Np mrd loader

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Record Information
Version1.0
Created at2006-03-08 13:03:03 UTC
Updated at2021-08-19 20:22:29 UTC
NP-MRD IDNP0000020
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha-Tocopherol
DescriptionAlpha-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. Natural vitamin E exists in eight different forms or isomers: Four tocopherols and four tocotrienols. In foods, the most abundant sources of vitamin E are vegetable oils such as palm oil, sunflower, corn, soybean, and olive oil. Nuts, sunflower seeds, and wheat germ are also good sources.
Structure
Thumb
Synonyms
ValueSource
(+)-alpha-TocopherolChEBI
(2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
(2R,4'r,8'r)-alpha-TocopherolChEBI
(all-R)-alpha-TocopherolChEBI
5,7,8-TrimethyltocolChEBI
D-alpha-TocopherolChEBI
RRR-alpha-TocopherolChEBI
Vitamin eChEBI
(+)-a-TocopherolGenerator
(+)-Α-tocopherolGenerator
(2R,4'r,8'r)-a-TocopherolGenerator
(2R,4'r,8'r)-Α-tocopherolGenerator
(all-R)-a-TocopherolGenerator
(all-R)-Α-tocopherolGenerator
D-a-TocopherolGenerator
D-Α-tocopherolGenerator
RRR-a-TocopherolGenerator
RRR-Α-tocopherolGenerator
a-TocopherolGenerator
Α-tocopherolGenerator
(R,R,R)-alpha-TocopherolHMDB
(R,R,R)-a-TocopherolHMDB
(R,R,R)-Α-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-TocopherylHMDB
Vitamin eaHMDB
(+)-2R,4'r,8'r-alpha-TocopherolHMDB
(+)-2R,4'r,8'r-Α-tocopherolHMDB
(+)-2R,4’R,8’r-α-tocopherolHMDB
(2R,4’R,8’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
AlmefrolHMDB
EmipherolHMDB
EtamicanHMDB
EvitaminumHMDB
ProfecundinHMDB
Vitamin ealphaHMDB
Vitamin eαHMDB
alpha-TocopherolChEBI
Chemical FormulaC29H50O2
Average Mass430.7061 Da
Monoisotopic Mass430.38108 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abramis bramaFooDB
AcipenserFooDB
AcipenseridaeFooDB
Actinidia chinensisFooDB
Aesculus hippocastanum Hort.KNApSAcK Database
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Alosa sapidissimaFooDB
AmaranthusFooDB
Amaranthus hypochondriacus L.KNApSAcK Database
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
AnatidaeFooDB
Anethum graveolensFooDB
AnguillaFooDB
AnguilliformesFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaKNApSAcK Database
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
AstacideaFooDB
Avena sativa L.KNApSAcK Database
Averrhoa carambolaFooDB
Belone beloneFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Bixa orellana L.KNApSAcK Database
Bos taurusFooDB
Botryococcus brauniiKNApSAcK Database
BrachyuraFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaKNApSAcK Database
Brassica oleracea var. sabaudaFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. rapaFooDB
BuccinidaeFooDB
Byrsonima crassifoliaFooDB
Calophyllum inophyllum L.KNApSAcK Database
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Carica papaya L.FooDB
CarideaFooDB
Carthamus tinctoriusKNApSAcK Database
Carum carviFooDB
Carum carvi L.KNApSAcK Database
Carya illinoinensisFooDB
CastaneaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chenopodium quinoaFooDB
Chondrus crispusFooDB
Cicer arietinumFooDB
CichlidaeFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clupea harengus harengusFooDB
ClupeinaeFooDB
Cocos nuciferaFooDB
Cocos nucifera L.KNApSAcK Database
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbidaeFooDB
CoregonusFooDB
Coriandrum sativum L.KNApSAcK Database
CorylusFooDB
Corylus avellanaFooDB
Crassostrea gigasFooDB
Crassostrea virginicaFooDB
