Abstract
2,4-Furfurylidene-D-sorbitol and its tetra-methyl ether: synthesis, conformational studies, and radical scavenging activity
Highlights
The structure of 1-[2-(furan-2-yl)-5-hydroxy-6-(hydroxymethyl)-1,3-dioxan-4-yl]ethane-1,2-diol] (2,4-furfurylidene-D-sorbitol) and its tetra-methyl ether was established by a detailed NMR analysis
The complete methylation of compound 1 in water could be achieved only using a large excess of dimethyl sulphate in an aqueous solution of NaOH
We describe the synthesis of 2,4-furfurylidene-D-sorbitol (1) and its tetra-methyl ether 2 and show the results of a detailed NMR analysis that suggest that both compounds exist predominantly in one ring conformation
Summary
The structure of 1-[2-(furan-2-yl)-5-hydroxy-6-(hydroxymethyl)-1,3-dioxan-4-yl]ethane-1,2-diol] (2,4-furfurylidene-D-sorbitol) and its tetra-methyl ether was established by a detailed NMR analysis. 1-[2-(furan-2-yl)-5-hydroxy-6-(hydroxymethyl)-1,3-dioxan-4-yl]ethane-1,2-diol (1) and its tetramethyl ether 2 (Figure 1) are 1,3-dioxane cyclic acetals that were claimed to prevent radical-caused skin aging.[1]. Concerning the anti-radical activity of 2,4-furfurylidene-D-sorbitol (1), the claimed protection from the free radical-caused skin damage initially proposed for this compound[1] has been demonstrated using an in vitro model of fibroblast cultures exposed to tert-butyl hydroperoxide.[10] The scavenging activity of compound 1 against the hydroxyl radical OH11,12 and other harmful radicals[13] was later demonstrated by -pulsed radiolysis studies. Interesting biological activities related to anti-radical properties of this compound were proposed,[14] including the protection against acute toxicity due to Amanita phalloides ingestion in mice.[15]
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