Showing metabocard for Beta-tocopherol (BMDB0006335)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:21:37 UTC
Update Date2020-05-11 20:41:28 UTC
BMDB IDBMDB0006335
Secondary Accession Numbers
  • BMDB06335
Metabolite Identification
Common NameBeta-tocopherol
Descriptionbeta-Tocopherol, also known as β-tocopherol or 5,8-dimethyltocol, belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. Thus, beta-tocopherol is considered to be a quinone. Based on a literature review a significant number of articles have been published on beta-Tocopherol.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2R)-2,5,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
(2R)-3,4-Dihydro-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olChEBI
(2R,4'r,8'r)-beta-TocopherolChEBI
(R,R,R)-beta-TocopherolChEBI
5,8-DimethyltocolChEBI
RRR-beta-TocopherolChEBI
(2R,4'r,8'r)-b-TocopherolGenerator
(2R,4'r,8'r)-Β-tocopherolGenerator
(R,R,R)-b-TocopherolGenerator
(R,R,R)-Β-tocopherolGenerator
RRR-b-TocopherolGenerator
RRR-Β-tocopherolGenerator
b-TocopherolGenerator
Β-tocopherolGenerator
beta TocopherolHMDB
3,4-Dihydro-2,5,8-trimethyl-2-(4,8,12- trimethyltridecyl)-2H-1-benzopyran-6-olHMDB
b-Tocopherol skeletonHMDB
Β-tocopherol skeletonHMDB
CumotocopherolHMDB
DL-beta-TocopherolHMDB
DL-Β-tocopherolHMDB
NeotocopherolHMDB
p-XylotocopherolHMDB
beta-TocopherolMeSH
2,5,8-Trimethyl-2-(4,8,12-trimethyltridecyl)-6-chromanolHMDB
Chemical FormulaC28H48O2
Average Molecular Weight416.6795
Monoisotopic Molecular Weight416.36543078
IUPAC Name(2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Nameβ-tocopherol
CAS Registry Number148-03-8
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(O)=CC(C)=C2O1
InChI Identifier
InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1
InChI KeyWGVKWNUPNGFDFJ-DQCZWYHMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentTocopherols
Alternative Parents
Substituents
  • Tocopherol
  • Diterpenoid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.81ALOGPS
logP9.99ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)10.47ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity130.33 m³·mol⁻¹ChemAxon
Polarizability53.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00di-1490200000-f75de727e16d87c65fbaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1490200000-f75de727e16d87c65fbaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lyo-6954200000-ffcf92e6a6e2f34dd922View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5644900000-b5341f1bdc151c1a796bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-0gb9-3900600000-10f458ddcb7e7aa4df84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0f6t-0900600000-9a11a437c645252a72a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0842900000-82c505b0548997aace83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1910000000-1b1a0fe2f352daa49e2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-4920000000-b63881a7743c06bdea15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0100900000-2345f13b44d6c70d81e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0912800000-4e68210f69fcd3f6c374View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kk-0914000000-f6f5255b874c4fc7f4f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-a74b65a822c3cc7625b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0201900000-2dcdf4f502cc6e57342dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-024m-2913100000-fb9e3e53715df460db95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3113900000-16d3b372ee248c26f313View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-9213100000-65be5213a11752835e85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-9400000000-947da441c6df0de93bedView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0006335
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012381
KNApSAcK IDC00007364
Chemspider ID5256784
KEGG Compound IDC14152
BioCyc IDBETA-TOCOPHEROL
BiGG ID2296531
Wikipedia LinkBeta-Tocopherol
METLIN IDNot Available
PubChem Compound6857447
PDB IDNot Available
ChEBI ID47771
References
Synthesis ReferenceJohn, Walter. Cumotocopherol, a new factor of the vitamin-E group. Z. physiol. Chem. (1937), 250 11-24. CAN 32:8751 AN 1938:8751
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available