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Record Information
Version3.6
Creation Date2007-05-23 00:49:32 UTC
Update Date2016-02-11 01:07:28 UTC
HMDB IDHMDB06327
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlpha-Tocotrienol
DescriptionAlpha-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
Thumb
Synonyms
ValueSource
zeta1-TocopherolChEBI
Z1-TocopherolGenerator
ζ1-tocopherolGenerator
(2R,3'e,7'e)-alpha-TocotrienolHMDB
(R)-alpha-TocotrienolHMDB
D-alpha-TocotrienolHMDB
delta-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 Number1721-51-3
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C
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 KeyInChIKey=RZFHLOLGZPDCHJ-XZXLULOTSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 Solubility0.000272 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity137.92 m3·mol-1ChemAxon
Polarizability53.67 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.23 +/- 0.7 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002434
KNApSAcK IDNot Available
Chemspider ID4445512
KEGG Compound IDC14153
BioCyc IDNot Available
BiGG ID2296493
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06327
Metagene LinkHMDB06327
METLIN IDNot Available
PubChem Compound5282347
PDB IDNot Available
ChEBI ID33270
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. [16771695 ]