Record Information
Version1.0
Creation date2010-04-08 22:10:08 UTC
Update date2020-04-21 18:03:03 UTC
Primary IDFDB012381
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namebeta-Tocopherol
DescriptionIsolated from vegetable sources, e.g. spinach chloroplasts (Spinacia oleracea), soybean oil, corn oil and wheat germ. Antioxidant. Member of Vitamin E group Beta-tocopherol is an antioxidant which is synthesized by photosynthetic organisms and play important roles in human and animal nutrition. betatocopherols can be oxidized in dry CH2Cl2 or CH3CN by one electron to form cation radicals that deprotonate to form the neutral phenoxyl radicals, which are then immediately further oxidized by one electron to the phenoxonium cations (an ECE electrochemical mechanism, where E signifies an electron transfer and C represents a chemical step, with the electrochemical mechanism having been determined by in situ spectroscopic analysis).The phenoxonium cation of beta-tocopherol is stable for several minutes. (PMID: 16771430); beta-Tocopherol (?-tocopherol) is a type of tocopherol with formula C28H48O2. beta-Tocopherol is found in many foods, some of which are carrot, curry powder, hot chocolate, and arepa.
CAS Number148-03-8
Structure
Thumb
Synonyms
SynonymSource
(2R)-3,4-dihydro-2,5,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olChEBI
2,5,8-Trimethyl-2-(4,8,12-trimethyltridecyl)chroman-6-ol, 8CIdb_source
3,4-Dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol, 9CIdb_source
5,8-Dimethyltocoldb_source
b-TocopherolGenerator
Beta-tocopherolbiospider
Cumotocopheroldb_source
Neotocopheroldb_source
p-Xylotocopheroldb_source
Vitamin ebetabiospider
β-tocopherolGenerator
Predicted Properties
PropertyValueSource
Water Solubility7.3e-06 g/LALOGPS
logP8.81ALOGPS
logP9.99ChemAxon
logS-7.8ALOGPS
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 Count12ChemAxon
Refractivity130.33 m³·mol⁻¹ChemAxon
Polarizability54.04 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC28H48O2
IUPAC name2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol
InChI IdentifierInChI=1S/C28H48O2/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/h19-22,29H,8-18H2,1-7H3
InChI KeyWGVKWNUPNGFDFJ-UHFFFAOYSA-N
Isomeric SMILESCC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=C(C)C(O)=CC(C)=C2O1
Average Molecular Weight416.6795
Monoisotopic Molecular Weight416.36543078
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 80.71%; H 11.61%; O 7.68%DFC
Melting Point< 25 oC
Boiling PointBp0.1 200-210°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +6.37DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0842900000-329a562098bb84cbf7e52015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1910000000-dc55f443e6bd0b9dc0092015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-4930000000-4f8c9c4247e32716ebb82015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0110900000-786c6a7de7da319e8b732015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0911800000-ddc076a8da9d5b77f0f72015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kk-0913000000-06c63a46c204a74dec7a2015-05-27View Spectrum
NMRNot Available
ChemSpider ID5256784
ChEMBL IDNot Available
KEGG Compound IDC14152
Pubchem Compound ID6857447
Pubchem Substance IDNot Available
ChEBI ID22855
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06335
CRC / DFC (Dictionary of Food Compounds) IDHGS15-G:HGS15-G
EAFUS IDNot Available
Dr. Duke IDBETA-TOCOPHEROL
BIGG ID2296531
KNApSAcK IDC00007364
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDbeta-tocopherol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.