Showing metabocard for Alpha-Tocopherol (BMDB0001893)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:48:43 UTC
Update Date2020-06-04 20:46:14 UTC
BMDB IDBMDB0001893
Secondary Accession Numbers
  • BMDB01893
Metabolite Identification
Common NameAlpha-Tocopherol
DescriptionAlpha-Tocopherol, also known as D-α-tocopherol or vitamin e, 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, Alpha-tocopherol is considered to be a quinone lipid molecule. Alpha-Tocopherol exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Alpha-Tocopherol exists in all living organisms, ranging from bacteria to humans. Alpha-Tocopherol is a potentially toxic compound. Alpha-Tocopherol has been found to be associated with several diseases known as parkinson's disease, thyroid cancer, cerebrotendinous xanthomatosis, and vitamin e deficiency; also alpha-tocopherol has been linked to the inborn metabolic disorders including abetalipoproteinemia.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+)-alpha-TocopherolChEBI
(2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
(2R,4'r,8'r)-alpha-TocopherolChEBI
(all-R)-alpha-TocopherolChEBI
5,7,8-TrimethyltocolChEBI
D-alpha-TocopherolChEBI
RRR-alpha-TocopherolChEBI
Vitamin eChEBI
(+)-a-TocopherolGenerator
(+)-Α-tocopherolGenerator
(2R,4'r,8'r)-a-TocopherolGenerator
(2R,4'r,8'r)-Α-tocopherolGenerator
(all-R)-a-TocopherolGenerator
(all-R)-Α-tocopherolGenerator
D-a-TocopherolGenerator
D-Α-tocopherolGenerator
RRR-a-TocopherolGenerator
RRR-Α-tocopherolGenerator
a-TocopherolGenerator
Α-tocopherolGenerator
(R,R,R)-alpha-TocopherolChEBI
(R,R,R)-a-TocopherolGenerator
(R,R,R)-α-TocopherolGenerator
(2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olHMDB
a-D-TocopherolHMDB
alpha-delta-TocopherolHMDB
delta-alpha-TocopherolHMDB
DenamoneHMDB
EprolinHMDB
PhytogerminHMDB
PhytogermineHMDB
RRR-alpha-TocopherylHMDB
Vitamin eaHMDB
alpha-TocopherolChEBI
(+)-2R,4'R,8'R-alpha-TocopherolHMDB
(+)-2R,4'R,8'R-α-TocopherolHMDB
(+)-2R,4’R,8’R-α-TocopherolHMDB
(2R,4’R,8’R)-α-TocopherolHMDB
3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-(2R)-2H-1-benzopyran-6-olHMDB
alpha-D-TocopherolHMDB
alpha-Vitamin EHMDB
α-D-TocopherolHMDB
α-Vitamin EHMDB
AlmefrolPhytoBank
EmipherolPhytoBank
EtamicanPhytoBank
EvitaminumPhytoBank
ProfecundinPhytoBank
Vitamin EalphaPhytoBank
Vitamin EαPhytoBank
Chemical FormulaC29H50O2
Average Molecular Weight430.7061
Monoisotopic Molecular Weight430.381080844
IUPAC Name(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional NameVitaE
CAS Registry Number59-02-9
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1
InChI Identifier
InChI=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/t21-,22-,29-/m1/s1
InChI KeyGVJHHUAWPYXKBD-IEOSBIPESA-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
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability55.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-000i-1390000000-fc8c4f9b9405598ede7fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00dr-9150010000-c4abc0e689e9b2476b9dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0f79-1190040000-663296a69129a59be1a6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-1390000000-fc8c4f9b9405598ede7fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-9150010000-c4abc0e689e9b2476b9dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f79-1190040000-663296a69129a59be1a6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-9886300000-b3225facac6ebdd8ddbdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000l-7735900000-1585eb83c1211ebe95f2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9600100000-aaf885290800a10d3fb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01wr-9300000000-f0c814976a58a9d837caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f79-1494700000-6b5f8f817c5a5429ed70View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-00lr-4910600000-1eda05dacf9642d7cea0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-a5860634bfd1ceb6833fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0159-0900500000-5a3bc17152cb61859b2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0842900000-f51286676592fd184193View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1920000000-1994f86bec2bb4a77b9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-3930000000-02190bf16d5d85d44bceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0110900000-c3541294fc60a7a8cc7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0730900000-553c4898757f6876036cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03e9-0920200000-276273a531fed5b3a2b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3013900000-4985082235edff7c4b8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r1-9313200000-cbc230d5dd20c629ffabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9320000000-5958d2e1d5b687b012c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-d3ddef81c134412455e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0310900000-30597e14cf876e4e4764View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08g0-2982400000-371737325df4dbb523b2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0159-2900500000-03e8a824731610752eb3View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Bladder
  • Blood
  • Epidermis
  • Erythrocyte
  • Eye Lens
  • Fibroblasts
  • Intestine
  • Leukocyte
  • Liver
  • Milk
  • Muscle
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate Tissue
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Eye LensExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LeukocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.161 - 7.685 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.509 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.37 - 1.69 uMNot SpecifiedNot Specified
Normal
    • Chotyakul N, Pate...
