Skip to main content
SpringerLink
Log in
SpringerLink
Log in

Advances in the Industrial Synthesis of Medium to Large Ring Molecules

  • Chapter
Current Topics in Flavours and Fragrances

Abstract

The synthetic chemist’s interest in materials with musk odours began when it was realised that crude natural musks, such as those isolated in limited amounts from the musk deer and civet cat, were prized as indispensable fragrance ingredients in the 1800’s[1]. Over a period of time the active musks in these crude materials were identified as macrocyclic compounds such as methyl substituted cyclopentadecanones and cycloheptadecenones[2]. Similar musk materials of vegetable origin were also found for example, ambrettolide which can be isolated from ambrette seed oil[3]. Since the availability of these musks from their natural source is limited, they command a very high price and their use in perfumery is relatively very small.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. B.D. Mookherjee and R.A. Wilson, in Fragrance Chemistry — The Science of the Sense of Smell Ed ET Theimer, Academic Press 1982, 433.

    Google Scholar 

  2. H. Walbaum, J. Prakt. Chem., 1906, 73, 488., L. Ruzicka, Helv. Chim. Acta., 1926, 9, 715.

    Article  Google Scholar 

  3. US 3, 415, 813 (1968)

    Google Scholar 

  4. A. Baur, Ber. Dtsch. Chem. Ges., 1891, 24, 2836 and 284.

    Google Scholar 

  5. T. Yamagishi et al., Bull. Environ. Contain. Toxicol., 1981, 26, 656.

    Article  CAS  Google Scholar 

  6. US 2, 450, 878 (1948), M.S. Carpenter et al., J. Org. Chem., 1951, 16, 59.

    Google Scholar 

  7. A. Rebmann, C. Wauschkuhn, W. Waizenegger, Dragoco Rep. (Engl Ed), 1998, (2), 49.

    Google Scholar 

  8. T.F. Wood et al., J. Org. Chem., 1963, 28, 2248.

    Article  CAS  Google Scholar 

  9. US 3, 360, 530.

    Google Scholar 

  10. For a review see K. J. Rossiter, Chem. Revs., 1996, 96, 3201–3240.

    Article  CAS  Google Scholar 

  11. D.P. Anonis, Perfumer &Flavourist, 1992, 17, 23.

    CAS  Google Scholar 

  12. C. Allan et al., Stud. Nat. Prod. Chem., 1991, 219.

    Google Scholar 

  13. Chemical-Business-India, 1996, 10(2), 69.

    Google Scholar 

  14. Japan Chemical Week, 1998, 39 (1966), 3.

    Google Scholar 

  15. Japan Chemical Week, 1998, 39 (1979), 3.

    Google Scholar 

  16. Parfums-Cosmetiques-Aromes, 1998, 143, 67.

    Google Scholar 

  17. J.L. Greene Jr., et al., J. Polymer Sci. A-1, 1967, 5, 391.

    Article  CAS  Google Scholar 

  18. US Patent, 4, 525, 251 (1985).

    Google Scholar 

  19. US Patent, 4, 310, 685 (1982).

    Google Scholar 

  20. Chemical-Market-Reporter, 20 Apr 1998.

    Google Scholar 

  21. R. Jeffcoat and B.J. Willis in Flavors and Fragrances: A World Perspective. Proceedings of the 10th International Congress Essential Oils, Fragrances and Flavors, Washington DC, USA, 16–20 November 1986, pp743, Eds. B.M. Lawrence, B.D. Mookherjee and B.J. Willis.

    Google Scholar 

  22. H. Okino, A. Taoka and N. Uemura in Flavors and Fragrances: A World Perspective. Proceedings of the 10th International Congress Essential Oils, Fragrances and Flavors, Washington DC, USA, 16–20 November 1986, pp753, Eds. B.M. Lawrence, B.D. Mookherjee and B.J. Willis.

