Elucidation of Selected Maillard Reaction Pathways in Alanine and Phenylalanine Model Systems Through Isotope Labelling and Pyrolysis-GC/MS Based Techniques

Elucidation of Selected Maillard Reaction Pathways in Alanine and Phenylalanine Model Systems Through Isotope Labelling and Pyrolysis-GC/MS Based Techniques PDF Author: Fong Lam Chu
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Languages : en
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Application of Mass Spectrometry and Isotope Labelling Technique to Study the Role of Various Derivatives of [alpha]-dicarbonyl Moiety in the Generation of Strecker and Maillard Reaction Products

Application of Mass Spectrometry and Isotope Labelling Technique to Study the Role of Various Derivatives of [alpha]-dicarbonyl Moiety in the Generation of Strecker and Maillard Reaction Products PDF Author: Paula Vanessa Guerra Quiroz
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ISBN:
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Languages : en
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"The interaction of carbonyl moieties with free amino groups initiates one of the most important chemical transformations in food, the Maillard reaction. Numerous studies have shown the interaction of a single amino acid with one of the most reactive structures produced in the Maillard reaction, 1,2-dicarbonyl moieties. However, no systematic studies have been reported on the ability of these [alpha]-dicarbonyls to undergo multiple addition reactions with amino acids. Since 1,2-dicarbonyl moiety can be found as part of other chemical structures such as cyclic lactones, [alpha]-keto acids and o-quinones, a comprehensive understanding of the potential of these moieties to participate in Maillard and Strecker-type reactions was assessed. For this purpose, appropriate model systems were evaluated using isotope labelling technique with various precursors in conjunction with pyrolysis gas chromatography mass spectrometry or high resolution liquid chromatography mass spectrometry of thermally reacted model systems. Initially, a model system composed of glycine and 2,3-butanedione was evaluated under dry pyrolytic conditions at 250 °C. These studies indicated the unexpected formation of 2,3-dimethylpyrazine and 2,3,5-trimethylpyrazine in addition to the expected tetramethylpyrazine. Based on isotope labelling studies using labelled glycine, the formation of 2,3-dimethylpyrazine was rationalized through the double addition of glycine to 2,3-butanedione, or by a sequential Schiff base formation. The development of the previously reported 4,5-dimethyl-1,2-benzoquinone from the 2,3-butanedione/glycine model system was also examined, as well as its involvement as a precursors of 2,3,6,7-tetramethylquinoxaline through Strecker-type transformations. Based on those observations and given that ring-B of catechins is susceptible to oxidation and formation of such o-benzoquinone moieties, the potential of ring-B of catechins to undergo similar interactions to form adducts with amino acids was evaluated. For this purpose high resolution ESI-TOF mass spectrometry and MS/MS analysis were used to assess the reactivity of glycine with (+)-catechin heated at 120 °C for 70 min. Isotope labelling incorporation pattern of individually labelled glycine indicated that (+)-catechin formed various adducts with glycine through formation of Schiff bases. Further evaluation of the double addition and double Schiff base formation principle was carried out through the reaction of glucose and two amino acids with different side chains, glycine and cysteine. Both its volatile and non-volatile products were studied. The formation of a non-volatile adduct demonstrated the occurrence of this principle for the first time through sequential Amadori rearrangements. The reactive dicarbonyl moiety present in [alpha]-keto acid structures was also investigated as precursors of Strecker or Maillard reaction products. A model system consisting of glyoxylic acid and glycine was reacted under pyrolytic conditions at 200 °C. The isotope labelling analysis with individually labelled glycine confirmed the hypothesized pathways through the formation of dihydropyrazine moieties, similar to those of the dimerization product of the [alpha]-amino carbonyl compounds generated through the Strecker reaction. Finally, when studying the role of [alpha]-keto acids, 3-amino-4,5-dimethyl-2(5H)-furanone, a known precursor of sotolone, was observed for the first time under thermal conditions from two model systems, from pyruvic acid and glycine and from glyoxylic acid and alanine model systems. Isotope labelling studies have indicated the formation of 3-amino-4,5-dimethyl-2(5H)-furanone from 4,5-dimethylfuran-2,3-dione after its reaction with an amino acid through a variant of the Strecker reaction. These results suggests that the use of model systems with 1,2-dicarbonyl type precursors serves as an effective approach for unraveling new pathways of formation of aroma related products." --

Maillard Reaction

Maillard Reaction PDF Author: H E Nursten
Publisher: Royal Society of Chemistry
ISBN: 1847552579
Category : Technology & Engineering
Languages : en
Pages : 227

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Book Description
Research in the field of the Maillard reaction has developed rapidly in recent years as a result of not only the application of improved analytical techniques, but also of the realisation that the Maillard reaction plays an important role in some human diseases and in the ageing process. The Maillard Reaction: Chemistry, Biochemistry, and Implications provides a comprehensive treatise on the Maillard reaction. This single-author volume covers all aspects of the Maillard reaction in a uniform, co-ordinated, and up-to-date manner. The book encompasses: the chemistry of non-enzymic browning; recent advances; colour formation in non-enzymic browning; flavour and off-flavour formation in non-enzymic browning; toxicological aspects; nutritional aspects; other physiological aspects; other consequences of technological significance; implications for other fields; non-enzymic browning due mainly to ascorbic acid; caramelisation; inhibition of non-enzymic browning in foods; and inhibition of the Maillard reaction in vivo. The Maillard Reaction: Chemistry, Biochemistry, and Implications will be welcomed as an important publication for both new and experienced researchers who are involved in solving the mysteries and complexities of Maillard chemistry and biochemistry. It will also appeal to students, university lecturers, and researchers in a variety of fields, including food science, nutrition, biochemistry, medicine, pharmacology, toxicology, and soil science.

