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Record Information
Version1.0
Created at2020-11-23 19:40:25 UTC
Updated at2021-08-19 23:59:23 UTC
NP-MRD IDNP0002786
Secondary Accession NumbersNone
Natural Product Identification
Common Namedelta-Tocopherol
DescriptionDelta-Tocopherol, also known as δ-tocopherol or 8-methyltocol, belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. Thus, delta-tocopherol is considered to be a quinone. Delta-Tocopherol exists in all living organisms, ranging from bacteria to humans. Delta-Tocopherol has been detected, but not quantified in, several different foods, such as yams (Dioscorea), arabica coffees (Coffea arabica), mammee apples (Mammea americana), chestnuts (Castanea), and dills (Anethum graveolens). This could make delta-tocopherol a potential biomarker for the consumption of these foods. Delta-Tocopherol 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 1999 (PMID: 10385606). Based on a literature review a significant number of articles have been published on delta-Tocopherol (PMID: 17984079) (PMID: 14695946) (PMID: 16400056) (PMID: 12600864).
Structure
Thumb
Synonyms
ValueSource
(+)-delta-TocopherolChEBI
(2R)-2,8-Dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
(2R)-3,4-Dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olChEBI
(2R,4'r,8'r)-delta-TocopherolChEBI
(R,R,R)-delta-TocopherolChEBI
8-MethyltocolChEBI
e309ChEBI
RRR-delta-TocopherolChEBI
(+)-Δ-tocopherolGenerator
(2R,4'r,8'r)-Δ-tocopherolGenerator
(R,R,R)-Δ-tocopherolGenerator
RRR-Δ-tocopherolGenerator
Δ-tocopherolGenerator
Vitamine eHMDB
(2R,4’R,8’r)-δ-tocopherolHMDB
D-delta-TocopherolHMDB
D-Δ-tocopherolHMDB
delta-D-TocopherolHMDB
delta-Vitamin eHMDB
Δ-D-tocopherolHMDB
Δ-vitamin eHMDB
delta-TocopherolHMDB
Chemical FormulaC27H46O2
Average Mass402.6529 Da
Monoisotopic Mass402.34978 Da
IUPAC Name(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Namedelta tocopherol
CAS Registry NumberNot Available
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1
InChI Identifier
InChI=1S/C27H46O2/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/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1
InChI KeyGZIFEOYASATJEH-VHFRWLAGSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Aesculus hippocatanum Hort.KNApSAcK Database
Amaranthus hypochondriacus L.KNApSAcK Database
Arabidopsis thalianaKNApSAcK 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
Elaeis guineensis Jacq.KNApSAcK Database
Foeniculum vulgare L.KNApSAcK Database
Gevuina avellana Mol.KNApSAcK Database
Glycine maxKNApSAcK 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
Pellia epiphyllaKNApSAcK Database
Potamogeton pectinatusKNApSAcK Database
Rosmarinus officinalis L.KNApSAcK Database
Secale cereale L.KNApSAcK Database
Vaccinium macrocarpon AitonKNApSAcK Database
Zea mays L.KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentTocopherols
Alternative Parents
Substituents
  • Tocopherol
  • 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 Point504.00 to 505.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility3.8e-06 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP10.493 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP8.76ALOGPS
logP9.48ChemAxon
logS-7.6ALOGPS
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 Count12ChemAxon
Refractivity125.29 m³·mol⁻¹ChemAxon
Polarizability51.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0002902
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112209
KNApSAcK IDC00007363
Chemspider ID83144
KEGG Compound IDC14151
BioCyc IDDELTA-TOCOPHEROL
BiGG IDNot Available
Wikipedia LinkDelta-Tocopherol
METLIN ID232
PubChem Compound92094
PDB IDNot Available
ChEBI ID47772
Good Scents IDrw1118171
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Passi S, De Pita O, Grandinetti M, Simotti C, Littarru GP: The combined use of oral and topical lipophilic antioxidants increases their levels both in sebum and stratum corneum. Biofactors. 2003;18(1-4):289-97. doi: 10.1002/biof.5520180233. [PubMed:14695946 ]
  3. Clarke MW, Ward NC, Wu JH, Hodgson JM, Puddey IB, Croft KD: Supplementation with mixed tocopherols increases serum and blood cell gamma-tocopherol but does not alter biomarkers of platelet activation in subjects with type 2 diabetes. Am J Clin Nutr. 2006 Jan;83(1):95-102. doi: 10.1093/ajcn/83.1.95. [PubMed:16400056 ]
  4. Brigelius-Flohe R, Traber MG: Vitamin E: function and metabolism. FASEB J. 1999 Jul;13(10):1145-55. [PubMed:10385606 ]
  5. Liu M, Wallmon A, Olsson-Mortlock C, Wallin R, Saldeen T: Mixed tocopherols inhibit platelet aggregation in humans: potential mechanisms. Am J Clin Nutr. 2003 Mar;77(3):700-6. doi: 10.1093/ajcn/77.3.700. [PubMed:12600864 ]