Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2018-05-28 23:08:26 UTC
Primary IDFDB002431
Secondary Accession Numbers
  • FDB010395
Chemical Information
FooDB Namegamma-Tocopherol
DescriptionOccurs in many nut and other vegetable oils such as soya and sunflower oil. It is used as antioxidant food additive. Member of Vitamin E group. Added to fats and oils to prevent rancidity. The naturally occurring tocopherol is a single steroisomer; synthetic forms are a mixture of all eight possible isomers [DFC] gamma-Tocopherol is one of the chemical compounds that is considered vitamin E. As a food additive, it has E number E308. [Wikipedia]. gamma-Tocopherol is found in many foods, some of which are common pea, shiitake, feijoa, and other bread.
CAS Number1406-66-2
Structure
Thumb
Synonyms
SynonymSource
DL-alpha-TocopherolKegg
DL-a-TocopherolGenerator
DL-Α-tocopherolGenerator
g-TocopherolGenerator
Γ-tocopherolGenerator
3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-olHMDB
7,8-DimethyltocolHMDB
7,8-Dimethyltocolo-xylotocopherolHMDB
MethyltocolsHMDB
O-XylotocopherolHMDB
TocopherolHMDB
TocopherolsHMDB
Vitamin e gammaHMDB
BioweyxinHMDB
e-MulsinHMDB
EmbialHMDB
GNR-Pharma brand OF tocopherol actetateHMDB
Organon brand OF tocopherol acetateHMDB
Schwarzhaupt brand OF tocopherol acetateHMDB
Snow-e muscle, energy and feritilityHMDB
SpondyvitHMDB
TocolionHMDB
Tocopherol rodisma-med brandHMDB
Tocopherol worwag brandHMDB
Togasan vitamin eHMDB
Unique eHMDB
VibolexHMDB
Vita-eHMDB
Vitamin e drageesHMDB
Atarost brand OF tocopherol acetateHMDB
Biocur brand OF tocopherol acetateHMDB
Cambridge laboratories brand OF tocopherol actetateHMDB
Dal eHMDB
DetulinHMDB
e Vitamin eHMDB
EVI-mirale, vitamin-eHMDB
Elex verlaHMDB
EplonatHMDB
Richelet brand OF tocopherol acetateHMDB
Roche nicholas brand OF tocopherol acetateHMDB
Rodisma med brand OF tocopherolHMDB
Sciencex brand OF tocopherol acetateHMDB
Steigerwald brand OF tocopherol acetateHMDB
Strathmann brand OF tocopherolHMDB
Tocopherol grunwalder brandHMDB
Tocopherol stadapharm brandHMDB
Verla brand OF tocopherolHMDB
Vit. e stadaHMDB
VitaPlus eHMDB
Vitamin-e evi-miraleHMDB
Vitamine e GNRHMDB
VitazellHMDB
Worwag brand OF tocopherolHMDB
Alcala brand OF tocopherol acetateHMDB
Bio eHMDB
Biopto-eHMDB
e VicotratHMDB
e-FerolHMDB
EUNOVA vitamin eHMDB
Equivit eHMDB
EvionHMDB
Internation animal health brand OF tocopherol acetateHMDB
MIP brand OF tocopherol acetateHMDB
Sanum-kehlbeck brand OF tocopherol actetateHMDB
Tocopherol infirmarius-rovit brandHMDB
Tocopherol twardy brandHMDB
TocovitalHMDB
Vitamin-e drageesHMDB
Wiedemann brand OF tocopherolHMDB
AbortosanHMDB
Arkopharma brand OF tocopherol acetateHMDB
Dal vita brand OF vitamin e succinateHMDB
Eu rho brand OF tocopherolHMDB
EusovitHMDB
Infirmarius-rovit brand OF tocopherolHMDB
Richtavit eHMDB
Riemser brand OF tocopherolHMDB
Tocopherol ausrichter brandHMDB
Tocopherol balkanpharma brandHMDB
Vitagutt vitamin eHMDB
Vitamin e naturHMDB
Vitamin e, togasanHMDB
Ratiopharm brand OF tocopherolHMDB
Aliud brand OF tocopherolHMDB
Bottger brand OF tocopherol acetateHMDB
DermorelleHMDB
e FerolHMDB
e-Vitamin-ratiopharmHMDB
Heyl brand OF tocopherol acetateHMDB
Kohler brand OF tocopherolHMDB
LasarHMDB
Puncto eHMDB
Rodisma-med brand OF tocopherolHMDB
Sanum kehlbeck brand OF tocopherol actetateHMDB
Scot tussin brand OF tocopherol acetateHMDB
Stadapharm brand OF tocopherolHMDB
TocopaHMDB
Tocopherol bayerHMDB
Tocopherol grace brandHMDB
Tocopherol ratiopharm brandHMDB
Twardy brand OF tocopherolHMDB
Uno vitHMDB
Uno-vitHMDB
Veyx brand OF tocopherolHMDB
Vit e hydrosolHMDB
Vita eHMDB
Vitamin e alHMDB
Wiedemann brand OF vitamin e succinateHMDB
Ausrichter brand OF tocopherolHMDB
Auxina eHMDB
Balkanpharma brand OF tocopherolHMDB
Blackmores brand OF tocopherolHMDB
Dal-eHMDB
DavitamonHMDB
e-VicotratHMDB
EcoroHMDB
EphynalHMDB
Grunwalder brand OF tocopherolHMDB
ICN brand OF tocopherol acetateHMDB
Mucos brand OF tocopherol acetateHMDB
