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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-23 00:49:32 UTC
Update Date2022-03-07 02:49:31 UTC
HMDB IDHMDB0006327
Secondary Accession Numbers
  • HMDB06327
Metabolite Identification
Common Namealpha-Tocotrienol
Descriptionalpha-Tocotrienol (CAS: 1721-51-3), also known as 5,7,8-trimethyltocotrienol, belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. They differ from tocopherols that contain a saturated trimethyltridecyl chain. Thus, alpha-tocotrienol is considered to be a quinone lipid molecule. alpha-Tocotrienol is found in the blood plasma and all lipoprotein subfractions. Compared to tocopherols, alpha-tocotrienols are poorly studied. Its presence in the blood plasma at nanomolar concentrations is thought to help to prevent stroke-related neurodegeneration (PMID: 16771695 ). alpha-Tocotrienol has been found to have vitamin E activity.
Structure
Data?1582752380
Synonyms
ValueSource
(2R)-2,5,7,8-Tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
zeta1-TocopherolChEBI
Ζ1-tocopherolGenerator
a-TocotrienolGenerator
Α-tocotrienolGenerator
(2R,3'e,7'e)-alpha-TocotrienolHMDB
(R)-alpha-TocotrienolHMDB
Tocotrienol, alphaHMDB
(2R,3'e,7'e)-Α-tocotrienolHMDB
(2R,3’E,7’e)-α-tocotrienolHMDB
(R)-Α-tocotrienolHMDB
5,7,8-TrimethyltocotrienolHMDB
alpha-TocotrienolHMDB
Chemical FormulaC29H44O2
Average Molecular Weight424.6585
Monoisotopic Molecular Weight424.334130652
IUPAC Name(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Nameα tocotrienol
CAS Registry Number58864-81-6
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1
InChI Identifier
InChI=1S/C29H44O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16+/t29-/m1/s1
InChI KeyRZFHLOLGZPDCHJ-XZXLULOTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentTocotrienols
Alternative Parents
Substituents
  • Tocotrienol
  • Diterpenoid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • 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

Biological location

Source

Physical Properties
StateSolid
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 Solubility0.00027 g/LALOGPS
logP7.7ALOGPS
logP9.29ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)10.8ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity137.92 m³·mol⁻¹ChemAxon
Polarizability54.56 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+203.75231661259
DarkChem[M-H]-201.26431661259
DeepCCS[M+H]+209.47730932474
DeepCCS[M-H]-207.11930932474
DeepCCS[M-2H]-240.55230932474
DeepCCS[M+Na]+215.7830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-TocotrienolCC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O14016.9Standard polar33892256
alpha-TocotrienolCC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O13229.7Standard non polar33892256
alpha-TocotrienolCC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O13287.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Tocotrienol,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC[C@]1(C)CCC2=C(C)C(O[Si](C)(C)C)=C(C)C(C)=C2O13176.4Semi standard non polar33892256
alpha-Tocotrienol,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC[C@]1(C)CCC2=C(C)C(O[Si](C)(C)C(C)(C)C)=C(C)C(C)=C2O13404.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Tocotrienol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4494300000-fa600d27bfadf9333e8c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Tocotrienol GC-MS (1 TMS) - 70eV, Positivesplash10-053r-5433900000-93585710604da7b48af42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Tocotrienol 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 - alpha-Tocotrienol LC-ESI-QTOF , positive-QTOFsplash10-01r2-9800300000-d4d5035c7c70dc5d39172017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocotrienol 10V, Positive-QTOFsplash10-004i-0943800000-8c0624844c5b25ade7882017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocotrienol 20V, Positive-QTOFsplash10-014i-0910000000-ea722b3b06305a4d0c1d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocotrienol 40V, Positive-QTOFsplash10-014i-2920000000-8541d4f689f1b7b7375d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocotrienol 10V, Negative-QTOFsplash10-00di-0000900000-a7c5f24f31abf7cac8fc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocotrienol 20V, Negative-QTOFsplash10-0229-0731900000-78aff556476fa975cfde2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocotrienol 40V, Negative-QTOFsplash10-08gj-0921200000-530dfe74d6457c43c4542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocotrienol 10V, Positive-QTOFsplash10-00or-6279700000-fbe5f6cab6018eff20d32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocotrienol 20V, Positive-QTOFsplash10-014i-6198100000-b37bca2605f0f838e2112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocotrienol 40V, Positive-QTOFsplash10-0a4l-9440000000-b860a3b18a066d1b0db62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocotrienol 10V, Negative-QTOFsplash10-00di-0000900000-306532243e42ab86a18e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocotrienol 20V, Negative-QTOFsplash10-00di-0422900000-abbe3bd275000d3b06e52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Tocotrienol 40V, Negative-QTOFsplash10-052r-3965100000-d69aac770a2bbd897e262021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.23 +/- 0.7 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
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112231
KNApSAcK IDC00035044
Chemspider ID4445512
KEGG Compound IDC14153
BioCyc IDCPD-15836
BiGG ID2296493
Wikipedia LinkAlpha-Tocotrienol
METLIN IDNot Available
PubChem Compound5282347
PDB IDNot Available
ChEBI ID33270
Food Biomarker OntologyNot Available
VMH IDAVITE2
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceChenevert Robert; Courchesne Gabriel; Pelchat Nicholas Chemoenzymatic synthesis of both enantiomers of alpha-tocotrienol. Bioorganic & medicinal chemistry (2006), 14(15), 5389-96.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Khosla P, Patel V, Whinter JM, Khanna S, Rakhkovskaya M, Roy S, Sen CK: Postprandial levels of the natural vitamin E tocotrienol in human circulation. Antioxid Redox Signal. 2006 May-Jun;8(5-6):1059-68. [PubMed:16771695 ]