CA2063025A1

CA2063025A1 - Smoking compositions containing a flavorant release additive

Info

Publication number: CA2063025A1
Application number: CA002063025A
Authority: CA
Inventors: Barbu A. Demian
Original assignee: Individual
Current assignee: Philip Morris Products Inc
Priority date: 1991-03-14
Filing date: 1992-03-13
Publication date: 1992-09-15
Also published as: US5144964A; EP0503795A2; JPH05146285A; EP0503795A3

Abstract

ABSTRACT OF THE DISCLOSURE

This invention provides smoking compositions which contain a novel flavorant-release additive.
Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as a molecular inclusion complex of a .beta.-cyclodextrin derivative and vanillin releases vanillin as a volatile flavorant component of the cigarette smoke. The released vanillin flavorant improves the taste of the mainstream smoke and imparts a pleasant aroma to the sidestream smoke.

Description

i~

.i'..

SMOKING COMPOSITIONS CONTAINING A
FLAVORANT-RELEASE ADDITIVE

BACKGROUND OF THE INvENTION
A variety of flavorants have been developed and proposed for incorporation into tobacco products. Illustrative of such tobacco flavorants are those described in United States Patents 3,580,259; 3,62S,224; 3,722,516; 3,750,674; 3,879,425;
3,881,025; 3,884,247; 3,890,981; 3,903,900; 3,914,451; 3,915,175;
3,920,027; 3,924,644; 3,937,228; 3,943,943; 3,568,387; 3~3791754;
and the like.
J. C. Leffingwell et al "Tobacco Flavoring For Smoking Products (R. J. Reynolds publication, 1972) recites a listing of desirable flavorants for smoking compositions, which include phenols, terpenols and lactones such as guaiacol, 1-undecanol and 5-dodecalactone.
The high degree of volatility and ease of sublimation o~ flavorant additives in tobacco products have presented problems in the manufacturing operations, and have resulted in a decreased shelf-life o~ the products due to losses of flavorant by evaporation on storage.
Recent devéiopments have involved incorporating a low volatility organic additive to a smoking composition, which under~
smoXing conditions is pyrolyzed into one or more fragments that function to improve the taste and character of mainstream tobacco smoke, and in some cases a consequential improvement of sidestream smoke aroma.

" ~ t.i i ~ j I
C

i.
. !
~;
U.S. 3,312,226:describes smoking tobacco compositions which contain an ester additive such as ~-menthyl linalool carbonate. Under smoking conditions pyrolysis of the carbonate ester releases menthol which flavors the mainstream smoXe.
U.S. 3,332,428 and U.S. 3,419,S43 describe smoking tobacco compositions which contain a menthyl carbonate ester of a glycol or saccharide, which under smoXing conditions decomposes to release free menthol into the mainstream smo~e.
U.S. 3,499,452 discloses similar smoking tobacco compositions in which a carbonate ester additive releases flavorant volatiles other than menthol.
United States Patents 4,119,106; 4,171,702; 4,177,339;
and 4,212,310 describe other oligomeric and polymeric carbonate ester derivatives which as constituents of smoking compositions are stable and non-volatile under storage conditions, and are adapted to release pyrolysis products under smoking conditions that improve the taste and aroma of smoke.
United States Patents 4,036,237; 4,141,906; and 4,178,458 describe ~-hydroxyesters which as additives in smoking i compositions pyrolyze into volatile aldehyde and ester flavorants, under smoking conditions.
Of specific interest with respect to the present invention is the proposed utilization of an organic add~tive to al cigarettP paper wrapper to enhance sidestream smo~e aroma under smoking conditions. U.S. 4,804,002 and U.S. 4,941,486 descr~be a tobacco product wrapper containing a flavorant additive ` l comprising a glycoside of a carbohydrate and phenolic compound.
Under cigarette smoking conditions a flavorant additive such as , ethyl vanillyl-D-glucoside yields ethyl vanillin and levoglucosan¦
-!j as pyrolysis products. ;
There is continuing research e~fort to develop low delivery smoking compositions which generate mainstream smoke . . .
with enhanced taste and sidestream smoke with a pleasant aroma , under smoking conditions.
i! Accordingly, it has been desired to provide smoking compositions having incorporated therein a flavorant-release component which is characterized by lack of mobility and/or volatility at ambient temperature.
It has also been desired to provide cigarette smoking p,roducts having a paper wrapper which has incorporated therein a flavorant-release additive which under normal smoking conditions imparts a pleasant aroma to sidestream smoke.
It has also be~n des,ired to provide novel molecular inclusion complex compositions which are adapted i to be incorporated into cigarette filler and~or paper wrapper components, and which under normal smoking conditions release a volatile ~lavorant into cigarette smoke.
- !

