18920-62-2

Basic information

• Product Name: VE
• CAS NO: 18920-62-2
• Molecular Formula: C29H50O2
• Molecular Weight: 430.7061
• Mol File: 18920-62-2.mol
• Article Data: 181

Chemical Properties

• Appearance: /
• CAS DataBase Reference: VE(CAS DataBase Reference)
• NIST Chemistry Reference: VE(18920-62-2)
• EPA Substance Registry System: VE(18920-62-2)

Safety Data

• Hazardous Substances Data: 18920-62-2(Hazardous Substances Data)

Upstream product

• 21980-71-2 neophytadiene 
• 700-13-0 Trimethylhydroquinone 
• 150-86-7 phytol 
• 395645-30-4 (3RS,7R,11R)-3,7,11,15-tetramethylhexadec-1-en-3-ol 
• 16825-16-4 (6R,10R)-6,10,14-trimethylpentadecan-2-one 
• 1629168-07-5 C₂₉H₄₈O₄ 
• 1629168-02-0 C₂₉H₄₆O₃ 
• 1629168-08-6 C₃₀H₅₂O₂ 
• 112109-69-0 4-hydroxy-2,3,5-trimethylphenyl pivalate 
• 6750-34-1 (3R,7R)-hexahydrofarnesol 
• 1629281-17-9 C₁₅H₂₂O₃ 
• 130422-86-5 4-methoxy-2,3,5-trimethylphenol 
• 1629168-03-1 1-(2-hydroxy-5-methoxy-3,4,6-trimethylphenyl)ethanone 
• 105470-79-9 (3R,7R,5E)-3,7,11-trimethyldodecan-1-al 

Downstream Products

• 72657-56-8 α-tocopherylquinone 
• 527-18-4 Durohydroquinone 
• 18920-63-3 vitamin E 
• 186537-56-4 (2RS,4R,8R)-α-tocopherol 

Relevant articles and documents

Tunneling effect in regeneration reaction of vitamin e by ubiquinol

A kinetic study of the regeneration reaction of vitamin E by ubiquinol was carried out by means of double-mixing stopped-flow spectroscopy. A substantial deuterium kinetic-isotope effect was observed on the second-order rate constant and the activation energy. In the regeneration reaction of α-tocopherol, deuteration of ubiquinol increased and decreased the activation energy and the second-order rate constant by 6.1 kJ/mol and a factor of 18.3, respectively. From this result, it is considered that proton tunneling plays an important role in the regeneration reaction of vitamin E by ubiquinol. The conditions under which the tunneling effect becomes an important factor were discussed in conjunction of our experimental results.

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Catalytic performance of nanoscopic, aluminium trifluoride-based catalysts in the synthesis of (all-rac)-α-tocopherol

A novel nanoscopic, partly hydroxylated aluminium fluoride was prepared in a sol-gel fluorination synthesis and characterised by IR probe molecules. It was shown that this material has, in contrast to high surface area aluminium fluoride (HSAlF3) which is one of the strongest Lewis acids, a low amount of strong Lewis acid sites combined with weak and medium strength Br?nsted sites. Both materials were tested in the synthesis of (all-rac)-α-tocopherol through the condensation of 2,3,6- trimethylhydroquinone (TMHQ) with isophytol (IP). The activity data indicate the partly hydroxylated aluminium fluoride to be a very efficient and highly selective catalyst for (all-rac)-α-tocopherol (>99.9%, for an IP conversion of 100%) whereas high surface area aluminium fluoride is a poor catalyst for this reaction.

Novel sol-gel synthesis of acidic MgF2-x(OH)x materials

Novel magnesium fluorides have been prepared by a new fluorolytic sol-gel synthesis for fluoride materials based on aqueous HF. By changing the amount of water at constant stoichiometric amount of HF, it is possible to tune the surface acidity of the resulting partly hydroxylated magnesium fluorides. These materials possess medium-strength Lewis acid sites and, by increasing the amount of water, Br?nsted acid sites as well. Magnesium hydroxyl groups normally have a basic nature and only with this new synthetic route is it possible to create Br?nsted acidic magnesium hydroxyl groups. XRD, MAS NMR, TEM, thermal analysis, and elemental analysis have been applied to study the structure, composition, and thermal behaviour of the bulk materials. XPS measurements, FTIR with probe molecules, and the determination of N 2/Ar adsorption-de-sorption isotherms have been carried out to investigate the surface properties. Furthermore, activity data have indicated that the tuning of the acidic properties makes these materials versatile catalysts for different classes of reactions, such as the synthesis of (all-rac)-[α]-tocopherol through the condensation of 2,3,6- trimethylhydroquinone (TMHQ) with isophytol (IP).

