Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2021-06-20 20:21:54 UTC
Updated at2021-08-20 00:00:34 UTC
NP-MRD IDNP0037441
Secondary Accession NumbersNone
Natural Product Identification
Common Namebeta-tocotrienol
Provided ByJEOL DatabaseJEOL Logo
Descriptionβ-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, β-tocotrienol is considered to be a quinone. It was first documented in 2018 (PMID: 29992988). Based on a literature review a significant number of articles have been published on β-tocotrienol (PMID: 30236726) (PMID: 29934169) (PMID: 28946344) (PMID: 28946335).
Structure
Thumb
Synonyms
ValueSource
(2R)-2,5,8-Trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
(2R)-3,4-Dihydro-2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-2H-1-benzopyran-6-olChEBI
epsilon-TocopherolChEBI
Tocotrienol, betaMeSH
b-TocotrienolGenerator
Β-tocotrienolGenerator
Chemical FormulaC28H42O2
Average Mass410.6420 Da
Monoisotopic Mass410.31848 Da
IUPAC Name(2R)-2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Nameβ tocotrienol
CAS Registry NumberNot Available
SMILES
[H]OC1=C([H])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]
InChI Identifier
InChI=1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h11,13,15,19,29H,8-10,12,14,16-18H2,1-7H3/b21-13+,22-15+/t28-/m1/s1
InChI KeyFGYKUFVNYVMTAM-WAZJVIJMSA-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
Amaranthus hypochondriacus L.KNApSAcK Database
Avena sativa L.KNApSAcK Database
Bixa orellana L.KNApSAcK Database
Carum carvi L.KNApSAcK Database
Cocos nucifera L.KNApSAcK Database
Delphinium ajacis L.KNApSAcK Database
Elaeis guineensis Jacq.KNApSAcK Database
Foeniculum vulgare L.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
  • 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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point528.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.9e-06 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP10.300 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
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
Polarizability50.04 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093543
KNApSAcK IDC00035060
Chemspider ID4445513
KEGG Compound IDC14154
BioCyc IDCPD-15837
BiGG IDNot Available
Wikipedia LinkBeta-Tocotrienol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID33275
Good Scents IDrw1679271
References
General References
  1. Pokkanta P, Sookwong P, Tanang M, Setchaiyan S, Boontakham P, Mahatheeranont S: Simultaneous determination of tocols, gamma-oryzanols, phytosterols, squalene, cholecalciferol and phylloquinone in rice bran and vegetable oil samples. Food Chem. 2019 Jan 15;271:630-638. doi: 10.1016/j.foodchem.2018.07.225. Epub 2018 Aug 1. [PubMed:30236726 ]
  2. Jaafar F, Abdullah A, Makpol S: Cellular Uptake and Bioavailability of Tocotrienol-Rich Fraction in SIRT1-Inhibited Human Diploid Fibroblasts. Sci Rep. 2018 Jul 11;8(1):10471. doi: 10.1038/s41598-018-28708-z. [PubMed:29992988 ]
  3. Costa ASG, Alves RC, Vinha AF, Costa E, Costa CSG, Nunes MA, Almeida AA, Santos-Silva A, Oliveira MBPP: Nutritional, chemical and antioxidant/pro-oxidant profiles of silverskin, a coffee roasting by-product. Food Chem. 2018 Nov 30;267:28-35. doi: 10.1016/j.foodchem.2017.03.106. Epub 2017 Mar 21. [PubMed:29934169 ]
  4. Hidalgo A, Ferraretto A, De Noni I, Bottani M, Cattaneo S, Galli S, Brandolini A: Bioactive compounds and antioxidant properties of pseudocereals-enriched water biscuits and their in vitro digestates. Food Chem. 2018 Feb 1;240:799-807. doi: 10.1016/j.foodchem.2017.08.014. Epub 2017 Aug 3. [PubMed:28946344 ]
  5. Lachman J, Hejtmankova A, Orsak M, Popov M, Martinek P: Tocotrienols and tocopherols in colored-grain wheat, tritordeum and barley. Food Chem. 2018 Feb 1;240:725-735. doi: 10.1016/j.foodchem.2017.07.123. Epub 2017 Jul 25. [PubMed:28946335 ]
  6. Ohnmacht, S., et al. (2008). Ohnmacht, S., et al, Magn. Reson. Chem. 46, 287 (2008). Mag. Reson. Chem..