beta-Tocopherol

Base Information

• Chemical Name: beta-Tocopherol
• CAS No.: 148-03-8
• Deprecated CAS: 16662-70-7
• Molecular Formula: C₂₈H₄₈O₂
• Molecular Weight: 416.688
• European Community (EC) Number: 205-708-5,240-747-1
• UNII: 8K9365K9PX,9U6A490501
• DSSTox Substance ID: DTXSID10873424,DTXSID30884931
• Nikkaji Number: J236.825K
• Wikipedia: %CE%92-Tocopherol
• Wikidata: Q155667
• NCI Thesaurus Code: C68315
• RXCUI: 1792723
• Metabolomics Workbench ID: 38864
• Mol file: 148-03-8.mol

Synonyms:3,4-Dihydro-2,5,8-trimethyl-2-(4,8,12- trimethyltridecyl)-2H-1-benzopyran-6-ol;beta Tocopherol;beta-Tocopherol

Chemical Property of beta-Tocopherol

Chemical Property:

• Vapor Pressure: 2.8E-11mmHg at 25°C
• Melting Point: <25℃
• Refractive Index: 1.495
• Boiling Point: 516.3°Cat760mmHg
• PKA: 11.05±0.40(Predicted)
• Flash Point: 204.7°C
• PSA: 29.46000
• Density: 0.933g/cm³
• LogP: 8.53180
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Ethanol (Slightly), Ethyl Acetate (Slightly), Methanol (
• 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:

96% ^*data from raw suppliers

β-Tocopherol(RacemicMixture) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,N
• Hazard Codes: F,Xn,N
• Statements: 11-38-48/20-51/53-62-67-65
• Safety Statements: 36/37-61-62-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C2=C1OC(CC2)(C)CCCC(C)CCCC(C)CCCC(C)C)C)O
• Isomeric SMILES: CC1=CC(=C(C2=C1O[C@](CC2)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)O
• Description: (±)-β-Tocopherol is a lipid-soluble form of vitamin E with antioxidant activity. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals with an EC50 value of 68.2 μM. (±)-β-Tocopherol (100 μM) inhibits LPS-induced COX-2 gene expression in mouse RAW 264.7 macrophage cells. Unlike (±)-α-tocopherol , (±)-β-tocopherol does not inhibit smooth muscle cell proliferation, decrease PKC activity, increase phosphoprotein phosphatase 2A (PP2A) activity, or modify expression of the α-tropomyosin gene. [Matreya, LLC. Catalog No. 1071]
• Uses: One of the naturally occurring forms of Vitamin E. Is biologically less active than α-Tocopherol. This is the racemic mixture of all stereoisomers.

Technology Process of beta-Tocopherol

There total 7 articles about beta-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:

5,8-dimethyltocol (16698-35-4) → (2RS,4'R,8'R)-β-Tocopherol (148-03-8,16662-70-7,16698-35-4,48223-98-9)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 140 ℃; for 14h; Inert atmosphere;

Reference yield:

2,5-dimethylhydroquinone monobenzoate (21111-71-7) + phytol (150-86-7,844467-91-0) → (2RS,4'R,8'R)-β-Tocopherol (148-03-8,16662-70-7,16698-35-4,48223-98-9)

Guidance literature:

With zinc(II) chloride; decalin; anschl. mit wss.-methanol. H₂SO₄;

DOI:10.1021/ja01864a065

Reference yield:

2,5-dimethylhydroquinone (615-90-7) + phytol (150-86-7,844467-91-0) → (2RS,4'R,8'R)-β-Tocopherol (148-03-8,16662-70-7,16698-35-4,48223-98-9)

Guidance literature:

With zinc(II) chloride; at 180 ℃;

upstream raw materials:

2,5-dimethylhydroquinone monobenzoate

phytol

2,5-dimethylhydroquinone

formaldehyd

Downstream raw materials:

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

C₂₈H₄₇O₂

Refernces

• 1、 -. "Process of separating chiral isomers of chroman compounds and their derivatives and precursors". Page/Page column 15. . Retrieved 2012/12/13.