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1. High‐Impact Sulfur Compounds: Constitutional and Configurational Assignment of Sulfur‐Containing Heterocycles

Author

Michael Backes, Berthold Weber, Stefan Brennecke, Christoph Krafft, Jakob Ley, Gerhard Krammer, Jörg Grunenberg, Reiner Salzer, and Frank Ott

Subjects
Magnetic Resonance Spectroscopy, chemistry.chemical_element, Bioengineering, Stereoisomerism, Spectrum Analysis, Raman, Biochemistry, symbols.namesake, Heterocyclic Compounds, Computational chemistry, Humans, Organic chemistry, Molecular Biology, Flavor, Molecular Structure, Sulfur Compounds, Chemistry, General Chemistry, General Medicine, Nuclear magnetic resonance spectroscopy, Sulfur containing, Sulfur, NMR spectra database, Taste, symbols, Molecular Medicine, Food Additives, Gas chromatography, Raman spectroscopy
Abstract

To unambiguously identify their structures and to evaluate their organoleptic properties, several constitutional und configurational isomers of dialkyl-tetrathianes and dialkyl-pentathiepanes were synthesized by two different synthetic protocols, and separated by preparative gas chromatography. Raman and NMR spectroscopy were used to differentiate between the constitutional 3,6-dialkyl-1,2,4,5-tetrathiane and the 4,6-dialkyl-1,2,3,5-tetrathiane isomers. Furthermore, cis- and trans-isomers of 3,6-dialkyl-1,2,4,5-tetrathianes were distinguished by temperature-dependent NMR experiments. Static, quantum-chemical simulations of the NMR spectra for these cis- and trans-isomers were calculated in the gas layer in order to confirm our experimental assignments. In addition, the assignment of 4,7-alkyl-1,2,3,5,6-pentathiepanes were deducted from their Raman spectra. Dialkyl-tetrathianes and dialkyl-pentathiepanes are interesting components to be used in flavor applications due to their unique olfactory impact and facets.

Published
2008
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2. Determination of configurational isomers in cyclic polysulfides by Raman spectroscopy

Author

Frank Ott, Stefan Brennecke, Christoph Krafft, Reiner Salzer, Berthold Weber, Enrico Pigorsch, and Gerhard Krammer

Subjects
symbols.namesake, Crystallography, Chemistry, Raman band, symbols, Disulfide bond, Organic chemistry, Stereoisomerism, Gas chromatography, Raman spectroscopy, Spectroscopy, Cis–trans isomerism
Abstract

Cyclic polysulfides such as trithiolanes, tetrathianes and their derivatives are found in natural sources like archaea, mushrooms and vegetables. They gained interest for research and industrial applications because of their pronounced flavors and biological activity. This study compares Raman spectra of reference compounds and cyclic polysulfides which were synthesized in-house and separated by preparative gas chromatography. The data show that the positions of the Raman bands due to S S stretching vibrations in the wavenumber region from 550 to 450 cm −1 can determine the relative stereochemistry of 2,5-dialkyl trithiolanes and 4,6-dialkyl tetrathianes. Configurational cis isomers were distinguished from their corresponding trans isomers. In addition, 4,6-dialkyl-1,2,4,5-tetrathiane with disulfide bonds were distinguished from the constitutive isomer 3,6-dialkyl-1,2,3,5-tetrathiane with trisulfide bonds.

Published
2007
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3. List of Contributors

