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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
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Aesculus hippocastanum Hort.KNApSAcK Database
Amaranthus hypochondriacus L.KNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaKNApSAcK Database
Avena sativa L.KNApSAcK Database
Bixa orellana L.KNApSAcK Database
Botryococcus brauniiKNApSAcK Database
Brassica oleracea var. italicaKNApSAcK Database
Calophyllum inophyllum L.KNApSAcK Database
Carthamus tinctoriusKNApSAcK Database
Carum carvi L.KNApSAcK Database
Cocos nucifera L.KNApSAcK Database
Coriandrum sativum L.KNApSAcK Database
Delphinium ajacis L.KNApSAcK Database
Elaeis guineensis Jacq.KNApSAcK Database
Feijoa sellowianaKNApSAcK Database
Foeniculum vulgare L.KNApSAcK Database
Gevuina avellana Mol.KNApSAcK Database
Glycine maxKNApSAcK Database
Hevea brasiliensis Mull.Arg.KNApSAcK Database
Hibiscus syriacusKNApSAcK Database
Hippophae rhamnoidesKNApSAcK Database
Hordeum vulgare L.KNApSAcK Database
Juglans regia L.KNApSAcK Database
Litchi chinensis Sonn.KNApSAcK Database
Lupinus albusKNApSAcK Database
Lychnis coronariaKNApSAcK Database
Machilus zuihoensisKNApSAcK Database
Nicotiana tabacum L.KNApSAcK Database
Oryza sativa L.KNApSAcK Database
Pinus koraiensisKNApSAcK Database
Rosmarinus officinalis L.KNApSAcK Database
Schisandra chinensisKNApSAcK Database
Sebertia acuminataKNApSAcK Database
Secale cereale L.KNApSAcK Database
Spinacia oleraceaKNApSAcK Database
Triticum aestivumKNApSAcK Database
Uvaria pandensisKNApSAcK Database
Vaccinium macrocarpon AitonKNApSAcK Database
Vitis vinifera L.KNApSAcK Database
Zea mays L.KNApSAcK Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
External Links
HMDB IDHMDB0001893
DrugBank IDDB00163
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000565
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]