Chemical Structure of Compounds and Their Sweet and Bitter Taste

In presenting the material in this chapter, four fundamental propositions are made. These are: (1) Sucrose (sugar) tastes sweet. (2) Quinine tastes bitter. (3) Sodium chloride tastes salty 1. (4) Hydrochloric acid tastes sour.

[1]  L. Audrieth,et al.  PREPARATION AND PROPERTIES OF SOME N-SUBSTITUTED SULFAMIC ACIDS1 , 1944 .

[2]  Ernest L. Eliel,et al.  Stereochemistry of Carbon Compounds , 1962 .

[3]  S. S. Stevens.  On the psychophysical law. , 1957, Psychological review.

[4]  F. J. Pilgrim,et al.  Sweetness of various compounds and its measurement. , 1957 .

[5]  C. Hudson.  THE SIGNIFICANCE OF CERTAIN NUMERICAL RELATIONS IN THE SUGAR GROUP.2 , 1909 .

[6]  C. P. Berg.  Physiology of the D-amino acids. , 1953, Physiological reviews.

[7]  E. Hughes,et al.  Configuration of Carbohydrates, Hydroxy-Acids and Amino-Acids: Stereochemical Standards of Configuration , 1950, Nature.

[8]  J. Danielli,et al.  PERMEABILITY OF NATURAL MEMBRANES , 1953 .

[9]  A. Heiduschka,et al.  Beziehungen zwischen Konstitution und Geschmack von α‐Aminosäuren , 1925 .

[10]  Yrjö Renqvist,et al.  Über den Geschmack , 1919 .

[11]  R. Bentley.  The Conformations of the Disaccharides, Cellobiose and Maltose1 , 1959 .

[12]  D. N. Hume,et al.  Acetato Complexes of Lead in Aqueous Solution , 1956 .

[13]  J. S. Brimacombe,et al.  Aspects of stereochemistry—II : Intramolecular hydrogen bonding in some monohydroxy derivatives of tetrahydrofuran, tetrahydropyran and 1:3-dioxan , 1959 .

[14]  H. Britton,et al.  CCCXCIV.—Physico-chemical studies of complex formation involving weak acids. Part II. The constitution of acetates in solution , 1931 .

[15]  R. Lenz,et al.  The application of nuclear magnetic resonance to structural studies of carbohydrates in aqueous solution , 1961 .

[16]  R. Oppermann.  Proteins, amino acids and peptides , 1943 .

[17]  S. Price,et al.  Sweet-Sensitive Protein from Bovine Taste Buds: Isolation and Assay , 1966, Science.

[18]  Y. Zotterman,et al.  ELECTROPHYSIOLOGICAL RESPONSES TO SUGARS AND THEIR DEPRESSION BY SALT , 1963 .

[19]  W. Boyd,et al.  Different Tastes of Enantiomorphic Hexoses , 1962, Science.

[20]  S. D. Beck.  A BIMODAL RESPONSE TO DIETARY SUGARS BY AN INSECT , 1956 .

[21]  S. Swisher,et al.  Incorporation of Acetate-2-14C into Human Erythrocyte Stroma as a Function of Storage , 1954, Nature.

[22]  O. Hassel,et al.  The Structure of Molecules Containing Cyclohexane or Pyranose Rings. , 1947 .

[23]  G. A. Jeffrey,et al.  CRYSTAL-STRUCTURE ANALYSIS IN CARBOHYDRATE CHEMISTRY. , 1964, Advances in carbohydrate chemistry.

[24]  DAVID G. KENDALL,et al.  Theory of Probability and Statistics , 1951, Nature.

[25]  C. P. Richter,et al.  SUCROSE TASTE THRESHOLDS OF RATS AND HUMANS , 1939 .

[26]  G. Inglett,et al.  Dihydrochalcones. Synthesis of potential sweetening agents , 1968 .

[27]  H. Isbell,et al.  Bromine oxidation and mutarotation measurements of the alpha- and beta-aldoses , 1937 .