Author

Terry E. Acree, Evelyne Aguera, Johanna K. Ahola, Isabella Almstätter, Andréa A.R. Alves, José M. Amigo, Thomas M. Amrein, Isabelle Andriot, Serge Antonczak, Renske Asma, Violaine Athes, Elodie Aubin, Alain Audebert, Noelle Béno, Juerg Baggenstoss, Irene Baiamonte, David A. Baines, Jean-Christophe Barbe, António S. Barros, Elisabete B.P. Barros, Max Batenburg, Beata Beisert, Lu Benet, Olivier Berdeaux, Jörg Bernhardt, Silvia Billmayer, Qing Bin, Anja N. Birch, Sandra Bishara, Consol Blanch, Domingo Blanco, Imre Blank, Rita Boerrigter-Eenling, Lauriane Boisard, Sebastian Bormann, Elias Bou-Maroun, Renaud Boulanger, Tiago Brandão, Katharina Breme, Stefan Brennecke, Anne Brockhoff, Laurent Brondel, Keith Brown, Pascal Brunerie, Remo Bucci, Markus Buchhaupt, Mónica Bueno, Andrea Buettner, Geoffroy Cabio’ch, Juan Cacho, Keith R. Cadwallader, Raquel M. Callejón, Maria Mar Campo, Charlotte Cartier, Beatriz Carvalho, Victor C. Castro Alves, Nathalie Cayot, Claire Chabanet, Alain Chaintreau, Adeline Chambault, Landry Charlier, Claire Chassemont, Irene Chetschik, In Hee Cho, Monika Christlbauer, Thomas Claeys Bouuaert, Solenn Coic, Sonia Collin, Belén Concejero-Pardos, Gérard Coureaud, Chris Courter, Laura Culleré, Chris D. Curtin, Marie-Louise Cypriani, Michael Czerny, Catherine Dacremont, Antonio D’Aloise, Marina M. Daltoé, Philippe Darriet, Tomas Davidek, Catrienus de Jong, Arancha De La Fuente, Andreas Degenhardt, Renske Dekkers, Isabelle Déléris, Nicolas Deprêtre, Maria Dermiki, Gilles de Revel, Neil C. Desforges, Annereinou Dijkstra, Diana Dobravalskytė, Andrew T. Dodson, Jossiê Z. Donadel, Thibaut Dosne, Xiaofen Du, Frank Dunemann, Pierre Dussort, J. Stephen Elmore, Karl-Heinz Engel, Hector B. Escalona-Buendia, Ana Escudero, Josefa Espitia-Lopez, Maria M.W. Etschmann, Gilles Féron, Vicente Ferreira, Daniel Festring, Sébastien Fiorucci, Ulrich Fischer, Ian D. Fisk, Pascal Floquet, Ernesto Franco-Luesma, Stephanie Frank, Sophie Frapolli, Felix Frauendorfer, Peter Frey, Stephanie Fritsch, Ozan Gürbüz, Sebastian Ganß, Deborah S. Garruti, Klaus Gassenmeier, Vincent Gerbaud, Joanne Giaccio, Ana M. Gil, A. Glabasnia, André Gohr, Jérôme Golebiowski, Bruna L. Gomes, Liseth Goncalves, Karine Gourrat-Pernin, Cécile Gouttefangeas, Elisa Gracia-Moreno, Julie Graham, David A. Gray, Chantalle Groeneschild, Jacques Gros, Barbara Guggenbühl, Elisabeth Guichard, Hervé Guillemin, Ziya Gunata, Robert D. Hancock, Dody D. Handoko, Åse S. Hansen, Beate Hartmann, Gesa Haseleu, Bethany J. Hausch, Lucie A. Hazelwood, Juan He, Anja Heinlein, Katrin Hempfling, Purificación Hernandez-Orte, Paula Herrero, Jens-Michael Hilmer, Josh L. Hixson, Thomas Hofmann, Hermen Hogekamp, Joanne Hort, Chantal Hory, Jan-Carlos Hufnagel, Carlos Ibàñez, Dominique Ibarra, Georg Innerhofer, Eduardo Jacob-Lopes, Nathalie Jacquet, Deshou Jiang, Lewis L. Jones, Rainer Jung, Fenja Kähne, Heikki P. Kallio, Sukhraj Kaloya, Markus Kelderer, Orla B. Kennedy, Josef Kerler, Christine Kersch-Counet, Artur Kessler, Günter Kindel, Dorothee Klein, Birgit Kohlenberg, Mourad Korichi, Miriam Kort, Stefan Koschinski, Gerhard E. Krammer, Johanna K. Kreißl, Anne J. Kurtz, B. Kusbiantoro, Misha T. Kwasniewski, Oskar A. Laaksonen, Hélène Labouré, Céline Lafarge, Annika Lagemann, Eric Landrieu, Ewald Lardschneider, Edward H Lavin, Harry T. Lawless, Patricia Le Bail, Yves Le Fur, Jean Luc Le Quéré, Catherine Leclercq, Selma G.F. Leite, Erich Leitner, Jakob