77171-97-2

Basic information

• Product Name: α-tocopherol
• Synonyms: α-tocopherol
• CAS NO: 77171-97-2
• Molecular Weight: 430.715
• Mol File: 77171-97-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: α-tocopherol(CAS DataBase Reference)
• NIST Chemistry Reference: α-tocopherol(77171-97-2)
• EPA Substance Registry System: α-tocopherol(77171-97-2)

Safety Data

• Hazardous Substances Data: 77171-97-2(Hazardous Substances Data)

Usage

Chemical Description

α-tocopherol and γ-tocotrienol are forms of vitamin E.

Upstream product

• 188416-16-2 (R)-(+)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol 
• 118100-81-5 (R)-6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carbaldehyde 
• 918876-45-6 benzyl (R)-6-(benzyloxy)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylate 
• 53101-49-8 (R)-trolox 
• 474255-87-3 (3S,7R)-3,7,11-trimethyl-10-dodecen-1-ol 
• 6750-34-1 3,7,11-trimethyldodecyl alcohol 
• 479353-40-7 (R)-[3,4-dihydro-6-benzyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]methyl trifluoromethane-sulfonate 
• 17081-92-4 1-bromo-3,7,11-trimethyldodecane 
• 10191-41-0 (+/-)-α-tocopherol 
• 79397-61-8 (R)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ethanol-p-toluenesulfonate 
• 79434-75-6 (S)-6-Benzyloxy-2,5,7,8-tetramethyl-2-((4S,8S)-4,8,12-trimethyl-tridecyl)-chroman 
• 59-02-9 vitamin E 

Downstream Products

• 1406-70-8 (all-rac)-α-tocopheryl acetate 
• 1406-70-8 α-tocopheryl acetate 
• 16676-75-8 DL-α-tocopherol nicotinate 
• 87291-70-1 DL-α-Tocopheryl phosphate dianilide 

Relevant articles and documents

Screening of a virtual mirror-image library of natural products

We established a facile access to an unexplored mirror-image library of chiral natural product derivatives using d-protein technology. In this process, two chemical syntheses of mirror-image substances including a target protein and hit compound(s) allow the lead discovery from a virtual mirror-image library without the synthesis of numerous mirror-image compounds.

PROCESS OF SEPARATING CHIRAL ISOMERS OF CHROMAN COMPOUNDS AND THEIR DERIVATIVES AND PRECURSORS

The present invention relates to a process of separating chiral isomers of chroman compounds, particularly tocopherols and tocotrienols as well as the esters and intermediates thereof. It has been found that this process allows a separation of the desired isomer with a higher yield and enables the use of the non-desired isomers in a very efficient way. Said process is particularly useful when implemented in an industrial process. Furthermore, it has been found that this process allows using isomer mixtures as they result from traditional industrial synthesis.

Electron-transfer reactions of alkyl peroxy radicals

One-electron-transfer reactions of alkyl peroxy radicals were studied by pulse radiolysis of aqueous solutions. At pH 13, the methyl peroxy radical was found to rapidly, k = 1 × 105-4.9 × 107 s-1, and quantitatively oxidize various organic substrates with E13 = 0.13-0.76 V vs NHE. On the other hand, this radical was unreactive with compounds with E13 ≥ 0.85 V. Consequently, E13 of the methyl peroxy radical is higher than 0.76 V and lower than 0.85 V, which means that E7 is in the range 1.02-1.11 V. At pH 8, the rate constants of the oxidation of four ferrocene derivatives by the alkyl peroxy radicals ranged from 7.1 × 104 M-1 s-1 for ferrocenedicarboxylate (E8 = 0.66 V) to 2.3 × 106 M-1 s-1 for (hydroxymethyl)ferrocene (E8 = 0.42 V). These rate constants were used to evaluate the reduction potential and self-exchange rate of alkyl peroxy radicals in neutral media from the Marcus equation. The calculated E7 = 1.05 V is in excellent agreement with the estimated E7 = 1.02-1.11 V and with one of the perviously published values E7 = 1.0 V, but the value is in excellent agreement higher than the other E7 ～ 0.6 V. It is suggested that the high reorganization energy, λ = 72 kcal mol-1 redox couple originates from the requirement for solvent reorganization due to the solvation of hydroperoxide anion in the transition state. In support of this are the activation parameters of the reaction of the methyl peroxy radical with uric acid. The activation entropy is 9 eu lower at pH 7.3 than it is at pH 13.2, whereas the activation enthalpies are unchanged. The importance of entropy control was verified in the reactions of cyclohexyl peroxy radicals with α- and δ-tocopherol in aerated cyclohexane (ΔH+ ≈ 0 kcal/mol, and ΔS+ = -25 and -26 eu). The implications of these findings on the inactivation of alkyl peroxy radicals in general are discussed.