(+)-gamma-Tocopherol (CED0001968)

Record Information
Version1.0
Creation Date2016-05-22 06:57:03 UTC
Update Date2026-05-14 19:50:50 UTC
Accession NumberCHEM020241
Identification
Common Name(+)-gamma-Tocopherol
ClassSmall Molecule
Description
(+)-gamma-Tocopherol is an organic compound with the formula C28H48O2 and an average molecular weight of 416.68 g/mol. (+)-gamma-Tocopherol belongs to the quinone and hydroquinone lipids, a subclass of prenol lipids within the organic compounds. In industrial applications, the compound is used as a fragrance. This substance is found in or released from several recorded sources, including household cleaning and consumer products such as other smoking requisites and non electric simulated smoking devices. It is also associated with food, food processing and cookware, specifically in the preparation of wine or sparkling wine, as well as electrical and electronic equipment including discharge lamps and antennas. Regarding health effects, (+)-gamma-Tocopherol has a therapeutic effect on prostate cancer (PMC3823537, PMC4670692) and is associated with prostate cancer in an inverse manner (PMC3823537).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-gamma-TocopherolChEBI
(2R)-2,7,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
(2R)-3,4-Dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olChEBI
(2R,4'r,8'r)-gamma-TocopherolChEBI
(R,R,R)-gamma-TocopherolChEBI
7,8-DimethyltocolChEBI
D-gamma-TocopherolChEBI
e308ChEBI
RRR-gamma-TocopherolChEBI
(+)-g-TocopherolGenerator
(+)-Γ-tocopherolGenerator
(2R,4'r,8'r)-g-TocopherolGenerator
(2R,4'r,8'r)-Γ-tocopherolGenerator
(R,R,R)-g-TocopherolGenerator
(R,R,R)-Γ-tocopherolGenerator
D-g-TocopherolGenerator
RRR-g-TocopherolGenerator
RRR-Γ-tocopherolGenerator
g-TocopherolGenerator
3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-olHMDB
(2R,4’R,8’r)-γ-tocopherolHMDB
all-(R)-gamma-TocopherolHMDB
all-(R)-Γ-tocopherolHMDB
gamma-TocopherolHMDB
Chemical FormulaC28H48O2
Average Molecular Mass416.680 g/mol
Monoisotopic Mass416.365 g/mol
CAS Registry Number54-28-4
IUPAC Name(2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Namegamma-tocopherol
SMILES[H][C@@](C)(CCCC(C)C)CCC[C@@]([H])(C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2
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/t21-,22-,28-/m1/s1
InChI KeyQUEDXNHFTDJVIY-DQCZWYHMSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability54.12 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-00di-2290200000-ca2e59769b7f9d283302Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0100900000-866035964c66e6e4a63cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0000900000-92e50ec0b18c795338b0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014j-0400900000-1fb1b39165372804b2c1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900500000-42bb4a664eeebbe24ff8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900200000-e8897dc0cd8b10c11820Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900100000-ea386123915e3fbbc82bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-896627229022e40d2d4cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-cc98083bdb10a92cc694Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-0c37948386f3f3e84231Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-006t-0900000000-82abe7b9bcb60c5e016fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-006t-0900000000-8ebacaefdf6ce927eb8fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fs-0900000000-6045c9c0b33abee0cf8cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-0900000000-814007aa4a0b534c8b92Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-1900000000-7f6bf2020beb1db07038Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-1900000000-da96e9792269933d640eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0200900000-b8c469956aa52f5cea7bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0200900000-c061dcce18ca02fdc7f8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-eaab1ecd4d7ca06a99f6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0911200000-794ce3ca05c79d17f851Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0100900000-9437d4bf2b1f52fbf7d7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uxr-1900600000-cf89d38fb3944ec6a0d6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900100000-ceb290cc9fce59042e26Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900100000-0b40aa60dada72fb18b9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-2ecb78a36e03ff309a03Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-dc95d3bbaf9bea576518Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-aeae0dab22369271499cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-3071eef7ee1173a1a8bdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-8973ef13e9c8efa76b20Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-3900000000-137ea4110c247189d58cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uk9-6900000000-41cd494fabc95e4e42e3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0avj-9600000000-906f9d184b75845dcbdbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9400000000-1b66dc68a8dec57d13c6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-9300000000-a39476bb544a236555acNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-9300000000-075969bd88c0377d20d2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-607ae8c15d8d8efe19cdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9100000000-f32c7c3796b4e5146fa0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-2900000000-306f993dbd302c2ff616Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-6701bba716a6affa8766Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9100000000-39877b0735d1c45e8182Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-022i-0900000000-97e2b897d8df8a2c2d21Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-265abade94883f51417bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052b-0900000000-ebf8b9b1d6ec688fdb6bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0910000000-255382c7549b338691e7