P. Ley, Pascale Lieben, Margit Liebig, Robert S.T. Linforth, Ricardo Lopez, Yaowapa Lorjaroenphon, Samuel Lubbers, Elisabetta Lubian, Georgia Lytra, Jakob Müller, Hilton Cesar R. Magalhães, Andrea D. Magrì, Antonio L. Magrì, Kanjana Mahattanatawee, Silvia Mallia, Fani Mantzouridou, Isabelle Maraval, Pedro Marco, Federico Marini, James W. Marshall, Marty Martens, Laura Mateo-Vivaracho, Bianca May, Christine M. Mayr, Ana Luisa Medina, Roberto Meier, Daniel Mendez-Iturbe, Christine Messner, Lisa Methven, Wolfgang Meyerhof, Liliana Moncayo, Sumallika Morakul, Maria Lourdes Morales, Cédric Moretton, Emily S. Mort, Mireille Moser, Donald S. Mottram, Jean-Roch Mouret, Stefan Mueller, Chloé Murat, Stefano M. Nalli, Nicoletta Nardo, Osamu Negishi, Yukiko Negishi, Stefano Nicoli, Pamela Nicolle, Henri Nigay, Ben Nijssen, Sabrina Nizet, Ondrej Novotny, Katja Obst, Francisco J. Olachea-Martínez, Alcilucia Oliveira, Ignacio Ontanón, Anne-Marie Orth, Nicole Pabi, Susanne Paetz, Flavio Paoletti, Adamantini Paraskevopoulou, Laurianne Paravisini, Jane K. Parker, Alistair Paterson, Elisabete B. Paula Barros, Francisco Peña, Jim Peck, Florence Peeters, Pere Peiró, Maria Flávia A. Penha, Liesbeth Pepin, M. Perez, Pilar Ruiz Pérez-Cacho, Mikael A. Petersen, Devin G. Peterson, Michael W. Pfaffl, Náyra O.F. Pinto, Monika Pischetsrieder, Daniel Plyer, Julie Poette, Luigi Poisson, Carina Ponne, Janchai Poonlaphdecha, Iulia Poplacean, Sari Puputti, El Mostafa Qannari, Michael C. Qian, Maria I. Queiroz, Jean-Marc Rabillier, Antonio Raffo, Doris Rauhut, Katharina V. Reichelt, Francisco J.B. Reifschneider, Anne Renault, Marie Repoux, Virginia C. Resconi, Claudia M. Rezende, Felipe M. Rivera, Sabine Rochat, João A. Rodrigues, José M. Rojas, S. Sandrine Roques, June Rouseff, Russell L. Rouseff, Daniel Ruiz, Francisco Ruiz-Teran, Christa Runge, Andreas Rytz, Khaled Saadi, Jean-Marie Sablayrolles, Gavin L. Sacks, Hilal Sahin, Anne Saint-Eve, Christian Salles, Felipe San Juan, Mari A. Sandell, Stefanie Sandgruber, Andriéli B. Santos, Uwe Schäfer, Armin Schüttler, Benoist Schaal, Jean-Pierre Schaller, Peter Schieberle, Hans-Georg Schmarr, Christina Schmidt, Eric Schoen, Caroline Scholtes, Dirk Schrader, Jens Schrader, Eva Schrampf, Wilfried Schwab, Hugo Schwager, Mark A. Sefton, Stefan Seilwind, Etienne Sémon, Barbara Siegmund, I. Silamba, António C. Silva Ferreira, Charlotte Sinding, Susan Skelton, Daniela Smogrovicova, Josep Solà, Hortensia Galán Soldevilla, Rollin Soles, Kerstin Söllner, Isabelle Souchon, Andreas Stangl, Christian Starkenmann, Martin Steinhaus, M. Evelyn Stelzl, Andreas Stephan, Georg Stettner, Andrea Strube, Barbara Suess, Chutipapha Suwankanit, Karen M. Swanepoel, Matthew D. Talbot, Thierry Talou, Amparo Tarrega, Andrew Taylor, Dennis K. Taylor, E. Thomas, Karin Thomas, Thierry Thomas-Danguin, Emeline Tissot, Torben Toldam-Andersen, Jérémie Topin, Miriam Torres-Moreno, Aiana F. Torri, Carole Tournier, Stephan Trautzsch, Anne Tromelin, Ana M. Troncoso, Cristina Úbeda, Detlef Ulrich, Camilla Varming, Petras Rimantas Venskutonis, Maria E. Venturini, Jose Ramon Verde-Calvo, Carmen Villmann, Rob van der Velden, Matthias Wüst, Roger Wagner, Stuart Walsh, Brian Wansink, Anne-Marie Wassink, Ludger Wessjohann, Vance Whitaker, Christofora Hanny Wijayaa, Robert C. Williams, Rüdiger Wittlake, Nadine Wollmann, Baoru Yang, Nicole Yang, Lu Yu, Niclass Yvan, Claude Yven, Julián Zapata, Leila Q. Zepka, and Herta Ziegler

