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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:18:21 UTC
Update Date2022-03-07 02:56:00 UTC
HMDB IDHMDB0038959
Secondary Accession Numbers
  • HMDB38959
Metabolite Identification
Common Name2-Methyl-6-phytylhydroquinone
Description2-Methyl-6-phytylhydroquinone, also known as 6-phytyltoluquinol or MPBQ, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2-Methyl-6-phytylhydroquinone is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methyl-6-phytylhydroquinone is found in green vegetables. 2-Methyl-6-phytylhydroquinone is a precursor of tocopherol synthesis in spinach chloroplasts.
Structure
Data?1583433045
Synonyms
ValueSource
(R,R)-2-Methyl-6-phytylquinolChEBI
2-Methyl-6-phytyl-1,4-benzene-1,4-diolChEBI
6-PhytyltoluquinolChEBI
2-Methyl-6-phytyl-1,4-benzoquinolHMDB
2-Methyl-6-phytyl-1,4-hydroquinoneHMDB
2-Methyl-6-phytylbenzene-1,4-diolHMDB
2-Methyl-6-phytylquinolHMDB
MPBQHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.663
Monoisotopic Molecular Weight402.349780721
IUPAC Name2-methyl-6-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]benzene-1,4-diol
Traditional Name2-methyl-6-phytylquinol
CAS Registry Number75513-85-8
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C(C)=CC(O)=C1
InChI Identifier
InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-15-23(5)16-17-25-19-26(28)18-24(6)27(25)29/h16,18-22,28-29H,7-15,17H2,1-6H3/b23-16+/t21-,22-/m1/s1
InChI KeyGTWCNYRFOZKWTL-UOFXASEASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Prenylbenzoquinol
  • O-cresol
  • M-cresol
  • Hydroquinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
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 Solubility9.4e-05 g/LALOGPS
logP8.58ALOGPS
logP9.8ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)9.78ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity128.16 m³·mol⁻¹ChemAxon
Polarizability52.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+214.43230932474
DeepCCS[M-H]-212.07430932474
DeepCCS[M-2H]-245.32830932474
DeepCCS[M+Na]+220.63230932474
AllCCS[M+H]+211.132859911
AllCCS[M+H-H2O]+208.832859911
AllCCS[M+NH4]+213.132859911
AllCCS[M+Na]+213.732859911
AllCCS[M-H]-207.832859911
AllCCS[M+Na-2H]-210.332859911
AllCCS[M+HCOO]-213.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Methyl-6-phytylhydroquinoneCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C(C)=CC(O)=C14045.0Standard polar33892256
2-Methyl-6-phytylhydroquinoneCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C(C)=CC(O)=C12952.8Standard non polar33892256
2-Methyl-6-phytylhydroquinoneCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C(C)=CC(O)=C13131.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methyl-6-phytylhydroquinone,1TMS,isomer #1C/C(=C\CC1=CC(O)=CC(C)=C1O[Si](C)(C)C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C3082.3Semi standard non polar33892256
2-Methyl-6-phytylhydroquinone,1TMS,isomer #2C/C(=C\CC1=CC(O[Si](C)(C)C)=CC(C)=C1O)CCC[C@H](C)CCC[C@H](C)CCCC(C)C3053.3Semi standard non polar33892256
2-Methyl-6-phytylhydroquinone,2TMS,isomer #1C/C(=C\CC1=CC(O[Si](C)(C)C)=CC(C)=C1O[Si](C)(C)C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C3063.4Semi standard non polar33892256
2-Methyl-6-phytylhydroquinone,1TBDMS,isomer #1C/C(=C\CC1=CC(O)=CC(C)=C1O[Si](C)(C)C(C)(C)C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C3309.1Semi standard non polar33892256
2-Methyl-6-phytylhydroquinone,1TBDMS,isomer #2C/C(=C\CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1O)CCC[C@H](C)CCC[C@H](C)CCCC(C)C3299.9Semi standard non polar33892256
2-Methyl-6-phytylhydroquinone,2TBDMS,isomer #1C/C(=C\CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1O[Si](C)(C)C(C)(C)C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C3538.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-6-phytylhydroquinone GC-MS (1 TMS) - 70eV, PositiveNot Available2020-06-30Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-6-phytylhydroquinone GC-MS (1 TMS) - 70eV, PositiveNot Available2020-06-30Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-6-phytylhydroquinone GC-MS (2 TMS) - 70eV, PositiveNot Available2020-06-30Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-6-phytylhydroquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-6-phytylhydroquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-6-phytylhydroquinone 10V, Positive-QTOFsplash10-0udi-0333900000-e1cef6da314a31925a462019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-6-phytylhydroquinone 20V, Positive-QTOFsplash10-05pa-4983100000-117eed532cfa0203b4b92019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-6-phytylhydroquinone 40V, Positive-QTOFsplash10-0a4i-9885000000-986610d4a66b0022965f2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-6-phytylhydroquinone 10V, Negative-QTOFsplash10-0udi-0000900000-e78444e8749e7b626c132019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-6-phytylhydroquinone 20V, Negative-QTOFsplash10-0udi-0003900000-c37a2e1279a4cbb8f1f22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-6-phytylhydroquinone 40V, Negative-QTOFsplash10-00dr-3319000000-044959d324410a8121d22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-6-phytylhydroquinone 10V, Negative-QTOFsplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-6-phytylhydroquinone 20V, Negative-QTOFsplash10-0udr-0914700000-589da17035a7b7a304ea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-6-phytylhydroquinone 40V, Negative-QTOFsplash10-0002-1905000000-9801817b8698191f4f472021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-6-phytylhydroquinone 10V, Positive-QTOFsplash10-0udi-1632900000-3df518199b83e2944b002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-6-phytylhydroquinone 20V, Positive-QTOFsplash10-0a5i-3902000000-697efa354199f64c4aa22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-6-phytylhydroquinone 40V, Positive-QTOFsplash10-05gr-6901000000-515f56138553d09510522021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB018442
KNApSAcK IDC00007590
Chemspider ID30785732
KEGG Compound IDNot Available
BioCyc IDMPBQ
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71768135
PDB IDNot Available
ChEBI ID75920
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.