1,7-Cyclogermacra-1(10),4-dien-15-al, a sesquiterpene with a novel skeleton, and other sesquiterpenes from Haitian vetiver oil

Flavour and Fragrance Journal

Volumn 15, Issue 2, 2000, Pages 61-83

  Weyerstahl, Peter ^a   Marschall, Helga ^a   Splittgerber, Ute ^a   Wolf, Dietmar ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

(nor) sesquiterpenes; Alcohols; Aldehydes; Essential oil; Ketones; NMR; Vetiver oil; Vetiveria zizanioides (L.) Nash

Indexed keywords

1,7 CYCLOGERMACRA 1(10),4 DIEN 15 AL; ALCOHOL; ALDEHYDE; BETA FUNEBREN 14 OL; CARBONYL DERIVATIVE; DIMETHYL ETHER; ESSENTIAL OIL; ETHYLENE OXIDE; KETONE; PREZIZAEN 12 OL; SESQUITERPENE; UNCLASSIFIED DRUG; VETIVER OIL;

ARTICLE; ARTIFACT; CHEMICAL STRUCTURE; CHROMATOGRAPHY; DISTILLATION; HAITI; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0034066002     PISSN: 08825734     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1026(200003/04)15:2<61::AID-FFJ865>3.0.CO;2-S     Document Type: Article

References (67)