Published
2014
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4. Studies on Stability of Citrus Flavors and Insights into Degradation Pathways of Key Aroma Compounds

Author

Dirk Schrader, Gerhard Krammer, Margit Liebig, Birgit Kohlenberg, Stefan Brennecke, Günter Kindel, Andreas Degenhardt, Beate Hartmann, Stephan Trautzsch, and Uwe Schäfer

Subjects
chemistry.chemical_compound, chemistry, biology, Organic chemistry, Degradation (geology), Food science, Citral, biology.organism_classification, Aroma, Flavor
Abstract

Model studies have been performed with individual citrus related aroma compounds such as citral, α-terpineol, α-terpinene, and others, in order to de-couple the complexity of citrus flavors. Degradation pathways and transformation rates have been determined for the most relevant compounds leading to the most prominent off-note compound p-methyl acetophenone. Citral is one of the main precursors. Catechins (flavan-3-ols) are often used as antioxidants for stabilization of flavor mixtures. The reactivity of catechins towards aldehydes is underestimated. In our study, we demonstrate the formation of covalent catechin–citral adducts – a reaction that might influence the aroma stability of citrus flavors in the presence of catechins. As a result, the freshness of citrus flavors and stability of key aroma-active substances can be improved, on the result of this study.

Published
2014
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5. Novel Insights into Flavor Chemistry of Asafetida

Author

Beate Hartmann, Michael Roloff, Laurence Guibouret, Margit Liebig, Birgit Kohlenberg, Stefan Brennecke, Berthold Weber, Andreas Degenhardt, and Gerhard Krammer

Subjects
Chemistry, Organic chemistry, Chemistry (relationship), Flavor
Published
2012
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7. Chirospecific analysis in essential oil, fragrance and flavor research

Author

Stefan Brennecke, Peter Werkhoff, Wilfried Bretschneider, Rudolf Dr Hopp, Horst Surburg, and Matthias Güntert

Subjects
Chemistry, Enantioselective synthesis, General Chemistry, Chiral stationary phase, Biochemistry, Industrial and Manufacturing Engineering, law.invention, law, Organic chemistry, Gas chromatography, Flavor, Essential oil, Food Science, Biotechnology
Abstract

Knowledge of the difference in character and intensity of organoleptically important enantiomeric flavor and fragrance components has initiated the development of new analytical and preparative methods for the separation of optical isomers. In recent years, progress in the area of chirospecific analysis has been especially achieved by the development of modified cyclodextrins as a new type of chiral stationary phase. The state of the art in research on inclusion gas chromatography for separating flavor and fragrance substances is presented. Furthermore, this review reports on new results and recent research developments in enantioselective GC analysis.

