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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-08-16 03:45:10 UTC
Secondary Accession Numbers
  • HMDB01492
  • 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.
Vitamin e gammaHMDB
GNR-Pharma brand OF tocopherol actetateMeSH
Organon brand OF tocopherol acetateMeSH
Schwarzhaupt brand OF tocopherol acetateMeSH
Snow-e muscle, energy and feritilityMeSH
Tocopherol rodisma-med brandMeSH
Tocopherol worwag brandMeSH
Togasan vitamin eMeSH
Unique eMeSH
Vitamin e drageesMeSH
Atarost brand OF tocopherol acetateMeSH
Biocur brand OF tocopherol acetateMeSH
Cambridge laboratories brand OF tocopherol actetateMeSH
Dal eMeSH
e Vitamin eMeSH
EVI-mirale, vitamin-eMeSH
Elex verlaMeSH
Richelet brand OF tocopherol acetateMeSH
Roche nicholas brand OF tocopherol acetateMeSH
Rodisma med brand OF tocopherolMeSH
Sciencex brand OF tocopherol acetateMeSH
Steigerwald brand OF tocopherol acetateMeSH
Strathmann brand OF tocopherolMeSH
Tocopherol grunwalder brandMeSH
Tocopherol stadapharm brandMeSH
Verla brand OF tocopherolMeSH
Vit. e stadaMeSH
VitaPlus eMeSH
Vitamin-e evi-miraleMeSH
Vitamine e GNRMeSH
Worwag brand OF tocopherolMeSH
Alcala brand OF tocopherol acetateMeSH
bio eMeSH
e VicotratMeSH
EUNOVA vitamin eMeSH
Equivit eMeSH
Internation animal health brand OF tocopherol acetateMeSH
MIP brand OF tocopherol acetateMeSH
Sanum-kehlbeck brand OF tocopherol actetateMeSH
Tocopherol infirmarius-rovit brandMeSH
Tocopherol twardy brandMeSH
Vitamin-e drageesMeSH
Wiedemann brand OF tocopherolMeSH
Arkopharma brand OF tocopherol acetateMeSH
Dal vita brand OF vitamin e succinateMeSH
Eu rho brand OF tocopherolMeSH
Infirmarius-rovit brand OF tocopherolMeSH
Richtavit eMeSH
Riemser brand OF tocopherolMeSH
Tocopherol ausrichter brandMeSH
Tocopherol balkanpharma brandMeSH
Vitagutt vitamin eMeSH
Vitamin e naturMeSH
Vitamin e, togasanMeSH
Ratiopharm brand OF tocopherolMeSH
Aliud brand OF tocopherolMeSH
Bottger brand OF tocopherol acetateMeSH
e FerolMeSH
Heyl brand OF tocopherol acetateMeSH
Kohler brand OF tocopherolMeSH
puncto eMeSH
Rodisma-med brand OF tocopherolMeSH
Sanum kehlbeck brand OF tocopherol actetateMeSH
Scot tussin brand OF tocopherol acetateMeSH
Stadapharm brand OF tocopherolMeSH
Tocopherol bayerMeSH
Tocopherol grace brandMeSH
Tocopherol ratiopharm brandMeSH
Twardy brand OF tocopherolMeSH
uno VitMeSH
Veyx brand OF tocopherolMeSH
Vit e hydrosolMeSH
Vita eMeSH
Vitamin e alMeSH
Wiedemann brand OF vitamin e succinateMeSH
Ausrichter brand OF tocopherolMeSH
Auxina eMeSH
Balkanpharma brand OF tocopherolMeSH
Blackmores brand OF tocopherolMeSH
Grunwalder brand OF tocopherolMeSH
ICN brand OF tocopherol acetateMeSH
Mucos brand OF tocopherol acetateMeSH
Tocopherol togal brandMeSH
Tocopherol verla brandMeSH
Togal brand OF tocopherolMeSH
Troyapharm brand OF tocopherol acetateMeSH
Vita-plus eMeSH
Vitamin e sanumMeSH
Vitamin e MPMeSH
Vitamin empMeSH
Woelm brand OF tocopherol acetateMeSH
Bayer brand OF tocopherol acetateMeSH
GNR Pharma brand OF tocopherol actetateMeSH
Grace brand OF tocopherolMeSH
Malton eMeSH
Merck brand OF tocopherol acetateMeSH
Mowivit vitamin eMeSH
Tocopherol wiedemann brandMeSH
Vitamin e evi miraleMeSH
Vitamin e suspensionMeSH
Vitamin e, mowivitMeSH
Vitamin e, vitaguttMeSH
Vitamin e-MPMeSH
adisseo Brand OF tocopherolMeSH
Antioxidans e-hevertMeSH
Aquasol eMeSH
AstraZeneca brand OF tocopherol acetateMeSH
Dal-vita brand OF vitamin e succinateMeSH
Dragees, vitamin-eMeSH
e MulsinMeSH
Hervert brand OF tocopherol acetateMeSH
Hydrovit eMeSH
Infirmarius rovit brand OF tocopherolMeSH
Jenapharm brand OF tocopherolMeSH
Kentucky brand OF tocopherolMeSH
Micorvit eMeSH
Sanavitan SMeSH
Scot-tussin brand OF tocopherol acetateMeSH
Tocopherol kentucky brandMeSH
Vita plus eMeSH
medphano Brand OF tocopherol acetateMeSH
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
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentTocopherols
Alternative Parents
  • Tocopherol
  • Diterpenoid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
StatusDetected and Quantified
  • Drug
  • Food
  • Cell signaling
  • Essential vitamins
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility128 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility7.37e-06 mg/mLALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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 Quantified Adult (>18 years old)Both
Breast MilkDetected and Quantified0.5430037 +/- 0.0966421 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
FecesDetected but not Quantified Infant (0-1 year old)Both
FecesDetected but not Quantified Infant (0-1 year old)Not AvailableNormal details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
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 Quantified Adult (>18 years old)Both
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
  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. [PubMed: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. [PubMed: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. doi: 10.1080/00016340902767187. [PubMed: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 LinkHMDB0001492
PubChem Compound14986
PDB IDNot Available
ChEBI ID298402
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. [PubMed:15189696 ]
  2. Reiter N, Jonsson B, Jansen E, Espersen K: [Vitamin E and excessive bleeding]. Ugeskr Laeger. 2005 Dec 5;167(49):4664-5. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:10875465 ]
  7. Chow CK: Distribution of tocopherols in human plasma and red blood cells. Am J Clin Nutr. 1975 Jul;28(7):756-60. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:15932790 ]
  12. Kontush K, Schekatolina S: Vitamin E in neurodegenerative disorders: Alzheimer's disease. Ann N Y Acad Sci. 2004 Dec;1031:249-62. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:15493460 ]
  17. Leo MA, Rosman AS, Lieber CS: Differential depletion of carotenoids and tocopherol in liver disease. Hepatology. 1993 Jun;17(6):977-86. [PubMed: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. [PubMed: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. [PubMed: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 (1985). 2006 May;100(5):1679-87. Epub 2005 Dec 29. [PubMed:16384840 ]