Vitamin E

Base Information

• Chemical Name: Vitamin E
• CAS No.: 59-02-9
• Deprecated CAS: 121854-78-2,18920-62-2,364-49-8,2484908-93-0,11105-14-9,18920-62-2,364-49-8
• Molecular Formula: C29H50O2
• Molecular Weight: 430.715
• Hs Code.: 29362800
• European Community (EC) Number: 233-466-0,200-412-2,215-798-8,218-197-9,606-803-8
• UNII: N9PR3490H9
• DSSTox Substance ID: DTXSID0026339
• Nikkaji Number: J24.260H
• Wikipedia: %CE%91-Tocopherol
• Wikidata: Q158348
• NCI Thesaurus Code: C68313,C2832,C74960
• RXCUI: 237099,1236136,11256
• Pharos Ligand ID: 85BJCGZ83ZT5
• Metabolomics Workbench ID: 29096
• ChEMBL ID: CHEMBL47
• Mol file: 59-02-9.mol

Synonyms:VITAMIN E;alpha-Tocopherol;D-alpha-Tocopherol;59-02-9;5,7,8-Trimethyltocol;(+)-alpha-Tocopherol;alpha Tocopherol;Phytogermine;TOCOPHEROL;2074-53-5;(R,R,R)-alpha-Tocopherol;Syntopherol;Viteolin;Eprolin;Esorb;a-Tocopherol;(2R,4'R,8'R)-alpha-Tocopherol;Tocopherol alpha;dl-a-Tocopherol;Profecundin;Denamone;Epsilan;Tokopharm;Vascuals;Viprimol;Etavit;alpha-Tokoferol;Evion;alpha-Tocopherol, D-;alpha-Vitamin E;Vitamin E alpha;Eprolin S;Viterra E;E Prolin;D-alpha tocopherol;Aquasol E;Lan-E;Med-E;Antisterility vitamin;alpha-Tocopherol acid;Tenox GT 1;Vi-E;Rhenogran Ronotec 50;(2R)-2,5,7,8-TETRAMETHYL-2-[(4R,8R)-4,8,12-TRIMETHYLTRIDECYL]CHROMAN-6-OL;Covitol F 1000;Waynecomycin;E 307 (tocopherol);(R)-2,5,7,8-Tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-ol;Vitamin Ea;ido-E;Tocopherol (R,S);CCRIS 3588;1406-18-4;CHEBI:18145;Vitamin-E;2,5,7,8-Tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanol;HSDB 2556;E-Vimin;EINECS 200-412-2;NSC 20812;(all-R)-alpha-Tocopherol;Evitaminum;Almefrol;E307;Emipherol;Etamican;Vitayonon;Ilitia;(+-)-Med-E;UNII-N9PR3490H9;(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol;H4N855PNZ1;BPBio1_000362;18920-62-2;Vitaplex E;Covi-ox;DTXSID0026339;E 307;.ALPHA.-TOCOPHEROL, D-;Spavit E;EC 200-412-2;alpha-D-Tocopherol;Endo E;N9PR3490H9;Vita E;EINECS 215-798-8;EINECS 218-197-9;a-Vitamin E;NSC 82623;(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-;(+-)-alpha-Tocopherol;(+/-)-alpha-Tocopherol;3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-rel-;CCRIS 5853;DTXCID706339;.alpha.-Tocopherol;d-a-tocopherol;EINECS 233-466-0;MFCD00072045;rel-alpha-Vitamin E;RRR-alpha-tocopherol;BRN 0094012;CAS-59-02-9;(2R*(4R*,8R*))-(1)-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-, (2R)-;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, (2R-(2R*(4R*,8R*)))-;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, [2R-[2R*(4R*,8R*)]]-;SMR000471844;VIV;.Alpha.-tocopherol, DL-;3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol;DTXSID8021355;Phytogermin;Palmvtee;alpha-Tocoferol;Vitamin Ealpha;a- tocopherol;NSC-20812;Alpha-tocopherols;a-D-Tocopherol;Pheryl-E;DL--Tocopherol;Vita plus E;rel--Vitamin E;d-..-Tocopherol;Vitamin e d-alpha;NCGC00016688-02;(+)--tocopherol;Prestwick_653;.alpha.-Vitamin E;Envirose 100;(+)-a-Tocopherol;COVIREL;RRR-alpha-tocopheryl;Vitamin E [USP];()-alpha-Tocopherol;delta-alpha-tocopherol;alpha-delta-Tocopherol;Tocopherol, d-alpha-;CONTROX VP;EPROLIN-S;Vitamin E (D-form);TENOX GT;CHEMBL47;(R,R,R)-a-Tocopherol;Prestwick3_000404;(+)- alpha -Tocopherol;(+)-.alpha.-Tocopherol;bmse000600;R,r,r-.alpha.-tocopherol;alpha-TOCOPHEROL (II);SCHEMBL3097;COVI-OX T 30P;RIKKI N 70;UNII-H4N855PNZ1;BIDD:PXR0174;COVI-OX T 50;BSPBio_000328;E-MIX 40A;MLS001066396;MLS001335981;MLS001335982;BIDD:ER0562;INS NO.307A;T1539_SIGMA;2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)chroman-6-ol;DTXCID201355;INS-307A;(+)-ALPHA-TOCOPHEROL-;ALPHA-TOCOPHEROL [HSDB];Vitamin e (as alpha tocopherol);(2R,4'R,8'R)-a-Tocopherol;.ALPHA.-TOCOPHEROL [MI];((addition))-(alpha)-Tocopherol;(2R,4'R,8'R)-2,5,7,8-Tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanol;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl- 2-(4,8,12-trimethyltridecyl)-;3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1- -benzopyran-6-ol;ALPHA TOCOPHEROL (USP-RS);(+)--Tocopherol;D--Tocopherol;HMS2096A10;HMS2231G08;C29H50O2 (D-alpha-tocopherol);3, 4- dihydro- 2, 5, 7, 8- tetramethyl- 2- (4, 8, 12- trimethyltridecyl)- 2H- benzopyran- 6- ol;D-ALPHA TOCOPHEROL [MART.];HY-N0683;Tox21_110563;Tox21_113208;Tox21_202081;BDBM50458513;E-307A;LMPR02020001;AKOS004910417;CS-8161;CS-O-02555;DB00163;LS-7727;(2R)-2-((4R,8R)-4,8,12-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol;NCGC00142625-01;NCGC00142625-04;NCGC00142625-05;NCGC00142625-06;NCGC00142625-07;NCGC00142625-10;NCGC00259630-01;ALPHA-TOCOPHEROL, UNSPECIFIED FORM;AS-13990;J24.260H;rel-(+)--Tocopherol;rel-D--Tocopherol;J203.513H;LS-173092;E-307;T2309;C02477;F82497;d-alpha, d-beta, d-gamma & d-delta tocopherols;EN300-7417123;Q158348;Q-201932;W-107596;W-109164;Z2235811339;07AA93F0-3339-4EEC-B50B-ADB70F657087;3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1--benzopyran-6-ol;(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol;(2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopy-ran-6-ol;(2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol;(R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromen-6-ol;[2R*(4R*,8R*)]-(+-)-3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol;2H-1-benzopirano-6-ol, 3,4-dihidro-2,5,7,8-tetrametil-2-[(4R, 8R)-4,8,12-trimetiltridecil]-, (2R)-;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl- 2-(4,8,12-trimethyltridecyl)-, [2R-[2R(4R,8R)]]-;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, 2R- 2R*(4R*,8R*) -;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, (2R*(4R*,8R*))-(+-)-;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, [2R*(4R*,8R*)]-(.+-.)-;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, [2R*(4R*,8R*)]-(.+.)-;rel-(2R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromen-6-ol

Chemical Property of Vitamin E

Chemical Property:

• Appearance/Colour: light yellow liquid
• Melting Point: 2.5-3.5 °C
• Refractive Index: n20/D 1.505(lit.)
• Boiling Point: 485.856 °C at 760 mmHg
• PKA: 11.40±0.40(Predicted)
• Flash Point: 210.229 °C
• PSA: 29.46000
• Density: 0.93 g/cm³
• LogP: 8.84020
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, freely soluble in acetone, in anhydrous ethanol, in methylene chloride and in fatty oils.
• Water Solubility.: INSOLUBLE
• XLogP3: 10.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 12
• Exact Mass: 430.381080833
• Heavy Atom Count: 31
• Complexity: 503

Purity/Quality:

99% ^*data from raw suppliers

α-Tocopherol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Vitamins and Derivatives
• Canonical SMILES: CC1=C(C2=C(CCC(O2)(C)CCCC(C)CCCC(C)CCCC(C)C)C(=C1O)C)C
• Isomeric SMILES: CC1=C(C2=C(CC[C@@](O2)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C(=C1O)C)C
• Recent ClinicalTrials: Vitamin E Pharmacokinetics and Biomarkers in Normal and Obese Women
• Recent EU Clinical Trials: The pAToMiUM Trial: pilot trial of Antioxidant Therapy of Men in Unexplained Miscarriage
• Recent NIPH Clinical Trials: An investigation study of antioxidant effect and improving blood circulation: A randomized double-blind placebo-controlled trial
• Uses: vitamin E, antioxidant α-Tocopherol is the most bioactive of the naturally occurring forms of Vitamin E. Richest sources are green vegetables, grains, and oils, particularly palm, safflower and sunflower oils. Use in insect cell culture applications as an antioxidant.
• Therapeutic Function: Antioxidant

Technology Process of Vitamin E

There total 255 articles about Vitamin E which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(2R,4'R,8'R)-α-tocopheryl methyl ether (32466-45-8) → Tocopherol (59-02-9,18920-62-2)

Guidance literature:

(2R,4'R,8'R)-α-tocopheryl methyl ether; With triethylsilane; tris(pentafluorophenyl)borate; at 20 ℃;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;

DOI:10.1248/cpb.c18-00460

Reference yield: 99.8%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9,18920-62-2)

Guidance literature:

With hydrogenchloride; Zinc chloride; In tetrachloromethane;

Reference yield: 99.6%

2-methylpropyl acetate (110-19-0) + isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9,18920-62-2)

Guidance literature:

With hydrogenchloride; Zinc chloride; In water; toluene;

upstream raw materials:

(2R,8aΞ)-8a-ethoxy-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyl-tridecyl)-8aH-chroman-6-one

delta tocopherol

5,8-dimethyltocol

gamma-tocopherol

Downstream raw materials:

tocopheroxyl radical

tert-butyl alcohol

2,2-diphenyl-1-picrylhydrazine

2,5,7,8-Tetramethyl-2-(4,8,12-trimethyl-tridecyl)-chroman-6-ol

Refernces

• 1、 Pan, Wenjing,Li, Chenchen,Zhu, Haoyin,Li, Fangfang,Li, Tao,Zhao, Wanxiang. "A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh2andtBuOK". . p. 7633 - 7640. Retrieved 2021/09/22.
• 2、 -. "SYNTHESIS OF CHROMANOL AND 2-METHYL-1,4-NAPHTHOQUINONE DERIVATIVES". Page/Page column 49-71. . Retrieved 2020/03/05.