Nature's chemical signatures in human olfaction: a foodborne perspective for future biotechnology.

The biocatalytic production of flavor naturals that determine chemosensory percepts of foods and beverages is an ever challenging target for academic and industrial research. Advances in chemical trace analysis and post-genomic progress at the chemistry-biology interface revealed odor qualities of nature's chemosensory entities to be defined by odorant-induced olfactory receptor activity patterns. Beyond traditional views, this review and meta-analysis now shows characteristic ratios of only about 3 to 40 genuine key odorants for each food, from a group of about 230 out of circa 10 000 food volatiles. This suggests the foodborn stimulus space has co-evolved with, and roughly match our circa 400 olfactory receptors as best natural agonists. This perspective gives insight into nature's chemical signatures of smell, provides the chemical odor codes of more than 220 food samples, and beyond addresses industrial implications for producing recombinants that fully reconstruct the natural odor signatures for use in flavors and fragrances, fully immersive interactive virtual environments, or humanoid bioelectronic noses.

[1]  B. Feringa,et al.  Combining Designer Cells and Click Chemistry for a One-Pot Four-Step Preparation of Enantiopure β-Hydroxytriazoles , 2010 .

[2]  Anne Didier,et al.  Humans and Mice Express Similar Olfactory Preferences , 2009, PloS one.

[3]  P. Fernández-Zurbano,et al.  Modeling quality of premium spanish red wines from gas chromatography-olfactometry data. , 2009, Journal of agricultural and food chemistry.

[4]  M. Bensafi,et al.  Physicochemical influence on odor hedonics , 2011 .

[5]  J. Frijters A critical analysis of the odour unit number and its use , 1978 .

[6]  H. Bouwmeester Engineering the essence of plants , 2006, Nature Biotechnology.

[7]  Tsviya Olender,et al.  Personal receptor repertoires: olfaction as a model , 2012, BMC Genomics.

[8]  M. Miyazawa,et al.  Aroma evaluation of gamazumi (Viburnum dilatatum) by aroma extract dilution analysis and odour activity value. , 2012, Phytochemical analysis : PCA.

[9]  N. Ryba,et al.  Common Sense about Taste: From Mammals to Insects , 2009, Cell.

[10]  H. Schiöth,et al.  G protein-coupled receptor deorphanizations. , 2013, Annual review of pharmacology and toxicology.

[11]  M. Kleerebezem,et al.  Lactococcus lactis as a Cell Factory for High-Level Diacetyl Production , 2000, Applied and Environmental Microbiology.

[12]  P. Kraft,et al.  Allerlei Trends: die neuesten Entwicklungen in der Riechstoffchemie , 2000 .

[13]  A. Dewan,et al.  Non-redundant coding of aversive odours in the main olfactory pathway , 2013, Nature.

[14]  P. Schieberle,et al.  Quantitative analysis of aroma compounds in wheat and rye bread crusts using a stable isotope dilution assay , 1987 .

[15]  B. Schäfer Menthol: Minze versus Tagasako-Prozess , 2013 .

[16]  Alois Jungbauer,et al.  Continuous downstream processing of biopharmaceuticals. , 2013, Trends in biotechnology.

[17]  D. Mottram The Maillard reaction: source of flavour in thermally processed foods , 2007 .

[18]  P. Schieberle,et al.  Flavor contribution and formation of the intense roast-smelling odorants 2-propionyl-1-pyrroline and 2-propionyltetrahydropyridine in Maillard-type reactions , 1998 .

[19]  A. A. Birkbeck Challenges in the Synthesis of Natural and Non‐Natural Volatiles , 2010 .

[20]  D. G. Laing,et al.  The analysis of odor mixtures by humans: evidence for a configurational process , 2001, Physiology & Behavior.

[21]  Andreas Stephan,et al.  Comprehensive sensomics analysis of hop-derived bitter compounds during storage of beer. , 2011, Journal of agricultural and food chemistry.

[22]  Donald A Wilson,et al.  Olfactory perceptual stability and discrimination , 2008, Nature Neuroscience.

[23]  P. Schieberle,et al.  Reconstitution of the flavor signature of Dornfelder red wine on the basis of the natural concentrations of its key aroma and taste compounds. , 2011, Journal of agricultural and food chemistry.

[24]  The formation of wine lactone from grape-derived secondary metabolites. , 2011, Journal of agricultural and food chemistry.

