(R)-alpha-Tocotrienol (CHEM024552)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:46:45 UTC
Update Date2016-11-09 01:17:55 UTC
Accession NumberCHEM024552
Identification
Common Name(R)-alpha-Tocotrienol
ClassSmall Molecule
DescriptionA tocotrienol that is chroman-6-ol substituted by methyl groups at positions 2, 5, 7 and 8 and a farnesyl chain at position 2. It has been found in palm oil derived from Elaeis guineensis.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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-olChEBI
zeta1-TocopherolChEBI
Ζ1-tocopherolGenerator
a-TocotrienolGenerator
Α-tocotrienolGenerator
(2R,3'e,7'e)-alpha-TocotrienolHMDB
(R)-alpha-TocotrienolHMDB
Tocotrienol, alphaHMDB
(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 Mass424.659 g/mol
Monoisotopic Mass424.334 g/mol
CAS Registry Number1721-51-3
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
SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C/CCC1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C
InChI IdentifierInChI=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-
InChI KeyRZFHLOLGZPDCHJ-AOOUSOOLSA-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
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 Solubility0.00027 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
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, Positivesplash10-0a4i-4494300000-fa600d27bfadf9333e8cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-053r-5433900000-93585710604da7b48af4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-6279700000-fbe5f6cab6018eff20d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-6198100000-b37bca2605f0f838e211Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9440000000-b860a3b18a066d1b0db6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-306532243e42ab86a18eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0422900000-abbe3bd275000d3b06e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-3965100000-d69aac770a2bbd897e26Spectrum
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 IDHMDB0006327
FooDB IDFDB112231
Phenol Explorer IDNot Available
KNApSAcK IDC00035044
BiGG ID2296493
BioCyc IDCPD-15836
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlpha-Tocotrienol
Chemspider ID4445512
ChEBI ID33270
PubChem Compound ID5282347
Kegg Compound IDC14153
YMDB IDNot Available
ECMDB IDM2MDB005240
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11160563
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12030315
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12521598
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12524170
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12566479
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12739983
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=12788481
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15527824
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16166580
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16257640
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=16616508
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=16771695
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=16923160
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=17331802
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=20028458
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=20823491
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22013739
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22252050
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24013375
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=30110365
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=31905614
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=7808307
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=PMC7259054
24. Chenevert Robert; Courchesne Gabriel; Pelchat Nicholas Chemoenzymatic synthesis of both enantiomers of alpha-tocotrienol. Bioorganic & medicinal chemistry (2006), 14(15), 5389-96.
25. 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.