Dihydro-dihydroxy-methyl-pyranone

An additional aromatic zone OZ 6 is also present in some wood extracts and in models of Maillard reactions with proline and glucose. The molecule responsible for the interesting odor of jam and burnt sugar has been identified to 3,5-dihydroxy-2-methyl-2,3-dihydro-4(H)-pyranone or hydroxymaltol [8]. 

Thermolysis of D-fructose in acid solution provides 11 and 2-(2-hydrox-yacetyl)furan (44) as major products. Earlier work had established the presence of 44 in the product mixtures obtained after acid-catalyzed dehydrations of D-glucose and sucrose. Eleven other products were identified in the D-fructose reaction-mixture, including formic acid, acetic acid, 2-furaldehyde, levulinic acid, 2-acetyl-3-hydroxyfuran (isomaltol), and 4-hydroxy-2-(hydroxymethyl)-5-methyl-3(2//)-furanone (59). Acetic acid and formic acid can be formed by an acid-catalyzed decomposition of 2-acetyl-3-hydroxyfuran, whereas levulinic acid is a degradation prod-uct of 11. 2,3-Dihydro-3,5-dihydroxy-6-methyl-4//-pyran-4-one has also been isolated after acid treatment of D-fructose.The pyranone is a dehydration product of the pyranose form of l-deoxy-D-eo f o-2,3-hexodiulose. In aqueous acid seems to be the major reaction product of the pyranone. 

Thus, the potential role of DMHF as a flavor impact compound and as an intermediate to form additional flavor compounds in heat-abused citrus products should be carefully considered. 2,3-Dihydro-3,5-dihydroxy-6-methyl-4-H-pyran-4-one was also isolated from dehydrated orange juice (37) and is known as a novel nonenzymic browning reaction product. This pyranone has a high threshold value, over 200 ppm (38), and appears to possess negligible odor character. 

The aromatic zone ZO 5 has a toasty character with fruity caramel overtones, which we identified as 2,3-dihydro-3,5-dihydroxy-2-methyl-4(H)-pyranone (7), or DDMP. 

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