Importance of Chirality to Flavor Compounds

Edited by Gary Takeoka and Karl-Heinz Engel

ACS Symposium Series

Chiral molecules are extremely ubiquitous and have multiple applications for flavor chemistry.
Appeals to those both in flavor research as well as in regulatory affairs.

Importance of Chirality to Flavor Compounds

Edited by Gary Takeoka and Karl-Heinz Engel

Description

Chiral molecules are ubiquitous in nature. Thus, it is not surprising to come across this phenomenon in the world of flavor substances. This book provides an overview on the analytical procedures currently applied to analyze chiral flavor substances at trace levels. It demonstrates several examples for the application of these techniques to determine naturally occurring enantiomeric compositions of chiral key flavor compounds in various natural systems. In addition to the analytical aspects, the contributions focus on the sensory properties of enantiomers and enlarge our knowledge on the correlation between configurations and odor properties and intensities of chiral flavor compounds.

The practical importance of the topic is reflected by a discussion of merits and limitations of chiral analysis for the authenticity control of food flavorings. In addition, examples for the use of enzymes and microorganisms to obtain enantiopure flavor substances and thus to meet legal requirements for "natural" labeling are presented. Finally, the book covers aspects recently getting more and more in the focus of flavor science: What are the physiological mechanisms underlying the perception of sensory properties and does chirality matter in that respect?

Importance of Chirality to Flavor Compounds

Edited by Gary Takeoka and Karl-Heinz Engel

ACS Symposium Series

Preface
Authenticity Assessments
1. Authenticity Control of Food Flavorings - Merits and Limitations of Chiral Analysis
Analytical Approaches
2. Cyclodextrin Derivatives as Stationary Phases for the GC Separation of Enantiomers in the Flavor and Fragrance Field
3. Vibrational CD (VCD) Spectroscopy as a Powerful Tool for Chiral Analysis of Flavor Compounds
Biocatalysis and Biogeneration
4. Multi-Enzymatic Cascade Procedures for the Synthesis of Chiral Odorous Molecules
5. Enantioselectivities of Uridine Diphosphate-Glucose:Monoterpenol Glucosyltransferases from Grapevine (Vitis vinifera L.)
6. Biotechnological Production of C8 Aroma Compounds by Submerged Cultures of Shiitake (Lentinula edodes)
Natural Occurrence
7. (3R,4R)-3-Methyl-4-decanolide, a Novel Lactone Contributing to Fresh Wasabi (Wasabia japonica) Aroma
8. Quantitation of cis- and trans-3,5-Diethyl-1,2,4-trithiolanes in Cooked Allium Varieties Using a Stable Isotope Dilution Assay
9. Characteristic Chiral Sulfur Compounds Aroma-Active in Cempedak (Artocarpus integer (Thunb.) Merr.) Fruits
10. Influence of Structural Modification and Chirality on the Odor Potency and Odor Quality of Thiols
11. Structure Elucidation of Novel Norcysteine-Containing Dipeptides from the Chinese Vegetable Toona sinensis
Physiology
12. Chirality Matters — Enantioselective Orthologous Odorant Receptors for Related Terpenoid Structures
13. Ligand Recognition of Taste Receptors

Importance of Chirality to Flavor Compounds

Edited by Gary Takeoka and Karl-Heinz Engel

ACS Symposium Series

Author Information

Edited by Gary Takeoka, Research Chemist, Healthy Processed Foods Research Unit, U.S. Department of Agriculture, Agricultural Research Service, and Karl-Heinz Engel, Professor of General Food Technology at the TUM School of Life Sciences Weihenstephan, Technische Universitaet Muenchen

Karl-Heinz Engel is Professor of General Food Technology at the TUM School of Life Sciences Weihenstephan of the Technische Universität München, Germany. He has published more than 280 scientific articles and contributed to various American Chemical Society Series books as author as well as co-editor. He is also involved in the safety assessment of flavorings, enzymes and novel foods performed by the European Food Safety Authority (EFSA) in Parma, Italy.; Gary Takeoka is a Research Chemist in the Healthy Processed Foods Research Unit, Western Regional Research Center, U.S. Department of Agriculture in Albany, CA. He received his B.S. and M.S. in Food Science and Technology and Ph.D. in Agricultural and Environmental Chemistry, all degrees from the University of California, Davis. He has published more than 100 scientific articles and has served as chairperson, vice-chairperson and secretary of the Flavor Subdivision of the ACS Division of Agricultural and Food Chemistry.