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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-23 00:55:35 UTC
Update Date2022-03-07 02:49:31 UTC
HMDB IDHMDB0006335
Secondary Accession Numbers
  • HMDB06335
Metabolite Identification
Common Namebeta-Tocopherol
Descriptionbeta-Tocopherol is an antioxidant which is synthesized by photosynthetic organisms and plays an important role in human and animal nutrition. beta-Tocopherols 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 ). beta-Tocopherol has been identified in the human placenta (PMID: 32033212 ).
Structure
Data?1582752381
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
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available209.755http://allccs.zhulab.cn/database/detail?ID=AllCCS00001885
[M+H]+Not Available212.235http://allccs.zhulab.cn/database/detail?ID=AllCCS00001885
Predicted Molecular 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
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]+202.70931661259
DarkChem[M-H]-199.36231661259
DeepCCS[M+H]+211.74530932474
DeepCCS[M-H]-209.38730932474
DeepCCS[M-2H]-242.27130932474
DeepCCS[M+Na]+217.83830932474
AllCCS[M+H]+213.132859911
AllCCS[M+H-H2O]+211.032859911
AllCCS[M+NH4]+215.032859911
AllCCS[M+Na]+215.532859911
AllCCS[M-H]-211.732859911
AllCCS[M+Na-2H]-214.332859911
AllCCS[M+HCOO]-217.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-TocopherolCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(O)=CC(C)=C2O13793.0Standard polar33892256
beta-TocopherolCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(O)=CC(C)=C2O13000.2Standard non polar33892256
beta-TocopherolCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(O)=CC(C)=C2O13097.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
beta-Tocopherol,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=C(C)C2=C1O[C@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC22999.6Semi standard non polar33892256
beta-Tocopherol,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=C(C)C2=C1O[C@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC23259.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - beta-Tocopherol GC-MS (1 TMS)splash10-00di-1490200000-f75de727e16d87c65fba2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Tocopherol GC-MS (Non-derivatized)splash10-00di-1490200000-f75de727e16d87c65fba2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Tocopherol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lyo-6954200000-ffcf92e6a6e2f34dd9222017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Tocopherol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5644900000-b5341f1bdc151c1a796b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Tocopherol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Tocopherol EI-EBEB (JMS-HX/HX 110A, JEOL) , Positive-QTOFsplash10-0gb9-3900600000-10f458ddcb7e7aa4df842012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Tocopherol n/a 29V, negative-QTOFsplash10-0f6t-0900600000-9a11a437c645252a72a52020-07-21HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Tocopherol 10V, Positive-QTOFsplash10-014i-0842900000-82c505b0548997aace832017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Tocopherol 20V, Positive-QTOFsplash10-0udi-1910000000-1b1a0fe2f352daa49e2c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Tocopherol 40V, Positive-QTOFsplash10-0pb9-4920000000-b63881a7743c06bdea152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Tocopherol 10V, Negative-QTOFsplash10-014i-0100900000-2345f13b44d6c70d81e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Tocopherol 20V, Negative-QTOFsplash10-014j-0912800000-4e68210f69fcd3f6c3742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Tocopherol 40V, Negative-QTOFsplash10-00kk-0914000000-f6f5255b874c4fc7f4f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Tocopherol 10V, Negative-QTOFsplash10-014i-0000900000-a74b65a822c3cc7625b72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Tocopherol 20V, Negative-QTOFsplash10-014i-0201900000-2dcdf4f502cc6e57342d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Tocopherol 40V, Negative-QTOFsplash10-024m-2913100000-fb9e3e53715df460db952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Tocopherol 10V, Positive-QTOFsplash10-014i-3113900000-16d3b372ee248c26f3132021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Tocopherol 20V, Positive-QTOFsplash10-0aor-9213100000-65be5213a11752835e852021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Tocopherol 40V, Positive-QTOFsplash10-052g-9400000000-947da441c6df0de93bed2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.20 (0.00-0.48) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
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
Food Biomarker OntologyNot Available
VMH IDBVITE
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]