[28]  E. Fischer.  Ueber die Glucoside der Alkohole , 1893 .

[29]  Wenner-Grenska samfundet,et al.  Olfaction and taste , 1963 .

[30]  L. N. Ferguson.  Electron structures of organic molecules , 1952 .

[31]  R. E. Reeves,et al.  Cuprammonium-glycoside complexes. , 1951, Advances in carbohydrate chemistry.

[32]  R. E. Reeves.  Cuprammonium--Glycoside Complexes. V. The Conformation of the Pyranose Ring in Some D-Hexose β Anhydrides , 1949 .

[33]  J. Böeseken.  Über die Lagerung der Hydroxyl‐Gruppen von Polyoxy‐Verbindungen im Raum. Die Konfiguration der gesättigten Glykole und der α‐ und β‐Glykose , 1913 .

[34]  Ernest Dzendolet,et al.  A structure common to sweet-evoking compounds , 1968 .

[35]  T. Acree,et al.  Sweet Taste of D and L-Sugars and Amino-acids and the Steric Nature of their Chemo-receptor Site , 1969, Nature.

[36]  T. Acree,et al.  Molecular Theory of Sweet Taste , 1967, Nature.

[37]  W. L. Marshall,et al.  Electrical conductances of aqueous sodium chloride solutions from 0 to 800.degree. and at pressures to 4000 bars , 1968 .

[38]  H. Isbell,et al.  Pyranose-furanose interconversions with reference to the mutarotations of galactose, levulose, lactulose,and turanose , 1938 .

[39]  C. J. Carr,et al.  Sugar Alcohols. V. Chemical Constitution and Sweet Taste1 , 1936 .

[40]  S. Carlill.  Olfaction and Taste II , 1968 .

[41]  W. Whelan.  Chemistry of Carbohydrates , 2012, Nature.

[42]  H. Meiselman,et al.  Cation and anion contributions to gustatory quality of simple salts , 1967 .

[43]  H. Sachse.  Ueber die geometrischen Isomerien der Hexamethylenderivate , 1890 .

[44]  H. Isbell.  Oxidation of aldoses with bromine , 1962 .

[45]  E. Percival.  Structural Carbohydrate Chemistry , 1962 .

[46]  Roger Hayward,et al.  The Hydrogen Bond , 1960 .

[47]  C. Hudson.  Historical Aspects Of Emil Fischer'S Fundamental Conventions For Writing Stereo-Formulas In A Plane , 1948 .

[48]  R. Pangborn,et al.  Relative Sweetness of α- and β-Forms of Selected Sugars , 1961, Nature.

[49]  J. S. Hough,et al.  The Chemistry of Hop Constituents , 1967 .

[50]  FRANK R. DASTOLI,et al.  Bitter-sensitive Protein from Porcine Taste Buds , 1968, Nature.

[51]  W. Haworth.  The constitution of sugars , 2022 .

[52]  A. L. Fox.  The Relationship between Chemical Constitution and Taste. , 1932, Proceedings of the National Academy of Sciences of the United States of America.

[53]  G. Hamor,et al.  Correlation of Chemical Structure and Taste in the Saccharin Series , 1961, Science.

[54]  H. A. Levy,et al.  Sucrose: Precise Determination of Crystal and Molecular Structure by Neutron Diffraction , 1963, Science.

[55]  L. D. Hall.  NUCLEAR MAGNETIC RESONANCE. , 1964 .

[56]  Beidler’s theory and human taste stimulation , 1966 .

[57]  R. Moncrieff,et al.  The chemical senses , 1967 .

[58]  R. Mazur,et al.  Structure-taste relationships of some dipeptides. , 1969, Journal of the American Chemical Society.

[59]  J. Bemiller,et al.  Methods in Carbohydrate Chemistry , 1965 .

[60]  H. A. Levy,et al.  α-D-Glucose: Precise Determination of Crystal and Molecular Structure by Neutron-Diffraction Analysis , 1965, Science.

[61]  Chang Yong Lee,et al.  Thermodynamics and kinetics of D-galactose tautomers during mutarotation , 1969 .

