Vitamin E

Base Information

• Chemical Name: Vitamin E
• CAS No.: 2074-53-5
• 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
• 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: 2074-53-5.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:

• Vapor Pressure: 4.59E-10mmHg at 25°C
• Melting Point: 3oC
• Refractive Index: 1.495
• Boiling Point: 485.9 °C at 760 mmHg
• PKA: 11.40±0.40(Predicted)
• Flash Point: 210.2 °C
• PSA: 29.46000
• Density: 0.93 g/cm³
• LogP: 8.84020
• 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:

99.00% ^*data from raw suppliers

Vitamin E ^*data from reagent 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
• Physical properties: Vitamin E has demonstrated some success in the treatment of yellow nail syndrome when taken orally (600 EU to 1200 EU daily) for several months. Topically-applied vitamin E has also shown significant improvement in symptoms of yellow nail syndrome, as well as increased nail growth rates after six months.
• Uses: Vitamin E supplement. vitamin E (D-alpha-tocopherol; DL-alpha-tocopherol; tocopherol) is considered the most important oil-soluble anti-oxidant and freeradical scavenger. Studies indicate that vitamin e performs these functions when topically applied. It is also a photoprotectant, and it helps protect the cellular membrane from free-radical damage. In addition, vitamin e serves a preservative function given its ability to protect against oxidation. This benefits not only the skin, but also the product in terms of longevity. As a moisturizer, vitamin e is well-absorbed through the skin, demonstrating a strong affinity with small blood vessels and an ability to enhance blood circulation in the skin. It is also thought to improve the skin’s water-binding ability. In addition, vitamin e emulsions have been found to reduce transepidermal water loss, thereby improving the appearance of rough, dry, and damaged skin. This vitamin is also believed to help maintain the connective tissue. There is evidence that vitamin e is effective in preventing irritation owing to sun exposure: studies show that vitamin e topically applied prior to uV irradiation is protective against epidermal cell damage caused by inflammation. This indicates possible anti-inflammatory properties. Lipid peroxidation in tissues may be one cause of skin aging. Vitamin e, however, appears to counteract decreased functioning of the sebaceous glands and to reduce excessive skin pigmentation, which is found to increase almost linearly with age. It is available also as a tocopherol-polypeptide complex that delivers the vitamin in a waterdispersable form. In this way, when incorporated into cosmetic formulations, it does not need other compounds to assist in its solubilization. It is useful in anti-aging creams and lotions, and in uV protective products, tocopherol is a naturally occurring vitamin e found in a variety of cereal germ oils including wheat germ oil. It can also be produced synthetically.
• Indications: Vitamin E is a potent antioxidant that is capable of protecting polyunsaturated fatty acids from oxidative breakdown.This vitamin also functions to enhance vitamin A use.Although several other physiological actions have been suggested, to date no unifying concept exists to explain these actions. Vitamin E (α-tocopherol) is found in a variety of foodstuffs, the richest sources being plant oils, including wheat germ and rice, and the lipids of green leaves.
• Clinical Use: Deficiency of vitamin E is characterized by low serum tocopherol levels and a positive hydrogen peroxide hemolysis test.This deficiency is believed to occur in patients with biliary, pancreatic, or intestinal disease that is characterized by excessive steatorrhea. Premature infants with a high intake of fatty acids exhibit a deficiency syndrome characterized by edema, anemia, and low tocopherol levels.This condition is reversed by giving vitamin E.

Technology Process of Vitamin E

There total 5 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:

cyclohexane (110-82-7,25012-93-5) + (+/-)-α-tocopherol (10191-41-0,18920-62-2) → cyclohexyl hydroperoxide (766-07-4) + (R)-2,5,7,8-Tetramethyl-2-((4R,8R)-4,8,12-trimethyl-tridecyl)-chroman-6-ol (59-02-9,2074-53-5,10191-41-0,18920-63-3,77171-97-2,77171-98-3,78656-09-4,78656-10-7,78656-11-8,78656-12-9,78656-13-0,79434-82-5,79434-83-6,113085-06-6)

Guidance literature:

With oxygen; at 20 ℃; Rate constant; Thermodynamic data; Irradiation; pulse radiolysis; ΔH⁺, ΔS⁺;

DOI:10.1021/ja00049a037

Reference yield:

vitamin E (59-02-9,18920-62-2) → vitamin E (895518-38-4,18920-62-2) + DL-α-tocopherol (59-02-9,2074-53-5,10191-41-0,18920-63-3,77171-97-2,77171-98-3,78656-09-4,78656-10-7,78656-11-8,78656-12-9,78656-13-0,79434-82-5,79434-83-6,113085-06-6,18920-62-2)

Guidance literature:

With Daicel Chiracel OD-H; In ethanol; n-heptane; Purification / work up; Resolution of racemate;

Reference yield:

→ (2S,4'R,8'R)-α-Tocopherol (59-02-9,2074-53-5,10191-41-0,18920-63-3,77171-97-2,77171-98-3,78656-09-4,78656-10-7,78656-11-8,78656-12-9,78656-13-0,79434-82-5,79434-83-6,113085-06-6)

Guidance literature:

(2S,4'R,8'R)-α-Tocopheryl-<4-phenylazo-benzoat>,LiAlH4 in sd. Ae.;

DOI:10.1002/hlca.19630460134

upstream raw materials:

vitamin E

cyclohexane

(+/-)-α-tocopherol

Downstream raw materials:

DL-α-tocopherol nicotinate

(all-rac)-α-tocopheryl acetate

DL-α-Tocopheryl phosphate dianilide

Refernces

• 1、 Jovanovic, Slobodan V.,Jankovic, Ivana,Josimovic, Ljubica. "Electron-transfer reactions of alkyl peroxy radicals". . p. 9018 - 9021. Retrieved 2007/10/02.