~J ~` ' . r~ /
DESCRIPTION OF THE INVENT~
The present invention provides a smoking composition comprising.
! an ad~ixture of (1) combustible filler selected from natural tobacco, reconstituted tobacco and tobacco substitutes, and (2) between about 0.0001-5 weight percent, based on the total weight of filler, of a flavorant-release additive which is a water-soluble molecular inclusion complex of a B-cyclodextrin : derivative and a lipophilic organic flavorant compound.
In another embodiment this invention provides a cigarette smoking product comprising (1) a combustible filler selected from natural tobacco, reconstituted tobacco and tobacco substitutes, and (2) a paper wrapper which has incorporated therein a flavorant-release additive which is a water-soluble molecular inclusion complex of a ~-cyclodextr~n derivative and a lipophilic organic flavorant compound.
In another embodiment this invention provides an aqueous solution containing at least about 50 milligrams per milliliter of a molecular inclusion complex of a ~-cyclodextrin derivative and a lipophilic organic flavorant compound such as vanillin, ethyl vanillin, bergamot oil or linalool.
A cigarette smoking product with treated paper wrapper in accordance with the present invention typ~cally contains between about 0.01-5 weight percent of ~avorant-release additiVe in the paper wrapper.
` !
. 4 t~

b In a further embodiment an invention cigarette product contains between about 0.01-5 weight percent of flavorant-release additive in the paper wrapper, and contains between about 0.0001-5 weight percent of flavorant-release additive in the combustible filler, based on the weight of filler.
The B-cyclodextrin derivative consists of a cone-shape i ring of seven glucose molecules with a 1-4 linkage. The ring structure of linked glucose units has a three dimensional torus configuration with a hydrophobic cavity (7.5 A in diameter), and with upper and lower edges that are hydrophilic. I
Unsubstituted B-cyclodextrin has a water solubility f !
only about 20 milligrams per milliliter of water at room ! -temperature. B-cyclodextrin which is substituted with hydroxyalXyl groups has an increased solubility in water. A
B-cyclodextrin derivative such as Molecusol HPBT~ ~
(Pharmatec, Inc.) or Encapsin HPBTH (American Maize Company) can ¦
form an aqueous solution with a concentration of 50% (w/v)~ The Molecusol HPBTH derivative contains about seven 2-hydroxypropoxy groups., The preferred ~-cyclodextrin derivatives of the present invention contain between about 1-7 Cl-C6 hydroxyalkyl ether substituents.
A present invention water-soluble molecular inclusion complex contains a lipophilic organic flavorant compound as an essential constituent.
The term "water-soluble" as employed herein refers to a moleculax inclu~ion complex solubility of at least about ` O c3 !~

.
I

1.
; , 50 milligrams per milliliter of water at room temperature.
Unsubstituted B-cyclodextrin does not have sufficient water solubility for purposes of the present invention.
The term "lipophilic" as employed herein refers to a flavorant compound which as a component of an aqueous solution f !
a hydroxyalkyl substituted B-cyclodextrin derivative preferentially concentrates within the hydrophobic cavity of the B-cyclodextrin molecules. :
Suitable lipophilic organic flavorant compounds for the practice of the present invention include van~llin, ethyl vanillin, guaiacol, thymol, methyl salicylate, coumarin, linalool, eugenol, menthol, clove, anise, cinnamon, bergamot oil, geranium, lemon oil, spearmint, ginger, and the like.
An aqueous solution of water-soluble molecular inclusion complex is formed by adding calculated amounts of B-cyclodextrin derivative and organic flavorant compound to an aqueous medium. Formation of the molecular inclusion complex of the B-cyclodextrin and flavorant compound can be facilitated by stirring or sonication means. A typical aqueous solution will contain at least about 20 milligrams of complexed flavorant compound per milliliter of solution.
A presen~ invention molecular inclusion complex can be recovered from the a~ueous solution in the for~ of an amorphous powder. Preferably, the or?ginal aqueous solution is utilized directly for application to combustible filler and~or cigarette paper wrapper.
.~ i !

~ C ~'~`3~J ~, ~
~ !

