TOBACCO-DERIVED COMPONENTS AND MATERIALS

• US 20120272976A1
• Filed: 04/27/2011
• Published: 11/01/2012
• Est. Priority Date: 04/27/2011
• Status: Active Grant

• Current Assignee: R J Reynolds Tobacco Company (R. J. Reynolds Tobacco)
• Original Assignee: R J Reynolds Tobacco Company (R. J. Reynolds Tobacco)
• Inventors: Byrd, Crystal Dawn Hege, Gerardi, Anthony Richard, Dube, Michael Francis
• Granted Patent: US 9,254,001 B2
• Time in Patent Office: Days
• US Class Current: 131/275
• CPC Class Codes: A23G 1/0016 Transformation of liquid, paste, cream, lump, powder, granule or shred into powder, granule or shred; Manufacture or treatment of powder
• CPC Class Codes: A24B 13/00 Tobacco for pipes, for cigars, e.g. cigar inserts, or for cigarettes; Chewing tobacco; Snuff reconstituted tobacco products A24B3/14
• CPC Class Codes: A24B 15/24 by extraction; Tobacco extracts
• CPC Class Codes: A24B 15/241 Extraction of specific substances
• CPC Class Codes: A24B 15/26 Use of organic solvents for extraction
• CPC Class Codes: A24B 15/30 by organic substances A24B15/281 takes precedence
• CPC Class Codes: C07C 35/02 monocyclic
• CPC Class Codes: C07C 35/21 polycyclic, at least one hydroxy group bound to a non-condensed ring
• CPC Class Codes: C07C 35/36 the condensed ring system being a (4.4.0) system, e.g. naphols
• CPC Class Codes: C07H 1/08 from natural products
• CPC Class Codes: C07H 3/04 Disaccharides

Abstract

The invention provides a method of extracting and isolating certain compounds from tobacco. The resulting isolate can include more than 90% by weight of a given compound and can be used as a flavor component for tobacco material used in smoking articles and smokeless tobacco compositions. Exemplary compounds that may be present in the isolate according to the invention include, but are not limited to, solanone, neophytadiene, megastigmatrienone, β-damascenone, norsolanadione, cis-abienol, α-cembratrienediol, β-cembratrienediol, sucrose esters, and lutein.

Claims

1. A method of extracting and isolating compounds from plants of the Nicotiana species, comprising:

receiving a plant material of the Nicotiana species;

contacting the plant material with a solvent for a time and under conditions sufficient to extract one or more desired compounds from the plant material into the solvent;

separating the solvent containing the one or more desired compounds from the extracted plant material; and

purifying the solvent containing the one or more desired compounds to provide an isolate comprising at least about 75 percent by weight of the one or more desired compounds, the one or more desired compounds being selected from the group consisting of solanone, neophytadiene, megastigmatrienone, β

-damascenone, norsolanadione, cis-abienol, α

-cembratrienediol, β

-cembratrienediol, sucrose esters, lutein, degradation products thereof, and mixtures thereof.

2. The method of claim 1, wherein the plant material of the Nicotiana species is in a form selected from the group consisting of whole leaf, laminae, cut filler, volume expanded, stems, cut-rolled stems, cut-puffed stems, reconstituted tobacco, and particulate.

3. The method of claim 1, wherein the plant material of the Nicotiana species is provided in green form.

4. The method of claim 1, wherein the plant material of the Nicotiana species is provided in cured form.

5. The method of claim 1, wherein the solvent is methanol.

6. The method of claim 5, wherein the one or more desired compounds are selected from the group consisting of cis-abienol, α

-cembratrienediol, β

-cembratrienediol, sucrose esters, and lutein.

7. The method of claim 1, wherein the solvent is dry steam.

8. The method of claim 7, wherein the one or more desired compounds are selected from the group consisting of solanone, neophytadiene, megastigmatrienone, β

-damascenone, and norsolanadione.

9. The method of claim 7, wherein the contacting step further comprises collecting a distillate.

10. The method of claim 9, wherein the distillate comprises a water layer and an oily layer.

11. The method of claim 10, wherein the solvent containing the one or more desired compounds is selected from the group consisting of the oily layer, the water layer, and a waste stream generated from the distillation process.

12. The method of claim 1, wherein the purifying step comprises using preparative scale liquid chromatography.

13. The method of claim 1, wherein the purifying step comprises using flash chromatography.

14. The method of claim 1, wherein the purifying step provides an isolate comprising greater than about 90% by weight of the one or more desired compounds.

15. The method of claim 1, wherein the purifying step provides an isolate comprising greater than about 95% by weight of the one or more desired compounds.

16. The method of claim 1, further comprising adding the isolate to a tobacco composition adapted for use in a smoking article or a smokeless tobacco composition.

17. The method of claim 1, further comprising treating the isolate to provide one or more degradation products therefrom, wherein the treating is selected from oxidation, heat treatment, and a combination thereof.

