Formation of 2,3-Dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one from Fructose and .beta.-Alanine under Conditions Used for Baking

Nishibori, Sukie; Kawakishi, Shunrô

doi:10.1021/jf00041a006

Cited by 17 publications

(11 citation statements)

References 11 publications

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“…This reaction (Maillard-Amadori reaction) is generally associated with browning of food during cooking (Nishibori and Kawakishi 1994;Tomasik et al 1989;Eichner et al 1994;de Kok and Rosing 1994). This reaction (Maillard-Amadori reaction) is generally associated with browning of food during cooking (Nishibori and Kawakishi 1994;Tomasik et al 1989;Eichner et al 1994;de Kok and Rosing 1994).…”

Section: Discussionmentioning

confidence: 99%

The Chemical Nature of Kiln Brown Stain in Radiata Pine

McDonald¹,

Fernández²,

Kreber³

et al. 2000

Holzforschung

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This paper presents results of a study on the chemical nature of kiln brown stain (KBS) that develops in kiln dried radiata pine (Pinus radiata D. Don) sapwood. KBS is a chocolate brown discolouration which develops approximately 0.5 mm under the timber surface. Stain free radiata pine was achieved during drying trials on "green" radiata pine sapwood which had been treated to extensive cold and hot water extraction. Differences in chemical composition between the sap and hot water extract were observed. Chemical analyses (of the water-soluble extracts) by a combination of chromatographic and spectroscopic techniques, demonstrated that carbohydrates, cyclitols, amino acids, protein, and phenolics were the main compound classes present. The presence of reducing sugars (glucose and fructose) and amino acids (glutamic acid) in the sap and hot water extracts support the theory that Amadori-Maillard type reactions significantly contribute to the formation of colour in KBS. Furthermore, lignin was also detected and is suspected to contribute to KBS formation. The relative contributions of colour formation to KBS intensity from either phenolics or Maillard-Amadori mechanisms is unknown. KeywordsAmino acids Kiln brown stain Kiln drying Maillard reaction Radiata pine Reducing sugars Sap Brought to you by |

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Section: Discussionmentioning

confidence: 99%

The Chemical Nature of Kiln Brown Stain in Radiata Pine

McDonald¹,

Fernández²,

Kreber³

et al. 2000

Holzforschung

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“…Figure 5 shows the GC/MS chromatogram of the evolved gas by heating the uncured adhesives at 170 • C. Table 3 reports the identified volatile components with a greater than 90 similarity index (SI) or the compounds with highest SI value (the SI value of all the identified compounds in one peak lower than 90 condition). The pyrogram of SADP 100/0 exhibits two main pyrolysis products: 4H-Pyran-4-one,2,3-dihydro-3,5-dihydroxy-6-methyl-(DDMP) and 5-Hydrxoymethylfurfura (5-HMF), both of which are the characteristic products by heating saccharide [36][37][38]. The profiles visualized in Figure 5b exhibited a significant variation that was ascribed to the addition of ADP when compared with the chromatogram of SADP 100/0, and even more chemical compounds were observed from the evolved gas by heating SADP 90/10.…”

Section: Py-gc/msmentioning

confidence: 99%

Investigation and Characterization of Synthesis Conditions on Sucrose-ammonium Dihydrogen Phosphate (SADP) Adhesive: Bond Performance and Chemical Transformation

et al. 2019

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Sucrose is one of the most abundantly available renewable chemicals in the world, and it is expected to be utilized as a raw material for wood-based material products. Herein, a novel adhesion system that was based on sucrose and ammonium dihydrogen phosphate (ADP) was synthesized into an adhesive with 80% solid content, and this eco-friendly was utilized on the fabrication of plywood. The effects of the synthesis conditions on the plywood bond performance and synthesis mechanism were investigated. The optimal synthesis conditions were as follows: the mass proportion between sucrose and ADP was 90/10, the synthesis temperature was 90 °C, and the synthesis time was 3 h. The bonding performance of the plywood that was bonded by optimal SADP adhesive satisfied the GB/T 9846-2015 standard. The chemical analysis was performance tested by using High-Performance Liquid Chromatography (HPLC), Attenuated Total Reflection-Fourier Transform Infrared Spectra (ATR-FTIR), and Pyrolysis Gas Chromatography and Mass Spectrometry (Py-GC/MS) to understand the chemical transformation during the synthesis process. The chemical analysis results confirmed that the hydrolysis and conversation reaction of sucrose occurred in the synthesized SADP adhesive, and ADP promoted the pyrolysis efficiency of sucrose.

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“…The most informative classification variable for discriminating raw from processed cocoas was 2,3-dihydro-3,5-dihydroxy-6-methyl-4 H -pyran-4-one. Its formation, promoted by heating, is related to the presence of fructose and β-alanine in raw cocoa . Variables with a secondary role for discriminating processing stages were 2,6-dimethylpyrazine, 2,3,5-trimethylpyrazine, 2-ethyl-5-methylpyrazine, and the potent odorant ( E )-2-phenyl-2-butenal (intense chocolate note).…”

Section: Resultsmentioning

confidence: 99%

Comprehensive Chemical Fingerprinting of High-Quality Cocoa at Early Stages of Processing: Effectiveness of Combined Untargeted and Targeted Approaches for Classification and Discrimination

Magagna

Guglielmetti

Liberto

et al. 2017

J. Agric. Food Chem.

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This study investigates chemical information of volatile fractions of high-quality cocoa (Theobroma cacao L. Malvaceae) from different origins (Mexico, Ecuador, Venezuela, Columbia, Java, Trinidad, and Sao Tomè) produced for fine chocolate. This study explores the evolution of the entire pattern of volatiles in relation to cocoa processing (raw, roasted, steamed, and ground beans). Advanced chemical fingerprinting (e.g., combined untargeted and targeted fingerprinting) with comprehensive two-dimensional gas chromatography coupled with mass spectrometry allows advanced pattern recognition for classification, discrimination, and sensory-quality characterization. The entire data set is analyzed for 595 reliable two-dimensional peak regions, including 130 known analytes and 13 potent odorants. Multivariate analysis with unsupervised exploration (principal component analysis) and simple supervised discrimination methods (Fisher ratios and linear regression trees) reveal informative patterns of similarities and differences and identify characteristic compounds related to sample origin and manufacturing step.

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Formation of 2,3-Dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one from Fructose and .beta.-Alanine under Conditions Used for Baking

Cited by 17 publications

References 11 publications

The Chemical Nature of Kiln Brown Stain in Radiata Pine

The Chemical Nature of Kiln Brown Stain in Radiata Pine

Investigation and Characterization of Synthesis Conditions on Sucrose-ammonium Dihydrogen Phosphate (SADP) Adhesive: Bond Performance and Chemical Transformation

Comprehensive Chemical Fingerprinting of High-Quality Cocoa at Early Stages of Processing: Effectiveness of Combined Untargeted and Targeted Approaches for Classification and Discrimination

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