Synthesis of 2,2-dialkyl chromanes by intramolecular Ullmann C–O coupling reactions toward the total synthesis of D-α-tocopherol

The complete synthesis of D-α-tocopherol was achieved using our developed-Ullmann C–O coupling reaction as a key reaction. The synthesis of the core structure of D-α-tocopherol, which is a chiral chromane, has never been reported using intramolecular Ullmann C–O coupling reactions owing to the low reactivity of electron-rich iodoarenes with tertiary alcohols. Because the developed intramolecular C–O coupling reactions prefer electron-rich iodoarenes with tertiary alcohols, we successfully synthesized the chiral chromane core and achieved the total synthesis of D-α-tocopherol.

ISOLATION AND IDENTIFICATION OF INTERMEDIATE COMPOUNDS IN THE SYNTHESIS OF DL-α-TOCOPHEROL

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Modern notions of the mechanism of α-tocopherol synthesis. Homogeneous catalysis by Lewis acids

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MECHANISM OF THE CONDENSATION OF 2,3,6-TRIMETHYLHYDROQUINONE WITH ISOPHYTOL

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Kinetic study of the α-tocopherol-regeneration reaction of ubiquinol-10 in methanol and acetonitrile solutions: Notable effect of the alkali and alkaline earth metal salts on the reaction rates

A kinetic study of regeneration reaction of α-tocopherol (α-TocH) by ubiquinol-10 has been performed in the presence of four kinds of alkali and alkaline earth metal salts (LiClO4, NaClO4, NaI, and Mg(ClO4)2) in methanol and acetonitrile solutions, using double-mixing stopped-flow spectrophotometry. The second-order rate constants (kr's) for the reaction of α-tocopheroxyl (α-Toc?) radical with ubiquinol-10 increased and decreased notably with increasing concentrations of metal salts in methanol and acetonitrile, respectively. The kr values increased in the order of no metal salt 4 ～ NaI 4 4)2 at the same concentration of metal salts in methanol. On the other hand, in acetonitrile, the kr values decreased in the order of no metal salt > NaClO4 ～ NaI > LiClO4 > Mg(ClO4)2 at the same concentration of metal salts. The metal salts having a smaller ionic radius of cation and a larger charge of cation gave a larger kr value in methanol, and a smaller k r value in acetonitrile. The effect of anion was almost negligible in both the solvents. Notable effects of metal cations on the UV-vis absorption spectrum of α-Toc? radical were observed in aprotic acetonitrile solution, suggesting complex formation between α-Toc? and metal cations. On the other hand, effects of metal cations were negligible in protic methanol, suggesting that the complex formation between α-Toc? and metal cations is hindered by the hydrogen bond between α-Toc? and methanol molecules. The difference between the reaction mechanisms in methanol and acetonitrile solutions was discussed on the basis of the results obtained. High concentrations of alkali and alkaline earth metal salts coexist with α-TocH and ubiquinol-10 in plasma, blood, and many tissues, suggesting the contribution of the metal salts to the above regeneration reaction in biological systems.

Highly Acidic BINOL-Derived Phosphoramidimidates and their Application in the Bronsted Acid Catalyzed Synthesis of α-Tocopherol

The design and synthesis of highly acidic BINOL-derived N,N′-bistriflylphosphoramidimidate and N,N′-bisarylsulfonylphosphoramidimidate Bronsted acid catalysts are reported.

Direct Construction of the Chroman Structure from 1,3-Diene. Regioselective Protonation of Acyclic Polyene

The regioselective protonation of acyclic polyene was achieved, dependent on the choice of catalyst.The addition of myrcene to trimethylhydroquinone, using boron trifluoride-diethyl ether (1/1), predominantly gave a spiro structure.When (+)-10-camphorsulfonic acid was used as a catalyst, the major compound produced was chroman.