PreparationOfSmOkingCmPSit`i~s In a further èmbodiment the present invention provides ,,.~. I
a method of preparing a smoking composition which is adapted to impart flavor and aroma to mainstream and sidëstream smoke under smoking conditions, which method comprises incorporating into . .~ .
natural tobacco, reconstituted tobacco or tobacco substitute between about 0.0001-5 weight percent, based on composition weight of a flavorant-release additive which is a water-soluble ,~
molecular inclusion complex of a B-cyclodextr ~ derivative and a lipophilic organic flavorant compound;
The invention flavorant-release additive can be incorporated into the tobacco or tobacco substitute in accordance, with methods known and used in the art. Preferably the flavorant-release additive is contained in an agueous medium and then sprayed or injected lnto the tobacco and/or tobacco substitute matrix. Such method ensures an even distribution of the flavorant additive throughout the filler, and thereby facilitates the production of a more uniform smoking composition.¦
Alternatively, the flavorant-release additive may be incorporated as part of a concentrated tobacco extract which is applied to a fibrous tobacco web as in the manufacture of reconstituted tobacco. Another suitable procedure is to incorporate the f}avorant-release additive in tobacco or tobacco substitute fi~ler in a concentr~tion between about 0.5-5 weight percent, - !

Ci based on the weight of ~lller, and then subsequently to blend the ¦
treated filler with filler which does not contain flavorant-release additive.
The term "tobacco substitute" is meant to include non-tobacco smoking filler materials such as are disclosed in United States Patents 3,703,177; 3,796,222; 4,019,521; 4,079,742;
and references cited therein. ' As previously described hereinabove,;an invention molecular inclusion complex flavorant-release'additive also can be incorporated in the paper wrapper of cigarette products, for the purpose of enhancing th~ aroma of cigarette sidestream smoke under smoking conditions. The addit'ive can be applied to the paper wrapper in the form of a solution, or a suspension of fine particles, or the additive can be included as an ingredient during the cigarette paper making process.
A further method of incorporating a flavorant-release additive in a cigarette smoking composition is by including the additive as an ingredient in the paper wrapper sideseam adhesive formulation which is employed in cigarette fabrication.
Other means can be utilized for applying the flavorant-release additive to cigarette paper wrapper, such as electrostatic deposition, printing wheel application, size press application, gravure printing, ink jet application, and the like. ¦
A flavorant-release additive in comb~stible filler andJor cigarette paper wrapper exhibits no evident volatility, and there is no loss of flavorant by evaporation during storage.

? ~ L~;~

...

An eddltionel edventage is that the Ln~lusion state of the flavorant molecules in the complex provides stability for the molecules and protection from adverse reactions such as oxidation.
Under normal smoking conditions the flavorant-release additive in a present invention cigarette product releases volatile flavorant, and the taste and character of the mainstream ;
smoke are enhanced, and a pleasant aroma is imparted to the sidestream smoke and the surrounding environment.
The following.Examples are further illustrative of the present invention. The specific ingredients and processing parameters are presented as being typical, and various modifications can be derived in view of the foregoing disclosure within the scope of the invention.

i ., 9 ', r 3 C) ~

.

. ~....... .
.

EXAMPLE I

Vanillin (lOO mg) is mixed with 2 ml of a 45% w/w aqueous solution of Encapsin HP8T~ and sonicated 10 minutes at room temperature to yield a clear, colorless, viscous solution which is stable under room temperature storagë conditions. The solution (50 mg/ml vanillin) is applied using-a calibrated micropipette in lengthwise stripes on the exterior of the cigarette wrapper of a conventional cigarette- The cigarette is dried at room temperature.
Under smoking conditions, the sidestream smoke of the cigarette has a sweet, vanilla-like odor. The mainstream smoke of the cigarette is enriched with a sweet, aromatic, vanilla-like¦
note.
In a separate procedure, the aqueous solution of the vanillin-Encapsin HPBT~ complex is injected lengthwise into the tobacco rod of a conventional cigarette with the microsyringe, and the cigarette is dried at room temperature.
The sidestram smoke of the cigarette has a sweet, vanilla-like odor, and the mainstrea~ smoke taste is enriched with a sweet, erometic, vanilla-liXe note.

