Alpha-Tocopherol (CHEM002132)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (11)XML
Record Information
Version1.0
Creation Date2009-07-21 20:26:11 UTC
Update Date2026-03-26 23:37:49 UTC
Accession NumberCHEM002132
Identification
Common NameAlpha-Tocopherol
ClassSmall Molecule
DescriptionA generic descriptor for all tocopherols and tocotrienols that exhibit alpha-tocopherol activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of isoprenoids.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antioxidant
  • Dietary Supplement
  • Drug
  • Ether
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Micronutrient
  • Natural Compound
  • Nutraceutical
  • Organic Compound
  • Supplement
  • Vitamin
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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-TocopherolChEBI
(R,R,R)-a-TocopherolGenerator
(R,R,R)-α-TocopherolGenerator
(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
alpha-TocopherolChEBI
(+)-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
AlmefrolPhytoBank
EmipherolPhytoBank
EtamicanPhytoBank
EvitaminumPhytoBank
ProfecundinPhytoBank
Vitamin EalphaPhytoBank
Vitamin EαPhytoBank
Chemical FormulaC29H50O2
Average Molecular Mass430.706 g/mol
Monoisotopic Mass430.381 g/mol
CAS Registry Number59-02-9
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
SMILESCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C
InChI IdentifierInChI=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
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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Adipose Tissue
  • Bladder
  • Erythrocyte
  • Eye Lens
  • Fibroblasts
  • Intestine
  • Liver
  • Lymphocyte
  • Muscle
  • Nerve Cells
  • Nervous Tissues
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point3°C
Boiling PointNot Available
SolubilityInsoluble in water, but water-dispersible.
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-000i-1390000000-fc8c4f9b9405598ede7fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00dr-9150010000-c4abc0e689e9b2476b9dSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0f79-1190040000-663296a69129a59be1a6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-1390000000-fc8c4f9b9405598ede7fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-9150010000-c4abc0e689e9b2476b9dSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f79-1190040000-663296a69129a59be1a6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-9886300000-b3225facac6ebdd8ddbdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000l-7735900000-1585eb83c1211ebe95f2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9600100000-aaf885290800a10d3fb2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01wr-9300000000-f0c814976a58a9d837caSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f79-1494700000-6b5f8f817c5a5429ed70Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-00lr-4910600000-1eda05dacf9642d7cea0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-a5860634bfd1ceb6833fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0159-0900500000-5a3bc17152cb61859b2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0842900000-f51286676592fd184193Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1920000000-1994f86bec2bb4a77b9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-3930000000-02190bf16d5d85d44bceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0110900000-c3541294fc60a7a8cc7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0730900000-553c4898757f6876036cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03e9-0920200000-276273a531fed5b3a2b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3013900000-4985082235edff7c4b8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r1-9313200000-cbc230d5dd20c629ffabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9320000000-5958d2e1d5b687b012c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-d3ddef81c134412455e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0310900000-30597e14cf876e4e4764Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08g0-2982400000-371737325df4dbb523b2Spectrum
MSMass Spectrum (Electron Ionization)splash10-0159-2900500000-03e8a824731610752eb3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral, Topical, Intramuscular 50 to 80% absorbed from gastrointestinal tract.
Mechanism of ToxicityAlthough all forms of Vitamin E exhibit antioxidant activity, it is known that the antioxidant activity of vitamin E is not sufficient to explain the vitamin's biological activity.
Vitamin E's anti-atherogenic activity involves the inhibition of the oxidation of LDL and the accumulation of oxLDL in the arterial wall. It also appears to reduce oxLDL-induced apoptosis in human endothelial cells. Oxidation of LDL is a key early step in atherogenesis as it triggers a number of events which lead to the formation of atherosclerotic plaque. In addition, vitamin E inhibits protein kinase C (PKC) activity. PKC plays a role in smooth muscle cell proliferation, and, thus, the inhibition of PKC results in inhibition of smooth muscle cell proliferation, which is involved in atherogenesis.
Vitamin E's antithrombotic and anticoagulant activities involves the downregulation of the expression of intracellular cell adhesion molecule(ICAM)-1 and vascular cell adhesion molecule(VCAM)-1 which lowers the adhesion of blood components to the endothelium. In addition, vitamin E upregulates the expression of cytosolic phospholipase A2 and cyclooxygenase (COX)-1 which in turn enhances the release of prostacyclin. Prostacyclin is a vasodilating factor and inhibitor of platelet aggregation and platelet release. It is also known that platelet aggregation is mediated by a mechanism involving the binding of fibrinogen to the glycoprotein IIb/IIIa (GPIIb/IIIa) complex of platelets. GPIIb/IIIa is the major membrane receptor protein that is key to the role of the platelet aggregation response. GPIIb is the alpha-subunit of this platelet membrane protein. Alpha-tocopherol downregulates GPIIb promoter activity which results in reduction of GPIIb protein expression and decreased platelet aggregation. Vitamin E has also been found in culture to decrease plasma production of thrombin, a protein which binds to platelets and induces aggregation. A metabolite of vitamin E called vitamin E quinone or alpha-tocopheryl quinone (TQ) is a potent anticoagulant. This metabolite inhibits vitamin K-dependent carboxylase, which is a major enzyme in the coagulation cascade.
