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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-10-17 23:06:35 UTC
HMDB IDHMDB01492
Secondary Accession Numbers
  • HMDB02634
Metabolite Identification
Common NameGamma-Tocopherol
DescriptionGamma-Tocopherol is a collective name for a group of closely related lipids that contain substitutions on the 2H-1-benzopyran-6-ol nucleus and a long hydrocarbon chain of isoprenoid units. They are antioxidants by virtue of the phenolic hydrogen. Tocopherols react with the most reactive form of oxygen and protect unsaturated fatty acids from oxidation.
Structure
Thumb
Synonyms
ValueSource
DL-alpha-TocopherolKegg
DL-a-TocopherolGenerator
DL-α-tocopherolGenerator
3,4-dihydro-2,7,8-Trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-olHMDB
7,8-DimethyltocolHMDB
7,8-dimethyltocolo-XylotocopherolHMDB
MethyltocolsHMDB
O-XylotocopherolHMDB
TocopherolHMDB
TocopherolsHMDB
Vitamin e gammaHMDB
Chemical FormulaC28H48O2
Average Molecular Weight416.6795
Monoisotopic Molecular Weight416.36543078
IUPAC Name2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Name2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-1-benzopyran-6-ol
CAS Registry Number1406-66-2
SMILES
CC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=CC(O)=C(C)C(C)=C2O1
InChI Identifier
InChI=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
InChI KeyInChIKey=QUEDXNHFTDJVIY-UHFFFAOYSA-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
  • Drug
  • Food
Biofunction
  • Cell signaling
  • Essential vitamins
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility128 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.37e-06 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity130.33 m3·mol-1ChemAxon
Polarizability54.13 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Breast Milk
  • Feces
Tissue Location
  • Adipose Tissue
  • Erythrocyte
  • Fibroblasts
  • Heart
  • Intestine
  • Liver
  • Lymphocyte
  • Muscle
  • Nervous Tissues
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Skin
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.41 (2.3-2.5) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.29 (0.63-2.63) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified7.2 (3.8-11.7) uMAdult (>18 years old)FemaleNormal details
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Breast MilkDetected and Quantified0.5430037 +/- 0.0966421 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Not AvailableNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.3 (2.2-2.43) uMAdult (>18 years old)BothProstate cancer details
BloodDetected and Quantified6.2 (3.6-8.4) uMAdult (>18 years old)FemaleEndometrial cancer details
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [22007635 ]
Prostate cancer
  1. Key TJ, Appleby PN, Allen NE, Travis RC, Roddam AW, Jenab M, Egevad L, Tjonneland A, Johnsen NF, Overvad K, Linseisen J, Rohrmann S, Boeing H, Pischon T, Psaltopoulou T, Trichopoulou A, Trichopoulos D, Palli D, Vineis P, Tumino R, Berrino F, Kiemeney L, Bueno-de-Mesquita HB, Quiros JR, Gonzalez CA, Martinez C, Larranaga N, Chirlaque MD, Ardanaz E, Stattin P, Hallmans G, Khaw KT, Bingham S, Slimani N, Ferrari P, Rinaldi S, Riboli E: Plasma carotenoids, retinol, and tocopherols and the risk of prostate cancer in the European Prospective Investigation into Cancer and Nutrition study. Am J Clin Nutr. 2007 Sep;86(3):672-81. [17823432 ]
Endometrial cancer
  1. Jeong NH, Song ES, Lee JM, Lee KB, Kim MK, Yun YM, Lee JK, Son SK, Lee JP, Kim JH, Hur SY, Kwon YI: Preoperative levels of plasma micronutrients are related to endometrial cancer risk. Acta Obstet Gynecol Scand. 2009;88(4):434-9. [19235557 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002431
KNApSAcK IDC00007365
Chemspider ID14266
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2296479
Wikipedia LinkTocopherol
NuGOwiki LinkHMDB01492
