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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-23 00:49:32 UTC
Update Date2020-06-15 17:04:52 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
zeta1-TocopherolChEBI
ζ1-tocopherolGenerator
a-TocotrienolGenerator
α-tocotrienolGenerator
(2R,3'E,7'E)-alpha-TocotrienolHMDB
(R)-alpha-TocotrienolHMDB
Tocotrienol, alphaMeSH, HMDB
(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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4494300000-fa600d27bfadf9333e8cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-053r-5433900000-93585710604da7b48af4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01r2-9800300000-d4d5035c7c70dc5d3917Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0943800000-8c0624844c5b25ade788Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0910000000-ea722b3b06305a4d0c1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2920000000-8541d4f689f1b7b7375dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-a7c5f24f31abf7cac8fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-0731900000-78aff556476fa975cfdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08gj-0921200000-530dfe74d6457c43c454Spectrum
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 IDFDB002434
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 ID
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 ]