gamma-Tocotrienol (CHEM023625)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:11:28 UTC
Update Date2016-11-09 01:17:45 UTC
Accession NumberCHEM023625
Identification
Common Namegamma-Tocotrienol
ClassSmall Molecule
DescriptionA tocotrienol that is chroman-6-ol substituted by methyl groups at positions 2, 7 and 8 and a farnesyl chain at position 2. A vitamin E family member that has potent anti-cancer properties against a wide-range of cancers.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-2,7,8-Trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
g-TocotrienolGenerator
Γ-tocotrienolGenerator
Tocotrienol, gammaHMDB
(2R)-3,4-Dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-2H-1-benzopyran-6-olHMDB
(R)-gamma-TocotrienolHMDB
(R)-Γ-tocotrienolHMDB
7,8-DimethyltocotrienolHMDB
D-gamma-TocotrienolHMDB
D-Γ-tocotrienolHMDB
Plastochromanol 3HMDB
gamma-TocotrienolHMDB
Chemical FormulaC28H42O2
Average Molecular Mass410.632 g/mol
Monoisotopic Mass410.318 g/mol
CAS Registry Number14101-61-2
IUPAC Name(2R)-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Namegamma-tocotrienol
SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C\CCC1(C)CCC2=CC(O)=C(C)C(C)=C2O1
InChI IdentifierInChI=1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h11,13,15,19,29H,8-10,12,14,16-18H2,1-7H3/b21-13+,22-15+
InChI KeyOTXNTMVVOOBZCV-NTZRDTQNSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00034 g/LALOGPS
logP7.71ALOGPS
logP8.78ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)10.47ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity132.88 m³·mol⁻¹ChemAxon
Polarizability52.51 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4m-5689000000-0d7bfe0a60d4ee1a2109Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-5434900000-88e1ef1d491000736dfaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0000900000-9ea294ff4831f39965a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ik9-0952700000-a647628546759321e97fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0920000000-5f57114e0b44fb382e34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-3920000000-61a9fdea487cbd6093efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0100900000-893e3a2bd3a1a3a2f336Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0932800000-da33f54bd082556fef71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000e-1933000000-4941dbd0b8867df99c57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fs-5295600000-7c0dc451a62c5aa801b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-6893000000-24e47314ac2c35b77a8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9800000000-741a3827b0fb740c39e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-01a5cd11479be7bee1beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-0901300000-ffe985ef6c11eebe38f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1903000000-8f9de8bc5233fa1f0419Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012958
FooDB IDFDB001298
Phenol Explorer IDNot Available
KNApSAcK IDC00035101
BiGG IDNot Available
BioCyc IDCPD-15838
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGamma-Tocotrienol
Chemspider ID4445514
ChEBI ID33277
PubChem Compound ID5282349
Kegg Compound IDC14155
YMDB IDNot Available
ECMDB IDM2MDB005294
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19195866
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19557601
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21429729
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23341695
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24959559
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25423021
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26930378
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=27128741
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=27356050
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=27864002
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=27869747
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=29283379
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=29642403
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=29787425
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=29957361
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=30070965
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=30183139
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=30497457
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=30845647
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=30866453
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=30901461
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=31414341
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=31877708
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=32283796
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=33343356
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=33847203
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=PMC8308567
28. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
29. 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.
30. 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.
31. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
32. The lipid handbook with CD-ROM