Development of structure-taste relationships for sweet and non-sweet heterosulfamates

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 7, 2000, Pages 1369-1374

  Spillane, William J ^a   Ryder, Caroline A ^a   Curran, Patrick J ^a   Wall, Siobhan N ^a   Kelly, Lorraine M ^a   Feeney, Brendan G ^a   Newell, John ^a  

^a NATIONAL UNIVERSITY OF IRELAND   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

MATHEMATICAL MODELS; MOLECULAR STRUCTURE; SODIUM; STATISTICAL METHODS; SYNTHESIS (CHEMICAL);

HETEROSULFAMATE; LINEAR DISCRIMINANT ANALYSIS; MOLECULAR CONNECTIVITY; QUADRATIC DISCRIMINANT ANALYSIS;

SALTS;

EID: 0034236736     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002482l     Document Type: Article

References (37)

1. G. G. Birch, Chem. Ind. (London), 1997, 90.
2. See the website at http://www.fst.rdg.ac.uk/people/pparke/tostq.htm.
3. European Parliament and Council Directive 94/35 EC.
4. W. J. Spillane, C. A. Ryder, M. R. Walsh, P. J. Curran, D. G. Concagh and S. N. Wall, Food Chem., 1996, 56, 255.
5. M. G. B. Drew, G. R. H. Wilden, W. J. Spillane, M. R. Walsh. C. A. Ryder and J. M. Simmie, J. Agric. Food Chem., 1998, 46, 3016.
6. W. J. Spillane and M. B. Sheahan, J. Chem. Soc., Perkin Trans. 2, 1989, 741.
7. W. J. Spillane, G. McGlinchey, I. Ó'Muircheartaigh and G. A. Benson, J. Pharm. Sci., 1983, 72, 852.
8. (a) B. Unterhalt and M. Moellers, Arch. Pharm. (Weinheim), 1990, 323, 317
9. (b) B. Unterhalt and M. Moellers, Sci. Pharm., 1991, 59, 173.
10. C. D. Hurd and N. Kharasch, J. Am. Chem. Soc., 1946, 68, 653.
11. (a) B. Unterhalt and L. Boschemeyer, Naturwissenschaften, 1972, 59, 271
12. (b) B. Unterhalt and L. Boschemeyer, Z. Lebensm. Unters. Forsch., 1976, 161, 275.
13. G. R. Wendt and M. W. Winkley, US Patent 3 787 442, 1974
14. G. R. Wendt and M. W. Winkley, Chem. Abstr., 1974, 80, 82669.
15. W. W. Thompson, US Patent 2 805 124, 1957
16. W. W. Thompson, Chem. Abstr., 1958, 52, 9221.
17. H. Yamaguchi, Jap P 13 056, 1963
18. H. Yamaguchi, Chem. Abstr., 1964, 60, 2771.
19. F. Blicke, H. E. Millson, Jr. and N. J. Doorenbos, J. Am. Chem. Soc., 1954, 76, 2489.
20. F. Pautet and D. Daudon, Pharm. Acta Helv., 1986, 61, 215.
21. M. DeNardo, C. Ruuti and F. Ulian, Farmaco, Ed. Sci., 1984, 39, 125
22. M. DeNardo, C. Ruuti and F. Ulian, Chem. Abstr., 1984, 100, 137568.
23. F. Evangelisti, A. Bargagna and P. Schenone, Riv. Soc. Ital. Sci. Aliment., 1980, 9, 435
24. F. Evangelisti, A. Bargagna and P. Schenone, Chem. Abstr., 1981, 95, 115755.
25. Wendt and Winkley (ref. 11) made six sulfamates viz. 11 and 21-25 (see Table 4 in Supplementary Data) and they report them all to be sweet. In a personal unpublished communication from James G. Sweeney, via Grant E. DuBois of the Coca-Cola Co., he has remade two of their compounds 21 and 25 and found that they are not sweet.
26. L. F. Audrieth and M. Sveda, J. Org. Chem., 1944, 89, 89.
27. C. R. Ryder, PhD Thesis, National University of Ireland, 1993.
28. L. B. Kier and L. H. Hall, J. Pharm. Sci., 1981, 70, 583.
29. L. Brieman, J. H. Friedman, R. A. Olshen and C. J. Stone. Classification and Regression Trees, Wadsworth Statistics/Probability Series, 1984.
30. F. Boyland, D. Manson and S. F. D. Orr, Biochem. J., 1957, 65, 417.
31. G. A. Benson and W. J. Spillane, J. Med. Chem., 1976, 19, 89.
32. -4 M (0.01%).
33. W. J. Spillane and G. McGlinchey, J. Pharm. Sci., 1981, 70, 933.
34. (a) L. H. Hall and L. B. Kier, J. Pharm. Sci., 1977, 66, 642
35. (b) L. B. Kier, J. Pharm. Sci., 1980, 69, 416
36. (c) Y. Takahashi, Y. Miyashita, Y. Tanaka, H. Hayasaka, H. Abe and S.-I. Sasaki, J. Pharm. Sci., 1984, 73, 737.
37. L. B. Kier and L. H. Hall, Molecular Connectivity in Structure-Activity Analysis, Research Studies Press, Letchworth, UK, 1986.