[25]  R. Rouseff,et al.  Comparison of aroma volatiles in commercial Merlot and Cabernet Sauvignon wines using gas chromatography-olfactometry and gas chromatography-mass spectrometry. , 2006, Journal of agricultural and food chemistry.

[26]  P. Walla,et al.  Sensory-specific satiety with simple foods in humans: no influence of BMI? , 2007, International Journal of Obesity.

[27]  D. Schneider Elektrophysiologische Untersuchungen von Chemo- und Mechanorezeptoren der Antenne des Seidenspinners Bombyx mori L. , 2004, Zeitschrift für vergleichende Physiologie.

[28]  I. Blank Sensory Relevance of Volatile Organic Sulfur Compounds in Food , 2002 .

[29]  G. Blancher,et al.  Multimodal sensory integration during sequential eating--linking chewing activity, aroma release, and aroma perception over time. , 2012, Chemical senses.

[30]  R. Khan,et al.  Perceptual convergence of multi-component mixtures in olfaction implies an olfactory white , 2012, Proceedings of the National Academy of Sciences.

[31]  C. Guyot-Declerck,et al.  Investigation of the beta-damascenone level in fresh and aged commercial beers. , 2002, Journal of agricultural and food chemistry.

[32]  B. Schaal,et al.  Maternal and Paternal Perception of Individual Odor Signatures in Human Amniotic Fluid – Potential Role in Early Bonding? , 1998, Neonatology.

[33]  K. Mori,et al.  Odorant Category Profile Selectivity of Olfactory Cortex Neurons , 2007, The Journal of Neuroscience.

[34]  Michelle K. Beresford,et al.  A Mendelian Trait for Olfactory Sensitivity Affects Odor Experience and Food Selection , 2013, Current Biology.

[35]  G H FULLER,et al.  THE GAS CHROMATOGRAPH WITH HUMAN SENSOR: PERFUMER MODEL , 1964, Annals of the New York Academy of Sciences.

[36]  K. Cadwallader,et al.  Convenient synthesis of stable deuterium-labeled alkylpyrazines for use in stable isotope dilution assays. , 2013, Journal of agricultural and food chemistry.

[37]  T. Thomas-Danguin,et al.  Just noticeable differences in component concentrations modify the odor quality of a blending mixture. , 2008, Chemical senses.

[38]  M. Sefton,et al.  The effects of size, temperature and air contact on the outcome of heating oak fragments , 2005 .

[39]  B. Chiarelli,et al.  Volatile Signals During Pregnancy: A Possible Chemical Basis for Mother–Infant Recognition , 2008, Journal of Chemical Ecology.

[40]  A. Mosandl,et al.  Mechanism of wine lactone formation: demonstration of stereoselective cyclization and 1,3-hydride shift. , 2006, Journal of agricultural and food chemistry.

[41]  Gisbert Schneider,et al.  Predicting olfactory receptor neuron responses from odorant structure , 2007, Chemistry Central journal.

[42]  T. Davidek,et al.  Basic Chemistry and Process Conditions for Reaction Flavours with Particular Focus on Maillard‐Type Reactions , 2010 .

[43]  L. Buck,et al.  Combinatorial Receptor Codes for Odors , 1999, Cell.

[44]  I. S. Pretorius,et al.  Yeast and its Importance to Wine Aroma - A Review , 2019, South African Journal of Enology & Viticulture.

[45]  Yoshihito Niimura,et al.  Olfactory Receptor Multigene Family in Vertebrates: From the Viewpoint of Evolutionary Genomics , 2012, Current genomics.

[46]  Yusuf Chisti,et al.  Biotechnology-a sustainable alternative for chemical industry. , 2005, Biotechnology advances.

[47]  Andreas Schmid,et al.  The production of fine chemicals by biotransformations. , 2002, Current opinion in biotechnology.

[48]  S. Vaglio,et al.  Chemical communication and mother-infant recognition , 2009, Communicative & integrative biology.

[49]  Cori Bargmann Comparative chemosensation from receptors to ecology , 2006, Nature.

[50]  Dietmar Krautwurst,et al.  Human Olfactory Receptor Families and Their Odorants , 2008, Chemistry & biodiversity.

[51]  Hiroshi Ishida,et al.  Smelling Screen: Development and Evaluation of an Olfactory Display System for Presenting a Virtual Odor Source , 2013, IEEE Transactions on Visualization and Computer Graphics.

[52]  H. Takeuchi,et al.  Structural determination of vanillin, isovanillin and ethylvanillin by means of gas electron diffraction and theoretical calculations , 2006 .

