DL-alpha-Tocopherol

Base Information

• Chemical Name: DL-alpha-Tocopherol
• CAS No.: 10191-41-0
• Deprecated CAS: 16826-11-2,181591-70-8,25094-97-7,364-50-1,4072-33-7,181591-70-8,25094-97-7,364-50-1,4072-33-7
• Molecular Formula: C29H50O2
• Molecular Weight: 430.715
• Hs Code.: 29362800
• European Community (EC) Number: 233-466-0,215-798-8,606-803-8
• NSC Number: 755839,82623,20812
• UNII: 7QWA1RIO01
• DSSTox Substance ID: DTXSID8021355
• Nikkaji Number: J24.789H
• Wikidata: Q27165663
• NCI Thesaurus Code: C74578
• RXCUI: 402899,1236136
• Metabolomics Workbench ID: 139099
• ChEMBL ID: CHEMBL49563
• Mol file: 10191-41-0.mol

Synonyms:DL-ALPHA-TOCOPHEROL;10191-41-0;alpha-tochopherol;Ephanyl;Tocopheroxy radical;TOCOPHEROL;all-rac-alpha-Tocopherol;alpha-Tocopherol, DL-;113085-06-6;Tocopheroxyl radical;DL-alpha tocopherol;Vitamin E DL-alpha;dl-.alpha.-Tocopherol;2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol;UNII-7QWA1RIO01;DL-5,7,8-trimethyltocol;7QWA1RIO01;CHEMBL49563;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-;DL-alpha-Tocopherol (Vitamin E);1406-18-4;2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol;all-rac-alpha-Tocopherol (Vitamin E);(2S, 4'R, 8'S)-alpha-Tocopherol;(2S, 4'S, 8'S)-alpha-Tocopherol;d-.alpha.-Tocopherol;(+-)-alpha-Tocopherol;6-Chromanol, 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-;alpha-Tocopherol-[D6] (Vitamin E-[D6]);EC 233-466-0;(2R)-alpha-Tocopherol (Mixture of Diastereomers);Evitaminum;Almefrol;Emipherol;Etamican;Vitayonon;5-17-04-00168 (Beilstein Handbook Reference);Ilitia;CCRIS 5853;Vitaplex E;Aquasol E;Covi-ox;Spavit E;Endo E;Vita E;.alpha.-Tocopherol;EINECS 233-466-0;DL-Tocopherol;RRR-alpha-tocopherol;(2R, 4'S, 8'R)-alpha-Tocopherol;(2R, 4'S, 8'S)-alpha-Tocopherol;(2S, 4'R, 8'R)-alpha-Tocopherol;(2S, 4'S, 8'R)-alpha-Tocopherol;2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromen-6-ol;BRN 0094012;2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)chroman-6-ol;(+/-)-alpha-Tocopherol;.Alpha.-tocopherol, DL-;3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol;SR-05000001813;5,6 Trans-Calcipotriol;DTXSID8021355;2,5,7,8-Tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol;MFCD00072045;NSC-20812;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl- 2-(4,8,12-trimethyltridecyl)-;.alpha.-Tokoferol;.alpha. Tocopherol;5,8-Trimethyltocol;Tocopherol (JP17);Spectrum_001195;DL- alpha -Tocopherol;DL-all-rac-A-Tocopherol;Spectrum2_000722;Spectrum3_001338;Spectrum4_001771;Spectrum5_000381;RONOTEC DF 120;IRGANOX E 210;UVINUL 2000AO;TOCOPHEROL, DL-ALPHA;SCHEMBL22303;BSPBio_003095;KBioGR_002282;KBioSS_001675;SPECTRUM310039;(all-R)-.alpha.-Tocopherol;DivK1c_000533;INS NO.307C;SPBio_000644;RAC-.ALPHA.-TOCOPHEROL;alpha-Tocopherol, >=95.5%;INS-307C;SCHEMBL14315133;(.+-.)-Med-E;(.+/-.)-.alpha.-Tocopherol;CHEBI:93909;HMS501K15;HSDB 8261;KBio1_000533;KBio2_001675;KBio2_004243;KBio2_006811;KBio3_002315;(2R,8'R)-.alpha.-Tocopherol;NINDS_000533;HMS1923I03;HMS2091C11;Pharmakon1600-00310039;3, 4- dihydro- 2, 5, 7, 8- tetramethyl- 2- (4, 8, 12- trimethyltridecyl)- 2H- benzopyran- 6- ol;C29H50O2 (DL-alpha-tocopherol);DL-ALPHA-TOCOPHEROL(307C);NSC20812;NSC82623;TOCOPHEROL,DL-ALPHA [VANDF];DL-.ALPHA.-TOCOPHEROL [MI];DL-ALPHA TOCOPHEROL [MART.];BBL027614;BDBM50436220;CCG-40162;E-307C;MFCD00072051;NSC-82623;NSC755839;s6104;STL372809;DL-ALPHA TOCOPHEROL [WHO-DD];AKOS015960364;ALL-RAC-ALPHA-TOCOPHEROL [FCC];DB14476;HY-W020044;NSC-755839;SDCCGMLS-0066634.P001;.ALPHA.-TOCOPHEROL, DL- [II];IDI1_000533;NCGC00095254-01;NCGC00095254-02;NCGC00095254-03;NCGC00095254-05;NCGC00095254-06;AC-10544;J24.789H;SY012869;SY057064;VS-08569;SBI-0051261.P003;(+/-)-alpha-Tocopherol, analytical standard;CS-0031997;FT-0600386;FT-0624406;FT-0625430;FT-0696605;T0251;EN300-20897;D02332;D70247;AB00051898_02;SR-05000001813-1;SR-05000001813-2;(+/-)-alpha-Tocopherol, synthetic, >=96% (HPLC);(+/-)-alpha-Tocopherol, tested according to Ph.Eur.;BRD-A82892199-001-01-7;Q27165663;(+/-)-alpha-Tocopherol, SAJ special grade, >=96.0%;F0001-2420;7A4513C3-131C-41D4-B6A0-7ED994AC2947;all-rac-alpha-TOCOPHERYL ACETATE IMPURITY C [EP IMPURITY];alpha-Tocopherol, British Pharmacopoeia (BP) Reference Standard;DL-alpha-Tocopherol (Vitamin E) 10 microg/mL in Acetonitrile;2,5,7,8-Tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol #;alpha-Tocopherol, European Pharmacopoeia (EP) Reference Standard;Alpha Tocopherol, United States Pharmacopeia (USP) Reference Standard;Alpha Tocopherol, Pharmaceutical Secondary Standard;Certified Reference Material;16826-11-2;2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, radical ion(1+), (2R-(2R*(4R*,8R*)))-;2H-1-Benzopyran-6-ol,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, [2R*(4R*,8R*)]-(.+-.)-;2H-1-Benzopyran-6-ol,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, [2R-[2R*(4R*,8R*)]]-

