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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:10 UTC
HMDB IDHMDB0001492
Secondary Accession Numbers
  • HMDB0002634
  • HMDB01492
  • HMDB02634
Metabolite Identification
Common Namegamma-Tocopherol
Descriptiongamma-Tocopherol, also known as 7,8-dimethyltocol, 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. They differ from tocotrienols which contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. It is estimated that 50% of gamma-tocopherol is metabolized into gamma-CEHC and excreted into the urine. gamma-Tocopherol is the predominant form of vitamin E in plant seeds and derived products (e.g. nuts and vegetable oils). Unlike alpha-tocopherol, gamma-tocopherol inhibits cyclooxygenase activity and, therefore, exhibit anti-inflammatory properties (PMID: 11722951 ).
Structure
Data?1582752205
Synonyms
ValueSource
(+)-gamma-TocopherolChEBI
(2R)-2,7,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
(2R)-3,4-Dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olChEBI
(2R,4'r,8'r)-gamma-TocopherolChEBI
(R,R,R)-gamma-TocopherolChEBI
7,8-DimethyltocolChEBI
D-gamma-TocopherolChEBI
e308ChEBI
RRR-gamma-TocopherolChEBI
(+)-g-TocopherolGenerator
(+)-Γ-tocopherolGenerator
(2R,4'r,8'r)-g-TocopherolGenerator
(2R,4'r,8'r)-Γ-tocopherolGenerator
(R,R,R)-g-TocopherolGenerator
(R,R,R)-Γ-tocopherolGenerator
D-g-TocopherolGenerator
RRR-g-TocopherolGenerator
RRR-Γ-tocopherolGenerator
g-TocopherolGenerator
3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-olHMDB
(2R,4’R,8’r)-γ-tocopherolHMDB
all-(R)-gamma-TocopherolHMDB
all-(R)-Γ-tocopherolHMDB
gamma-TocopherolHMDB
Chemical FormulaC28H48O2
Average Molecular Weight416.6795
Monoisotopic Molecular Weight416.36543078
IUPAC Name(2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional Namegamma-tocopherol
CAS Registry Number54-28-4
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(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/t21-,22-,28-/m1/s1
InChI KeyQUEDXNHFTDJVIY-DQCZWYHMSA-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
  • 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
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point-67.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point226.20 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility128 mg/mLNot Available
LogP4.352 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.4e-06 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity130.33 m³·mol⁻¹ChemAxon
Polarizability54.12 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+208.97930932474
DeepCCS[M-H]-206.62130932474
DeepCCS[M-2H]-239.50430932474
DeepCCS[M+Na]+215.07230932474
AllCCS[M+H]+212.932859911
AllCCS[M+H-H2O]+210.832859911
AllCCS[M+NH4]+214.932859911
AllCCS[M+Na]+215.532859911
AllCCS[M-H]-211.932859911
AllCCS[M+Na-2H]-214.532859911
AllCCS[M+HCOO]-217.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
gamma-TocopherolCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O13807.9Standard polar33892256
gamma-TocopherolCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O13004.6Standard non polar33892256
gamma-TocopherolCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O13121.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
gamma-Tocopherol,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)OC2=C1C2996.5Semi standard non polar33892256
gamma-Tocopherol,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)OC2=C1C3267.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - gamma-Tocopherol GC-MS (1 TMS)splash10-00di-2290200000-ca2e59769b7f9d2833022014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Tocopherol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, negative-QTOFsplash10-0udi-0100900000-866035964c66e6e4a63c2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 13V, negative-QTOFsplash10-014i-0000900000-92e50ec0b18c795338b02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 16V, negative-QTOFsplash10-014j-0400900000-1fb1b39165372804b2c12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 19V, negative-QTOFsplash10-0002-0900500000-42bb4a664eeebbe24ff82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 24V, negative-QTOFsplash10-0002-0900200000-e8897dc0cd8b10c118202020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 30V, negative-QTOFsplash10-0002-0900100000-ea386123915e3fbbc82b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 37V, negative-QTOFsplash10-0002-0900000000-896627229022e40d2d4c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 44V, negative-QTOFsplash10-0002-0900000000-cc98083bdb10a92cc6942020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 51V, negative-QTOFsplash10-0002-0900000000-0c37948386f3f3e842312020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 58V, negative-QTOFsplash10-006t-0900000000-82abe7b9bcb60c5e016f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 64V, negative-QTOFsplash10-006t-0900000000-8ebacaefdf6ce927eb8f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 75V, negative-QTOFsplash10-05fs-0900000000-6045c9c0b33abee0cf8c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 85V, negative-QTOFsplash10-0ab9-0900000000-814007aa4a0b534c8b922020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 96V, negative-QTOFsplash10-0ab9-1900000000-7f6bf2020beb1db070382020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol Orbitrap 