Studies on Ozonation of Nicotine

니코틴의 오존화 반응에 관한 연구

  • Taek-Kyu Park (Department of Chemistry, Kun University) ;
  • Ki-Hwan Kim (Department of Chemistry, Kun University) ;
  • Tae-Sung Huk (Department of Chemistry, Song Sim College for Woman)
  • 박택규 (건국대학교 문리과대학 화학과) ;
  • 김기환 (건국대학교 문리과대학 화학과) ;
  • 허태성 (성심여자대학 이과대학 화학과)
  • Published : 1984.10.20

Abstract

Nicotine was reacted with an equimolar amount of ozone in methylene chloride and distilled water. The reaction mixture was separated by column chromatography or thin layer chromatography and then purified by vacuum distillation. The six compounds obtained from this reaction were characterized by NMR, IR and Mass spectrometry. These were identified as unchanged nicotine, nornicotine, anabasine, ${\beta}$-nicotyrine, cotinine and nicotine-N-oxide. From these results, reaction mechanism for the ozonolysis ofon nicotine was proposed; the pyrrolidine ring is attacked by ozone at the 1'-position followed by further transformation.

극성 용매인 물과 비극성 용매인 염화메틸렌에서 각각 니코틴을 당량의 오존과 반응시켜 그 생성물을 기체 크로마토그라피로 조사한 후 관 크로마토그래피 및 얇은 막 크로마토그래피를 이용하여 분리하였다. 이들 6가지 물질을 NMR, IR 및 Mass로 구조를 확인한 결과, 미반응의 니코틴 l-nornicotine, anabasine, ${\beta}$-nicotyrine, cotinine 및 nicotine-N-oxide임이 밝혀졌다. 이 생성물들을 토대로 두 액상에서의 니코틴 오존화 반응은 피롤리딘 고리의 1'위치에서 1차 산화가 일어나는 반응 메카니즘을 제안하였다.

Keywords

References

  1. Mag. Pharm. v.24 Posselt;Reimann
  2. Chem. Rev. v.29 K. E. Jackson
  3. Chem. Abstracts v.6 Auzies
  4. Ber. v.61 Spath;Bretschneider
  5. Intn. Agency Res. Cancer Sci. Publ. v.14 R. Preussmann;G. Eisenbrand;D. Schmahl
  6. Cancer Res. v.36 W. Liginsky;H. Taylor
  7. J. Nat. Cancer Inst. v.58 D. Hoffmann;M. Dong;S. S. Hecht
  8. Beit. Tabakfor Inter. v.9 no.57 T. Kisaki;S. Maeda;A. Koiwai;Y. Mikami;T. Sasaki;H. Matsusbita
  9. J. Am. Chem. Soc. v.77 W. G. Frankenburg;A. M. Gottscho
  10. Proceeding Actes du Congres G. S. Hyin
  11. J. Bact. v.76 no.1 J. W. Hylin
  12. Arch, Biochem. Biophys. v.72 E. Wada
  13. Tob. Sci. v.9 W. G. Frankenburg;A. M. Gottscho;A. A. Vaitekunas
  14. Austria Tabakwerke A.G., Faehliche Mitt. v.13 H. Bindera;W. Linder
  15. Ber. v.24 Pinner;Wolffenstein
  16. Indian J. Agric. Soi. v.39 no.3 M. K. Chakraborty;B. S. Ranachandradn;C. B. Sarma
  17. Z. Untersuch Lebensm v.74 Preiss
  18. Phytochemistry v.14 J. D. Phillipson;S. S. Handa
  19. J. Org. Chem. v.35 J. C. Craig;K. K. Purushothmann
  20. J. Chem. Soc. A. W. Johnson;T. J. King;J. R. Turner
  21. Tob. Sci. v.24 A. I. Schepartz;J. J. Ellington;W. S. Schlotghauer
  22. Tob. Sci. v.25 A. I. Schepartz;A. C. Mottola;W. S. Schlotghaue;D.W. Dejong;J.J. Lam
  23. J. Am. Chem. Soc. v.79 W. G. Frankenburg;A. A. Vaitekunas
  24. Ozonation in Organic chemistry v.II P. S. Bailey
  25. J. Amer. Chem. Soc. v.86 J. C. Craig;N. Y. Mary;N. L. Goldman;L. Wolf