gamma-Tocopherol

Base Information

• Chemical Name: gamma-Tocopherol
• CAS No.: 54-28-4
• Molecular Formula: C28H48 O2
• Molecular Weight: 416.688
• Hs Code.: 2932999099
• European Community (EC) Number: 231-523-4,200-201-5
• UNII: 8EF1Z1238F
• DSSTox Substance ID: DTXSID9049031
• Nikkaji Number: J213.540J
• Wikipedia: %CE%93-Tocopherol
• Wikidata: Q155753
• NCI Thesaurus Code: C68317
• Metabolomics Workbench ID: 29106
• ChEMBL ID: CHEMBL2151591
• Mol file: 54-28-4.mol

Synonyms:3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol;gamma-Tocopherol

Chemical Property of gamma-Tocopherol

Chemical Property:

• Appearance/Colour: clear light brown viscous liquid
• Vapor Pressure: 2.35E-11mmHg at 25°C
• Refractive Index: n20/D 1.505
• Boiling Point: 200 ºC (0.1 mmHg)
• PKA: 11.05±0.40(Predicted)
• Flash Point: 206°C
• PSA: 29.46000
• Density: 0.933g/cm³
• LogP: 8.53180
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Ethanol (Slightly), Methanol (Sparingly)
• XLogP3: 10.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 12
• Exact Mass: 416.365430770
• Heavy Atom Count: 30
• Complexity: 475

Purity/Quality:

≥98% ^*data from raw suppliers

γ-Tocopherol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 93072
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 24/25-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C=C2CCC(OC2=C1C)(C)CCCC(C)CCCC(C)CCCC(C)C)O
• Isomeric SMILES: CC1=C(C=C2CC[C@@](OC2=C1C)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)O
• Recent ClinicalTrials: A Study of Gamma Tocopherol-enriched Supplement on Lower Airway Responses to Inhaled Wood Smoke in Healthy Adults
• Uses: One of the naturally occurring forms of Vitamin E. Most abundant Tocopherol in soybean and corn oils. (+)-γ-Tocopherol has been used:as reference material for the quantification of γ-tocopherol in the oil sample using high performance liquid chromatography with diode array detector (HPLC/DAD)(192}as a component of diet to feed vitamin-E-depleted rats to study its effectsas an additive in the feed to study its effects in reducing dietary induced oxidative stress in vivo and improving meat lipid stability in broilers This Certified Spiking Solution? is suitable for use as a starting material in the preparation of linearity standards, calibrators, and controls in a variety of testing applications from diagnostic testing of Vitamin E deficiency by LC-MS/MS or HPLC to quality control testing of tocopherol-based dietary supplements or pharmaceutical preparations.

Technology Process of gamma-Tocopherol

There total 26 articles about gamma-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: 91.0%

(2R,4'R,8'R)-γ-tocopherol-5-carboxylic acid (187677-37-8) → gamma-tocopherol (54-28-4)

Guidance literature:

at 170 ℃; for 3h;

DOI:10.1016/j.tet.2004.11.047

Reference yield: 90.0%

phytylplastoquinol (96480-20-5,73980-80-0) → gamma-tocopherol (54-28-4)

Guidance literature:

With 2,6-di-O-methyl-β-cyclodextrin; ascorbic acid; In water; at 35 ℃; for 15h; tocopherol-cyclase enzyme;

DOI:10.1002/hlca.19940770705

Reference yield: 72.0%

(3R,7R,11R)-(E)-3,7,11,15-tetramethyl-1-(2,5-dimethoxy-3,4-dimethylphenyl)hexadecan-3-ol → gamma-tocopherol (54-28-4)

Guidance literature:

(3R,7R,11R)-(E)-3,7,11,15-tetramethyl-1-(2,5-dimethoxy-3,4-dimethylphenyl)hexadecan-3-ol; With ammonium cerium (IV) nitrate; In water; acetonitrile; at 0 ℃; for 2h;

With sodium dithionite; In water; acetone; at 20 ℃; for 0.5h;

With toluene-4-sulfonic acid; In toluene; at 65 ℃; for 0.5h;

DOI:10.1002/chem.201404458

upstream raw materials:

2-methyl-6-phythyl-1,4-benzoquinone

6-phytyltoluquinol

delta tocopherol

phytylplastoquinol

Downstream raw materials:

2,6-di(t-butyl)-4-phenylphenol

C₂₈H₄₇O₂

5-(morpholino[13C]methyl)-(2R,4'R,8'R)-γ-tocopherol

7,8-dimethyltocol

Refernces

• 1、 Wu, Zhongtao,Harutyunyan, Syuzanna R.,Minnaard, Adriaan J.. "Total synthesis of (R, R, R)-γ-tocopherol through cu-catalyzed asymmetric 1,2-addition". . p. 14250 - 14255. Retrieved 2015/03/18.
• 2、 Mazzini, Francesco,Netscher, Thomas,Salvadori, Piero. "Easy route to labeled and unlabeled R,R,R-γ-tocopherol by aryl demethylation of α-homologues". . p. 813 - 817. Retrieved 2007/10/03.