109V, negative-QTOFsplash10-0ab9-1900000000-da96e9792269933d640e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, negative-QTOFsplash10-0udi-0200900000-b8c469956aa52f5cea7b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, negative-QTOFsplash10-0udi-0200900000-c061dcce18ca02fdc7f82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, negative-QTOFsplash10-03di-0900000000-eaab1ecd4d7ca06a99f62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Tocopherol n/a 29V, positive-QTOFsplash10-014i-0911200000-794ce3ca05c79d17f8512020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocopherol 10V, Positive-QTOFsplash10-014i-1842900000-c0a3ade1f225f3c78ac22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocopherol 20V, Positive-QTOFsplash10-0udi-1910000000-db436d443f9dc640b9792016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocopherol 40V, Positive-QTOFsplash10-0pb9-5930000000-1cbe4445929c9b90be472016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocopherol 10V, Negative-QTOFsplash10-014i-0110900000-23d01b80a965180b27d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocopherol 20V, Negative-QTOFsplash10-014j-0931800000-70e6ff42d0190b91ef522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Tocopherol 40V, Negative-QTOFsplash10-0002-0932000000-e16b76b24d1cd56f30b12016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Breast Milk
  • Feces
Tissue Locations
  • Adipose Tissue
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Heart
  • Intestine
  • Leukocyte
  • Liver
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 Quantified36.920 +/- 11.540 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified39.100 +/- 11.940 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified4.500 +/- 3.0700 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified42.380 +/- 14.790 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified47.670 +/- 18.690 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified5.320 +/- 3.620 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified5.360 +/- 3.0700 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified5.390 +/- 2.880 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified40.540 +/- 12.450 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified42.280 +/- 16.230 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified5.600 +/- 3.0400 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified5.970 +/- 3.510 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified4.0600 +/- 2.690 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified4.440 +/- 3.0400 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified41.120 +/- 14.950 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified43.650 +/- 17.390 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.2 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified3.7 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified6.720 +/- 3.360 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified1.458 uMChildren (1-13 years old)FemaleNormal details
BloodDetected and Quantified1.469 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified1.48 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified5.508 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.440 +/- 0.720 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.0159 +/- 0.696 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.360 +/- 0.760 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified2.600 +/- 0.100 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.700 +/- 0.100 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.806 +/- 1.721 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified29.0367 +/- 10.384 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.351 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified1.473 uMChildren (1-13 years old)MaleNormal details
BloodDetected and Quantified1.63 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00576 +/- 0.00240 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified1.440 +/- 0.790 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified2.280 +/- 0.980 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified2.700 +/- 0.100 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified7.2 (3.8-11.7) uMAdult (>18 years old)FemaleNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Breast MilkDetected and Quantified0.5430037 +/- 0.0966421 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 QuantifiedAdult (>18 years old)Both
Schizophrenia
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
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 ]
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. [PubMed:22007635 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002431
KNApSAcK IDC00007365
Chemspider ID83708
KEGG Compound IDC02483
BioCyc IDGAMA-TOCOPHEROL
BiGG IDNot Available
Wikipedia LinkGamma-Tocopherol
METLIN IDNot Available
PubChem Compound92729
PDB IDNot Available
ChEBI ID18185
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000332
Good Scents IDrw1013461
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. [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 ]
  21. Jiang Q, Christen S, Shigenaga MK, Ames BN: gamma-tocopherol, the major form of vitamin E in the US diet, deserves more attention. Am J Clin Nutr. 2001 Dec;74(6):714-22. doi: 10.1093/ajcn/74.6.714. [PubMed:11722951 ]
  22. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]