Cucumis meloFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
CyclopteridaeFooDB
Cydonia oblongaFooDB
Cynara scolymusFooDB
Cyprinus carpioFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Delphinium ajacis L.KNApSAcK Database
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Dromaius novaehollandiaeFooDB
ElaeisFooDB
Elaeis guineensis Jacq.KNApSAcK Database
Elettaria cardamomumFooDB
EngraulidaeFooDB
Engraulis encrasicolusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Esox luciusFooDB
EucheumaFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Feijoa sellowianaKNApSAcK Database
Ficus caricaFooDB
Foeniculum vulgareFooDB
Foeniculum vulgare L.KNApSAcK Database
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gadus macrocephalusFooDB
Gadus morhuaFooDB
Gallus gallusFooDB
GastropodaFooDB
Gevuina avellana Mol.KNApSAcK Database
Glycine maxKNApSAcK Database
GossypiumFooDB
Grifola frondosaFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hevea brasiliensis Mull.Arg.KNApSAcK Database
Hibiscus sabbariffaFooDB
Hibiscus syriacusKNApSAcK Database
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hippoglossus stenolepisFooDB
Hippophae rhamnoidesKNApSAcK Database
Homarus americanusFooDB
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Hordeum vulgare L.KNApSAcK Database
Ictalurus punctatusFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Juglans regia L.KNApSAcK Database
Lactuca sativaFooDB
Lagopus mutaFooDB
LaminariaFooDB
Lens culinarisFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Limanda limandaFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Litchi chinensis Sonn.KNApSAcK Database
Lota lotaFooDB
Lupinus albusKNApSAcK Database
LutjanidaeFooDB
Lychnis coronariaKNApSAcK Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Machilus zuihoensisKNApSAcK Database
MalusFooDB
Malus pumilaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Matricaria recutitaFooDB
Medicago sativaFooDB
Melanogrammus aeglefinusFooDB
Meleagris gallopavoFooDB
Mentha x piperitaFooDB
Merlangius merlangusFooDB
Micromesistius poutassouFooDB
Micropogonias undulatusFooDB
Microstomus kittFooDB
Molva molvaFooDB
Moringa oleiferaFooDB
Mugil cephalusFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
Myristica fragransFooDB
MytilidaeFooDB
Mytilus edulisFooDB
NephropidaeFooDB
Nephrops norvegicusFooDB
Nicotiana tabacum L.KNApSAcK Database
Nuphar luteaFooDB
Ocimum basilicumFooDB
Octopus vulgarisFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Origanum majoranaFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Oryza sativa L.KNApSAcK Database
OsmeridaeFooDB
Osmerus mordaxFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panicum miliaceumFooDB
PapaverFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
PectinidaeFooDB
PerciformesFooDB
Persea americanaFooDB
Petroselinum crispumFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phoenix dactyliferaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus koraiensisKNApSAcK Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectidaeFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
PollachiusFooDB
Pollachius pollachiusFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus virginianaFooDB
Psidium guajavaFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
RanidaeFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rosmarinus officinalis L.KNApSAcK Database
Rubus idaeusFooDB
Rubus spectabilisFooDB
Rumex acetosaFooDB
Saccharina japonicaFooDB
Salmo salarFooDB
SalmonidaeFooDB
SalvelinusFooDB
Salvelinus namaycushFooDB
