Process for producing flavorants and related materials

Patent metadata

Field	Value
Publication number	US-9265284-B2
Application number	US-201414158058-A
Country	US
Kind code	B2
Filing date	Jan 17, 2014
Priority date	Jan 17, 2014
Publication date	Feb 23, 2016
Grant date	Feb 23, 2016

Abstract

A process for producing flavorants made or derived from tobacco or, more generally, made or derived from any biomass derived from any one or more species of genus Nicotiana , or that otherwise incorporate tobacco, is provided. Provided are flavorants obtained or derived from plants or portions of plants from the Nicotiana species, such as from one or more flowers from one or more Nicotiana species, and products comprising one or more such flavorants.

First claim

What is claimed is:

1. A process for producing one or more sensory-positive ester flavorants from a quantity of biomass of a plant of a Nicotiana species, the process comprising:
(a) contacting the quantity of biomass with a quantity of a non-polar solvent to form a first mixture;
(b) collecting a liquid phase of the first mixture to form a collected liquid;
(c) concentrating the collected liquid to form a concrete;
(d) dissolving the concrete in a minimal quantity of an alcohol solvent to form a reconstituted liquid;
(e) precipitating the reconstituted liquid to form a precipitated wax and an unprecipitated mixture;
(f) collecting the unprecipitated mixture in the form of a biomass isolate;
(g) contacting the biomass isolate with a quantity of an acid and a quantity of an alcohol to form a reaction mixture for a period of time sufficient for the formation of ester linkages between one or more components of the reaction mixture;
thereby producing one or more sensory-positive ester flavorants.

2. The process according to claim 1 , wherein the Nicotiana species is N. alata, N. suaveolens, N. sylvestris or N. tabacum.

3. The process according to claim 1 , wherein the alcohol solvent comprises ethanol.

4. The process according to claim 1 , wherein the alcohol used in the contacting step comprises ethanol, isopropanol and/or isoamyl alcohol.

5. The process according to claim 1 , wherein the non-polar solvent comprises hexanes.

6. The process according to claim 1 , wherein the non-polar solvent is a hydrocarbon solvent or supercritical carbon dioxide.

7. The process according to claim 1 , wherein the acid comprises sulfuric acid.

8. The process according to claim 1 , wherein the biomass isolate is a flower isolate.

9. The process according to claim 1 , wherein the biomass isolate is subjected to one or more additional separation steps prior to said contacting step.

10. The process according to claim 9 , wherein the one or more separation steps are selected from molecular distillation, solvent-solvent partitioning, filtration, chromatography, recrystallization, and combinations thereof.

11. The process according to claim 1 , wherein the one or more sensory-positive ester flavorants comprise one or more ethyl esters.

12. The process according to claim 1 , wherein the one or more sensory-positive ester flavorants comprise one or more isopropyl esters.

13. The process according to claim 1 , wherein the one or more sensory-positive ester flavorants comprise one or more isoamyl esters.

14. The process according to claim 1 , wherein the one or more sensory-positive ester flavorants comprise at least one member of the following set of compounds: (a) ethyl octanoate, ethyl hexanoate and ethyl decanoate; (b) isopropyl octanoate, isopropyl hexanoate and isopropyl decanoate; (c) isoamyl octanoate and isoamyl hexanoate.

15. The process according to claim 1 , wherein the one or more sensory-positive ester flavorants are incorporated into a tobacco product.

16. The process according to claim 15 , wherein the tobacco product is a smoking article.

17. The process according to claim 16 , wherein the one or-more sensory-positive ester flavorants are incorporated into the smoking article as part of a casing formulation or a top dressing formulation.

18. A process for producing one or more sensory-positive ester flavorants from a quantity of flower biomass of a plant of a Nicotiana species, the process comprising:
(a) contacting the quantity of flower biomass with a quantity of a hydrocarbon solvent to form a first mixture;
(b) collecting a liquid phase of the first mixture to form a collected liquid;
(c) concentrating the collected liquid to form a concrete;
(d) dissolving the concrete in a minimal quantity of an alcohol solvent to form a reconstituted liquid;
(e) precipitating the reconstituted liquid to form a precipitated wax and an unprecipitated mixture;
(f) collecting the unprecipitated mixture in the form of a flower isolate comprising one or more C 5 to C 12 acids;
(g) optionally, subjecting the flower isolate to one or more additional separation steps;
(h) contacting the flower isolate with a quantity of an acid and a quantity of an alcohol to form a reaction mixture for a period of time sufficient for the formation of ester linkages between one or more components of the reaction mixture;
thereby producing one or more sensory-positive ester flavorants.

19. The process according to claim 18 , wherein the acid comprises sulfuric acid.

20. The process according to claim 18 , wherein the one or more sensory-positive ester flavorants are incorporated into a tobacco product.

Assignees

• Reynolds Tobacco Co R

Inventors

• Junker Christopher S
• Dube Michael F

Classifications

• C11B1/10

  by extracting · CPC title

• A24B15/32 Primary

  by acyclic compounds · CPC title

• A24B15/26

  Use of organic solvents for extraction · CPC title

• A24B15/241 Primary

  Extraction of specific substances · CPC title

• A24B15/302

  by natural substances obtained from animals or plants · CPC title