    Google Scholar 

  23. R. Uchio and I. Shiio, Agr. Biol. Chem., 1972, 36, 426.

    Article  CAS  Google Scholar 

  24. US 5, 648, 247 (1997).

    Google Scholar 

  25. A. Tulloch, J. Spencer and P. Gorin, Can. J. Chem., 1962, 40, 1326, H. Asmer, S. Lang, F. Wagner and V. Wray, J. Am. Oil Chem. Soc., 1988, 65, 1460.

    Article  CAS  Google Scholar 

  26. S. Kuwarhara et al., Biosci. Biotechnol. Biochem., 1998, 68, 1261.

    Article  Google Scholar 

  27. US Patent 4, 246, 182 (1981).

    Google Scholar 

  28. L.H. Hinkamp, H.J. Shafer, B. Wippich and H. Luftmann, Liebigs Ann. Chem. 1992, 559.

    Google Scholar 

  29. J. Tsuji and S. Hashigucji, J. Organomet. Chem., 1981, 218, 69.

    Article  CAS  Google Scholar 

  30. D. Villemin, Tet. Lett., 1980, 1715.

    Google Scholar 

  31. US Patent 4, 559, 168 (1985).

    Google Scholar 

  32. J. Tsuji and S. Hashiguchi, Tet. Lett., 1980, 2955.

    Google Scholar 

  33. JP 08217716 (1996).

    Google Scholar 

  34. T.G. Back, Tetrahedron, 1977, 33, 3041.

    Article  CAS  Google Scholar 

  35. L. Ruzicka, Helv. Chim. Acta., 1926, 9, 230, L. Ruzicka, Ibid, 1926, 9, 715, L. Ruzicka, Ibid, 1926, 9, 1008.

    Article  CAS  Google Scholar 

  36. K.C. Nicolaou, Tetrahedron, 1977, 33, 683, K.C. Nicolaou, Y. He, F. Roschangar, P.N. King, D. Vouloumis, T. Li, Angew. Chem. Int. Ed., 1998, 37, 84, A Fuerstner, K. Langemann, J. Am. Chem. Soc., 1997, 119, 9130.

    Article  CAS  Google Scholar 

  37. J.W. Hill and W.H. Carothers, J. Am. Chem. Soc., 1933, 55, 5031.

    Article  CAS  Google Scholar 

  38. For recent examples of the polymerisation/depolymerisation procedure see: JP 7, 267, 945-A (1995), US Patent 4, 709, 058-A(1987).

    Google Scholar 

  39. H. Kuno et al., Chemistry Letters, 1992, 571-574.

    Google Scholar 

  40. J.D. White, N.J. Green, F.F. Fleming, Tet Lett, 1993, 34, 3515, K. Steliou, S. Hannesian et al., J. Am. Chem. Soc., 1980, 102, 7579.

    Article  CAS  Google Scholar 

  41. T. Tatsumi, H. Sakashita, K. Asano, J. Chem. Soc. Chem. Commun., 1993, 1264

    Google Scholar 

  42. T. Ogawa, A. Yoshikawa, H. Wada, C. Ogawa, N. Ono and H. Suzuki, J Chem Soc Chem Commun., 1995, 1407.

    Google Scholar 

  43. G.K. Robinson, M.J. Alston, C.J. Knowles, P.S.J. Cheetham, K.R. Motion, Enzyme Microb. Technol., 1987, 16, 855, C.S. Chen and C.J. Sih, Angew. Chem. Int. Ed. Engl., 1989, 28, 695.

    Article  Google Scholar 

  44. F. Binns, S.M. Roberts et al., J. Chem. Soc. Perkin Trans. I, 1993, 899.

    Google Scholar 

  45. A. Makita, T. Nihira and Y. Yamada, Tet. Lett., 1987, 805-808.

    Google Scholar 

  46. L. Bouvealt, R. Loquin, Bull. Soc. Chim. France, 1936, 35, 629., K. Ruhlmann, Synthesis, 1971, 236.

    Google Scholar 

  47. JP 5155802 (1991).

    Google Scholar 

  48. J.E. McMurry and J.G. Rico, Tet. Lett., 1989, 1169.

    Google Scholar 

  49. J.E. McMurry, Chem. Rev. 1989, 89, 1513.

    Article  CAS  Google Scholar 

  50. K.A.D. Swift, Proceedings from Fragrances and Flavours Association of India XIV Biennial Seminar “Fragrances and Flavours in the 21st Century”, Jaipur, India, 1999.

