Vitamin E

Base Information

• Chemical Name: Vitamin E
• CAS No.: 1406-18-4
• 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: Unspecified
• Molecular Weight: 490.61600
• 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: 1406-18-4.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: Tan, white granular powder
• Melting Point: 3ºC
• Boiling Point: 210ºC at 0.1 mm Hg
• Flash Point: 210.2ºC
• PSA: 133.06000
• Density: 0.93 g/cm3
• LogP: 5.26540
• Storage Temp.: 0-6°C
• 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:

1%-101.0% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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: Fat-soluble vitamin E, which is a light yellow oil readily degradable by heat. As a vitamin, it is essential for normal muscle growth and prevents vitamin A destruction by deterioration. It also functions as an antioxidant. It prevents the oxidation of certain fatty acids and is stable unless the food becomes rancid. Vegetable oils contain a higher concentration of natural antioxidants, including tocopherols, than animal fats and are thus more stable. Tocopherol is obtained from vegetable oils, beans, eggs, and milk. It is also termed alpha-tocopherol. Medicine, nutrition, antioxidants for fats, animal feed additive.

Refernces

A new route to vitamin E Key-intermediates by olefin cross-metathesis

10.1002/hlca.200690072

The research explores an innovative method for synthesizing key intermediates for vitamin E (α-tocopherol acetate) using olefin cross-metathesis (CM) catalyzed by ruthenium (Ru). The study utilized second-generation Grubbs catalyst (RuCl2(C21H26N2)(CHPh)PCy3) and Hoveyda–Grubbs catalyst (RuCl2(C21H26N2){CH-C6H4(O-Pr)-2}) to perform CM reactions with various C-allyl and O-allyl derivatives of trimethylhydroquinone-1-acetate as substrates, along with olefin partners like 2,6,10,14-tetramethylpentadec-1-ene and phytol derivatives. The goal was to develop an alternative route to vitamin E that prevents the formation of by-products typically obtained in classical syntheses. The vitamin E precursors were successfully prepared in yields up to 83% as (E/Z)-mixtures. The research highlights the efficiency of Ru-catalyzed CM in constructing complex organic molecules, specifically in the context of vitamin E synthesis, and provides valuable insights for further advancements in this field.

Synthesis of a new flavonoid-antioxidant

10.1016/S0040-4039(00)88547-0

The study reports the synthesis of a new, highly lipophilic flavonoid-antioxidant 1, which is a potent inhibitor of LDL oxidation. The synthesis involves key chemicals such as 3-bromomethyl-flavonoid 1 and isomerically pure 2(E)-phytyl mercaptan 8. The 3-bromomethyl-flavonoid 1 is synthesized from phloroglucine dimethyl-ether through a series of reactions including O-acetylation, Robinson synthesis, demethylation, and acetylation. The 2(E)-phytyl mercaptan 8 is obtained from phytol by the method of Folkers. These two compounds are then reacted together to form the final flavonoid-antioxidant 1. The new flavonoid-antioxidant 1 shows 15 times more potency in inhibiting LDL oxidation in vitro compared to vitamin E.

Hydroperoxyl Radicals (HOO^.): Vitamin E Regeneration and H-Bond Effects on the Hydrogen Atom Transfer

10.1002/chem.201603722

The study primarily investigates the behavior of hydroperoxyl (HOOC) and alkylperoxyl (ROOC) radicals in hydrogen atom transfer (HAT) reactions, with a focus on their interaction with 2,2,5,7,8-pentamethyl-6-chromanol (TOH), an analogue of vitamin E. The researchers used 1,4-cyclohexadiene (CHD) and styrene as substrates to monitor the autoxidation rate in various organic solvents, which served as a means to assess the reactivity of HOOC and ROOC with TOH. The purpose of these chemicals was to understand how HOOC radicals, which are implicated in oxidative damage in biological systems, behave differently from ROOC radicals during H-atom transfer and how they affect the regeneration of TOH, providing insights into the antioxidant properties of vitamin E and the role of solvent effects on these reactions.

A Convenient access to (All-rac)-α-tocopherol acetate from linalool and dihydromyrcene

10.1246/bcsj.82.829

The study explores a novel synthetic route to produce (All-rac)-α-tocopherol acetate, a form of vitamin E, using linalool and dihydromyrcene as starting materials. The researchers employed trimethylhydroquinone (2) as a key reactant and utilized camphorsulfonic acid as a catalyst to condense it with linalool (3b) in a solvent mixture of dodecane and dichloromethane. The resulting crude product, a mixture of chromanols and tricyclic compounds, was sequentially treated with acetic anhydride (Ac2O) and m-chloroperoxybenzoic acid (m-CPBA) to form a mixture of epoxides. This mixture was then converted to the desired (All-rac)-α-tocopherol acetate through a series of reactions involving aluminum isopropoxide, copper(I) iodide-catalyzed Wurtz coupling with citronellylmagnesium chloride, and hydrogenation. The study aimed to develop a more efficient and cost-effective method for synthesizing this important vitamin E derivative, which is widely used in the feed industry due to its antioxidant properties and health benefits.

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