[53]  Gary A Reineccius,et al.  Flavour-Isolation Techniques , 2007 .

[54]  T. Hofmann,et al.  Quantitative reconstruction of the nonvolatile sensometabolome of a red wine. , 2008, Journal of agricultural and food chemistry.

[55]  M. Jones-Gotman,et al.  The human brain distinguishes between single odorants and binary mixtures. , 2009, Cerebral cortex.

[56]  J. Mattes,et al.  Sensomics analysis of taste compounds in balsamic vinegar and discovery of 5-acetoxymethyl-2-furaldehyde as a novel sweet taste modulator. , 2012, Journal of agricultural and food chemistry.

[57]  Masatoshi Nei,et al.  Evolutionary dynamics of olfactory receptor genes in fishes and tetrapods , 2005, Proceedings of the National Academy of Sciences of the United States of America.

[58]  G. Sicard,et al.  Perceptual blending in odor mixtures depends on the nature of odorants and human olfactory expertise. , 2012, Chemical senses.

[59]  P. Schieberle,et al.  Compound identification: a Journal of Agricultural and Food Chemistry perspective. , 2007, Journal of agricultural and food chemistry.

[60]  L. Vosshall,et al.  Genetic variation in a human odorant receptor alters odour perception , 2007, Nature.

[61]  A. D. Wilson,et al.  Review of electronic-nose technologies and algorithms to detect hazardous chemicals in the environment , 2012 .

[62]  W. Grosch Gas Chromatography—Olfactometry of Aroma Compounds , 2007 .

[63]  Paul Richard,et al.  Using Olfactive Virtual Environments for Learning Organic Molecules , 2006, Edutainment.

[64]  John R. Piggott,et al.  Origins of Flavour in Whiskies and a Revised Flavour Wheel: a Review , 2001 .

[65]  S. Gravina,et al.  Human Biology of Taste , 2013, Annals of Saudi medicine.

[66]  M. Spehr,et al.  Odorant–Receptor Interactions and Odor Percept: A Chemical Perspective , 2008, Chemistry & biodiversity.

[67]  S. Liberles,et al.  Trace Amine‐associated Receptors Are Olfactory Receptors in Vertebrates , 2009, Annals of the New York Academy of Sciences.

[68]  P. Lennie,et al.  The machinery of colour vision , 2007, Nature Reviews Neuroscience.

[69]  Alphus D. Wilson,et al.  Applications and Advances in Electronic-Nose Technologies , 2009, Sensors.

[70]  Jasmine L. Gallaher,et al.  Computational Design of an Enzyme Catalyst for a Stereoselective Bimolecular Diels-Alder Reaction , 2010, Science.

[71]  J. Pronk,et al.  The Ehrlich Pathway for Fusel Alcohol Production: a Century of Research on Saccharomyces cerevisiae Metabolism , 2008, Applied and Environmental Microbiology.

[72]  R. Axel,et al.  A novel multigene family may encode odorant receptors: A molecular basis for odor recognition , 1991, Cell.

[73]  R. Rouseff,et al.  Pathways of 4-vinylguaiacol formation from ferulic acid in model solutions of orange juice , 1992 .

[74]  R. Triqui,et al.  Freshness assessments of Moroccan sardine (Sardina pilchardus): comparison of overall sensory changes to instrumentally determined volatiles. , 2003, Journal of agricultural and food chemistry.

[75]  P. Schieberle New Developments in Methods for Analysis of Volatile Flavor Compounds and their Precursors , 1995 .

[76]  P. Schieberle,et al.  Evaluation of Key Odorants in Milk Chocolate and Cocoa Mass by Aroma Extract Dilution Analyses , 1997 .

[77]  Gilles Laurent,et al.  Olfactory network dynamics and the coding of multidimensional signals , 2002, Nature Reviews Neuroscience.

[78]  D. Guadagni,et al.  Aroma components of olive oil , 1973 .

[79]  M. V. Filho,et al.  Methanol-based industrial biotechnology: current status and future perspectives of methylotrophic bacteria. , 2009, Trends in biotechnology.

[80]  K. Shinohara,et al.  The calming effect of a maternal breast milk odor on the human newborn infant , 2009, Neuroscience Research.

[81]  A. Demain History of Industrial Biotechnology , 2010 .

[82]  Relationship between the differential adsorption of odorants by the olfactory mucus and their perception in mixtures , 1988 .