 details
MilkDetected and Quantified0.16 - 0.21 uMNot SpecifiedNot Specified
Normal
    • Chotyakul N, Pate...
 details
MilkDetected and Quantified3.0183 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.232 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.232 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.857 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.232 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.232 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.232 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.232 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.929 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.697 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.697 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.871 +/- 0.0279 uMNot SpecifiedNot Specified
Normal
    • International Dai...
 details
MilkDetected and Quantified1.983 +/- 0.0720 uMNot SpecifiedNot Specified
Normal
    • International Dai...
 details
MilkDetected and Quantified1.625 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.625 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.120 +/- 0.100 uMNot SpecifiedNot Specified
Normal
    • International Dai...
 details
MilkDetected and Quantified2.0800 +/- 0.830 uMNot SpecifiedNot Specified
Normal
    • International Dai...
 details
MilkDetected and Quantified0.950 +/- 0.490 uMNot SpecifiedNot Specified
Normal
    • International Dai...
 details
MilkDetected and Quantified0.697 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.929 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.232 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.302 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.232 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified2.0896 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.393 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.974 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.90 - 2.16 uMNot SpecifiedNot SpecifiedNormal
    • Chotyakul N, Pate...
 details
MilkDetected and Quantified0.464 - 2.322 uMNot SpecifiedNot SpecifiedNormal
    • Graulet B: Improv...
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
 details
MilkDetected and Quantified0.464 - 4.179 uMNot SpecifiedNot SpecifiedNormal
    • Oste R, Jagerstad...
 details
MilkDetected and Quantified0.5 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.8 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.9 +/- 0.2 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.5 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Sub/clinical ketosis		 details
HMDB IDHMDB0001893
DrugBank IDDB00163
Phenol Explorer Compound IDNot Available
FooDB IDFDB000565
KNApSAcK IDC00007366
Chemspider ID14265
KEGG Compound IDC02477
BioCyc IDALPHA-TOCOPHEROL
BiGG ID2296507
Wikipedia LinkAlpha-Tocopherol
METLIN ID6376
PubChem Compound14985
PDB IDNot Available
ChEBI ID18145
References
Synthesis ReferenceMatsui, Makoto. Synthesis of a-tocopherol for the next century. Nihon Yukagakkaishi (1996), 45(9), 821-831.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Delgado Zamarreno MM, Sanchez Perez A, Gomez Perez C, Hernandez Mendez J: High-performance liquid chromatography with electrochemical detection for the simultaneous determination of vitamin A, D3 and E in milk. J Chromatogr. 1992 Oct 9;623(1):69-74. [PubMed:1333471 ]
  2. Noziere P, Grolier P, Durand D, Ferlay A, Pradel P, Martin B: Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. J Dairy Sci. 2006 Jul;89(7):2634-48. doi: 10.3168/jds.S0022-0302(06)72340-2. [PubMed:16772583 ]
  3. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  4. M.S Havemose, Martin Riis Weisbjerg, Wender L.P Bredie, J.H Nielsen (2004). International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570. International Dairy Journal.
  5. M.C. Herrero-Barbudo, F. Granado-Lorencio, I. Blanco-Navarro, B. Olmedilla-Alonso (2005). International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526. International Dairy Journal.
  6. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  7. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  8. Nattaporn Chotyakul, Miriam Pateiro-Moure, Jorge Alexandre Saraiva, J. Antonio Torres, Concepción Pérez-Lamela (2014). Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 . European Food Research and Technology.
  9. Graulet B (2010). Graulet B: Improving the level of vitamins in milk. In Griffiths MW (ed):‘‘Improving the Safety and Quality of Milk: Improving Quality in Milk Products,’’vol. 2. Boca Raton, FL: CRC Press, pp 229–251, 2010.. CRC Press.
  10. Oste R, Jagerstad M, Anderson I (1997). Oste R, Jagerstad M, Anderson I: Vitamins in milk and milk products. In Fox PF (ed):‘‘Advanced Dairy Chemistry: Lactose, Water, Salts and Vitamins,’’vol 3, 2nd ed. London: Chapman & Hall, pp 347–402, 1997. Chapman & Hall.
  11. USDA Food Composition Databases [Link]
  12. Fooddata+, The Technical University of Denmark (DTU) [Link]