    Google Scholar 

  51. S. Warwel et al., Seifen Oele Fette Wachse, 1989, 115, 538.

    CAS  Google Scholar 

  52. K.C. Nicolaou et al., Angew. Chem. Int. Ed. Engl., 1998, 37, 84–87.

    Article  CAS  Google Scholar 

  53. K.E. Litinas, B.E. Salteris, J. Chem. Soc. Perkin Trans. 1, 1997, 2869.

    Google Scholar 

  54. S.J. Danishefsky et al., J. Am. Chem. Soc., 1997, 119, 10073.

    Article  Google Scholar 

  55. M.F.C. Plugge and J.C. Mol, Synlett, 1991, 507.

    Google Scholar 

  56. A. Furstner and K. Langemann, J. Org. Chem., 1996, 61, 3942.

    Article  Google Scholar 

  57. A. Furstner and G. Seidel, Angew. Chem. Int. Ed., 1998, 37, 1734.

    Article  Google Scholar 

  58. see G. Frater and D. Lamparsky in Perfumes, Art, Science and Technology, Elsevier Applies Science London & New York, ed. P.M. Muller and D. Lamparsky.

    Google Scholar 

  59. I.J. Borowitz, G. Gonis, Tet Lett, 1964, 1151, I.J. Borowitz et al., J. Org. Chem., 1966, 31, 3032, I.J. Borowitz et al., J. Org. Chem., 1973, 38, 1324, US 4, 187, 222 (1980).

    Article  CAS  Google Scholar 

  60. W. Tochtermann et al., Tetrahedron, 1996, 52, 4581.

    Article  Google Scholar 

  61. JP 7267968 (1995), JP 6192161 (1994).

    Google Scholar 

  62. EP 862911 (1998), US 5, 266, 559 (1993).

    Google Scholar 

  63. US 5, 214, 163 (1993).

    Google Scholar 

  64. V. Rautenstrauch et al., Helv. Chim. Acta., 1990, 73, 896.

    Article  CAS  Google Scholar 

  65. C. Bohm et al., Tet. Letts. 1993, 3405, K. Kaneda et al., J. Chem. Soc. Chem. Commun., 1994, 797, K. Kaneda et al., J. Org. Chem. 1994, 59, 2915, F. Wang et al., Syn. Commun., 1996, 26, 1613.

    Article  CAS  Google Scholar 

  66. L. G. Wideman, J. Org. Chem., 1968, 33, 4541., S. Lee, R. Huff, Q. Rev. Chem. Soc., 1967, 21, 445.

    Article  CAS  Google Scholar 

  67. GB 1, 433, 463 (1974).

    Google Scholar 

  68. US 4, 668, 836 (1987).

    Google Scholar 

  69. R. Baker et al., J. Chem. Soc. Chem. Commun., 1972, 802.

    Google Scholar 

  70. R. Baker et al., J. Chem. Soc. Chem. Commun., 1974, 515.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Quest International, Ashford, Kent, TN24 OLT, UK

    Simon Ellwood & Tom Haines

Authors
  1. Simon Ellwood
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tom Haines
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Quest International, Ashford, Kent, UK

    Karl A. D. Swift

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Ellwood, S., Haines, T. (1999). Advances in the Industrial Synthesis of Medium to Large Ring Molecules. In: Swift, K.A.D. (eds) Current Topics in Flavours and Fragrances. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-4022-5_5

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-4022-5_5

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-5775-2

  • Online ISBN: 978-94-011-4022-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation