alpha-Tocopheronolactone

Base Information

• Chemical Name: alpha-Tocopheronolactone
• CAS No.: 3121-68-4
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.332
• UNII: EJ4295TK60
• DSSTox Substance ID: DTXSID90953293
• Wikidata: Q27894614
• Mol file: 3121-68-4.mol

Synonyms:alpha-tocopheronolactone;tocopheronolactone;tocopheronolactone, (+-)-isomer

Chemical Property of alpha-Tocopheronolactone

Chemical Property:

• Vapor Pressure: 2.28E-07mmHg at 25°C
• Melting Point: 64 °C
• Boiling Point: 423.1°Cat760mmHg
• Flash Point: 187.2°C
• PSA: 60.44000
• Density: 1.122g/cm³
• LogP: 2.66700
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 276.13615911
• Heavy Atom Count: 20
• Complexity: 565

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)C(=C(C1=O)C)CCC2(CCC(=O)O2)C)C

Technology Process of alpha-Tocopheronolactone

There total 7 articles about alpha-Tocopheronolactone 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: 82.0%

racemic 2,5,7,8-tetramethyl-2-(β-carboxyethyl)-6-hydroxy chroman (4072-32-6) → 2,3,5-trimethyl-6-(2-(2-methyl-5-oxotetrahydrofuran-2-yl)ethyl)cvclohexa-2,5-diene-1,4-dione (3121-68-4,15716-16-2,22625-17-8)

Guidance literature:

With iron(III) chloride; In methanol; water; at 20 ℃; for 0.5h; in dark;

Reference yield: 62.0%

5-methyl-5-vinyl-dihydro-furan-2-one (1073-11-6) + 2,3,5-Trimethyl-1,4-benzoquinone (935-92-2) → 2,3,5-trimethyl-6-(2-(2-methyl-5-oxotetrahydrofuran-2-yl)ethyl)cvclohexa-2,5-diene-1,4-dione (3121-68-4,15716-16-2,22625-17-8)

Guidance literature:

5-methyl-5-vinyl-dihydro-furan-2-one; 2,3,5-Trimethyl-1,4-benzoquinone; With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; at 20 ℃; for 0.5h;

With C₁₃H₁₄O₂; at 50 ℃; for 15h;

DOI:10.1021/acs.orglett.9b01672

Reference yield:

Trimethylhydroquinone (700-13-0) → 2,3,5-trimethyl-6-(2-(2-methyl-5-oxotetrahydrofuran-2-yl)ethyl)cvclohexa-2,5-diene-1,4-dione (3121-68-4,15716-16-2,22625-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / BF₃*Et₂O / dioxane / 1 h / 120 °C

2: 82 percent / FeCl₃*6H₂O / methanol; H₂O / 0.5 h / 20 °C / in dark

With boron trifluoride diethyl etherate; iron(III) chloride; In 1,4-dioxane; methanol; water;

upstream raw materials:

methanol

sulfuric acid

racemic 2,5,7,8-tetramethyl-2-(β-carboxyethyl)-6-hydroxy chroman

Trimethylhydroquinone

Downstream raw materials:

4-Hydroxy-4-methyl-6-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-hexanoic acid methyl ester

Refernces

• 1、 -. "CARBOXYLIC ACID DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISORDERS". Paragraph 0135. . Retrieved 2014/12/12.
• 2、 Kantoci, Darko,Wechter, William J.,Murray Jr., E. David,Dewind, Sally A.,Borchardt, Dan,Khan, Saeed I.. "Endogenous natriuretic factors 6: The stereochemistry of a natriuretic γ-tocopherol metabolite LLU-α". . p. 648 - 656. Retrieved 2007/10/03.