Showing metabocard for Alpha-Tocopherol (BMDB0001893)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:48:43 UTC
Update Date2020-06-04 20:46:14 UTC
MCDB ID BMDB0001893
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
(2R,4'R,8'R)-alpha-TocopherolChEBI
(R,R,R)-alpha-TocopherolChEBI
5,7,8-TrimethyltocolChEBI
d-alpha-TocopherolChEBI
Vitamin eChEBI
(2R,4'r,8'r)-a-TocopherolGenerator
(2R,4'R,8'R)-α-TocopherolGenerator
a-TocopherolGenerator
α-TocopherolGenerator
(R,R,R)-a-TocopherolGenerator
(R,R,R)-α-TocopherolGenerator
D-a-TocopherolGenerator
d-α-TocopherolGenerator
(+)-a-TocopherolHMDB
(+)-alpha-TocopherolHMDB
(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-TocopherolHMDB
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
(+)-α-TocopherolHMDB
(2R,4’R,8’R)-α-TocopherolHMDB
(all-R)-alpha-TocopherolHMDB
(all-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
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-000i-1390000000-fc8c4f9b9405598ede7f2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00dr-9150010000-c4abc0e689e9b2476b9d2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0f79-1190040000-663296a69129a59be1a62014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-1390000000-fc8c4f9b9405598ede7f2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-9150010000-c4abc0e689e9b2476b9d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f79-1190040000-663296a69129a59be1a62017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-9886300000-b3225facac6ebdd8ddbd2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000l-7735900000-1585eb83c1211ebe95f22017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9600100000-aaf885290800a10d3fb22012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01wr-9300000000-f0c814976a58a9d837ca2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f79-1494700000-6b5f8f817c5a5429ed702012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-00lr-4910600000-1eda05dacf9642d7cea02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-a5860634bfd1ceb6833f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0159-0900500000-5a3bc17152cb61859b2c2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0842900000-f51286676592fd1841932017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1920000000-1994f86bec2bb4a77b9c2017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-3930000000-02190bf16d5d85d44bce2017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0110900000-c3541294fc60a7a8cc7e2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0730900000-553c4898757f6876036c2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03e9-0920200000-276273a531fed5b3a2b02017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3013900000-4985082235edff7c4b8c2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r1-9313200000-cbc230d5dd20c629ffab2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9320000000-5958d2e1d5b687b012c12021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-d3ddef81c134412455e12021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0310900000-30597e14cf876e4e47642021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08g0-2982400000-371737325df4dbb523b22021-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0159-2900500000-03e8a824731610752eb32014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2015-03-12View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified1.161 - 7.685 uM details
Detected and Quantified1.509 uM details
Detected and Quantified1 +/- 0.03 uM
  • International Dai...
 details
Detected and Quantified1.983 +/- 0.072 uM
  • International Dai...
 details
Detected and Quantified1.1 +/- 0.1 uM
  • International Dai...
 details
Detected and Quantified2.1 +/- 0.83 uM
  • International Dai...
 details
Detected and Quantified1 +/- 0.5 uM
  • International Dai...
 details
Detected but not QuantifiedNot Applicable details
Detected and Quantified0.697 uM details
Detected and Quantified0.929 uM details
Detected and Quantified0.232 uM details
Detected and Quantified0.302 uM details
Detected and Quantified0.232 uM details
Detected and Quantified2.089 uM details
Detected and Quantified1.393 uM details
Detected and Quantified1.974 uM details
Detected and Quantified3.018 uM details
Detected and Quantified0.232 uM details
Detected and Quantified0.232 uM details
Detected and Quantified1.857 uM details
Detected and Quantified0.232 uM details
Detected and Quantified0.232 uM details
Detected and Quantified0.232 uM details
Detected and Quantified0.232 uM details
Detected and Quantified0.929 uM details
Detected and Quantified0.697 uM details
Detected and Quantified0.697 uM details
Detected and Quantified1.625 uM details
Detected and Quantified1.625 uM details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected and Quantified1.90 - 2.16 uM
  • Chotyakul N, Pate...
 details
Detected and Quantified0.464 - 2.322 uM
  • Graulet B: Improv...
 details
Detected and Quantified0.464 - 4.179 uM
  • Oste R, Jagerstad...
 details
Detected and Quantified0.5 +/- 0.1 uM details
Detected and Quantified0.8 +/- 0.1 uM details
Detected and Quantified0.9 +/- 0.2 uM details
Detected and Quantified0.5 +/- 0.1 uM details
Detected and Quantified1.37 - 1.69 uM
  • Chotyakul N, Pate...
 details
Detected and Quantified0.16 - 0.21 uM
  • Chotyakul N, Pate...
 details
HMDB IDHMDB0001893
DrugBank IDDB00163
Phenol Explorer Compound IDNot Available
FoodDB 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]