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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-23 00:55:35 UTC
Update Date2019-07-23 05:47:18 UTC
HMDB IDHMDB0006335
Secondary Accession Numbers
  • HMDB06335
Metabolite Identification
Common NameBeta-tocopherol
DescriptionBeta-tocopherol is an antioxidant which is synthesized by photosynthetic organisms and play important roles in human and animal nutrition. betatocopherols can be oxidized in dry CH2Cl2 or CH3CN by one electron to form cation radicals that deprotonate to form the neutral phenoxyl radicals, which are then immediately further oxidized by one electron to the phenoxonium cations (an ECE electrochemical mechanism, where E signifies an electron transfer and C represents a chemical step, with the electrochemical mechanism having been determined by in situ spectroscopic analysis).The phenoxonium cation of beta-tocopherol is stable for several minutes. (PMID: 16771430 ).
Structure
Data?1563860838
Synonyms
ValueSource
(2R)-3,4-dihydro-2,5,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olChEBI
5,8-DimethyltocolChEBI
b-TocopherolGenerator
β-tocopherolGenerator
beta TocopherolMeSH
3,4-dihydro-2,5,8-Trimethyl-2-(4,8,12- trimethyltridecyl)-2H-1-benzopyran-6-olMeSH
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(O1)C(C)=CC(O)=C2C
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
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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
Water Solubility7.3e-06 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00di-1490200000-f75de727e16d87c65fbaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1490200000-f75de727e16d87c65fbaJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lyo-6954200000-ffcf92e6a6e2f34dd922JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5644900000-b5341f1bdc151c1a796bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-0gb9-3900600000-10f458ddcb7e7aa4df84JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0842900000-82c505b0548997aace83JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1910000000-1b1a0fe2f352daa49e2cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-4920000000-b63881a7743c06bdea15JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0100900000-2345f13b44d6c70d81e5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0912800000-4e68210f69fcd3f6c374JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kk-0914000000-f6f5255b874c4fc7f4f3JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.20 (0.00-0.48) uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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 References
  1. Wilson GJ, Lin CY, Webster RD: Significant differences in the electrochemical behavior of the alpha-, beta-, gamma-, and delta-tocopherols (vitamin E). J Phys Chem B. 2006 Jun 15;110(23):11540-8. [PubMed:16771430 ]