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Record Information
Version3.6
Creation Date2006-05-22 15:12:18 UTC
Update Date2016-02-11 01:05:52 UTC
HMDB IDHMDB02902
Secondary Accession NumbersNone
Metabolite Identification
Common NameDelta-Tocopherol
DescriptionTocopherol, or Vitamin E, is a fat-soluble vitamin in eight forms that is an important antioxidant. Vitamin E is often used in skin creams and lotions because it is believed to play a role in encouraging skin healing and reducing scarring after injuries such as burns. -- Wikipedia; Natural vitamin E exists in eight different forms or isomers, four tocopherols and four tocotrienols. All isomers have a chromanol ring, with a hydroxyl group which can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain which allows for penetration into biological membranes. There is an alpha, beta, gamma and delta form of both the tocopherols and tocotrienols, determined by the number of methyl groups on the chromanol ring. Each form has its own biological activity, the measure of potency or functional use in the body. -- Wikipedia; Alpha-tocopherol is traditionally recognized as the most active form of vitamin E in humans, and is a powerful biological antioxidant. The measurement of "vitamin E" activity in international units (IU) was based on fertility enhancement by the prevention of spontaneous abortions in pregnant rats relative to alpha tocopherol. It increases naturally to about 150% of normal in the maternal circulation during human pregnancies. 1 IU of vitamin E is defined as the biological equivalent of 0.667 milligrams of d-alpha-tocopherol, or of 1 milligram of dl-alpha-tocopherol acetate. The other isomers are slowly being recognized as research begins to elucidate their additional roles in the human body. Many naturopathic and orthomolecular medicine advocates suggest that vitamin E supplements contain at least 20% by weight of the other natural vitamin E isomers. Commercially available blends of natural vitamin E include "mixed tocopherols" and "high gamma tocopherol" formulas. Also selenium, Coenzyme Q10, and ample vitamin C have been shown to be essential cofactors of natural tocopherols. -- Wikipedia; Synthetic vitamin E, usually marked as d,l-tocopherol or d,l tocopheryl acetate, with 50% d-alpha tocopherol moiety and 50% l-alpha-tocopherol moiety, as synthesized by an earlier process is now actually manufactured as all-racemic alpha tocopherol, with only about one alpha tocopherol molecule in 8 molecules as actual d-alpha tocpherol. The synthetic form is not as active as the natural alpha tocopherol form. The 1950's thalidomide disaster with numerous severe birth defects is a common example of d- vs l- epimer forms type problem with synthesized racemic mixtures. Information on any side effects of the synthetic vitamin E epimers is not readily available. Naturopathic and orthomolecular medicine advocates have long considered the synthetic vitamin E forms to be with little or no merit for cancer, circulatory and heart diseases. -- Wikipedia; Abetalipoproteinemia is a rare inherited disorder of fat metabolism that results in poor absorption of dietary fat and vitamin E. The vitamin E deficiency associated with this disease causes problems such as poor transmission of nerve impulses, muscle weakness, and degeneration of the retina that can cause blindness. Individuals with abetalipoproteinemia may be prescribed special vitamin E supplements by a physician to treat this disorder. -- Wikipedia; Recent studies also show that vitamin E acts as an effective free radical scavenger and can lower the incidence of lung cancer in smokers. The effects are opposite to that of the clinical trials based on administering carotenoid to male smokers, that resulted in increased risk of lung cancer. Hence vitamin E is an effective antagonist to the oxidative stress that is imposed by high carotenoids in certain patients. -- Wikipedia; A cataract is a condition of clouding of the tissue of the lens of the eye. They increase the risk of disability and blindness in aging adults. Antioxidants are being studied to determine whether they can help prevent or delay cataract growth. Observational studies have found that lens clarity, which is used to diagnose cataracts, was better in regular users of vitamin E supplements and in persons with higher blood levels of vitamin E. A study of middle aged male smokers, however, did not demonstrate any effect from vitamin E supplements on the incidence of cataract formation. The effects of smoking, a major risk factor for developing cataracts, may have overridden any potential benefit from the vitamin E, but the conflicting results also indicate a need for further studies before researchers can confidently recommend extra vitamin E for the prevention of cataracts. It is important to note that the term "cataract" may be used in common parlance for an opacity involving any tissue of the eye, for example a corneal scar. Thus a character in theater or on television who is blind from cataracts might have white instead of clear corneas, covering over the iris and pupil. Since the lens is behind the pupil, real cataracts are difficult to see without special instrumentation, so people with cataracts have rather normally appearing eyes. -- Wikipedia; Alzheimer's disease is a wasting disease of the brain. An observational trial conducted by The Johns Hopkins University Bloomberg School of Public Health found that when vitamin E is taken daily in large doses (400-1000IU) in combination with vitamin C (500-1000mg) the onset of Alzheimer's was reduced between 64 and 78%. External Link - Johns Hopkins press release -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