Process-Induced Food Toxicants

Process-Induced Food Toxicants PDF Author: Richard H. Stadler
Publisher: John Wiley & Sons
ISBN: 0470430095
Category : Technology & Engineering
Languages : en
Pages : 744

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Book Description
Process-Induced Food Toxicants combines the analytical, health, and risk management issues relating to all of the currently known processing-induced toxins that may be present in common foods. It considers the different processing methods used in the manufacture of foods, including thermal treatment, drying, fermentation, preservation, fat processing, and high hydrostatic pressure processing, and the potential contaminants for each method. The book discusses the analysis, formation, mitigation, health risks, and risk management of each hazardous compound. Also discussed are new technologies and the impact of processing on nutrients and allergens.

Safety Evaluation of Certain Contaminants in Food

Safety Evaluation of Certain Contaminants in Food PDF Author: Joint FAO/WHO Expert Committee on Food Additives. Meeting
Publisher: WHO Food Additives
ISBN: 9789241660631
Category : Medical
Languages : en
Pages : 0

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Book Description
The detailed monographs in this volume summarize the technical, analytical, dietary exposure and toxicological data on a number of contaminants in food: acrylamide, arsenic, deoxydivalenol, furan, mercury and perchlorate. This volume and others in the WHO Food Additives series contain information that is useful to those who produce and use food additives and veterinary drugs and those involved with controlling contaminants in food, government and food regulatory officers, industrial testing laboratories, toxicological laboratories and universities.

Chemical Evolution

Chemical Evolution PDF Author: Bernd Markert
Publisher: Springer
ISBN: 3319143557
Category : Science
Languages : en
Pages : 295

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Book Description
This book is written for researchers and students interested in the function and role of chemical elements in biological or environmental systems. Experts have long known that the Periodic System of Elements (PSE) provides only an inadequate chemical description of elements of biological, environmental or medicinal importance. This book explores the notion of a Biological System of the Elements (BSE) established on accurate and precise multi-element data, including evolutionary aspects, representative sampling procedures, inter-element relationships, the physiological function of elements and uptake mechanisms. The book further explores the concept Stoichiometric Network Analysis (SNA) to analyze the biological roles of chemical species. Also discussed is the idea of ecotoxicological identity cards which give a first-hand description of properties relevant for biological and toxicological features of a certain chemical element and its geo biochemically plausible speciation form. The focus of this book goes beyond both classical bioinorganic chemistry and toxicology.

Fundamentals and Applications of Fourier Transform Mass Spectrometry

Fundamentals and Applications of Fourier Transform Mass Spectrometry PDF Author: Philippe Schmitt-Kopplin
Publisher: Elsevier
ISBN: 0128140143
Category : Science
Languages : en
Pages : 780

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Book Description
Fundamentals and Applications of Fourier Transform Mass Spectrometry is the first book to delve into the underlying principles on the topic and their linkage to industrial applications. Drs. Schmitt-Kopplin and Kanawati have brought together a team of leading experts in their respective fields to present this technique from many different perspectives, describing, at length, the pros and cons of FT-ICR and Orbitrap. Numerous examples help researchers decide which instruments to use for their particular scientific problem and which data analysis methods should be applied to get the most out of their data. - Covers FT-ICR-MS and Orbitrap's fundamentals, enhancing researcher knowledge - Includes details on ion sources, data processing, chemical analysis and imaging - Provides examples across the wide spectrum of applications, including omics, environmental, chemical, pharmaceutical and food analysis

Flavours and Fragrances

Flavours and Fragrances PDF Author: Ralf Günter Berger
Publisher: Springer Science & Business Media
ISBN: 3540493395
Category : Science
Languages : en
Pages : 649

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Book Description
This book is an introduction to the world of aroma chemicals, essential oils, fragrances and flavour compositions for the food, cosmetics and pharmaceutical industry. Present technology, the future use of resources and biotechnological approaches for the production of the respective chemical compounds are described. The book has an integrated and interdisciplinary approach on future industrial production and the issues related to this topic.

Flavor Chemistry

Flavor Chemistry PDF Author: Roy Teranishi
Publisher: Springer Science & Business Media
ISBN: 1461546931
Category : Technology & Engineering
Languages : en
Pages : 423

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Book Description
Celebrating the founding of the Flavor Subdivision of the Agriculture and Food Chemistry Division of the American Chemical Society, this book provides an overview of progress made during the past 30-40 years in various aspects of flavor chemistry as seen by internationally renowned scientists in the forefront of their respective fields. In addition, it presents up-to-date findings in the areas of flavor chemistry, analytical methods, thermally produced flavors and precursors, enzymatically produced flavors and precursors, and sensory methods and results.

Advances in Carbohydrate Chemistry and Biochemistry

Advances in Carbohydrate Chemistry and Biochemistry PDF Author:
Publisher: Academic Press
ISBN: 0080562841
Category : Science
Languages : en
Pages : 559

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Book Description
Advances in Carbohydrate Chemistry and Biochemistry