Chemical Property of DL-alpha-Tocopherol

Chemical Property:

• Appearance/Colour: low yellow powder
• Vapor Pressure: 4.59E-10mmHg at 25°C
• Melting Point: 2-4 °C
• Refractive Index: n20/D 1.506
• 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
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: H2O: insoluble
• Water Solubility.: Miscible with chloroform, vegetable oils, ether, acetone and alcohol. Immiscible with water.
• 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:

98% ^*data from raw suppliers

a-Tocopherol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T,F
• Statements: 36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-37/39-45-36/37-16-7

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
• Recent ClinicalTrials: Vitamin E Pharmacokinetics and Biomarkers in Normal and Obese Women
• Recent EU Clinical Trials: Advances in the management of mandibular osteoradionecrosis: Pentoxyfilline and Tocopherol as medical treatment.
• Recent NIPH Clinical Trials: Chemotherapy for osteoradionecrosis of mandible using a pentoxifylline-tocopherol-clodronate combination (PENTOCLO).
• Uses: dl-α-Tocopherol is the racemic analog of α-Tocopherol (T526125), 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. dl-α-Tocopherol is an antioxidant that protects cell membrane lipids from oxidative damage. DL-α-Tocopherol is used as an antioxidant that protects cell membrane lipids from oxidative damage. These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Technology Process of DL-alpha-Tocopherol

There total 14 articles about DL-alpha-Tocopherol 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: 92.4%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → (+/-)-α-tocopherol (10191-41-0,18920-62-2)

Guidance literature:

methanetrisulfonic acid; In Ethylene carbonate; n-heptane; water; at 50 - 140 ℃; for 1 - 1.66667h;

Reference yield: 60.0%

4-((3R,7R,11R)-3-Hydroxy-3,7,11,15-tetramethyl-hexadecyl)-5,7,8-trimethyl-1-oxa-spiro[2.5]octa-4,7-dien-6-one (129658-43-1) → (+/-)-α-tocopherol (10191-41-0,18920-62-2)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; for 4h;

Reference yield: 17.0%

5-nitromethyl-γ-tocopherol acetate → (+/-)-α-tocopherol (10191-41-0,18920-62-2)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride;

upstream raw materials:

4-((3R,7R,11R)-3-Hydroxy-3,7,11,15-tetramethyl-hexadecyl)-5,7,8-trimethyl-1-oxa-spiro[2.5]octa-4,7-dien-6-one

(RS)-isophytol

Trimethylhydroquinone

DL-α-tocopherol acetate

Downstream raw materials:

tocopheryl linoleate

cyclohexyl hydroperoxide

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

dl-α-Tocopheryl palmitate

Refernces

• 1、 Fang, Jian-Guo,Bo, Zhou. "Structure-activity relationship and mechanism of the tocopherol- regenerating activity of resveratrol and its analogues". . p. 11458 - 11463. Retrieved 2008.
• 2、 -. "SYNTHESIS OF CHROMANOL DERIVATIVES". Page/Page column 40-41. . Retrieved 2020/03/05.
• 3、 -. "Process of separating chiral isomers of chroman compounds and their derivatives and precursors". Page/Page column 14. . Retrieved 2012/12/13.