Tocopherol togal brandHMDB
Tocopherol verla brandHMDB
Togal brand OF tocopherolHMDB
Troyapharm brand OF tocopherol acetateHMDB
Vita-plus eHMDB
Vitamin e sanumHMDB
Vitamin e MPHMDB
Vitamin empHMDB
Woelm brand OF tocopherol acetateHMDB
Bayer brand OF tocopherol acetateHMDB
GNR Pharma brand OF tocopherol actetateHMDB
Grace brand OF tocopherolHMDB
Malton eHMDB
Merck brand OF tocopherol acetateHMDB
Mowivit vitamin eHMDB
Tocopherol wiedemann brandHMDB
UnoVitHMDB
Vitamin e evi miraleHMDB
Vitamin e suspensionHMDB
Vitamin e, mowivitHMDB
Vitamin e, vitaguttHMDB
Vitamin e-MPHMDB
Adisseo brand OF tocopherolHMDB
Antioxidans e-hevertHMDB
Aquasol eHMDB
AstraZeneca brand OF tocopherol acetateHMDB
BiosanHMDB
Dal-vita brand OF vitamin e succinateHMDB
Dragees, vitamin-eHMDB
e MulsinHMDB
Hervert brand OF tocopherol acetateHMDB
Hydrovit eHMDB
Infirmarius rovit brand OF tocopherolHMDB
Jenapharm brand OF tocopherolHMDB
Kentucky brand OF tocopherolHMDB
Micorvit eHMDB
Sanavitan SHMDB
Scot-tussin brand OF tocopherol acetateHMDB
TocopharmHMDB
Tocopherol kentucky brandHMDB
Vita plus eHMDB
VitaEHMDB
Medphano brand OF tocopherol acetateHMDB
VitaminE evimiraleHMDB
2,7,8-Trimethyl-2-(4,8,12-trimethyltridecyl)-6-chromanolbiospider
3,4-dihydro-2,7,8-Trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-olHMDB
3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol, 9CIdb_source
6-Chromanol, 2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-biospider
D-gamma-tocopherolbiospider
DL-α-tocopherolGenerator
E308db_source
Gama-tocopherolbiospider
Gamma-tocopherolbiospider
O-xylotocopherolbiospider
Predicted Properties
PropertyValueSource
Water Solubility7.4e-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
Polarizability54.13 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H48O2
IUPAC name2,7,8-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)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3
InChI KeyQUEDXNHFTDJVIY-UHFFFAOYSA-N
Isomeric SMILESCC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=CC(O)=C(C)C(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
OntologyShould have ontology for this compound
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 PointMp -3°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25Hg546 -2.4 (C6H6)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lyo-7964200000-f0d5087bb29d80c38248View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5644900000-85c7bfa3df1a86febfebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1842900000-c0a3ade1f225f3c78ac2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1910000000-db436d443f9dc640b979View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-5930000000-1cbe4445929c9b90be47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0110900000-23d01b80a965180b27d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0931800000-70e6ff42d0190b91ef52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0932000000-e16b76b24d1cd56f30b1View in MoNA
ChemSpider ID14266
ChEMBL IDCHEMBL420898
KEGG Compound IDNot Available
Pubchem Compound ID14986
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01492
CRC / DFC (Dictionary of Food Compounds) IDCLT22-R:CLT22-R
EAFUS IDNot Available
Dr. Duke IDGAMMA-TOCOPHEROL
BIGG ID2296479
KNApSAcK IDC00007365
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGamma-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 / Bioactivities
DescriptorIDDefinitionReference
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti C-reactive-proteinDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardioprotective38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
hypocholesterolemicDUKE
natriureticDUKE
nitric-oxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
protein kinase C inhibitor37700 An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of protein kinase C (EC 2.7.11.13).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
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.