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-f3d87f907df61c4e51b8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-53f816d98bbae1109d8bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-25bcfba8c57cfaea3b59Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-3f8b4f3b2ed449eef382Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uka-5900000000-31647398b6c8c611cb08Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-06dj-9600000000-f535fe7f47537f4d53bfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aor-9400000000-84bbd07b34c41fd7adc0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ar0-9300000000-096af8f5525df139e974Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-9300000000-f638d00793b8dc406576Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-056r-9300000000-48e18bd7fdba0c3559fdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-2900000000-c9f7277819f6896e1d37Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1842900000-c0a3ade1f225f3c78ac2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1910000000-db436d443f9dc640b979Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pb9-5930000000-1cbe4445929c9b90be47Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0110900000-23d01b80a965180b27d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014j-0931800000-70e6ff42d0190b91ef52Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0932000000-e16b76b24d1cd56f30b1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0000900000-a74b65a822c3cc7625b7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kb-0900400000-1aa0d45dfe97fb5b6083Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006t-1913000000-f1a2aca9373c531b9acfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-3113900000-1ea441316ee3b0510812Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pvj-9612200000-b6b6362e686b9d897db7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052g-9500000000-ed62294773e63b2e826eNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
8739.0Log mg/kg[4900:16000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Prostate cancerhas_therapeutic_effect_onNot AvailablePMC3823537 , PMC4670692
Prostate cancerassociated_withinversePMC3823537
Exposure Sources
Source IDSourceSectorReference
506AntennasElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structurePH domain leucine-rich repeat-containing protein phosphatase 1O60346HumansPredicted (SEA)0.0778492
Alpha-tocopherol transfer protein structureClick to view 3D structureAlpha-tocopherol transfer proteinP49638HumansPredicted (SEA)0.155698
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)125.804
Scaffold protein ILK structureClick to view 3D structureScaffold protein ILKQ13418HumansPredicted (SEA)5.2159
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q6RI86Rattus norvegicusPredicted (SEA)184.036
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)78.0049
Click to view 3D structure3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomeraseP9WQP7Mycobacterium tuberculosisPredicted (SEA)23.5105
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)2928.14
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)2790.12
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)1494.94
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)5226.49
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)6358.72
Nuclear receptor ROR-gamma structureClick to view 3D structureNuclear receptor ROR-gammaP51449HumansPredicted (SEA)1423.86
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)6281.81
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)5965.82
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)4939.38
Transient receptor potential cation channel subfamily A member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily A member 1O75762HumansPredicted (SEA)1027.06
Insulin-like growth factor 1 receptor structureClick to view 3D structureInsulin-like growth factor 1 receptorP08069HumansPredicted (SEA)6033.7
ALK tyrosine kinase receptor structureClick to view 3D structureALK tyrosine kinase receptorQ9UM73HumansPredicted (SEA)6074.42
Click to view 3D structurePolyunsaturated fatty acid lipoxygenase ALOX15P12530Oryctolagus cuniculusPredicted (SEA)369.395
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)5484.17
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)2728.93
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)2940.21
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)462.347
Cytochrome c oxidase subunit NDUFA4 structureClick to view 3D structureCytochrome c oxidase subunit NDUFA4O00483HumansPredicted (SEA)45.6196
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0001492
FooDB IDFDB002431
Phenol Explorer IDNot Available
KNApSAcK IDC00007365
BiGG IDNot Available
BioCyc IDGAMA-TOCOPHEROL
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGamma-Tocopherol
Chemspider ID83708
ChEBI ID18185
PubChem Compound ID92729
Kegg Compound IDC02483
YMDB IDNot Available
ECMDB IDM2MDB005226
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
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30. https://www.ncbi.nlm.nih.gov/pubmed/?term=25916693
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37. https://www.ncbi.nlm.nih.gov/pubmed/?term=31957471
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55. 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.
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61. Ble-Castillo JL, Carmona-Diaz E, Mendez JD, Larios-Medina FJ, Medina-Santillan R, Cleva-Villanueva G, Diaz-Zagoya JC: Effect of alpha-tocopherol on the metabolic control and oxidative stress in female type 2 diabetics. Biomed Pharmacother. 2005 Jul;59(6):290-5.
62. Kontush K, Schekatolina S: Vitamin E in neurodegenerative disorders: Alzheimer's disease. Ann N Y Acad Sci. 2004 Dec;1031:249-62.
63. Kayden HJ, Hatam LJ, Traber MG: The measurement of nanograms of tocopherol from needle aspiration biopsies of adipose tissue: normal and abetalipoproteinemic subjects. J Lipid Res. 1983 May;24(5):652-6.
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