James C. Goodwin

Synthesis of a derivative of 1-deoxy-d-erythro-2,3-hexodiulose and its conversion into nonenzymic browning products

Abstract A new synthesis of 1-deoxy-4,5- O -isopropylidene- d - erythro -2,3-hexodiulose ( 5 ), a stable derivative of the elusive 1-deoxy- d - erythro -2,3-hexodiulose ( 6 ), starting from 3,6-anhydro-4,5- O -isopropylidene- d -mannitol ( 1 ) is described. Acid hydrolysis of 5 produced 6 , which without isolation was treated with piperidine acetate to yield piperidino-hexose-reductone ( 7 ) and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one ( 8 ). A third component in the reaction mixture has been tentatively assigned from mass-spectroscopic data the structure 4-hydroxy-2-hydroxymethyl-5-methyl-3(2 H )-furanone ( 9 ).

Preparation and structure of an unusual dimeric furan from the acid decomposition of isomaltol

Abstract 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]-(2 H )-furan-3-one ( 2 ). Compound 2 was obtained in 20.4% yield with toluenesulfonic acid (⩾3 m ) at 50°. The structure for 2 was assigned on the basis of spectral data (m.s., u.v., i.r., 13 C- and 1 H-n.m.r.) and conversion into its mono- O -acetyl derivative ( 3 ).

Preparation and Structure of (E)-1-(3′-Hydroxy-2-Furanyl)-3-(3″-Hydroxy-4″-Methoxyphenyl)-2-Propen-1-One

Abstract A facile procedure is presented for the synthesis of (E)-1-(3′-hydroxy-2′-furanyl)-3-(3″-hydroxy-4″-methoxyphenyl)-2- propen-1-one (6). Galactosylisomaltol (1) was condensed with isovanillin (2) under strong alkaline conditions at 25 [ddot]C to form (E)-1-(3′-O-β-D-galactopyranosyloxy-2′-furanyl)-3-(3″- hydroxy-4″-methoxyphenyl)-2-propen-1-one (4). (E)-1-(3′-hydroxy-2′-furanyl)-3-(3″-hydroxy-4″-methoxyphenyl)-2-propen-1-one (6) was obtained by acid hydrolysis of 4 in a 53.9% yield. This hetero-cyclic 2-propen-1-one was characterized on the basis of spectral data (IR and 1H NMR), physicochemical properties, and conversion to a mono-O-acetyl derivative.

Sodium Complexes of Isomaltol and Maltol

Abstract Sodium bis(3-O-hydroxy-2-furyl methyl ketone) (3) and sodium 3-O-hydroxy-2-methyl-4-pyrone hydrate (4) were isolated and characterized from the interaction of isomaltol and maltol with sodium methoxide in boiling benzene (toluene or acetone). Elemental analyses of 3 furnished the formula C12H11NaO6, and this composition was confirmed by conversion to isomaltol O-benzoyl ester.

Amine-catalyzed transformation of enolic nonenzymic browning products, isomaltol glycopyranosides into 1,6-anhydro-β-D-hexopyranoses

Abstract The nonenzymic browning products, isomaltol d -galacto- and d -glucopyranosides, are transformed by 5:1 (v/v) triethylamine-pyrrolidine into 1,6-anhydro-β- d -galactopyranose (41%) and 1,6-anhydro-β- d -glucopyranose (