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Reactions of vitamin A with acceptors of electrons. Interactions with iodine and the formation of iodide.

ABSTRACT: 1. The reactions of retinol and retinoic acid with iodine were investigated since knowledge of the chemical reactions of vitamin A with acceptors of electrons may shed light on its biochemical mode of action. 2. Colloidal retinol, but not retinoic acid, reacts with iodine to yield a blue-green complex that rapidly decomposes, giving iodide and an unknown species with lambda(max.) at 870mmu. 3. In addition, both retinol and retinoic acid reduce iodine to iodide by a reaction that does not involve an intermediate coloured complex; this reaction appears to yield unstable carbonium ion derivatives of the vitamin. 4. The presence of water greatly facilitates the production of iodide from vitamin A and iodine. 5. Possible chemical pathways involved in these reactions are discussed. 6. It is suggested that the chemical properties of retinol and retinoic acid that underlie their biochemical behaviour might be apparent only when the molecules are at a lipid-water interface, and that vitamin A might be expected to react with a number of different electron acceptors in vivo.

SUBMITTER: Lucy JA

PROVIDER: S-EPMC1187696 | biostudies-other | 1969 Apr

REPOSITORIES: biostudies-other

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Reactions of vitamin A with acceptors of electrons. Formation of radical anions from 7,7,8,8-tetracyanoquinodimethane and tetrachloro-1,4-benzoquinone.

Project description:1. The interactions of retinol and retinoic acid with two electron acceptors, 7,7,8,8-tetracyanoquinodimethane (TCNQ) and tetrachloro-1,4-benzoquinone (chloranil), were studied in an investigation on the ability of vitamin A to behave as a donor of electrons. 2. Retinol reacts with TCNQ in polar organic solvents with the formation, as judged by spectral studies, of the radical anion of TCNQ. 3. Addition of the products of this reaction to water is accompanied by a rapid consumption of OH(-) ions. 4. Consumption of OH(-) ions is also a feature of the reactions between retinol and chloranil, but the spectrum of the radical anion of chloranil is observed only when retinol and chloranil are suspended in aqueous salt solutions. 5. Retinoic acid behaves similarly to retinol in its reactions with TCNQ and chloranil, but it appears to be a weaker electron donor than retinol. 6. The reaction products that may be formed from retinol in its reactions with TCNQ and chloranil are discussed. 7. It is suggested that the ability of vitamin A to behave as a donor of electrons may be an important aspect of its biochemical mode of action.

| S-EPMC1187695 | biostudies-other

The Chlorate-Nitrous Acid-Iodine-Iodide Oscillating Reaction.

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Autoinhibition by Iodide Ion in the Methionine-Iodine Reaction.

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