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Record Information
Version1.0
Created at2021-01-05 23:30:52 UTC
Updated at2021-08-19 23:59:52 UTC
NP-MRD IDNP0014309
Secondary Accession NumbersNone
Natural Product Identification
Common NameR-δ-tocotrienol
Provided ByNPAtlasNPAtlas Logo
DescriptionDelta-Tocotrienol, also known as δ-tocotrienol or tocotrienol, delta, 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, delta-tocotrienol is considered to be a quinone. Delta-Tocotrienol exists in all living organisms, ranging from bacteria to humans. Delta-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. R-δ-tocotrienol is found in Cystophora monilifera. It was first documented in 2011 (PMID: 21598300). Based on a literature review a significant number of articles have been published on delta-Tocotrienol (PMID: 26093325) (PMID: 22816285) (PMID: 24486300) (PMID: 24294967).
Structure
Thumb
Synonyms
ValueSource
(2R)-2,8-Dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
Δ-tocotrienolGenerator
Tocotrienol, deltaHMDB
(2R)-3,4-Dihydro-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-2H-1-benzopyran-6-olHMDB
(R)-delta-TocotrienolHMDB
(R)-Δ-tocotrienolHMDB
8-MethyltocotrienolHMDB
D-delta-TocotrienolHMDB
D-Δ-tocotrienolHMDB
delta-TocotrienolHMDB
Chemical FormulaC27H40O2
Average Mass396.6150 Da
Monoisotopic Mass396.30283 Da
IUPAC Name(2R)-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Namedelta tocotrienol
CAS Registry NumberNot Available
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1
InChI Identifier
InChI=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+/t27-/m1/s1
InChI KeyODADKLYLWWCHNB-LDYBVBFYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)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
Cinnamosma fragransKNApSAcK Database
Cinnamosma macrocarpaKNApSAcK Database
Cinnamosma madagascariensisKNApSAcK Database
Cocos nucifera L.KNApSAcK Database
Coriandrum sativum L.KNApSAcK Database
Cratoxylum sumatranumKNApSAcK Database
Cystophora monilifera
Elaeis guineensis Jacq.KNApSAcK Database
Foeniculum vulgare L.KNApSAcK Database
Garcinia multifloraKNApSAcK Database
Hevea brasiliensis Mull.Arg.KNApSAcK Database
Hordeum vulgare L.KNApSAcK Database
Juglans regia L.KNApSAcK Database
Litchi chinensis Sonn.KNApSAcK Database
Nicotiana tabacum L.KNApSAcK Database
Oryza sativa L.KNApSAcK Database
Pleodendron costaricenseKNApSAcK Database
Rosmarinus officinalis L.KNApSAcK Database
Vaccinium macrocarpon AitonKNApSAcK 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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point517.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility6.9e-06 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP9.840 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
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
Polarizability49.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0030008
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001299
KNApSAcK IDC00035077
Chemspider ID4445515
KEGG Compound IDC14156
BioCyc IDCPD-15839
BiGG IDNot Available
Wikipedia LinkTocotrienol
METLIN IDNot Available
PubChem Compound5282350
PDB IDNot Available
ChEBI ID33276
Good Scents IDrw1679291
References
General References
  1. Brkljaca R, Urban S: HPLC-NMR and HPLC-MS investigation of antimicrobial constituents in Cystophora monilifera and Cystophora subfarcinata. Phytochemistry. 2015 Sep;117:200-208. doi: 10.1016/j.phytochem.2015.06.014. Epub 2015 Jun 18. [PubMed:26093325 ]
  2. Ji X, Wang Z, Geamanu A, Sarkar FH, Gupta SV: Inhibition of cell growth and induction of apoptosis in non-small cell lung cancer cells by delta-tocotrienol is associated with notch-1 down-regulation. J Cell Biochem. 2011 Oct;112(10):2773-83. doi: 10.1002/jcb.23184. [PubMed:21598300 ]
  3. Asakawa Y, Ludwiczuk A, Harinantenaina L, Toyota M, Nishiki M, Bardon A, Nii K: Distribution of drimane sesquiterpenoids and tocopherols in liverworts, ferns and higher plants: Polygonaceae, Canellaceae and Winteraceae species. Nat Prod Commun. 2012 Jun;7(6):685-92. [PubMed:22816285 ]
  4. Singh VK, Wise SY, Scott JR, Romaine PL, Newman VL, Fatanmi OO: Radioprotective efficacy of delta-tocotrienol, a vitamin E isoform, is mediated through granulocyte colony-stimulating factor. Life Sci. 2014 Mar 11;98(2):113-22. doi: 10.1016/j.lfs.2014.01.065. Epub 2014 Jan 28. [PubMed:24486300 ]
  5. Li XH, Ghosh SP, Ha CT, Fu D, Elliott TB, Bolduc DL, Villa V, Whitnall MH, Landauer MR, Xiao M: Delta-tocotrienol protects mice from radiation-induced gastrointestinal injury. Radiat Res. 2013 Dec;180(6):649-57. doi: 10.1667/RR13398.1. Epub 2013 Dec 2. [PubMed:24294967 ]