PREPARATION AND STRUCTURE OF AN UNUSUAL DIMERIC FURAN FROM THE ACID DECOMPOSITION OF ISOMALTOL

Article abstract of DOI:10.1016/0008-6215(86)85028-5

Isomaltol (1), an enolic nonenzymic browning-product, decomposes in dilute acid to form the new red-orange colored, symmetrical dimer, (E)-2-<1-(3-hydroxy-2-furanyl)ethylidene>-(2H)-furan-3-one (2).Compound 2 was obtained in 20.4percent yield with toluenesulfonic acid (>/=3M) at 50 deg C.The structure for 2 was assigned on the basis of spectral data (m.s., u.v., i.r., 13C- and 1H-n.m.r.) and conversion into its mono-O-acetyl derivative (3).