Alpha tocopherol (CED0001332)

Record Information
Version1.0
Creation Date2016-05-25 02:48:48 UTC
Update Date2026-05-14 19:42:18 UTC
Accession NumberCHEM020976
Identification
Common NameAlpha tocopherol
ClassSmall Molecule
Description
Alpha tocopherol (C29H50O2) is a compound with an average molecular weight of 430.72 g/mol. Alpha tocopherol belongs to the quinone and hydroquinone lipids, a subclass of prenol lipids within the organic compounds. Industrially, it is utilized as a fragrance, preservative, softener, and conditioner, as well as an antioxidant (PMC10855613, PMC3257702, PMC4104792, PMC4428026, PMC5651431, PMC7550371, PMC8980384). It also serves as a biological antioxidant (PMC10855613, PMC3257702, PMC4104792, PMC4428026, PMC5651431, PMC7550371, PMC8980384) and an environmental nutrient (PMC3257702). The compound is found in or released from 29 recorded sources. These include household cleaning and consumer products such as bleaching agents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. It is also associated with food, food processing and cookware, specifically food preservation and the preparation of malt, vinegar, wine or sparkling wine, as well as fermentation processes for beer. Additionally, it is found in electrical and electronic equipment, including antennas, coils, electric hearing aids, communication cables or conductors, and conductors or conductive bodies characterised by the conductive materials. Regarding health effects, alpha tocopherol is associated with lung disease (PMC4384764), heart disease (PMC6259353), and atherosclerosis (PMC7932781). It is linked to a decrease in asthma (PMC4299629, PMC9025817) and cancer (PMC2763252, PMC3257702). Furthermore, it is used as a treatment for male infertility (PMC9005387) and epilepsy (PMC4428026), and it has a therapeutic effect on myocardial infarction (PMC4315737).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
Vitamin eMeSH, HMDB
(-)-a-TocopherolGenerator
(-)-Α-tocopherolGenerator
Chemical FormulaC29H50O2
Average Molecular Mass430.717 g/mol
Monoisotopic Mass430.381 g/mol
CAS Registry Number10191-41-0
IUPAC Name2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Namevita E
SMILESCC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1
InChI IdentifierInChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3
InChI KeyGVJHHUAWPYXKBD-UHFFFAOYSA-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
  • 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 Roles
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 Solubility7.0e-06 g/LALOGPS
logP8.84ALOGPS
logP10.51ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)10.8ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity135.37 m³·mol⁻¹ChemAxon
Polarizability56.18 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0aor-9886300000-b3225facac6ebdd8ddbdNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0742900000-e04f7b35db8df7846abbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1910000000-cc361786eb3f51f45d19Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066r-3930000000-979a3e4c33d64d0c6215Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0110900000-d5b620320c97f00ad562Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-0730900000-36e33000e46f480ceb9dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03e9-0921200000-7c36ba360f71f0d4b512Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-3003900000-22e1cd43cc0d836c7bedNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05r1-9313200000-cbc230d5dd20c629ffabNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9320000000-5958d2e1d5b687b012c1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0000900000-d3ddef81c134412455e1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0310900000-30597e14cf876e4e4764Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08g0-2982400000-371737325df4dbb523b2Not 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
8744.0Log mg/kg[4900:16000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
cancerassociated_withdecreasePMC2763252 , PMC3257702
asthmaassociated_withdecreasePMC4299629 , PMC9025817
atherosclerosisassociated_withNot AvailablePMC7932781
myocardial infarctionhas_therapeutic_effect_onNot AvailablePMC4315737
heart diseaseassociated_withNot AvailablePMC6259353
male infertilityis_treatment_forNot AvailablePMC9005387
epilepsyis_treatment_forNot AvailablePMC4428026
lung diseaseassociated_withNot AvailablePMC4384764
macular degenerationhas_therapeutic_effect_onNot AvailablePMC7932781
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
568Tobacco Product Moisture ControlHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Alpha-tocopherol transfer protein structureClick to view 3D structureAlpha-tocopherol transfer proteinP49638HumansPredicted (SEA)0.0778492
Click to view 3D structurePH domain leucine-rich repeat-containing protein phosphatase 1O60346HumansPredicted (SEA)0.389246
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)1126.17
Glutathione S-transferase P structureClick to view 3D structureGlutathione S-transferase PP09211HumansPredicted (SEA)0.700643
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)1859.12
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)1815.83
Forkhead box protein M1 structureClick to view 3D structureForkhead box protein M1Q08050HumansPredicted (SEA)3.42537
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)1794.97
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)5678.48
Click to view 3D structure3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomeraseP9WQP7Mycobacterium tuberculosisPredicted (SEA)25.9238
Click to view 3D structureHTH-type quorum-sensing regulator RhlRP54292Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)Predicted (SEA)27.6365
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)5381.09
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q6RI86Rattus norvegicusPredicted (SEA)966.109
Nuclear receptor ROR-gamma structureClick to view 3D structureNuclear receptor ROR-gammaP51449HumansPredicted (SEA)2263.39
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)6353.59
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)6527.27
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)138.494
Click to view 3D structureBile salt export pumpO70127Rattus norvegicusPredicted (SEA)8.32987
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)7166.64
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)7431.49
Click to view 3D structurePolyunsaturated fatty acid lipoxygenase ALOX15P12530Oryctolagus cuniculusPredicted (SEA)682.271
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)4725.45
ALK tyrosine kinase receptor structureClick to view 3D structureALK tyrosine kinase receptorQ9UM73HumansPredicted (SEA)6917.21
Insulin-like growth factor 1 receptor structureClick to view 3D structureInsulin-like growth factor 1 receptorP08069HumansPredicted (SEA)6922.2
Histamine H1 receptor structureClick to view 3D structureHistamine H1 receptorP35367HumansPredicted (SEA)6463.2
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0259851
FooDB IDFDB031279
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkΑ-Tocopherol
Chemspider ID2032
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References