18. The method of claim 17, wherein the isolate comprises lutein and wherein the one or more degradation products are selected from the group consisting of megastigmatrienone, beta-damascenone, and mixtures thereof.

19. The method of claim 17, wherein the isolate comprises cis-abienol and wherein the one or more degradation products are selected from the group consisting of sclareolide, sclareol, ambroxide, and mixtures thereof.

20. A method for providing a flavor material derived from a plant of the Nicotiana species for addition to a tobacco composition, the method comprising:

receiving a plant material of the Nicotiana species;

contacting the plant material with a solvent for a time and under conditions sufficient to extract one or more desired compounds form the plant material into the solvent;

separating the solvent containing the one or more desired compounds from the extracted plant material;

purifying the solvent containing the one or more desired compounds to provide an isolate comprising at least about 75% by weight of the one or more desired compounds, the one or more desired compounds being selected from the group consisting of solanone, neophytadiene, megastigmatrienone, β

-damascenone, norsolanadione, cis-abienol, α

-cembratrienediol, β

-cembratrienediol, sucrose esters, lutein, degradation products thereof, and mixtures thereof; and

adding the isolate to a tobacco composition adapted for use in a smoking article or a smokeless tobacco composition.

21. The method of claim 20, wherein the plant material of the Nicotiana species is in a form selected from the group consisting of whole leaf, laminae, cut filler, volume expanded, stems, cut-rolled stems, cut-puffed stems, reconstituted tobacco, and particulate.

22. The method of claim 20, wherein the plant material of the Nicotiana species is provided in green form.

23. The method of claim 20, wherein the plant material of the Nicotiana species is provided in cured form.

24. The method of claim 20, wherein the solvent is methanol.

25. The method of claim 24, wherein the one or more desired compounds are selected from the group consisting of cis-abienol, α

-cembratrienediol, β

-cembratriene diol, sucrose esters, and lutein.

26. The method of claim 20, wherein the solvent is dry steam.

27. The method of claim 26, wherein the one or more desired compounds are selected from the group consisting of solanone, neophytadiene, megastigmatrienone, β

-damascenone, and norsolanadione.

28. The method of claim 26, wherein the contacting step further comprises collecting a distillate.

29. The method of claim 28, wherein the distillate comprises a water layer and an oily layer.

30. The method of claim 29, wherein the solvent containing the one or more desired compounds is selected from the group consisting of the oily layer, the water layer, and a waste stream generated from the distillation process.

31. The method of claim 20, wherein the purifying step comprises using preparative scale liquid chromatography.

32. The method of claim 20, wherein the purifying step comprises using flash chromatography.

33. The method of claim 20, wherein the purifying step provides an isolate comprising greater than about 90% by weight of the one or more desired compounds.

34. The method of claim 20, wherein the purifying step provides an isolate comprising greater than about 95% by weight of the one or more desired compounds.

35. The method of claim 20, further comprising treating the isolate to provide one or more degradation products therefrom, wherein the treating is selected from oxidation, heat treatment, and a combination thereof.

36. The method of claim 35, wherein the isolate comprises lutein and wherein the one or more degradation products are selected from the group consisting of megastigmatrienone, beta-damascenone, and mixtures thereof.

37. The method of claim 35, wherein the isolate comprises cis-abienol and wherein the one or more degradation products are selected from the group consisting of sclareolide, sclareol, ambroxide, and mixtures thereof.

38. The method of claim 20, wherein the isolate is added in the form of a casing formulation or a top dressing formulation applied to tobacco strip or in the form of a component of a reconstituted tobacco material.

39. The method of claim 20, wherein the tobacco composition comprises a tobacco material adapted for use in a smoking article.

40. The method of claim 39, wherein the amount of isolate in the tobacco composition is between about 5 ppm and about 5 weight percent based on the total dry weight of the tobacco material in the smoking article.

41. The method of claim 20, wherein the tobacco composition comprises a tobacco material adapted for use in a smokeless tobacco product.

42. The method of claim 41, wherein the amount of isolate in the tobacco composition is between about 5 ppm and about 5 weight percent based on the total dry weight of the tobacco material in the smokeless tobacco product.

43. An isolate from a plant of the Nicotiana species or components thereof, wherein the isolate comprises at least about 75 percent by weight of one or more desired compounds selected from the group consisting of solanone, neophytadiene, megastigmatrienone, β

-damascenone, norsolanadione, cis-abienol, α

-cembratrienediol, β

-cembratrienediol, sucrose esters, lutein, and degradation products thereof.

44. The isolate of claim 43, wherein the isolate comprises greater than about 90% by weight of the one or more desired compounds.

45. The isolate of claim 43, wherein the isolate comprises greater than about 95% by weight of the one or more desired compounds.

46. A tobacco composition for use in a smoking article or a smokeless tobacco composition comprising the isolate of claim 43.