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OH radical oxidation of Sorbitylfurfural furanic ring to sugar derivatives, induced by radiolysis in aerobic environment. (Articolo in rivista)
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- OH radical oxidation of Sorbitylfurfural furanic ring to sugar derivatives, induced by radiolysis in aerobic environment. (Articolo in rivista) (literal)
- Anno
- 2005-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1163/156856706775372816 (literal)
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Russo, M.; Poggi, G.; Navacchia, M. L.; D'Angelantonio, M.; Emmi, S.S. (2005)
OH radical oxidation of Sorbitylfurfural furanic ring to sugar derivatives, induced by radiolysis in aerobic environment.
in Research on chemical intermediates (Print); VSP BV, Leiden (Paesi Bassi)
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- Russo, M.; Poggi, G.; Navacchia, M. L.; D'Angelantonio, M.; Emmi, S.S. (literal)
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- Russo, M. - Istituto per la Sintesi Organica e la Fotoreattività - CNR - Bologna
Poggi, G. - Università di Bologna, Dipartimento di Chimica \"G. Ciamician\"
Navacchia, M. L. - Istituto per la Sintesi Organica e la Fotoreattività - CNR - Bologna
D'Angelantonio, M, - Istituto per la Sintesi Organica e la Fotoreattività - CNR - Bologna
Emmi, S.S. - Istituto per la Sintesi Organica e la Fotoreattività - CNR - Bologna (literal)
- Titolo
- OH radical oxidation of Sorbitylfurfural furanic ring to sugar derivatives, induced by radiolysis in aerobic environment. (literal)
- Abstract
- Chemical radiolytic oxidation induced by OH addition on 1-(2-furan-2-yl-5-hydroxy6-hydroxymethyl-[1,3]dioxan-4-yl)-ethan-1,2-diol (sorbitylfurfural, SF) leads, in the presence of controlled amounts of oxygen, to a permanent functional modification of the target molecule. The yield of conversion reaches 60% of the starting material. LC-MS analysis allowed the identification, as final products, of carboxylic acids, butenal and hydroxy-furan derivatives in which the sugar chain remains unbroken, while the furanic ring is attacked first by OH and then by oxygen, giving in succession an intra-/inter-molecular rearrangement of the allylperoxyl radicals thus formed. The proposed oxidation of the furanic ring envisages the peroxyl intermediates undergoing mono- and/or bi-molecular reactions; a reaction path has been outlined and is reported here. The presence of unsaturated bonds in the final products could provide a further site for radical scavenger activity. Therefore, the fast reaction with O-2 and the rearrangement of the produced peroxyl radicals to species, which are likely to be effective OH-capturers, reinforces the antioxidant ability of SF. (literal)
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