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The keto-enol tautomerism and the redox conversions of α-ketol fatty acids

✍ Scribed by A.N. Grechkin; R.A. Kuramshin; E.Y. Safonova; L.S. Mukhtarova; S.K. Latypov; A.V. Ilyasov

Publisher
Elsevier Science
Year
1993
Tongue
English
Weight
602 KB
Volume
66
Category
Article
ISSN
0009-3084

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✦ Synopsis

The main conversions of c~-ketol fatty acids (18:2 and 18:3), accompanying their redox interactions with 2,6dichlorophenolindophenol (DCPIP) and copper(II) acetate, were studied. The highest rates of oxidation with DCPIP were observed in the alkaline water solutions. In the acidic aqueous media or in organic solvents, reaction with DCPIP proceeded much more slowly. The presence of oxygen significantly altered the direction but not the kinetics of reaction. The predominant products of aerobic reaction with DCPIP under alkaline conditions were c~-ketol hydroperoxides. Similar incubations under argon atmosphere, excluding hydroperoxide formation, afforded 9,13-dihydroxy-12-oxo and 9,12-dioxo-13-hydroxy acids. The latter was also the main product of reaction with copper acetate, along with 9acetoxy-12-oxo-13-hydroxy acid. The free radical mechanism of the observed conversions is proposed.

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