1. J. Smadju, Riv. Ital. EPPOS, 15, (1994) and references cited therein.
2. P. Weyerstahl, H. Marschall, U. Splittgerber and D. Wolf, Liebigs Ann., 1195 (1996).
3. P. Weyerstahl, H. Marschall, U. Splittgerberand D. Wolf, Liebigs Ann./Recueil, 1783 (1997).
4. P. Weyerstahl and V. Schlicht, Liebigs Ann./Recueil, 1789 (1997).
5. P. Weyerstahl, H. Marschall, P. Degenkolb and P. Lebada, Eur. J. Org. Chem., 675 (1999).
6. P. Weyerstahl, C. Christiansen and H. Marschall, Flavour Fragr. J., 11, 15 (1996).
7. J. D. Connolly and R. A. Hill, Dictionary of Terpenoids, Vol. 1, Mono-and Sesquiterpenoids, Chapman & Hall, London (1991).
8. P. Weyerstahl, H. Marschall, Phan Tong Son and Phan Minh Giang, Flavour Fragr. J., 14, 219 (1999).
9. Nianbai Fang, Sanggong Yu, T. J. Mabry, K. A. Abboud and S. H. Simonsen, Phytochemistry, 27, 3187 (1988).
10. H. Wolf, M. Kolleck and W. Rascher, Chem. Ber., 109, 2805 (1976).
11. R. Kutschan, H.-M. Schiebel, N. Schröder and H. Wolf. Chem. Ber., 110, 1615 (1977).
12. L. Piovetti, G. Combaut and A. Diara, Phytochemistry, 19, 2117 (1980).
13. P. Weyerstahl, H. Marschall and K. Schneider, Liebigs Ann., 231 (1995).
14. V. K. Honwad, E. Siscovic and A. S. Rao, Tetrahedron, 23, 1273 (1967).
15. W. P. Griffith, S. V. Ley, G. W. Whilcombe and A. D. White, J. Chem. Soc. Chem. Commun., 1625 (1987).
16. K. A. Plavcan, Isolation and characterization of carbonyl components from the essential oil of Vetiveria zizanoides, Dissertation, Cornell University, Ithaca, NY (1985).
17. R. R. Izac, W. Fenical, B. Tagle and J. Clardy, Tetrahedron, 37, 2569 (1981).
18. F. Näf, R. Decorzant and W. Thommen, Helv. Chim. Acta, 65, 2212 (1982).
19. B. Maurer, M. Fracheboud, A. Grieder and G. Ohloff, Helv. Chim. Acta. 55, 2371 (1972).
20. R. Kaiser and P. Naegeli, Tetrahedron Lett., 2009 (1972).
21. S. K. Paknikar, S. V. Bhatwadekar and K. K. Chakravarti, Tetrahedron Lett., 2973 (1975).
22. T. Norin, S. Sundin, B. Karlsson, P. Kierkegaard, A.-M. Pilotti and A.-C. Wiehager, Tetrahedron Lett., 17 (1973).
23. P. Brun, J. Casanova, M. S. Raju, B. Waegell, E. Wenkert and J. P. Zahra. Magn. Reson. Chem., 25, 619 (1987).
24. R. Kaiser and D. Lamparsky, Helv. Chim. Acta, 66, 1843 (1983).
25. K. Sakurai, T. Kitahara and K. Mori, Tetrahedron, 46, 761 (1990).
26. N. Selvakumar and G. S. R. S. Rao, J. Chem. Soc. Perkin Trans. I, 3217 (1994).
27. R. N. Ganguly, G. K. Trivedi and S. C. Bhattacharyya, Indian J. Chem., 16B, 20 (1978).
28. T. Nakanishi, E. Yamagata, K. Yoneda, I. Miura and H. Mori, J. Chem. Soc. Perkin Trans I, 601 (1983).
29. K. Sakurai, T. Kitahara and K. Mori, Tetrahedron, 44, 6581 (1988).
30. Sung Ho Kang and S. A. Monti, J. Org. Chem., 49, 3830 (1984).
31. S. K. Paknikar, S. V. Bhatwadekar, K. K. Chakravarti and A. M. Shaligram, Ind. J. Chem., 22B, 288 (1983).
32. R. N. Ganguly and G. K. Trivedi, Proceedings of the 11th International Congress on Essential Oils, Fragrances and Flavours, Vol. 5, p. 119, eds. S. C. Bhattacharyya, N. Sen and K. L. Sethi, Oxford & IBH Publ. Co. Pvt. Ltd., New Delhi, India (1989).
33. S. C. Jain, S. Nowicki, T. Eisner and J. Meinwald, Tetrahedron Lett., 23, 4639 (1982).
34. P. Weyerstahl, H. Marschall and U. Splittgerber, Liebigs Ann., 523 (1994).
35. N. Hanayama, F. Kido, R. Tanaka, H. Uda and A. Yoshikoshi, Tetrahedron, 29, 945 (1973).
36. R. N. Ganguly, G. K. Trivedi and S. C. Bhattacharyya, Indian J. Chem., 16B, 23 (1978).
37. P. S. Shanker and G. S. R. S. Rao, Tetrahedron Lett., 35, 5055 (1994).
38. A. Homma, M. Kato, Ming-Der Wu and A. Yoshikoshi, Tetrahedron Lett., 231 (1970).
39. I. A. Southwell, Aust. J. Chem., 31, 2527 (1978).
40. A. Hammoumi, J.-P. Girault and R. Azerad, Tetrahedron Asymmetry, 4, 1295 (1993).
41. D. Caine, A. A. Boucugnani and W. R. Pennington, J. Org. Chem., 41, 3632 (1976).
42. G. Blay, R. Schrijvers, J. B. P. A. Wijnberg and A. de Groot, J. Org. Chem., 60, 2188 (1995).
43. L. H. Zalkow and M. G. Clower, Tetrahedron Lett., 75 (1975).
44. N. H. Andersen and M. S. Falcone, Chem. Ind., 62 (1971).
45. N. H. Andersen, From Nerolidol to Cedrene and Vetiver Tricyclics. Chemical Realization of the Step-wise Processes, 6th International Congress on Essential Oils (Pap. p. 159). 1974, Allured, Carol Stream, IL, Chem. Abstr., 84, 135845j, (1976).
46. L. Piovetti and A. Diara, Tetrahedron Lett., 21, 1453 (1980).
47. M. Mizutani, K. Koseki, H. Ago, M. Mori, T. Matsuzaki and T. Ebata. Tetrahedron, 53, 11563 (1997).
48. A. S. Vaidya and A. S. Rao, Indian J. Chem., 1, 307 (1969).
49. M. Ando, K. Tajima and K. Takase, J. Org. Chem., 48, 1210 (1983).
50. N. H. Andersen, Tetrahedron Lett., 1755 (1970).
51. P. Weyerstahl and K. Schneider, Liehigs Ann. Chem., 1049 (1992).
52. I. Bombarda, E. M. Gaydou, J. Smadja and R. Faure, J. Agric. Food Chem., 44, 217 (1996).
53. P. Roach Vettel and R. M. Coates, J. Org. Chem., 45, 5430 (1980).
54. P. J. Carrol, E. L. Ghisalberti and D. E. Ralph, Phytochemistry, 15, 777 (1976).
55. T. Nakanishi, E. Yamagata, K. Yoneda and I. Miura, Phytochemistry, 20, 1597 (1981).
56. A. F. Barrero, E. Alvarez-Manzaneda and A. Lara, Tetrahedron Lett., 37, 3757 (1996).
57. Y. Fukushi, C. Yajima and J. Mizutani, Tetrahedron Lett., 35, 8809 (1994).
58. N. Selvakumar, S. N. Jamaki, K. Pramod and G. S. R. Subba Rao, J. Chem. Soc. Perkin Trans. I, 839 (1995).
59. T. Nagashima and T. Yoshida, (Takasago Perfumery Co. Ltd.), Eur. Pat. Appl. EP 78,925, 18 May 1983; Chem. Abstr., 99, 122710 (1983).
60. P. Raharivelomanana, J.-P. Bianchini, R. Faure, A. Cambon and M. Azzaro. Phytochemistry, 35, 1059 (1994).
61. B. Tomita and Y. Hirose, Phytochemistry, 12, 1409 (1973).
62. P. Weyerstahl, H. Marschall, H.-C. Wahlburg, C. Christiansen, A. Rustaiyan and F. Mirdjalili, Flavour Fragr. J., 14, 121 (1999).
63. P. Weyerstahl, H. Marschall, A. Eckhardt and C. Christiansen, Flavour Fragr. J., 14, 15 (1999).
64. P. Weyerstahl and I. Schwope, Liebigs Ann., 191 (1995).
65. Pei-Ying Liu, Yong-Jin Wu and D. J. Burnell, Can. J. Chem., 75, 656 (1997).
66. P. Weyerstahl, H. Marschall, U. Splittgerber and D. Wolf, Flavour Fragr. J., in press
67. P. Raharivelomanana, R. Faure, A. Cambon and H. Azzaro, Phytochemistry, 33, 235 (1983).