Reaction of Carotenoids and Ferric Chloride: Equilibria, Isomerization, and Products
The Journal of Physical Chemistry B2003Vol. 107(22), pp. 5333–5338
Citations Over Time
Abstract
In the oxidation of carotenoids, ethyl all-trans-8‘-apo-β-caroten-8‘-oate and all-trans-β-carotene, with ferric chloride, several equilibria occur between Fe3+, Fe2+, Cl-, the neutral carotenoid, and its radical cation and dication. The radical cation and dication were found to abstract an electron from Fe2+. Isomerization of carotenoids occurs during the oxidation. In the presence of air, a stable product is formed in high yield during the oxidation. 1H NMR, LC-MS, and optical studies show that this product is the 5,8-peroxide of the starting material. A mechanism for the formation of this compound is proposed.
Related Papers
- → Formation and Characterization of the π-Radical Cation and Dication of π-Extended Tetrathiafulvalene Materials(2001)71 cited
- → π-dimerization of pleiadiene radical cations at low temperatures revealed by UV–vis spectroelectrochemistry and quantum theory(2011)10 cited
- → One‐ and Two‐Electron Oxidations of Pagodanes and Bissecododecahedradienes: Unusually Persistent Radical Cations(1987)38 cited
- → Dimethylcarbene, Its Radical Cation and Dication(1997)15 cited
- → Electrochemical Oxidation of 1‐(p‐Dimethylaminophenyl)‐3,3‐dimethyltriazene—Cyclic Voltammetric Detection of a Triazene Radical Cation and Dication(1992)10 cited