[83]  Y. Pilpel,et al.  Mouse-human orthology relationships in an olfactory receptor gene cluster. , 2001, Genomics.

[84]  Maik Behrens,et al.  Moleküle und biologische Mechanismen des Süß‐ und Umamigeschmacks , 2011 .

[85]  J. Rehfeld,et al.  Appetite suppression through smelling of dark chocolate correlates with changes in ghrelin in young women , 2010, Regulatory Peptides.

[86]  Oh Seok Kwon,et al.  Polypyrrole nanotubes conjugated with human olfactory receptors: high-performance transducers for FET-type bioelectronic noses. , 2009, Angewandte Chemie.

[87]  D. G. Laing,et al.  The capacity of humans to identify odors in mixtures , 1989, Physiology & Behavior.

[88]  W. Schwab Genetic Engineering of Plants and Microbial Cells for Flavour Production , 2007 .

[89]  P. Schieberle,et al.  2-Oxopropanal, Hydroxy-2-propanone, and 1-PyrrolineImportant Intermediates in the Generation of the Roast-Smelling Food Flavor Compounds 2-Acetyl-1-pyrroline and 2-Acetyltetrahydropyridine , 1998 .

[90]  P. Schieberle,et al.  Evaluation of key aroma compounds in hand-squeezed grapefruit juice (Citrus paradisi Macfayden) by quantitation and flavor reconstitution experiments. , 2001, Journal of agricultural and food chemistry.

[91]  Takashi Tanaka,et al.  Whisky lactone precursors from the wood of Platycarya strobilacea , 1996 .

[92]  Kea-Tiong Tang,et al.  Towards a Chemiresistive Sensor-Integrated Electronic Nose: A Review , 2013, Sensors.

[93]  Peter Bliss,et al.  The Chemical Interactions Underlying Tomato Flavor Preferences , 2012, Current Biology.

[94]  P. Schieberle,et al.  Evaluation of aroma differences between hand-squeezed juices from Valencia late and Navel oranges by quantitation of key odorants and flavor reconstitution experiments. , 2001, Journal of agricultural and food chemistry.

[95]  R. Soussignan,et al.  Orientation responses to biological odours in the human newborn. Initial pattern and postnatal plasticity. , 1997, Comptes rendus de l'Academie des sciences. Serie III, Sciences de la vie.

[96]  W. Meyerhof,et al.  The human vomeronasal type‐1 receptor family—detection of volatiles and cAMP signaling in HeLa/Olf cells , 2008, FASEB journal : official publication of the Federation of American Societies for Experimental Biology.

[97]  Donald A Wilson,et al.  Separate encoding of identity and similarity of complex familiar odors in piriform cortex , 2006, Proceedings of the National Academy of Sciences.

[98]  P. Schieberle,et al.  Identification of the key odorants in barley malt (caramalt) using GC/MS techniques and odour dilution analyses. , 1998, Die Nahrung.

[99]  I. Pretorius,et al.  The Development of Yeast Strains as Tools for Adjusting the Flavor of Fermented Beverages to Market Specifications , 2009 .

[100]  W. Grosch,et al.  Sensory study on the character impact odorants of roasted arabica coffee. , 1999, Journal of agricultural and food chemistry.

[101]  Nathanael Weill Chemogenomic approaches for the exploration of GPCR space. , 2011, Current topics in medicinal chemistry.

[102]  Yan Xu,et al.  Ferulic Acid Release and 4‐Vinylguaiacol Formation during Chinese Rice Wine Brewing and Fermentation , 2010 .

[103]  R. Rouseff,et al.  Aroma composition changes in early season grapefruit juice produced from thermal concentration. , 2002, Journal of agricultural and food chemistry.

[104]  Arnold L. Demain,et al.  REVIEWS: The business of biotechnology , 2007 .

[105]  Tai Hyun Park,et al.  Recent advances in electronic and bioelectronic noses and their biomedical applications. , 2011, Enzyme and microbial technology.

[106]  R. Reed,et al.  Signal transduction in olfactory neurons , 1991, The Journal of Steroid Biochemistry and Molecular Biology.

[107]  Stefan Krahulec,et al.  Harnessing Candida tenuis and Pichia stipitis in whole‐cell bioreductions of o‐chloroacetophenone: Stereoselectivity, cell activity, in situ substrate supply and product removal , 2013, Biotechnology journal.

[108]  Terry E. Acree,et al.  A Procedure for the Sensory Analysis of Gas Chromatographic Effluents , 1984 .