[62]  D. Horton,et al.  Conformational inversion of pyranoid ring sugars. Conformational equilibrium of .beta.-D-ribopyranose tetraacetate , 1967 .

[63]  R. G. Myers,et al.  A NEW THEORY RELATING CONSTITUTION TO TASTE. [PRELIMINARY PAPER.] SIMPLE RELATIONS BETWEEN THE CONSTITUTION OF ALIPHATIC COMPOUNDS AND THEIR SWEET TASTE. , 1919 .

[64]  T. Acree,et al.  Molecular structure and sweet taste , 1969 .

[65]  M. Wolfrom,et al.  Analysis and preparation of sugars , 1962 .

[66]  L. Verstraeten.  D-fructose and its derivatives. , 1967, Advances in carbohydrate chemistry and biochemistry.

[67]  I. Kubo,et al.  Bitterness and Chemical Structure , 1969, Nature.

[68]  N. Mōri,et al.  Sweetness and Configuration in Rhamnose , 1954, Nature.

[69]  T. Acree,et al.  The identity of γ-D-galactose , 1966 .

[70]  L. G. Sillén,et al.  STUDIES ON THE HYDROLYSIS OF METAL IONS. XVI. THE HYDROLYSIS OF THE BERYLLIUM ION, Be$sup +$$sup 2$ , 1956 .

[71]  L. P. Kuhn.  The Hydrogen Bond. I. Intra- and Intermolecular Hydrogen Bonds in Alcohols1 , 1952 .

[72]  A. Perlin.  Action of lead tetraacetate on the sugars. , 1959, Advances in carbohydrate chemistry.

[73]  Ralph G. Pearson,et al.  HARD AND SOFT ACIDS AND BASES , 1963 .

[74]  C. Hansch,et al.  Dependence of Relative Sweetness on Hydrophobic Bonding , 1966, Nature.

[75]  R. Shallenberger.  Hydrogen Bonding and the Varying Sweetness of the Sugars , 1963 .

[76]  T. Acree,et al.  Configuration, Conformation, and Sweetness of Hexose Anomers , 1965 .

[77]  D. French.  The raffinose family of oligosaccharides. , 1954, Advances in carbohydrate chemistry.

[78]  A. B. Foster,et al.  Aspects of stereochemistry—I : Properties and reactions of some diols , 1958 .

[79]  J. Harborne.  Biochemistry of Phenolic Compounds , 1964 .

[80]  T. Acree,et al.  Mutarotation of D-galactose. Tautomeric composition of an equilibrium solution in pyridine , 1968 .

[81]  H. Degn,et al.  Determination of the Optical Rotation of beta-Fructofuranose by Means of Kinetic Measurements. , 1962 .

[82]  L. M. Beidler.  DYNAMICS OF TASTE CELLS , 1963 .

[83]  L. N. Ferguson,et al.  The physicochemical aspects of the sense of taste , 1958 .

[84]  S. J. Angyal,et al.  The Composition and Conformation of Sugars in Solution , 1969 .

[85]  C. Hansch,et al.  p-σ-π Analysis. A Method for the Correlation of Biological Activity and Chemical Structure , 1964 .

[86]  J. Bijvoet,et al.  Determination of the Absolute Configuration of Optically Active Compounds by Means of X-Rays , 1951, Nature.

[87]  Y. Tsuzuki,et al.  [On the sweetness of fructose and some other sugars especially its variation with temperature]. , 1953, Biochemische Zeitschrift.

[88]  L. Pauling.  The Nature Of The Chemical Bond , 1939 .

[89]  B. Tollens.  Ueber das Verhalten der Dextrose zu ammonalkalischer Silberlösung , 1883 .

[90]  L. M. Beidler,et al.  A THEORY OF TASTE STIMULATION , 1954, The Journal of general physiology.

[91]  O. J. Magidson,et al.  Zur Frage der Süßigkeit des Saccharins. Das o-Benzoylsulfimid und seine elektrolytische Dissoziation , 1923 .