Record Information
Version1.0
Creation date2010-04-08 22:04:55 UTC
Update date2019-11-26 02:56:16 UTC
Primary IDFDB001299
Secondary Accession NumbersNot Available
Chemical Information
FooDB Named-Tocotrienol
Descriptiond-Tocotrienol 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. d-Tocotrienol is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number25612-59-3
Structure
Thumb
Synonyms
SynonymSource
(R)-delta-TocotrienolHMDB
3,4-Dihydro-2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol, 9ciHMDB
8-MethyltocotrienolHMDB
delta-TocotrienolHMDB
Tocotrienol, deltaHMDB
(r)-delta-tocotrienolbiospider
2,8-Dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-6-chromanoldb_source
3,4-Dihydro-2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol, 9CIdb_source
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
Polarizability50.08 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H40O2
IUPAC name2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol
InChI IdentifierInChI=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+
InChI KeyODADKLYLWWCHNB-QRCIITMISA-N
Isomeric SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C\CCC1(C)CCC2=CC(O)=CC(C)=C2O1
Average Molecular Weight396.6053
Monoisotopic Molecular Weight396.302830524
Classification
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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 81.77%; H 10.17%; O 8.07%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSd-Tocotrienol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a7i-5779000000-194bd961eb4a4dc6ab87Spectrum
Predicted GC-MSd-Tocotrienol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-7658900000-899fc3a01d3cb7be159eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000b-0729000000-0ac61af8e1349dae63a9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-a48a1fcb6a81dcbd8833Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4910000000-872ac24390c903ef6155Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0109000000-b3deb3254ff71b978f17Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-0709000000-a706906091096f93cd2dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-0913000000-f5f5985c3a947d086f5aSpectrum
NMRNot Available
ChemSpider ID8030319
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID9854614
Pubchem Substance IDNot Available
ChEBI ID33276
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30008
CRC / DFC (Dictionary of Food Compounds) IDBZG51-V:BZG51-V
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00035077
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.