Salvia hispanicaFooDB
Salvia rosmarinusFooDB
Sambucus nigra L.FooDB
Sander luciopercaFooDB
Schisandra chinensisKNApSAcK Database
Scomberomorus maculatusFooDB
ScombridaeFooDB
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
SebastesFooDB
Sebastes alutusFooDB
Sebastes viviparusFooDB
Sebertia acuminataKNApSAcK Database
Secale cerealeFooDB
Secale cereale L.KNApSAcK Database
Sechium eduleFooDB
Sesamum indicumFooDB
SiluriformesFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
SoleidaeFooDB
Sorghum bicolorFooDB
Spinacia oleraceaKNApSAcK Database
SpirulinaFooDB
SqualiformesFooDB
Squalus acanthiasFooDB
Stenodus leucichthysFooDB
Stenotomus chrysopsFooDB
StrombidaeFooDB
Struthio camelusFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Terminalia brasiliensisPlant
Tetragonia tetragonioidesFooDB
TeuthidaFooDB
ThunnusFooDB
Thunnus albacaresFooDB
Thunnus thynnusFooDB
Thymus vulgarisFooDB
Trachinotus carolinusFooDB
Trachurus symmetricusFooDB
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum aestivumKNApSAcK Database
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Undaria pinnatifidaFooDB
Uvaria pandensisKNApSAcK Database
VacciniumFooDB
Vaccinium corymbosumFooDB
Vaccinium macrocarponFooDB
Vaccinium macrocarpon AitonKNApSAcK Database
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium vitis-idaeaFooDB
VanillaFooDB
Vicia fabaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna unguiculata ssp. unguiculataFooDB
Virola surinamensisFooDB
VitisFooDB
Vitis vinifera L.KNApSAcK Database
Xiphias gladiusFooDB
Zea mays L.KNApSAcK Database
Zingiber officinaleFooDB
ZizaniaFooDB
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 Point3 °CNot Available
Boiling Point200 - 220 °Chttps://en.wikipedia.org/wiki/Alpha-Tocopherol
Water Solubility3.0e-07 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP10.962 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility7.0e-06 g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001893
DrugBank IDDB00163
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005752
KNApSAcK IDC00007366
Chemspider ID14265
KEGG Compound IDC02477
BioCyc IDALPHA-TOCOPHEROL
BiGG ID2296507
Wikipedia LinkAlpha-Tocopherol
METLIN ID6376
PubChem Compound14985
PDB IDNot Available
ChEBI ID18145
Good Scents IDrw1105941
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Hino K, Murakami Y, Nagai A, Kitase A, Hara Y, Furutani T, Ren F, Yamaguchi Y, Yutoku K, Yamashita S, Okuda M, Okita M, Okita K: Alpha-tocopherol [corrected] and ascorbic acid attenuates the ribavirin [corrected] induced decrease of eicosapentaenoic acid in erythrocyte membrane in chronic hepatitis C patients. J Gastroenterol Hepatol. 2006 Aug;21(8):1269-75. [PubMed:16872308 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. de Souza Junior O, Treitinger A, Baggio GL, Michelon C, Verdi JC, Cunha J, Ferreira SI, Spada C: alpha-Tocopherol as an antiretroviral therapy supplement for HIV-1-infected patients for increased lymphocyte viability. Clin Chem Lab Med. 2005;43(4):376-82. [PubMed:15899652 ]
  7. Palan PR, Woodall AL, Anderson PS, Mikhail MS: Alpha-tocopherol and alpha-tocopheryl quinone levels in cervical intraepithelial neoplasia and cervical cancer. Am J Obstet Gynecol. 2004 May;190(5):1407-10. [PubMed:15167851 ]
  8. Traber MG, Siddens LK, Leonard SW, Schock B, Gohil K, Krueger SK, Cross CE, Williams DE: Alpha-tocopherol modulates Cyp3a expression, increases gamma-CEHC production, and limits tissue gamma-tocopherol accumulation in mice fed high gamma-tocopherol diets. Free Radic Biol Med. 2005 Mar 15;38(6):773-85. [PubMed:15721988 ]