(2R)-3,4-dihydro-2,8-Dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olChEBI
8-MethyltocolChEBI
Vitamine eHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Namedelta tocopherol
CAS Registry Number119-13-1
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=CC(O)=C2
InChI Identifier
InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1
InChI KeyInChIKey=GZIFEOYASATJEH-VHFRWLAGSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Anti-oxidant
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.09e-05 mg/mLALOGPS
logP8.76ALOGPS
logP9.48ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)10.14ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity125.29 m3·mol-1ChemAxon
Polarizability51.31 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0ab9-3490300000-f13783678d446978a134View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udr-2500900000-d51c6b511d2655c65526View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0300900000-c7cd87c9e4b48f15bbbbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-0900000000-afcde4fb8f9be6edde67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-0f79-3900300000-7367fe51787d1f4d6faeView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adipose Tissue
  • Epidermis
  • Liver
  • Neuron
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified26.7 +/- 0.9 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified26.00 +/- 1.00 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified2.4 (0.24-4.7) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002432
KNApSAcK IDC00007363
Chemspider ID83144
KEGG Compound IDC14151
BioCyc IDDELTA-TOCOPHEROL
BiGG IDNot Available
Wikipedia Link Vitamine E
NuGOwiki LinkHMDB02902
Metagene LinkHMDB02902
METLIN ID232
PubChem Compound92094
PDB IDNot Available
ChEBI ID47772
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jiang Q, Wong J, Fyrst H, Saba JD, Ames BN: gamma-Tocopherol or combinations of vitamin E forms induce cell death in human prostate cancer cells by interrupting sphingolipid synthesis. Proc Natl Acad Sci U S A. 2004 Dec 21;101(51):17825-30. Epub 2004 Dec 13. [15596715 ]
  2. 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. [16400056 ]
  3. Fischer CP, Hiscock NJ, Basu S, Vessby B, Kallner A, Sjoberg LB, Febbraio MA, Pedersen BK: Vitamin E isoform-specific inhibition of the exercise-induced heat shock protein 72 expression in humans. J Appl Physiol. 2006 May;100(5):1679-87. Epub 2005 Dec 29. [16384840 ]
  4. Passi S, De Pita O, Grandinetti M, Simotti C, Littarru GP: The combined use of oral and topical lipophilic antioxidants increases their levels both in sebum and stratum corneum. Biofactors. 2003;18(1-4):289-97. [14695946 ]
  5. Brigelius-Flohe R, Traber MG: Vitamin E: function and metabolism. FASEB J. 1999 Jul;13(10):1145-55. [10385606 ]
  6. Liu M, Wallmon A, Olsson-Mortlock C, Wallin R, Saldeen T: Mixed tocopherols inhibit platelet aggregation in humans: potential mechanisms. Am J Clin Nutr. 2003 Mar;77(3):700-6. [12600864 ]
  7. Traber MG, Kayden HJ: Tocopherol distribution and intracellular localization in human adipose tissue. Am J Clin Nutr. 1987 Sep;46(3):488-95. [3630967 ]
  8. Gehring W, Fluhr J, Gloor M: Influence of vitamin E acetate on stratum corneum hydration. Arzneimittelforschung. 1998 Jul;48(7):772-5. [9706379 ]
  9. Sen CK, Khanna S, Roy S: Tocotrienol: the natural vitamin E to defend the nervous system? Ann N Y Acad Sci. 2004 Dec;1031:127-42. [15753140 ]
  10. Sontag TJ, Parker RS: Cytochrome P450 omega-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status. J Biol Chem. 2002 Jul 12;277(28):25290-6. Epub 2002 May 7. [11997390 ]
  11. Epler KS, Ziegler RG, Craft NE: Liquid chromatographic method for the determination of carotenoids, retinoids and tocopherols in human serum and in food. J Chromatogr. 1993 Sep 8;619(1):37-48. [8245162 ]
  12. Mavon A, Raufast V, Redoules D: Skin absorption and metabolism of a new vitamin E prodrug, delta-tocopherol-glucoside: in vitro evaluation in human skin models. J Control Release. 2004 Nov 24;100(2):221-31. [15544870 ]
  13. Limpens J, Schroder FH, de Ridder CM, Bolder CA, Wildhagen MF, Obermuller-Jevic UC, Kramer K, van Weerden WM: Combined lycopene and vitamin E treatment suppresses the growth of PC-346C human prostate cancer cells in nude mice. J Nutr. 2006 May;136(5):1287-93. [16614418 ]