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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:08 UTC
Update Date2020-09-27 20:02:09 UTC
HMDB IDHMDB0030008
Secondary Accession Numbers
  • HMDB30008
Metabolite Identification
Common Namedelta-Tocotrienol
Descriptiondelta-Tocotrienol, also known as 8-methyltocotrienol, 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, delta-tocotrienol is considered to be a quinone lipid molecule. delta-Tocotrienol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. delta-Tocotrienol is found in American cranberry and palm oil. It is a nutriceutical with anticancer properties and a positive influence on the blood lipid profile.
Structure
Data?1601236929
Synonyms
ValueSource
Tocotrienol, deltaMeSH
δ-TocotrienolGenerator
(2R)-3,4-Dihydro-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-2H-1-benzopyran-6-olHMDB
(R)-delta-TocotrienolHMDB
(R)-δ-TocotrienolHMDB
8-MethyltocotrienolHMDB
delta-TocotrienolHMDB
d-delta-TocotrienolPhytoBank
d-δ-TocotrienolPhytoBank
Chemical FormulaC27H40O2
Average Molecular Weight396.615
Monoisotopic Molecular Weight396.302830528
IUPAC Name(2R)-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Namedelta tocotrienol
CAS Registry Number25612-59-3
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1
InChI Identifier
InChI=1S/C27H40O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3/b21-12+,22-14+/t27-/m1/s1
InChI KeyODADKLYLWWCHNB-LDYBVBFYSA-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
  • 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:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00049 g/LALOGPS
logP7.71ALOGPS
logP8.26ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)10.14ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity127.84 m³·mol⁻¹ChemAxon
Polarizability50.41 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000b-0729000000-bdb3f601da6568da91feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1910000000-abbd9af3e2be0c682cfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3920000000-7d0b193d8a3c3a3a5967Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0109000000-5ada9ae99b1c0f7f1258Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-0709000000-22c37c4db5a8d82525ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-0913000000-c3d3a5ed1080b2af167fSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001299
KNApSAcK IDC00035077
Chemspider ID4445515
KEGG Compound IDC14156
BioCyc IDCPD-15839
BiGG IDNot Available
Wikipedia LinkTocotrienol
METLIN IDNot Available
PubChem Compound5282350
PDB IDNot Available
ChEBI ID33276
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.