  9. Mardla V, Kobzar G, Samel N: Potentiation of antiaggregating effect of prostaglandins by alpha-tocopherol and quercetin. Platelets. 2004 Aug;15(5):319-24. [PubMed:15370103 ]
  10. Pappert EJ, Tangney CC, Goetz CG, Ling ZD, Lipton JW, Stebbins GT, Carvey PM: Alpha-tocopherol in the ventricular cerebrospinal fluid of Parkinson's disease patients: dose-response study and correlations with plasma levels. Neurology. 1996 Oct;47(4):1037-42. [PubMed:8857741 ]
  11. Rota C, Barella L, Minihane AM, Stocklin E, Rimbach G: Dietary alpha-tocopherol affects differential gene expression in rat testes. IUBMB Life. 2004 May;56(5):277-80. [PubMed:15370891 ]
  12. Ekanayake-Mudiyanselage S, Tavakkol A, Polefka TG, Nabi Z, Elsner P, Thiele JJ: Vitamin E delivery to human skin by a rinse-off product: penetration of alpha-tocopherol versus wash-out effects of skin surface lipids. Skin Pharmacol Physiol. 2005 Jan-Feb;18(1):20-6. [PubMed:15608499 ]
  13. Liu ZQ: The "unexpected role" of vitamin E in free radical-induced hemolysis of human erythrocytes: alpha-tocopherol-mediated peroxidation. Cell Biochem Biophys. 2006;44(2):233-9. [PubMed:16456225 ]
  14. Kang MJ, Lin YC, Yeh WH, Pan WH: Vitamin E status and its dietary determinants in Taiwanese--results of the Nutrition and Health Survey in Taiwan 1993-1996. Eur J Nutr. 2004 Apr;43(2):86-92. Epub 2004 Jan 6. [PubMed:15083315 ]
  15. Hozyasz K, Chelchowska M: [Vitamin E status in mothers of children with cleft lip]. Pol Merkur Lekarski. 2004 Jul;17(97):25-7. [PubMed:15559605 ]
  16. Rose AT, McFadden DW: Alpha-tocopherol succinate inhibits growth of gastric cancer cells in vitro. J Surg Res. 2001 Jan;95(1):19-22. [PubMed:11120630 ]
  17. Murohara T, Ikeda H, Otsuka Y, Aoki M, Haramaki N, Katoh A, Takajo Y, Imaizumi T: Inhibition of platelet adherence to mononuclear cells by alpha-tocopherol: role of P-selectin. Circulation. 2004 Jul 13;110(2):141-8. Epub 2004 Jun 14. [PubMed:15197142 ]
  18. Hozyasz KK, Chelchowska M, Laskowska-Klita T, Ruszkowska L, Milanowski A: [Low concentration of alpha-tocopherol in erythrocytes of atopic dermatitis patients]. Med Wieku Rozwoj. 2004 Oct-Dec;8(4 Pt 1):963-9. [PubMed:15951615 ]
  19. Horwitt MK, Elliott WH, Kanjananggulpan P, Fitch CD: Serum concentrations of alpha-tocopherol after ingestion of various vitamin E preparations. Am J Clin Nutr. 1984 Aug;40(2):240-5. [PubMed:6465056 ]
  20. Iuliano L, Micheletta F, Maranghi M, Frati G, Diczfalusy U, Violi F: Bioavailability of vitamin E as function of food intake in healthy subjects: effects on plasma peroxide-scavenging activity and cholesterol-oxidation products. Arterioscler Thromb Vasc Biol. 2001 Oct;21(10):E34-7. [PubMed:11597949 ]
  21. Miller ER 3rd, Pastor-Barriuso R, Dalal D, Riemersma RA, Appel LJ, Guallar E: Meta-analysis: high-dosage vitamin E supplementation may increase all-cause mortality. Ann Intern Med. 2005 Jan 4;142(1):37-46. Epub 2004 Nov 10. [PubMed:15537682 ]
  22. Poston L, Briley AL, Seed PT, Kelly FJ, Shennan AH: Vitamin C and vitamin E in pregnant women at risk for pre-eclampsia (VIP trial): randomised placebo-controlled trial. Lancet. 2006 Apr 8;367(9517):1145-54. [PubMed:16616557 ]
  23. Rumbold AR, Crowther CA, Haslam RR, Dekker GA, Robinson JS: Vitamins C and E and the risks of preeclampsia and perinatal complications. N Engl J Med. 2006 Apr 27;354(17):1796-806. [PubMed:16641396 ]
  24. Linus Pauling Institute [Link]