28564-83-2Relevant academic research and scientific papers
Degradation of 3-Chloro-p-toluidine Hydrochloride in Watermelon Bait. Identification and Chemical Characterization of Novel N-Glucoside and Oxopropanimine
Tawara, Jeanne N.,Johnston, John J.,Goodall, Margaret J.
, p. 3983 - 3988 (1996)
Stability of the avicide 3-chloro-p-toluidine hydrochloride (CPTH) in watermelon bait was assessed. When exposed to light, the presence of CPTH accelerated nonenzymic browning (Maillard) reactions and degradation of the watermelon matrix. The addition of potassium metabisulfite appeared to hinder bait degradation. These experiments resulted in the identification and chemical characterization of two novel CPTH derivatives: N-β-D-glucopyranosyl-3-chloro-4-methylaniline and N-(3-chloro4-methylphenyl)-2-oxopropanimine.
Pyrolysis/GC/MS Analysis of 1--1-deoxy-D-fructose (Proline Amadori Compound)
Huyghues-Despointes, Alexis,Yaylayan, Varoujan A.,Keyhani, Anahita
, p. 2519 - 2524 (1994)
Pyrolysis/GC/MS was applied to the study of primary and secondary pyrolysis products of 1--1-deoxy-D-fructose (proline Amadori compound). The Amadori product was pyrolyzed on a ribbon probe at 150, 200, 250, 300, and 350 deg C for 10 s. The main products formed under these conditions were 1-(1'-pyrrolidinyl)-2-propanone, 2-hydroxy-1-(1/-pyrrolidinyl)-1-buten-3-one, and 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one in addition to acetic acid and pyrrolidine. The produce secondary pyrolysis products, the Amadori compound was pyrolyzed at 250 deg C in a quartz tube for 20 s; 14 secondary pyrolysis products were identified. The majority of the products were also reported to be formed during autoclaving of proline/monosaccharide mixtures at 150 deg C for 1.5 h in water. In addition, the pyrolysis of D-glucose/proline and the proline Amadori compound was compared. Keywords: Pyrolysis; proline; Amadori compound; decomposition; mechanism; Maillard reaction
Effect of hydroxyl on antioxidant properties of 2,3-dihydro-3,5-dihydroxy-6-methyl-4: H -pyran-4-one to scavenge free radicals
Bai, Bing,Cai, Lili,Chen, Zhifei,Fu, Yufeng,Liu, Qiang,Ma, Yuping,Sun, Zhitao,Wang, Qingfu,Xi, Gaolei,Zhao, Zhiwei
, p. 34456 - 34461 (2021/12/02)
It is well known that 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) is usually formed in the Maillard reaction and it contributes to the antioxidant properties of Maillard reaction intermediates. A series of hydroxyl group protected DDMP derivatives were synthesized to further understand the source of antioxidant activity. Antioxidant abilities of the DDMP derivatives were evaluated by scavenging the 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. It was found that the introduction of protecting groups to the free hydroxyl groups of DDMP decreases their reducing abilities. In particular, the hydroxyl group at the olefin position exhibited a remarkable impact on the antioxidant activity of DDMP, indicating that the unstable enol structure in the DDMP moiety is the key factor for its antioxidant activity.
Preparation method of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one
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Paragraph 0036-0038; 0045-0049, (2020/03/02)
The invention relates to a preparation method of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one. Monosaccharide is adopted as the raw material, secondary amine and acid are used as the catalyst,ethanol is taken as the solvent, and Maillard reaction one-pot method is employed to synthesize 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one. At the same time, silica gel chromatographic column-polyamide resin column-silica gel chromatographic column three-time chromatography is adopted for purification to obtain a 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one pure product, and the yield is up to 20.31%, which is far greater than 3.125% reported in literature. The synthesis and purification method has the advantages of simple preparation process, high yield, easy large-scale production and the like, and has wide application prospects.
Synthesis method of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
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, (2020/02/14)
The invention relates to a synthesis method of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, which creatively uses maltose as an initial raw material to synthesize the 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one. The synthesis method comprises: firstly, generating maltol acetate through acetylation; secondly, carrying out catalytic hydrogenation to obtain dihydromaltol acetate; adding asilylation reagent again to synthesize a dihydromaltol acetate silyl enol ether compound; increasing reaction activity of 5-position methylene and introducing hydroxy to the 5-position through peroxidation to obtain 5-hydroxy-dihydromaltol acetate; and performing a deacetylation reaction to obtain the 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one that is a target compound. According to the technical scheme, the five-step reaction process is simple, the yield is higher than 80%, the purity of the final product reaches 98% or above, large-scale production can be conducted, and the method has a wide application prospect.
Formation of Reactive Intermediates, Color, and Antioxidant Activity in the Maillard Reaction of Maltose in Comparison to d -Glucose
Kanzler, Clemens,Schestkowa, Helena,Haase, Paul T.,Kroh, Lothar W.