Metagene LinkHMDB01492
METLIN ID6276
PubChem Compound14986
PDB IDNot Available
ChEBI ID298402
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zhan X, Wang SY, Wang L, Qu P: [Decreased peripheral nerve conduction velocity may be associated with lower-serum level of vitamin E in patients with infantile hepatitis syndrome] Zhonghua Er Ke Za Zhi. 2004 May;42(5):362-6. [15189696 ]
  2. Reiter N, Jonsson B, Jansen E, Espersen K: [Vitamin E and excessive bleeding] Ugeskr Laeger. 2005 Dec 5;167(49):4664-5. [16336861 ]
  3. Chelchowska M, Laskowska-Klita T, Leibschang J: [The effect of tobacco smoking during pregnancy on concentration of vitamin E in blood of mothers and their newborns in umbilical cord blood] Ginekol Pol. 2006 Apr;77(4):263-8. [16875031 ]
  4. Vatassery GT, Adityanjee, Quach HT, Smith WE, Kuskowski MA, Melnyk D: Alpha and gamma tocopherols in cerebrospinal fluid and serum from older, male, human subjects. J Am Coll Nutr. 2004 Jun;23(3):233-8. [15190048 ]
  5. 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 ]
  6. Nair S, Norkus EP, Hertan H, Pitchumoni CS: Micronutrient antioxidants in gastric mucosa and serum in patients with gastritis and gastric ulcer: does Helicobacter pylori infection affect the mucosal levels? J Clin Gastroenterol. 2000 Jun;30(4):381-5. [10875465 ]
  7. Chow CK: Distribution of tocopherols in human plasma and red blood cells. Am J Clin Nutr. 1975 Jul;28(7):756-60. [1146729 ]
  8. Tauler P, Sureda A, Cases N, Aguilo A, Rodriguez-Marroyo JA, Villa G, Tur JA, Pons A: Increased lymphocyte antioxidant defences in response to exhaustive exercise do not prevent oxidative damage. J Nutr Biochem. 2006 Oct;17(10):665-71. Epub 2005 Nov 28. [16481153 ]
  9. Hozyasz KK, Chelchowska M, Laskowska-Klita T: [Vitamin E levels in patients with celiac disease] Med Wieku Rozwoj. 2003 Oct-Dec;7(4 Pt 2):593-604. [15213374 ]
  10. Sokol RJ, Heubi JE, Iannaccone S, Bove KE, Balistreri WF: Mechanism causing vitamin E deficiency during chronic childhood cholestasis. Gastroenterology. 1983 Nov;85(5):1172-82. [6618108 ]
  11. 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. [15932790 ]
  12. Kontush K, Schekatolina S: Vitamin E in neurodegenerative disorders: Alzheimer's disease. Ann N Y Acad Sci. 2004 Dec;1031:249-62. [15753151 ]
  13. 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. [6875389 ]
  14. Guggenheim MA, Ringel SP, Silverman A, Grabert BE, Neville HE: Progressive neuromuscular disease in children with chronic cholestasis and vitamin E deficiency: clinical and muscle biopsy findings and treatment with alpha-tocopherol. Ann N Y Acad Sci. 1982;393:84-95. [6959572 ]
  15. Burton GW, Traber MG, Acuff RV, Walters DN, Kayden H, Hughes L, Ingold KU: Human plasma and tissue alpha-tocopherol concentrations in response to supplementation with deuterated natural and synthetic vitamin E. Am J Clin Nutr. 1998 Apr;67(4):669-84. [9537614 ]
  16. Jeanes YM, Hall WL, Proteggente AR, Lodge JK: Cigarette smokers have decreased lymphocyte and platelet alpha-tocopherol levels and increased excretion of the gamma-tocopherol metabolite gamma-carboxyethyl-hydroxychroman (gamma-CEHC). Free Radic Res. 2004 Aug;38(8):861-8. [15493460 ]
  17. Leo MA, Rosman AS, Lieber CS: Differential depletion of carotenoids and tocopherol in liver disease. Hepatology. 1993 Jun;17(6):977-86. [8514270 ]
  18. Yeum KJ, Ahn SH, Rupp de Paiva SA, Lee-Kim YC, Krinsky NI, Russell RM: Correlation between carotenoid concentrations in serum and normal breast adipose tissue of women with benign breast tumor or breast cancer. J Nutr. 1998 Nov;128(11):1920-6. [9808643 ]
  19. Jeanes YM, Hall WL, Lodge JK: Comparative (2)H-labelled alpha-tocopherol biokinetics in plasma, lipoproteins, erythrocytes, platelets and lymphocytes in normolipidaemic males. Br J Nutr. 2005 Jul;94(1):92-9. [16115338 ]
  20. 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 ]