[109]  Donald A. Wilson,et al.  Odour Perception: An Object-Recognition Approach , 2007, Perception.

[110]  I. Blank,et al.  Formation of odorants in Maillard model systems based on l-proline as affected by pH. , 2003, Journal of agricultural and food chemistry.

[111]  J. Moorhouse,et al.  Method for Use in Studies of Insect Chemical Communication , 1969, Nature.

[112]  R. Petit,et al.  Variation in wood volatile compounds in a mixed oak stand: strong species and spatial differentiation in whisky-lactone content , 2007, Annals of Forest Science.

[113]  K. Krogerus,et al.  125th Anniversary Review: Diacetyl and its control during brewery fermentation , 2013 .

[114]  C. Sheridan A taste of the future , 2004, Nature Biotechnology.

[115]  F. Priest,et al.  Composition of peats used in the preparation of malt for scotch whisky productioninfluence of geographical source and extraction depth. , 2009, Journal of agricultural and food chemistry.

[116]  C. Derby,et al.  Generalization among related complex odorant mixtures and their components: Analysis of olfactory perception in the spiny lobster , 1996, Physiology & Behavior.

[117]  Horst Vogel,et al.  Characterization of an extended receptive ligand repertoire of the human olfactory receptor OR17‐40 comprising structurally related compounds , 2006, Journal of neurochemistry.

[118]  Bastian Blombach,et al.  Bio-based production of organic acids with Corynebacterium glutamicum , 2012, Microbial biotechnology.

[119]  R. Khan,et al.  Predicting Odor Pleasantness from Odorant Structure: Pleasantness as a Reflection of the Physical World , 2007, The Journal of Neuroscience.

[120]  H. Zorn,et al.  Fungal secretomes—nature’s toolbox for white biotechnology , 2008, Applied Microbiology and Biotechnology.

[121]  Hanns Hatt,et al.  Molecular and Cellular Basis of Human Olfaction , 2004, Chemistry & biodiversity.

[122]  Imre Blank,et al.  Potent odorants of the roasted powder and brew of Arabica coffee , 1992 .

[123]  I. Rodriguez,et al.  A putative pheromone receptor gene expressed in human olfactory mucosa , 2000, Nature Genetics.

[124]  Hiroshi Kataoka,et al.  Molecular Bases of Odor Discrimination: Reconstitution of Olfactory Receptors that Recognize Overlapping Sets of Odorants , 2001, The Journal of Neuroscience.

[125]  A. Keller,et al.  Humans Can Discriminate More than 1 Trillion Olfactory Stimuli , 2014, Science.

[126]  M. Rothe,et al.  Aromastoffe des Brotes , 1963 .

[127]  J. Gottfried Central mechanisms of odour object perception , 2010, Nature Reviews Neuroscience.

[128]  Michelle K. Beresford,et al.  Identification of Regions Associated with Variation in Sensitivity to Food-Related Odors in the Human Genome , 2013, Current Biology.

[129]  C. de Graaf,et al.  Sensory-specific satiety in obese and normal-weight women. , 2004, The American journal of clinical nutrition.

[130]  A comparison of taste test ratings, repeated consumption, and postconsumption ratings of different strengths of iced tea , 1995 .

[131]  Congjun Li,et al.  AKT/eNOS signaling module functions as a potential feedback loop in the growth hormone signaling pathway , 2009, Journal of molecular signaling.

[132]  D. Krautwurst,et al.  A hit map-based statistical method to predict best ligands for orphan olfactory receptors: natural key odorants versus "lock picks". , 2013, Methods in molecular biology.

[133]  J. Mainland,et al.  Odor Coding by a Mammalian Receptor Repertoire , 2009, Science Signaling.

[134]  B. Hauer,et al.  Rational Design of Pseudozyma antarctica Lipase B Yielding a General Esterification Catalyst , 2010, Chembiochem : a European journal of chemical biology.

[135]  W. Schwab Natural 4-Hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol®) , 2013, Molecules.

[136]  W. D. Murray,et al.  Microbiological and Enzymatic Production of Flavor and Fragrance Chemicals , 1989 .

[137]  Dan D. Stettler,et al.  Representations of Odor in the Piriform Cortex , 2009, Neuron.

[138]  Tai Hyun Park,et al.  Bioelectronic nose with high sensitivity and selectivity using chemically functionalized carbon nanotube combined with human olfactory receptor. , 2012, Journal of biotechnology.

