molecular weight:
62636.69
Reactions
beta-Carotene-15,15'-epoxide + Water → 15,15'-Dihydroxy-beta-carotenedetails
15,15'-Dihydroxy-beta-carotene + Acceptor → Retinal + Reduced acceptordetails