New synthesis of 3,4-dehydro-α-tocotrienol and vitamin E

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Synthesis of dl-α-tocopherol and dl-α-tocotrienol

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Formation and decay dynamics of vitamin e radical in the antioxidant reaction of vitamin E

In order to understand the dynamics of antioxidant actions of vitamin E (α-, β-, γ-, and δ-tocopherols, TocH) in biological systems, kinetic study of the formation and decay reactions of vitamin E radicals (α-, β-, γ-, and γ- tocopheroxyls, Toc ?) has been performed in organic solvents, using stopped-flow spectrophotometry. By mixing α-, β-, γ-, and δ-TocH with aryloxyl radical (ArO ?) in ethanol, the peaks of the UV-vis absorption due to α-, β-, γ-, and δ-Toe? radical appeared rapidly at ca. 430-340 nm, showed maxima, and then decayed gradually. The second-order rate constants (κa and 2κd) for the formation and decay (that is, bimolecular disproportionation) reactions of a-Toe were determined by comparing the observed curves with the simulation ones obtained by the numerical calculation of differential equations related to the above reactions. From the results, the wavelengths of absorption maxima (λmax i) and molar extinction coefficients (ε) (i = 1-4) of the optical spectra were determined for α-Toc? radical. Notable solvent effects have been observed for the reaction rates (κf and 2κd) and absorption spectra (λmax i and εi) of α-Toc? radical. The scheme of the formation and decay reactions of α-, β-, γ-, and δ-Toc? radicals has been discussed based on the results obtained.

Novel PEGylated derivatives of α-tocopherol for nanocarrier formulations; synthesis, characterization and in vitro cytotoxicity against MCF-7 breast cancer cells

Despite numerous beneficial therapeutic effects namely antioxidant and anti-inflammatory activity, Vitamin E has limited clinical applications due to its low water solubility. Throughout the present work, α-tocopherol's new PEGylated derivatives alongside with polyethylene glycol 300 (α-TPGT300), 400 (α-TPGT400), and 1000 (α-TPGT1000) were synthesized. A 1,2,3-triazole ring was utilized as a linker for the attachment of alpha tocopherol to the PEGs through a click reaction. The purified derivatives were characterized by the means of 1H NMR, 13C NMR, mass spectroscopy, UV–vis and FT-IR methods. Synthesized derivatives’ capacity to produce self-assembly nanoparticles was evaluated employing the critical micelle concentration (CMC) values. The stability of the micelles was studied by size analysis. In vitro cytotoxicity of the products was investigated using MTT assay against MCF-7 breast cancer cells. The IC50 value for TPGT1000 after 24 h treatment was 15.0 ± 1.8 μM, whereas no significant cytotoxicity effect was observed following the treatment of MCF-7 cells by TPGT300, 400. The present study showed that polymeric micelle TPGT1000 possessed better physicochemical and biological properties including relatively lower CMC value, higher stability in FBS environment in addition to higher cytotoxicity against MCF-7 breast cancer cells compared to the lower molecular weight PEGylated derivatives. These results confirmed that increasing PEG chain length left a positive effect on the polymeric micelle properties and also improved the cytotoxicity effect of new PEGylated vitamin E derivatives.

A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh2andtBuOK

A general method for the demethylation, debenzylation, and deallylation of aryl ethers using HPPh2andtBuOK is reported. The reaction features mild and metal-free reaction conditions, broad substrate scope, good functional group compatibility, and high chemical selectivity towards aryl ethers over aliphatic structures. Notably, this approach is competent to selectively deprotect the allyl or benzyl group, making it a general and practical method in organic synthesis.

SYNTHESIS OF CHROMANOL AND 2-METHYL-1,4-NAPHTHOQUINONE DERIVATIVES

The present invention relates to a process for the production of chromanol and 2-methyl-1,4-naphthoquinone derivatives, more specifically to a process for preparing a compound of the general formula (I) or (II) wherein the variables are as defined in the claims and the description.