Res. Chem. Intermed.
, Vol. 32, No. 2, pp. 153–170 (2006)
Also available online - www.vsppub.com
OH radical oxidation of the sorbitylfurfural furanic ring
to sugar derivatives induced by radiolysis in aerobic
, GABRIELLA POGGI
MARIA LUISA NAVACCHIA
, MILA D’ANGELANTONIO
and SALVATORE S. EMMI
Istituto di Sintesi Organica e Fotoreattivita’ (ISOF) del CNR, Area della Ricerca,
Via P. Gobetti 101, I-40129 Bologna, Italy
Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2,
I-40126 Bologna, Italy
Received 2 February 2005; accepted 18 July 2005
Abstract—Chemical radiolytic oxidation induced by OH addition on 1-(2-furan-2-yl-5-hydroxy-
6-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
and the rearrangement of the produced peroxyl radicals to species,
which are likely to be effective OH-capturers, reinforces the antioxidant ability of SF.
Keywords: Sorbitylfurfural; furalglucitol; CAS 7089-59-0; functionalization; antioxidant; radiolysis;
radical oxidation; peroxyl radicals.
In our previous studies [1, 2] we assessed the reactions of sorbitylfurfural (SF) with
OH and a series of potentially harmful oxidizing radicals. These studies were aimed
at clarifying the ability of SF to capture unstable species and, thus, act as antioxidant
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