Published
1993
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8. Identification of allyl esters in garlic cheese

Author

Stefan Brennecke, Klaus Herbrand, Gerd Lösing, Gerhard Krammer, Margit Liebig, Franz Josef Hammerschmidt, Claus Oliver Schmidt, Ian Gatfield, and Heinz-Jürgen Bertram

Subjects
Chromatography, Propanols, Extraction (chemistry), food and beverages, Esters, General Chemistry, Decanoic acid, Cream cheese, Mass spectrometry, Fatty Acids, Volatile, Gas Chromatography-Mass Spectrometry, chemistry.chemical_compound, food, chemistry, Cheese, Organic chemistry, Gas chromatography, Gas chromatography–mass spectrometry, Allyl alcohol, food.cheese, General Agricultural and Biological Sciences, Garlic, Flavor
Abstract

This study describes the identification of six allyl esters in a garlic cheese preparation and in a commercial cream cheese. The extracts were prepared by liquid/liquid extraction and concentrated by the SAFE process. The identification of the allyl esters of acetic, butyric, hexanoic, heptanoic, octanoic, and decanoic acids is based on the correlation of their mass spectrometric data and chromatographic retention time data obtained from the extracts with those of authentic standards. In addition to the gas chromatography (GC)/mass spectrometry analysis, the flavor ingredients were characterized by GC sniffing by a trained flavorist. Some of the esters were isolated by preparative GC.

Published
2007

9. Authentication of Essential Oils

Author

Franz-Josef Hammerschmidt, Gerhard E. Krammer, Lars Meier, Detlef Stöckigt, Stefan Brennecke, Klaus Herbrand, Angelika Lückhoff, Uwe Schäfer, Claus Oliver Schmidt, and Heinz-Jürgen Bertram

Published
2006
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11. Product-oriented flavor research: learnings from the past, visions for the future

Author

Bernhard Weckerle, Günter Kindel, Detlef Stöckigt, Franz Josef Hammerschmidt, Claus Oliver Schmidt, Berthold Weber, Ian Gatfield, Stefan Brennecke, Jakob Ley, Frank Ott, Gerald Reinders, Gerhard Krammer, Heinz-Jürgen Bertram, and Jens-Michael Hilmer

Subjects
Magnetic Resonance Spectroscopy, Food Contamination, Spectrum Analysis, Raman, Fragaria, Modern life, Mass Spectrometry, Caffeine, Product (category theory), Eating habits, Rosaceae, Flavor, Scientific disciplines, Vision, Chromatography, business.industry, Research, Stereoisomerism, Data science, Toolbox, Flavoring Agents, Fruit, Taste, New product development, Volatilization, business, Food Analysis, Food Science, Biotechnology
Abstract

In the past flavor research and the development of new flavorings were constantly driven by the interaction of flavor analysis, structure elucidation, and chemical synthesis accompanied by sensory. Highly potent flavor compounds were identified in numerous food products and helped to establish a powerful toolbox for flavorists. Nowadays we experience the merging of various scientific disciplines, for example medicine, biology, chemistry, and various technologies in the field of flavor research, which shows direct impact on our understanding of flavors. At the same time modern life has profoundly changed our eating habits. This situation generates new challenges for product development teams, which represent all facets of technologies. This paper will illustrate different examples for the evolution of product-oriented flavor research and future trends.

Published
2006

12. The flavour chemistry of culinary Allium preparations

Author

Heinz-Jürgen Bertram, Jakob Ley, Kathrin Freiherr, Detlef Stöckigt, Margit Liebig, Berthold Weber, Gerhard Krammer, Stefan Brennecke, Michael Roloff, Ian Gatfield, Frank Ott, Christopher Sabater, and Claus Oliver Schmidt

Subjects
Taste, biology, Chemistry, Flavour, food and beverages, Allium, Food science, biology.organism_classification, Aroma
Abstract

In culinary preparations cooked, roasted and fried Allium products play a major role in the taste and the aroma of the final product. In this study the correlation of various culinary preparation techniques such as cooking and frying and the resulting differences in the flavour chemistry (volatiles and non-volatiles) are demonstrated. Different preparation techniques performed on shallots, garlic and/or scallions influence the profile of volatiles and non-volatiles in culinary preparations significantly.

Published
2006
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