[139]  Roland Wohlgemuth,et al.  Biocatalysis--key to sustainable industrial chemistry. , 2010, Current opinion in biotechnology.

[140]  H. Zorn,et al.  Insect-derived enzymes: a treasure for industrial biotechnology and food biotechnology. , 2013, Advances in biochemical engineering/biotechnology.

[141]  Peter Schieberle,et al.  Odor-Active Constituents in Fresh Pineapple (Ananas comosus [L.] Merr.) by Quantitative and Sensory Evaluation , 2005, Bioscience, biotechnology, and biochemistry.

[142]  E. Lavin,et al.  Odorants in breast milk. , 2003, Archives of pediatrics & adolescent medicine.

[143]  Gustavo Glusman,et al.  The complete human olfactory subgenome. , 2001, Genome research.

[144]  M. Crabbe,et al.  The Maillard reaction in foods and medicine , 1998 .

[145]  W. Grosch Evaluation of the key odorants of foods by dilution experiments, aroma models and omission. , 2001, Chemical senses.

[146]  Andreas Keller,et al.  The Missense of Smell: Functional Variability in the Human Odorant Receptor Repertoire , 2013, Nature Neuroscience.

[147]  P. Schieberle,et al.  Evaluation of the character impact odorants in fresh strawberry juice by quantitative measurements and sensory studies on model mixtures , 1997 .

[148]  Dietmar Krautwurst,et al.  Structural determinants of odorant recognition by the human olfactory receptors OR1A1 and OR1A2. , 2007, Journal of structural biology.

[149]  H. Guth Quantitation and Sensory Studies of Character Impact Odorants of Different White Wine Varieties , 1997 .

[150]  Zhimin Huang,et al.  Crucial role of copper in detection of metal-coordinating odorants , 2012, Proceedings of the National Academy of Sciences.

[151]  T. Michael,et al.  The tomato genome fleshed out , 2012, Nature Biotechnology.

[152]  Philip Kraft,et al.  Odds and Trends: Recent Developments in the Chemistry of Odorants , 2000 .

[153]  Masayuki Numao,et al.  Adaptive interactive device control by using reinforcement learning in ambient information environment , 2012, VR.

[154]  E. Sugawara,et al.  Diversity of odor-active compounds from local cultivars and wild accessions of Iwateyamanashi (Pyrus ussuriensis var. aromatica) revealed by Aroma Extract Dilution Analysis (AEDA) , 2013, Breeding science.

[155]  D. G. Laing,et al.  Perception of components in binary odour mixtures , 1983 .

[156]  Yoshihito Niimura,et al.  Evolutionary dynamics of olfactory receptor genes in chordates: interaction between environments and genomic contents , 2009, Human Genomics.

[157]  M. Giurfa,et al.  Antennal lobe processing increases separability of odor mixture representations in the honeybee. , 2010, Journal of neurophysiology.

[158]  Benoist Schaal,et al.  Human newborns prefer human milk: conspecific milk odor is attractive without postnatal exposure. , 2005, Child development.

[159]  W. Grosch,et al.  Key odorants of french fries , 1998 .

[160]  P. Schieberle,et al.  Characterization of the key aroma compounds in an american bourbon whisky by quantitative measurements, aroma recombination, and omission studies. , 2008, Journal of agricultural and food chemistry.

[161]  Terry E. Acree,et al.  Peer Reviewed: GC/Olfactometry GC With a Sense of Smell , 1997 .

[162]  I. Ojima,et al.  Catalytic Asymmetric Synthesis , 1993 .

[163]  E. Boido,et al.  Production of fermentation aroma compounds by Saccharomyces cerevisiae wine yeasts: effects of yeast assimilable nitrogen on two model strains. , 2008, FEMS yeast research.

[164]  Werner Grosch,et al.  Detection of potent odorants in foods by aroma extract dilution analysis , 1993 .

[165]  S. Kays,et al.  Analytically Directed Flavor Selection in Breeding Food Crops , 2003 .

[166]  M. Behrens,et al.  Sweet and umami taste: natural products, their chemosensory targets, and beyond. , 2011, Angewandte Chemie.

[167]  I. Gaillard,et al.  Amino-acid changes acquired during evolution by olfactory receptor 912-93 modify the specificity of odorant recognition. , 2004, Human molecular genetics.

[168]  M. Behrens,et al.  The molecular receptive ranges of human TAS2R bitter taste receptors. , 2010, Chemical senses.

