Tobacco-derived components and materials

Patent metadata

Field	Value
Publication number	US-2016143347-A1
Application number	US-201615012140-A
Country	US
Kind code	A1
Filing date	Feb 1, 2016
Priority date	Apr 27, 2011
Publication date	May 26, 2016
Grant date	—

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.

First claim

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 .- 46 . (canceled)

Assignees

• R J Reynolds Company
• Reynolds Tobacco Co R

Inventors

• Byrd Crystal Dawn Hege
• Gerardi Anthony Richard
• Dube Michael Francis

Classifications

• A24B15/24

  by extraction; Tobacco extracts · CPC title

• A24B15/241 Primary

  Extraction of specific substances · CPC title

• C07H3/04

  Disaccharides · CPC title

• C07C35/02

  monocyclic · CPC title

• A24B15/26

  Use of organic solvents for extraction · CPC title