The neuroprotective effects of vitamin E are explained by its antioxidant effects. Many disorders of the nervous system are caused by oxidative stress. Vitamin E protects against this stress, thereby protecting the nervouse system.
The immunomodulatory effects of Vitamin E have been demonstrated in vitro, where alpha-tocopherol increases mitogenic response of T lymphocytes from aged mice. The mechanism of this response by vitamin E is not well understood, however it has been suggested that vitamin E itself may have mitogenic activity independent of its antioxidant activity.
Lastly, the mechanism of action of vitamin E's antiviral effects (primarily against HIV-1) involves its antioxidant activity. Vitamin E reduces oxidative stress, which is thought to contribute to HIV-1 pathogenesis, as well as to the pathogenesis of other viral infections. Vitamin E also affects membrane integrity and fluidity and, since HIV-1 is a membraned virus, altering membrane fluidity of HIV-1 may interfere with its ability to bind to cell-receptor sites, thus decreasing its infectivity.
MetabolismHepatic.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesVitamin E, known for its antioxidant activities, is protective against cardiovascular disease and some forms of cancer and has also demonstrated immune-enhancing effects. It may be of limited benefit in some with asthma and rheumatoid arthritis. It may be helpful in some neurological diseases including Alzheimer's, some eye disorders including cataracts, and diabetes and premenstrual syndrome. It may also help protect skin from ultraviolet irradiation although claims that it reverses skin aging, enhances male fertility and exercise performance are poorly supported. It may help relieve some muscle cramps.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00163
HMDB IDHMDB0001893
FooDB IDFDB000565
Phenol Explorer IDNot Available
KNApSAcK IDC00007366
BiGG ID2296507
BioCyc IDALPHA-TOCOPHEROL
METLIN ID6376
PDB IDNot Available
Wikipedia LinkAlpha-Tocopherol
Chemspider ID14265
ChEBI ID18145
PubChem Compound ID14985
Kegg Compound IDC02477
YMDB IDNot Available
ECMDB IDM2MDB005238
References
Synthesis Reference

Ralph E. Close, William Oroshnik, “Synthesis of dehydrophytol and Vitamin E.” U.S. Patent US4039591, issued February, 1945.

MSDSLink
General References
1. Matsui, Makoto. Synthesis of a-tocopherol for the next century. Nihon Yukagakkaishi (1996), 45(9), 821-831.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. Mardla V, Kobzar G, Samel N: Potentiation of antiaggregating effect of prostaglandins by alpha-tocopherol and quercetin. Platelets. 2004 Aug;15(5):319-24.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. Hozyasz K, Chelchowska M: [Vitamin E status in mothers of children with cleft lip]. Pol Merkur Lekarski. 2004 Jul;17(97):25-7.
17. Rose AT, McFadden DW: Alpha-tocopherol succinate inhibits growth of gastric cancer cells in vitro. J Surg Res. 2001 Jan;95(1):19-22.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
26. Linus Pauling Institute: http://lpi.oregonstate.edu/infocenter/vitamins/vitaminE/
27. Delgado Zamarreno MM, Sanchez Perez A, Gomez Perez C, Hernandez Mendez J: High-performance liquid chromatography with electrochemical detection for the simultaneous determination of vitamin A, D3 and E in milk. J Chromatogr. 1992 Oct 9;623(1):69-74.
28. Noziere P, Grolier P, Durand D, Ferlay A, Pradel P, Martin B: Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. J Dairy Sci. 2006 Jul;89(7):2634-48. doi: 10.3168/jds.S0022-0302(06)72340-2.
29. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.
30. International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570
31. International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526
32. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386
33. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
34. Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547
35. Graulet B: Improving the level of vitamins in milk. In Griffiths MW (ed):‘‘Improving the Safety and Quality of Milk: Improving Quality in Milk Products,’’vol. 2. Boca Raton, FL: CRC Press, pp 229–251, 2010.
36. Oste R, Jagerstad M, Anderson I: Vitamins in milk and milk products. In Fox PF (ed):‘‘Advanced Dairy Chemistry: Lactose, Water, Salts and Vitamins,’’vol 3, 2nd ed. London: Chapman & Hall, pp 347–402, 1997
37. USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/
38. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en
39. https://www.ncbi.nlm.nih.gov/pubmed/?term=11427352
40. https://www.ncbi.nlm.nih.gov/pubmed/?term=12899840
41. https://www.ncbi.nlm.nih.gov/pubmed/?term=14657365
42. https://www.ncbi.nlm.nih.gov/pubmed/?term=16512933
43. https://www.ncbi.nlm.nih.gov/pubmed/?term=17031012
44. https://www.ncbi.nlm.nih.gov/pubmed/?term=17310859
45. https://www.ncbi.nlm.nih.gov/pubmed/?term=19389964
46. https://www.ncbi.nlm.nih.gov/pubmed/?term=19663978
47. https://www.ncbi.nlm.nih.gov/pubmed/?term=20209471
48. https://www.ncbi.nlm.nih.gov/pubmed/?term=21591326
49. https://www.ncbi.nlm.nih.gov/pubmed/?term=23599266
50. https://www.ncbi.nlm.nih.gov/pubmed/?term=28694484
51. https://www.ncbi.nlm.nih.gov/pubmed/?term=31013594
52. https://www.ncbi.nlm.nih.gov/pubmed/?term=33197771