72657-56-8Relevant academic research and scientific papers
Design, synthesis, and biological characterization of potential antiatherogenic nitric oxide releasing tocopherol analogs
Lopez, Gloria V.,Batthyany, Carlos,Blanco, Fabiana,Botti, Horacio,Trostchansky, Andres,Migliaro, Eduardo,Radi, Rafael,Gonzalez, Mercedes,Cerecetto, Hugo,Rubbo, Homero
, p. 5787 - 5796 (2007/10/03)
Synthesis and biological characterization of a series of α-tocopherol analogs with NO-releasing capacity are reported. The selected NO-donor moieties were nitrooxy and furoxan. All products were tested for their in vitro NO-releasing capacities, vasodilat
Reaction of 5a-bromo-α-tocopherol with nucleophiles
Rosenau,Habicher
, p. 647 - 653 (2007/10/03)
The synthesis of different classes of 5a-substituted tocopherols is described. These compounds are potent antioxidants and highly interesting as vitamin E carriers. The reaction of the readily available 5a-bromo-α-tocopherol with alcohols and phenols is shown to produce 5a-alkoxy-α-tocopherols (3-5, 8, 9) and 5a-aryloxy-α-tocopherols (6, 7), respectively, with high yields. 5a-α-Tocopheryl esters (10, 11) are prepared by reaction with metal carboxylates. 5a-Bromo-α-tocopherol is used as well to introduce tocopheryl groups into tertiary amines by quaternization, that renders these compounds (13, 14) soluble in water and in common organic solvents. 5a-Bromo-α-tocopherol also reacts as an alkylating agent with sterically hindered phenols in a Friedel-Crafts reaction. Phenols not highly substituted are exclusively alkylated in the para position at room temperature or below, whereas at higher temperature the para- as well as the orthoalkylated product is observed.
Nitric oxide-induced oxidation of α-tocopherol
D'Ischia, Marco,Novellino, Luisa
, p. 1747 - 1753 (2007/10/03)
Exposure of α-tocopherol (α-T) to nitric oxide under aerobic conditions resulted in a complex oxidation process whose final outcome was dictated by the nature of the reaction medium. In a cyclohexane solution, a prevailing route led to a mixture of relatively unstable polar products positive to Griess reagent. On standing at room temperature these were partially converted to the novel 2,3-dimethyl-4-acetyl-4-hydroxy-5-nitroso-2-cyclopentenone derivative. Reaction of α-T via a secondary oxidation path led to the formation of α-tocopherylquinone (α-TQ) as well as of little amounts of the corresponding nitrite ester. A quite different product pattern was observed when the reaction was carried out on a suspension of α-T in 0.1 M phosphate buffer, pH 7.4. Besides a significant formation of α-TQ and its nitrite ester, product analysis revealed a characteristic pattern of apolar compounds consisting of a yellow dimer and a series of related oligomers. These results provide an improved chemical background to inquire into the role of α-T in nitric oxide-induced tissue injury.
Novel tocopherol compounds I. Bromination of α-tocopherol-reaction mechanism and synthetic applications
Rosenau,Habicher
, p. 7919 - 7926 (2007/10/02)
Bromination of α-tocopherol is shown to proceed as a two-step process including the occurrence of an ortho-quinone methide, not as a radical-chain reaction, contrary to earlier reports. The ortho-quinone methide intermediate is also produced by oxidation
A New Synthesis of α-Tocopherol
Olson, Gary L.,Cheung, Ho-Chuen,Morgan, Keith,Saucy, Gabriel
, p. 803 - 805 (2007/10/02)
α-Tocopherol (vitamin E,1) has been synthesized in racemic form following a new strategy in which the aromatic ring of the chroman is constructed by addition of the dianion of 2,4-pentanedione to 1,2-epoxy-2,6,10,14-tetramethylpentadecane (5) as a side-ch
