3121-68-4

Basic information

• Product Name: tocopheronolactone
• Synonyms: tocopheronolactone
• CAS NO: 3121-68-4
• Molecular Formula: C16H20O4
• Molecular Weight: 276.3276
• Mol File: 3121-68-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 64 °C
• Boiling Point: 423.1°Cat760mmHg
• Flash Point: 187.2°C
• Appearance: /
• Density: 1.122g/cm³
• Vapor Pressure: 2.28E-07mmHg at 25°C
• Refractive Index: 1.507
• CAS DataBase Reference: tocopheronolactone(CAS DataBase Reference)
• NIST Chemistry Reference: tocopheronolactone(3121-68-4)
• EPA Substance Registry System: tocopheronolactone(3121-68-4)

Safety Data

• Hazardous Substances Data: 3121-68-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H20O4/c1-9-10(2)15(19)12(11(3)14(9)18)5-7-16(4)8-6-13(17)20-16/h5-8H2,1-4H3

Upstream product

• 1073-11-6 5-methyl-5-vinyl-dihydro-furan-2-one 
• 935-92-2 2,3,5-Trimethyl-1,4-benzoquinone 
• 1088428-42-5 α-CEHC sulfate trimethylamine 
• 700-13-0 Trimethylhydroquinone 
• 4072-32-6 racemic 2,5,7,8-tetramethyl-2-(β-carboxyethyl)-6-hydroxy chroman 
• 67-56-1 methanol 
• 7664-93-9 sulfuric acid 

Downstream Products

• 52078-58-7 4-Hydroxy-4-methyl-6-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-hexanoic acid methyl ester 

Relevant articles and documents

Catalytic Redox Chain Ring Opening of Lactones with Quinones to Synthesize Quinone-Containing Carboxylic Acids

Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C-H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes a carbocation intermediate.

Isolation and identification of α-CEHC sulfate in rat urine and an improved method for the determination of conjugated α-CEHC

2,5,7,8-Tetramethyl-2-(2′-carboxyethyl)-6-hydroxychroman (α-CEHC), the water-soluble metabolite of α-tocopherol (α-TOH) with a shortened side chain but an intact hydroxychroman structure, has been identified in human urine and are thought to be produced in significant amount at excess intake of α-TOH. In previous studies, CEHCs in biological specimens were measured by HPLC, GC-MS or LC-MS, preceded by a hydrolysis procedure using either enzyme or methanolic HCl. In an attempt to analyze α-CEHC in rat urine accordingly, we observed that enzyme hydrolysis was relatively inefficient in releasing α-CEHC compared to high concentrations of HCl. The HCl releasable α-CEHC conjugate was isolated and chemically identified as 6-O-sulfated α-CEHC (α-CEHC sulfate). Using the synthetic α-CEHC sulfate standard, it was found that sulfatase could not hydrolyze to a significant extent. On the other hand, pretreatment with HCl at 60°C in the presence of ascorbate, followed by a one-step ether extraction, not only hydrolyzed the sulfate conjugate completely but also extracted α-CEHC with high recovery. The inclusion of ascorbate minimized the conversion of α-CEHC to α-tocopheronolactone in the HCl pretreatment. A complete procedure for the quantitative analysis of α-CEHC including HCl hydrolysis, ether extraction and reverse phase isocratic HPLC-ECD was thus established. In conclusion, α-CEHC sulfate was isolated and identified as the HCl-releasable conjugate of α-CEHC in rat urine. A rapid and sensitive method with high reproducibility for the determination of free, conjugated and total α-CEHC is then established.

Ubiquinone and related compounds. XXXI. Synthesis of urinary metabolites of ubiquinone, phylloquinone, α-tocopherol and their related compounds

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