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Record Information
Version1.0
Created at2021-06-20 20:21:51 UTC
Updated at2021-06-30 00:09:39 UTC
NP-MRD IDNP0037440
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha-tocotrienol
Provided ByJEOL DatabaseJEOL Logo
DescriptionAlpha-Tocotrienol, also known as zeta1-tocopherol or α-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. Thus, alpha-tocotrienol is considered to be a quinone. Alpha-Tocotrienol exists in all living organisms, ranging from bacteria to humans. Alpha-Tocotrienol has been detected, but not quantified in, several different foods, such as naranjillas (Solanum quitoense), purple mangosteens (Garcinia mangostana), saskatoon berries (Amelanchier alnifolia), mexican groundcherries (Physalis philadelphica var. Immaculata), and pepper (c. Frutescens). This could make alpha-tocotrienol a potential biomarker for the consumption of these foods. Alpha-Tocotrienol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 2006 (PMID: 16771695). Based on a literature review a significant number of articles have been published on alpha-Tocotrienol (PMID: 16923160) (PMID: 20823491) (PMID: 22013739) (PMID: 22252050).
Structure
Thumb
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, alphaMeSH, HMDB
(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 Mass424.6585 Da
Monoisotopic Mass424.33413 Da
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 NumberNot Available
SMILES
[H]OC1=C(C(=C2O[C@](C([H])([H])[H])(C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C2=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]
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 KeyRZFHLOLGZPDCHJ-XZXLULOTSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Aesculus hippocastanum Hort.KNApSAcK Database
Amaranthus hypochondriacus L.KNApSAcK Database
Avena sativa L.KNApSAcK Database
Bixa orellana L.KNApSAcK Database
Calophyllum inophyllum L.KNApSAcK Database
Carum carvi L.KNApSAcK Database
Cocos nucifera L.KNApSAcK Database
Coriandrum sativum L.KNApSAcK Database
Delphinium ajacis L.KNApSAcK Database
Elaeis guineensis Jacq.KNApSAcK Database
Foeniculum vulgare L.KNApSAcK Database
Gevuina avellana Mol.KNApSAcK Database
Hevea brasiliensis Mull.Arg.KNApSAcK Database
Hordeum vulgare L.KNApSAcK Database
Nicotiana tabacum L.KNApSAcK Database
Oryza sativa L.KNApSAcK Database
Rosmarinus officinalis L.KNApSAcK Database
Secale cereale L.KNApSAcK Database
Vaccinium macrocarpon AitonKNApSAcK Database
Vitis vinifera L.KNApSAcK Database
Zea mays L.KNApSAcK Database
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
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
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
Polarizability51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0006327
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112231
KNApSAcK IDC00035044
Chemspider ID4445512
KEGG Compound IDC14153
BioCyc IDCPD-15836
BiGG IDNot Available
Wikipedia LinkAlpha-Tocotrienol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID33270
Good Scents IDNot Available
References
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. doi: 10.1089/ars.2006.8.1059. [PubMed:16771695 ]
  2. Khanna S, Roy S, Parinandi NL, Maurer M, Sen CK: Characterization of the potent neuroprotective properties of the natural vitamin E alpha-tocotrienol. J Neurochem. 2006 Sep;98(5):1474-86. doi: 10.1111/j.1471-4159.2006.04000.x. [PubMed:16923160 ]
  3. Sen CK, Rink C, Khanna S: Palm oil-derived natural vitamin E alpha-tocotrienol in brain health and disease. J Am Coll Nutr. 2010 Jun;29(3 Suppl):314S-323S. doi: 10.1080/07315724.2010.10719846. [PubMed:20823491 ]
  4. Patel V, Rink C, Khanna S, Sen CK: Tocotrienols: the lesser known form of natural vitamin E. Indian J Exp Biol. 2011 Oct;49(10):732-8. [PubMed:22013739 ]
  5. Fairus S, Nor RM, Cheng HM, Sundram K: Alpha-tocotrienol is the most abundant tocotrienol isomer circulated in plasma and lipoproteins after postprandial tocotrienol-rich vitamin E supplementation. Nutr J. 2012 Jan 17;11:5. doi: 10.1186/1475-2891-11-5. [PubMed:22252050 ]
  6. Ohnmacht, S., et al. (2008). Ohnmacht, S., et al, Magn. Reson. Chem. 46, 287 (2008). Mag. Reson. Chem..