2,3-dihydro-3,5-dihydroxy-6-methyl-4-pyran-4-one, a novel nonenzymatic browning product

Mills, Frank D.; Weisleder, David; Hodge, John E.

doi:10.1016/s0040-4039(01)91599-0

Cited by 55 publications

(35 citation statements)

References 9 publications

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“…Another reductone, 2,3-dihydroxy-3,S-dihydro-6-methyl-4H-pyran-4-one (DDMP) has been identified from the thermal degradation products of several Amadori compounds. 1,2) Melanoidin, a high molecular weight reductone, also has reducing ability. These reductones are not only useful for flavoring, but also as antioxidants and antimutation substances.…”

mentioning

confidence: 99%

Formation of Reducing Substances in the Maillard Reaction between D-Glucose and γ-Aminobutyric Acid

Ninomiya

Matsuzaki

Shigematsu

1992

Bioscience, Biotechnology, and Biochemistry

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mentioning

confidence: 99%

Formation of Reducing Substances in the Maillard Reaction between D-Glucose and γ-Aminobutyric Acid

Ninomiya

Matsuzaki

Shigematsu

1992

Bioscience, Biotechnology, and Biochemistry

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“…The weakly acidic nature of reductones may cause their lower recovery at pH 7. The low value of DDMP (Mills et al, 1970), which is known to be unstable and highly polar, was an exceptional case. In contrast to other reductones, the recovery of DDMP under acidic conditions was lower than that at neutral pH.…”

Section: Resultsmentioning

confidence: 99%

“…The sample of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) was chromatographically separated from vacuum pyrolysate at 150-160˚C/133.3 Pa of 1-deoxy-1-prolino-D-fructose according to the method of Mills et al (1970) and purified by recrystallization, m.p. 73.0-73.6˚C; Lit.…”

Section: Methodsmentioning

confidence: 99%

Determination of Reductones, Furans and Organic Acids in Aqueous Model Matrices Using Solid-Phase Extraction and Gas Chromatography/Mass Spectrometry

Mori

Ito

2004

FSTR

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A method using solid-phase extraction (SPE) and GC-MS was developed for the determination of a series of polar and unstable flavor compounds: reductones, furans and volatile organic acids, in aqueous model matrices. The SPE procedures were optimized mainly on the pH-dependency of the analytes with regard to their adsorption characteristics. Good recovery of the reductones except DDMP was obtained at pH 2 and 4.5. Furan derivatives were generally recovered in high yields under the acidic to neutral pH conditions examined. All organic acids were recovered almost quantitatively at pH 2. An essentially comparable result was obtained in a model Maillard reaction mixture. In order to apply this method to alcoholic beverages, effect of the ethanol concentration on the SPE adsorption of the analytes was also investigated.Keywords: solid-phase extraction (SPE), gas chromatography/mass spectrometry (GC-MS), reductone, furan, organic acid Reductones, furans (Ledl & Schleicher, 1990) and organic acids (Hofmann et al., 2000) are commonly found in foods and beverages. Most reductones and volatile acids exhibit important sensory properties with low threshold values, and some of them are utilized as food flavors. Furan derivatives generated from sugars by non-enzymatic browning are closely related to the chemical changes in foods and beverages during their processing and storage (Lee & Nagy, 1990).Such types of compounds have relatively high polarity and ionic characters, so that their high water solubility results in low recovery in conventional solvent-extraction methods. Headspace sampling and solid-phase microextraction (SPME) are frequently used for the selective extraction of volatile flavors from a complex matrix. Unfortunately, the main disadvantage of these methods is low recovery of polar analytes (Pan et al., 1995).In addition, reductones and furans tend to be decomposed during the analytical procedures, particularly at the elevated temperature used in GC analysis (Blank et al., 1992). To compensate for losses during the workup procedure for GC analysis, stable isotope dilution assays (Sen et al., 1991) were developed. However, this technique requires the corresponding isotope-labeled derivative of each analyte as the internal standard.Column adsorption (Shimoda et al., 1987) and solid phase extraction (SPE) (Coulibaly & Jeon, 1996) are now widely used for the extraction and clean up of flavor compounds in foods and beverages. Even though some efficient methods had been developed for the analysis of reductones, most of them were optimized to one or a few analytes on high performance liquid chromatography (HPLC) (Walsh et al., 1997). The HPLC methods are not suitable to trace level multiple analytes.To our knowledge, there were only a few reports concerning the GC-quantitation of such polar and unstable volatiles from aqueous matrices using SPE treatments (Wada & Shibamoto, 1997;Adahchour et al., 1999). Recently, Thum and Back (1999) applied their SPE procedure for a selective concentration of a series of aroma compou...

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“…When maltulose was treated with an addition of proline, the main products were furanmethanol and DDMP, while maltose/proline gave maltol as the main product. DDMP, which was a major product in the reaction of glucose and proline (Mills et al, 1970), must be formed from the hexose-unit released in the course of the formation of furanmethanol. The higher yield of DDMP from maltulose than that of maltose at pH 8 indicates that ␤-elimination via maltulose mainly participates in the release of the hexose-unit.…”

Section: Resultsmentioning

confidence: 99%

“…Pure samples of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) (Mills et al, 1970) and 2-hydroxyacetylfuran (2-HAF) (Miller & Cantor, 1952) were synthesized by the literature methods. Proline-maltulose (95% purity checked by HPLC) was prepared from L-proline and D-maltose monohydrate by the method of Moll and Gross (1981) Model reactions A solution of D-maltose monohydrate with or without L-proline in water was placed in a glass vessel and heated at 90˚C with stirring in an oil bath.…”

Section: Methodsmentioning

confidence: 99%

Effects of pH on the Formation of Volatile Products in Non-Enzymatic Browning of Maltose

Mori

Ito

2004

FSTR

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The effects of pH on the formation of maltol and furanmethanol as well as other minor reductones and furans on heating an aqueous solution of maltose under conditions in the absence (caramelization) and presence (Maillard reaction) of proline were examined. The experiments employing a pH-stat device clearly demonstrated the pH dependency on the formations of the products. The products of maltulose and proline-maltulose, which were postulated as the initial intermediates for the two pathways of maltose degradation in the presence of proline, were also examined. On the basis of the results, the reaction pathways of the formation of volatile products from maltose were discussed.

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2,3-dihydro-3,5-dihydroxy-6-methyl-4-pyran-4-one, a novel nonenzymatic browning product

Cited by 55 publications

References 9 publications

Formation of Reducing Substances in the Maillard Reaction between D-Glucose and γ-Aminobutyric Acid

Formation of Reducing Substances in the Maillard Reaction between D-Glucose and γ-Aminobutyric Acid

Determination of Reductones, Furans and Organic Acids in Aqueous Model Matrices Using Solid-Phase Extraction and Gas Chromatography/Mass Spectrometry

Effects of pH on the Formation of Volatile Products in Non-Enzymatic Browning of Maltose

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