, p. 8957 - 8965 (2017/10/17)
In this study, the Maillard reaction of maltose and d-glucose in the presence of l-alanine was investigated in aqueous solution at 130 °C and pH 5. The reactivity of both carbohydrates was compared in regards of their degradation, browning, and antioxidant activity. In order to identify relevant differences in the reaction pathways, the concentrations of selected intermediates such as 1,2-dicarbonyl compounds, furans, furanones, and pyranones were determined. It was found, that the degradation of maltose predominantly yields 1,2-dicarbonyls that still carry a glucosyl moiety and thus subsequent reactions to HMF, furfural, and 2-acetylfuran are favored due to the elimination of d-glucose, which is an excellent leaving group in aqueous solution. Consequently, higher amounts of these heterocycles are formed from maltose. 3-deoxyglucosone and 3-deoxygalactosone represent the only relevant C6-1,2-dicarbonyls in maltose incubations and are produced in nearly equimolar amounts during the first 60 min of heating as byproducts of the HMF formation.
Antioxidant Properties of Heterocyclic Intermediates of the Maillard Reaction and Structurally Related Compounds
Kanzler, Clemens,Haase, Paul T.,Schestkowa, Helena,Kroh, Lothar W.
, p. 7829 - 7837 (2016/10/31)
It is well established that a wide range of reductones is formed in the course of the Maillard reaction and that these substances contribute to the oxidative stability of food. The aim of this study was to analyze 12 important heterocyclic intermediates with and without reductone structure as well as structurally related substances under equal conditions to compare their antioxidant properties in detail. For this purpose, five methods were selected including photometrical methods such as the trolox equivalent antioxidant capacity assay and an electron paramagnetic resonance spectroscopic method. Reductones with furan-3-one structure and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one were reducing in all assays, whereas isomaltol and maltol did not react in assays based on the reduction of metal ions because of their complexing abilities. The introduction of protecting groups to the free hydroxyl functions of selected reductones could nearly eliminate their reducing abilities. In addition, the oxidation products of the different reductive heterocycles were compared after treatment with iodine. Mainly short-chained organic acids such as lactic, glycolic, and glyceric acid are formed as result of the degradation, which indicates 1,3-dicarbonyl cleavage reactions of corresponding tricarbonyl compounds as intermediates of the oxidation.
PHARMACEUTICAL COMPOSITION, FOOD OR BEVERAGE CAPABLE OF ENHANCING SYMPATHETIC NERVE ACTIVITY
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Page/Page column 11-12, (2010/01/29)
It is intended to provide a safe composition for preventing or treating obesity or related complications which has an autonomic nervous control effect, in particular, an effect of enhancing sympathetic nervous activity and an effect of promoting energy metabolism. Thus, a medicinal composition, a food or a drink containing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one and having an autonomic nervous control effect and an effect of promoting energy metabolism is provided.
Oxygen-dependent fragmentation reactions during the degradation of 1-deoxy-d-erythro-hexo-2,3-diulose
Voigt, Michael,Smuda, Mareen,Pfahler, Christoph,Glomb, Marcus A.
experimental part, p. 5685 - 5691 (2011/08/05)
With this work, we report on further insights into the chemistry of 1-deoxy-d-erythro-hexo-2,3-diulose (1-deoxyglucosone, 1-DG). This α-dicarbonyl plays an important role as a highly reactive intermediate in the Maillard chemistry of hexoses. Degradation of 1-DG in the presence of the amino acid l-alanine led to the formation of several products. Lactic acid and glyceric acid were found to be major degradation products. Their formation was dependent on the presence of oxygen. Therefore, a mechanism is postulated based on oxidation leading to a tricarbonyl intermediate. Carbonyl cleavage of this structure should then give rise to carboxylic acids. This mechanism was supported by the isotope distribution observed during degradation of different 13C-labeled d-glucose isotopomers. Furthermore, we identified 3,5-dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one (γ-pyranone) to be capable of rehydration forming 1-DG to a minor extent and therefore leading to the same degradation products. The formation of carboxylic acids from γ-pyranone was also dependent on the presence of oxygen in agreement with the postulated oxidative fragmentation. Finally, we investigated the formation of aldehydes expected as retro-aldol products formed within the degradation of 1-DG. Results seemed to rule out this reaction as an important degradation pathway under the conditions investigated herein.
Reactivity of 1-deoxy-D-erythro-hexo-2,3-diulose; A key intermediate in the maillard chemistry of hexoses
Voigt, Michael,Glomb, Marcus A.
experimental part, p. 4765 - 4770 (2010/06/14)
Degradation of 1-deoxyhexo-2,3-diulose, a key intermediate in Maillard chemistry, in the presence of L-alanine under moderate conditions (37 and 50 °C) was investigated. Different analytical strategies were accomplished to cover the broad range of product