[169]  C. Ross,et al.  Wine matrix compounds affect perception of wine aromas. , 2013, Annual review of food science and technology.

[170]  T. Thomas-Danguin,et al.  Proportion of Odorants Impacts the Configural versus Elemental Perception of a Binary Blending Mixture in Newborn Rabbits , 2011 .

[171]  J. Keasling,et al.  Engineering a mevalonate pathway in Escherichia coli for production of terpenoids , 2003, Nature Biotechnology.

[172]  B. Vanderhaegen,et al.  Ferulic acid release and 4-vinylguaiacol formation during brewing and fermentation: indications for feruloyl esterase activity in Saccharomyces cerevisiae. , 2004, Journal of agricultural and food chemistry.

[173]  P. Schreier,et al.  Enzymes and Flavour Biotechnology , 2007 .

[174]  R. Ulber,et al.  Downstream processing in marine biotechnology. , 2005, Advances in biochemical engineering/biotechnology.

[175]  R. Axel,et al.  A novel family of genes encoding putative pheromone receptors in mammals , 1995, Cell.

[176]  Charles Spence,et al.  Multisensory Presence in Virtual Reality: Possibilities & Limitations. , 2011 .

[177]  Peter Schieberle,et al.  Identification based on quantitative measurements and aroma recombination of the character impact odorants in a Bavarian Pilsner-type beer. , 2005, Journal of agricultural and food chemistry.

[178]  D. Sell,et al.  Applied biocatalysis for the synthesis of natural flavour compounds – current industrial processes and future prospects , 2004, Biotechnology Letters.

[179]  P. Schieberle,et al.  Comparison of the most odor-active compounds in fresh and dried hop cones (Humulus lupulus L. variety spalter select) based on GC-olfactometry and odor dilution techniques. , 2000, Journal of agricultural and food chemistry.

[180]  David G. Laing Perceptual odour interactions and objective mixture analysis , 1994 .

[181]  Y. Gounaris Biotechnology for the production of essential oils, flavours and volatile isolates. A review.†‡ , 2010 .

[182]  R. Hudson,et al.  From molecule to mind: the role of experience in shaping olfactory function , 1999, Journal of Comparative Physiology A.

[183]  Linda B. Buck,et al.  A second class of chemosensory receptors in the olfactory epithelium , 2006, Nature.

[184]  Yehudit Hasin,et al.  Genetic Elucidation of Human Hyperosmia to Isovaleric Acid , 2007, PLoS biology.

[185]  P. Schieberle,et al.  Sensomics analysis of key hazelnut odorants (Corylus avellana L. 'Tonda Gentile') using comprehensive two-dimensional gas chromatography in combination with time-of-flight mass spectrometry (GC×GC-TOF-MS). , 2013, Journal of agricultural and food chemistry.

[186]  M. Wüst,et al.  Stereoselective formation of the varietal aroma compound rose oxide during alcoholic fermentation. , 2008, Journal of agricultural and food chemistry.

[187]  P. Schieberle,et al.  Correlation between the Concentrations of Two Oak Derived Key Odorants and the Intensity of a Woody-“Barrique-Type” Odor Note in Different Red Wines , 2011 .

[188]  S. Ebeler,et al.  Carotenoid Cleavage Products , 2013 .

[189]  J. Schrader Microbial Flavour Production , 2007 .

[190]  N. Magan,et al.  Electronic noses and disease diagnostics , 2004, Nature Reviews Microbiology.

[191]  R. Stevenson REVIEW An Initial Evaluation of the Functions of Human Olfaction , 2022 .

[192]  T. Thomas-Danguin,et al.  Elemental and configural processing of odour mixtures in the newborn rabbit , 2009, Journal of Experimental Biology.

[193]  Paul N. Devine,et al.  Biocatalytic Asymmetric Synthesis of Chiral Amines from Ketones Applied to Sitagliptin Manufacture , 2010, Science.

[194]  D. Reed,et al.  Genetics of taste and smell: poisons and pleasures. , 2010, Progress in molecular biology and translational science.

[195]  J. Giovannoni Breeding new life into plant metabolism , 2006, Nature Biotechnology.

[196]  F. Priest,et al.  Decarboxylation of Substituted Cinnamic Acids by Lactic Acid Bacteria Isolated during Malt Whisky Fermentation , 2000, Applied and Environmental Microbiology.

