Philip Morris Inc.

Philip Morris Products Inc.

Liggett Group Inc.

Everett W Southwick

Yoram Houminer

David L Williams

John Bryant Paine, Iii

Harvey J Grubbs

Kenneth F Podraza

Charles R Howe

Andrew G Kallianos

Edward B Sanders

W Geoffrey Chan

Jeffrey I Seeman

William B Edwards, Iii

Richard H Cox

John D Naworal

Dennis M Driscoll

Melvyn Irving Simpson

This invention provides smoking compositions which contain a novel .beta.-hydroxycarboxylate flavorant-release additive. Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as calcium bis(2,2-diethyl-3-hydroxy-4-phenylmethylenedecanoate) pyrolyzes and releases .alpha.-hexylcinnamaldehyde as a volatile flavorant component of the cigarette smoke.

Smoking compositions containing an .alpha.-alkylcinnamaldehyde-release

This invention provides smoking compositions which contain a vanillin carboxylate type flavorant-release additive. Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as 5-carboxyethylvanillin pyrolyzes and releases ethylvanillin as a volatile flavorant component of the cigarette smoke.

Smoking compositions containing a vanillin-release additive

This invention provides smoking compositions which contain a novel di-vanillyl ester flavorant-release additive. Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as di-ethylvanillyl oxalate pyrolyzes and releases ethylvanillin as a volatile flavorant component of the cigarette smoke.

This invention provides novel vanillyl 5-hydroxyesters, and smoking compositions which contain a vanillyl 5-hydroxyester as a flavorant-release additive. Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as 4'-formyl-2'-methoxyphenyl 5-hydroxy-2-isopropylhexanoate pyrolyzes into vanillin and 2-isopropyl-5-hydroxyhexanoic acid delta lactone flavorants as volatile components of the cigarette smoke.

Vanillin 5-hydroxyesters and smoking compositions containing a

In one of its embodiments this invention provides smoking compositions which contain a novel unsymmetrical 2,5-diacylpyrazine flavorant additive as illustrated by 1-[5-(1-propanoyl)-2-pyrazinyl]-2-methyl-1-propanone: ##STR1## Under normal cigarette smoking conditions, the 2,5-diacylpyrazine additive volatilizes and enhances the flavor and aroma of the mainstream and sidestream smoke. In another embodiment this invention provides novel unsymmetrical 2,5-diacylpyrazine compounds corresponding to the formula: ##STR2## where R is hydrogen or an alkyl radical containing between about 1-4 carbon atoms; and R.sup.1 and R.sup.2 are alkyl radicals containing between about 1-10 carbon atoms, and R.sup.1 and R.sup.2 are different alkyl groups.

Smoking compositions containing a 2,5-diacylpyrazine flavorant additive

A smoking composition comprising an admixture of (1) combustible filler selected from natural tobacco, reconstituted tobacco, non-tobacco substitutes, and mixtures thereof, and (2) between about 0.00001 and 2 percent, by weight of the composition of a flavorant selected from the group consisting of compounds of the formulae ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.6, and R.sup.7 are independently selected from the group consisting of: hydrogen; C.sub.1 to C.sub.6 alkyl; C.sub.1 to C.sub.6 alkoxy-C.sub.1 to C.sub.6 alkyl; C.sub.3 to C.sub.12 cycloalkyl; phenyl; benzyl; substituted phenyl and substituted benzyl, wherein the substituted phenyl and substituted benzyl are substituted with one or more substituents, each of said substituents being independently selected from the group consisting of C.sub.1 to C.sub.6 alkyl, methoxy and hydroxy.

Tobacco flavorants

This invention provides novel sclaral alkyl ether compounds, and smoking compositions which contain a sclaral alkyl ether compound as a flavorant additive. ##STR1## Under cigarette smoking conditions the sclaral ether is a volatile component which enhances the flavor of the mainstream smoke and the aroma of sidestream smoke.

Sclarai alkyl ethers and smoking compositions containing a sclaral alkyl

In one of its embodiments the present invention provides a smoking composition which contains a novel type of acylpyrazine ether flavorant additive as exemplified by 1-(3-methoxy-2-pyrazinyl)-2-methyl-1-propanone. ##STR1##

Process for preparing acylpyrazine ethers

Smoking compositions containing acylpyrazine ether flavorants

This invention provides smoking compositions which contain a monoacylpyrazine compound as a flavorant additive. In one of its embodiments, this invention provides tobacco compositions which contain a monoacylpyrazine flavorant additive such as 1-pyrazinyl-2,2-dimethyl-1-propanone: ##STR1## Under cigarette smoking conditions the above illustrated monoacylpyrazine additive flavors the mainstream smoke and enriches the aroma of the sidestream smoke.

Smoking composition containing a novel monoacylpyrazine flavorant

A method for modifying the smoking flavor characteristics of bright tobacco, involves treating the tobacco with liquid ammonia, separating the resulting ammonia solution from the tobacco, concentrating the solution by evaporating the ammonia, dissolving the concentrate in a solvent and reapplying the dissolved residue to the once-treated tobacco.

Process for modifying the flavor characteristics of bright tobacco

1-pyrazinyl-1-propanone derivatives useful as flavorants in smoking

In one of its embodiments the present invention provides a smoking composition which contains a novel type of acylpyrazine ether flavorant additive as exemplified by 1-(3-methoxy-2-pyrazinyl)-2-methyl-1-propanone: ##STR1##

In one of its embodiments the present invention provides a smoking composition which contains a novel type of bicyclic acylpyrazine flavorant additive as exemplified by 2-acetyl-5,6,7,8-tetrahydrocyclohexa[b]pyrazine: ##STR1##

Smoking compositions containing novel acylpyrazine flavorants

In one of its embodiments this invention provides a smoking composition which contains a novel type of flavorant additive as exemplified by polymerized ethyl 2-propenyl 2-(2-butyl)malonate: ##STR1##

Growing community of inventors

Richmond, VA, United States of America

Everett W Southwick