.~ . i .10 I

:~ ;

~` !
EXAMPLE II "5' Ethyl vanillin (50 mg) is mixed with 2 ml of a 45% w/w j aqueous solution of Encapsin HPBT~ and sonicated 10 minutes at room temperature, to yield a clear, colorless, viscous solution which is stable under room temperature storage conditions. The solution (25 mg/ml ethyl vanillin) is applied using a calibrated ¦
micropipette in lengthwise stripes on the exterior of the cigarette wrapper of a conventional cigarette' and the cigarette is dried at room te~perature.
Under smoking conditions, the sidestream smoke of the cigarette has a sweet, vanilla-like odor, and the mainstream smoke is enriched with a sweet, aromatic, vanilla-like note.

~, ` .
.-..
...

EXAMPLE III
Bergamot oil (40 mg) is mixed with 2 ml of a 45% w/w aqueous solution of Encapsin HPBT~ and sonicated 10 minutes at room temperature to provide a pale greenish-yellow viscous solution which is stable under room temperature storage conditions. The solution (20 mg/ml bergamot oil) is applied using a calibrated micropipette in lengthwise stripes on the exterior of the cigarette wrapper of a conventional cigarette.
The cigarette is dried at room temperature.
Under smoking conditions, the sidestream smoke of the cigarette has a fresh, fruity odor, and the mainstream smoke taste is enhanced with a fruity, fresh note.

~`r~
. -~ -EXAMPLE IV ., Linalool (lOO mg) is mixed with 2 mi of a 45% w/w aqueous solution of Encapsin HPBT~ and sonicated 10 minutes at room temperature, to yield a clear, colorless, viscous solution which is stable under room temperature storage conditions. The solution (~0 mg/ml linalool) is applied using a calibrated micropipette in lengthwise stripes on the exterior of the cigarette wrapper of a coventional cigarette. The cigarette is dried at room temperature.
The sidestream smoke of the cigarette has a fresh, fruity, sweet odor, and the mainstream taste is enhanced with a fruity, fresh note.
!

. I

Claims

1. A smoking composition comprising an admixture of (1) combustible filler selected from natural tobacco, reconstituted tobacco and tobacco substitutes, and (2) between about 0.0001-5 weight percent, based on the total weight of filler, of a flavorant-release additive which is a water-soluble molecular inclusion complex of a .beta.-cyclodextrin derivative and a lipophilic organic flavorant compound.

2. A smoking composition in accordance with claim 1 wherein the organic flavorant compound is vanillin.

3. A smoking composition in accordance with claim 1 wherein the organic flavorant compound is ethyl vanillin.

4. A smoking composition in accordance with claim 1 wherein the organic flavorant compound is bergamot oil.

5. A smoking composition in accordance with claim 1 wherein the organic flavorant compound is linalool.

6. A smoking composition in accordance with claim 1 wherein the .beta.-cyclodextrin structure is a hydroxyalkyl ether derivative.

7. A cigarette smoking product comprising (1) a combustible filler selected from natural tobacco, reconstituted tobacco and tobacco substitutes, and (2) a paper wrapper having incorporated therein a flavorant-release additive which is a water-soluble molecular inclusion complex of a .beta.-cyclodextrin derivative and a lipophilic organic flavorant compound.

8. A cigarette smoking product in accordance with claim 7 wherein the paper wrapper contains between about 0.01-5 weight percent of flavorant-release additive.

9. A cigarette smoking product in accordance with claim 7 wherein the organic flavorant compound is vanillin.

10. A cigarette smoking product in accordance with claim 7 wherein the organic flavorant compound is ethyl vanillin.

11. A cigarette smoking product in accordance with claim 7 wherein the organic flavorant compound is bergamot oil.

12. A cigarette smoking product in accordance with claim 7 wherein the organic flavorant is linalool.

13. A cigarette smoking product in accordance with claim 7 wherein the .beta.-cyclodextrin structure is a hydroxyalkyl ether derivative.

14. A water-soluble molecular inclusion complex of a .beta.-cyclodextrin derivative and a lipophilic organic flavorant compound.

15. A molecular inclusion complex in accordance with claim 14 wherein the flavorant compound is vanillin, ethyl vanillin, bergamot oil or linalool.

16. An aqueous solution containing at least about 50 milligrams per milliliter of a molecular inclusion complex of a .beta.-cyclodextrin derivative and a lipophilic organic flavorant compound.

17. An aqueous solution in accordance with claim 16 wherein the weight content of the flavorant compound in the molecular inclusion complex is at least about 20 milligrams per milliliter of solution.

18. An aqueous solution in accordance with claim 16 wherein the flavorant compound is vanillin, ethyl vanillin, bergamot oil or linalool.