[197]  Tomoko Takahashi,et al.  Deorphanization of Dresden G Protein-Coupled Receptor for an Odorant Receptor , 2007, Journal of receptor and signal transduction research.

[198]  Werner Grosch,et al.  Structure-odour-activity relationships of alkylpyrazines , 1999 .

[199]  R. Berger Biotechnology of flavours—the next generation , 2009, Biotechnology Letters.

[200]  Z. Peterlin,et al.  Pharmacology of mammalian olfactory receptors. , 2013, Methods in molecular biology.

[201]  Masatoshi Nei,et al.  The evolution of animal chemosensory receptor gene repertoires: roles of chance and necessity , 2008, Nature Reviews Genetics.

[202]  T. Hofmann,et al.  Quantitative studies and taste re-engineering experiments toward the decoding of the nonvolatile sensometabolome of Gouda cheese. , 2008, Journal of agricultural and food chemistry.

[203]  R. Stubbs,et al.  Energy density, diet composition and palatability: influences on overall food energy intake in humans , 2004, Physiology & Behavior.

[204]  W. Grosch,et al.  Fishy and hay-like off-flavours of dry spinach , 1998 .

[205]  C. Galizia,et al.  Weaker Ligands Can Dominate an Odor Blend due to Syntopic Interactions , 2013, Chemical senses.

[206]  W. Grosch Determination of potent odourants in foods by aroma extract dilution analysis (AEDA) and calculation of odour activity values (OAVs) , 1994 .

[207]  C. Nederkoorn,et al.  Sensory-specific satiety is unaffected by manipulations of flavour intensity , 2009, Physiology & Behavior.

[208]  A. Buettner A selective and sensitive approach to characterize odour‐active and volatile constituents in small‐scale human milk samples , 2007 .

[209]  P. Dürr,et al.  THE CONTRIBUTION OF SOME VOLATILES TO THE SENSORY QUALITY OF APPLE AND ORANGE JUICE ODOUR , 1981 .

[210]  Andréi Prida,et al.  Impact of Oak-Derived Compounds on the Olfactory Perception of Barrel-Aged Wines , 2010, American Journal of Enology and Viticulture.

[211]  N. Stroebele,et al.  Effect of ambience on food intake and food choice. , 2004, Nutrition.

[212]  Jian-He Xu,et al.  New opportunities for biocatalysis: driving the synthesis of chiral chemicals. , 2011, Current opinion in biotechnology.

[213]  Hiroshi Kataoka,et al.  Olfactory receptor antagonism between odorants , 2004, The EMBO journal.

[214]  John-Dylan Haynes,et al.  Odor quality coding and categorization in human posterior piriform cortex , 2009, Nature Neuroscience.

[215]  P. Schieberle,et al.  Character Impact Odour Compounds of Different Kinds of Butter , 1993 .

[216]  Loïc Briand,et al.  Comparison of odorant specificity of two human olfactory receptors from different phylogenetic classes and evidence for antagonism. , 2005, Chemical senses.

[217]  S. Akutagawa Enantioselective isomerization of allylamine to enamine: practical asymmetric synthesis of (–)-menthol by Rh–BINAP catalysts , 1997 .

[218]  Klaus Willecke,et al.  Identification of Specific Ligands for Orphan Olfactory Receptors , 2005, Journal of Biological Chemistry.

[219]  Jeffrey A. Riffell,et al.  Identification of a Testicular Odorant Receptor Mediating Human Sperm Chemotaxis , 2003, Science.

[220]  Bernhard Hauer,et al.  Recent progress in industrial biocatalysis. , 2011, Current opinion in chemical biology.

[221]  D. Dubourdieu,et al.  A New Type of Flavor Precursors in Vitis vinifera L. cv. Sauvignon Blanc: S-Cysteine Conjugates , 1998 .

[222]  N. Issa,et al.  Glomerular activation patterns and the perception of odor mixtures , 2008, The European journal of neuroscience.

[223]  J. Mainland,et al.  Genetic variation in the odorant receptor OR2J3 is associated with the ability to detect the "grassy" smelling odor, cis-3-hexen-1-ol. , 2012, Chemical senses.

[224]  J. Rospars,et al.  Competitive and Noncompetitive Odorant Interactions in the Early Neural Coding of Odorant Mixtures , 2008, The Journal of Neuroscience.

[225]  K. Cadwallader,et al.  Identification and quantification of aroma-active components that contribute to the distinct malty flavor of buckwheat honey. , 2002, Journal of agricultural and food chemistry.