Maltol, 5-hydroxy

Hydroxy-2-methyl-4H-pyran-4-one (maltol) 5-Hydroxy-2-methyl-4H-pyran-4-one (allomaltol) 5-Hydroxymethylfurancarboxyaldehyde (5-hydroxymethylfurfural) 5-Methylfurancarboxyaldehyde (5-methylfurfural)... 

Maltol — see Pyran-4-one, 3-hydroxy-2-methyl-Maltol, ethyl — see Pyran-4-one, 3-ethoxy-2-methyl-Maltol, methyl — see Pyran-4-one, 3-methoxy-2-methyl-Mandelic acid ethyl ester, 1, 310-311 Manganaindene reactions, 1, 671 Mannich bases dehydro... 

It is worthy of note that the substance maltol, 2-methyl-3-hydroxy- ... 

This was significant in the preparation of l,2-dimethyl-3-hydroxy-4-pyridone, employed clinically as an iron chelating agent. The aminoreductone is obtained by reaction of methylamine with maltol. Traces of metal within the system readily form highly colored complexes with reactant or product and these are difficult to remove. With the CMR, the preparation was achieved in 65 % yield without the need for decolorizing charcoal and the product was crystallized by collecting the effluent in acetone (Scheme 2.10) [22]. 

The fact that pyromeconic acid and allomaltol were only available with difficulty meant that direct synthesis of certain 3-hydroxy-4-pyridinones was not possible. However the demonstration that some of these compounds were accessible from maltol or ethylmaltol by functionalizing the position adjacent to the ring-oxygen by an aldol condensation and N-oxide intermediates led to the preparation of 2-(l -hydroxyalkyl) and 2-amido derivatives with usefully high affinities for Fe + (70). 

L — maltolate the coordination environment of the vanadium in K[V02(malt)2] H2O is approximately octahedral, the two 0x0 ligands being in cis positions. [K(H20)e] units link adjacent vanadium(V) complex anions to give a chain structure 166). The main products of aerobic oxidation of [V O(dmpp)2l in aqueous solution are [V02(dmpp)] and [VOo(dmpp)2]. High pH favors these V products, whereas at low pH V species predominate 171). Vanadium(V) also forms a VO(OR)(malt)2 series, readily prepared from ammonium vanadate, maltol, and the appropriate alcohol in a water-alcohol-dichloromethane medium 172), and 3-hydroxy-4-pyridinonate analogues V0(0R)L2 on oxidation of their oxovanadium(IV) precursors in solution in the appropriate alcohol ROH 168). 

Stepwise stability constants decrease regularly in the normal manner 178), log > log K2 > log K, as may be exemplified by the values for the Ni -maltolate system, viz. 5.5, 4.3, and 2.7, respectively 179). Stability constants (log Kf) for a selection of 3-hydroxy-4-pyranonate and 3-hydroxy-4-pyridinonate complexes of some first-row transition metal 2+ cations are listed in Table IV 10,128,180—184). The values for the 3d transition metal cations conform to the long-established Irving-Williams order... 

Stability constants for maltolate and 2-methyl-3-hydroxy-4-pyridi-nonate complexes have been discussed in the context of a score of... 

Despite their importance in many pharmacological uses and potential applications, solubilities of hydroxypyranones, hydroxypyridinones, and their complexes have not been extensively and systematically investigated and established. This situation contrasts sharply with that for partition coefficients, as will become apparent in the following section. The solubility of maltol in water is approximately 0.1moldm , of ethyl maltol 0.13 mol dm, at 298 K. 1,2-Alkyl-3-hydroxy-4-pyridinones show the expected decrease in water-solubility as the sizes of the alkyl groups increase solubilities - in water at 298 K - of l-aryl-2-methyl-3-hydroxy-4-pyridinones decrease from 9 X 10 mol dm for the 1-phenyl compound through 6 x lO- moldm for l-(4 -tolyl) to 6 x 10 mol dm for l-(4 -re-hexyl-phenyl) (37). 

In recent years hydroxypyranones and hydroxypyridinones have been increasingly investigated for the control of metal ion levels in the body (324-327). The 3-hydroxy-4-pyranones maltol and ethylmaltol are of relatively low toxicity 328,329), and indeed have the pharmacological advantage of being permitted food additives. Hydroxypyridinones are particularly attractive for pharmaceutical purposes since their structure allows tailoring of many of their properties, as outlined in Section II.A.3.b earlier. They have been used in, or tested or proposed for, chelation therapy to remove excess of several toxic elements. This will be illustrated later in the sections... 

The formation of oxygen-containing heterocyclic compounds is also a consequence of the Maillard reaction. Amines and amino acids have a catalytic effect upon the formation of 2-furaldehyde (5), 5-(hydroxy-methyl)-2-furaldehyde (11),2-(2-hydroxyacetyl)furan (44),2 and 4-hy-droxy-5-methyl-3(2//)-furanone (111) (see Ref. 214). This catalytic effect can be observed with several other non-nitrogenous products, including maltol. The amino acid or amine catalysis has been attributed to the transient formation of enamines or immonium ions, or the 1,2-2,3 eno-lization of carbohydrates. Of interest is the detection of A -(2-furoyl-... 

Hydroxy-2-methyl-4//-pyran-4-one (maltol) and 2-acetyl-3-hydroxy-furan (isomaltol) are also products of the Maillard reaction. Both have a considerable history, due to their early detection in beer and breads. A mechanism based upon the pyranose form of a methyl-a-dicarbonyl inter-... 

Figure 1 Transfer chemical potentials for selected iron complexes from water into aqueous methanol (on the molar scale, at 298 K). Ligand abbreviations not appearing in the list at the end of this chapter are acac = acetylacetonate (2,4-pentanedionate) dmpp = l,2-dimethyl-3-hydroxy-4-pyridinonate, the anion from (24) malt = maltolate (2-methyl-3-hydroxy-4-pyranonate, the anion from (233)).

Numerous furan and pyran derivatives, many of which originate from heat treatment of carbohydrates, largely determine the odor of processed foods. Of this group, 2,5-dimethyl-4-hydroxy-277-furan-3-one and maltols are used in fairly large quantities in flavors. The following compounds are used in relatively small amounts in flavor compositions ... 

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