Philip Morris Inc.

Philip Morris Products Inc.

Yoram Houminer

W Geoffrey Chan

Harvey J Grubbs

Kenneth F Podraza

Everett W Southwick

Edward B Sanders

David L Williams

John Bryant Paine, Iii

Jeffrey I Seeman

William B Edwards, Iii

John D Naworal

Henry V Secor

Makram H Meshreki

Charles R Howe

Susan S Tafur

Ernst K Just

This invention provides a cigarette product which releases vanillin or ethylvanillin aroma in sidestream smoke under cigarette smoking conditions. The paper wrapper of the cigarette product has a content of a flavorant-release additive which is a novel 3-vanillyl-2-hydroxypropyl or 3-ethylvanillyl-2-hydroxypropyl substituted ether derivative of cellulose.

Cigarette smoking products containing a vanillin-release additive

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 novel vanillin flavorant-release additive. 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 corresponding to the formula: ##STR1## where R is methyl or ethyl.

Smoking compositions containing a vanillin-release additive

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 2-(3-hexyl-2-hydroxy-4-phenyl-3-buten-1-yl)-3,5,6-trimethylpyrazine releases pyrazine and cinnamaldehyde type of volatile flavorants into the cigarette smoke: ##STR1##

Smoking compositions containing a pyrazine-ethanol flavorant-release

This invention provides smoking compositions which contain a novel tartrate salt flavorant-release additive, such as an acetal derivative corresponding to the formula: ##STR1## Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive as illustrated above pyrolyzes and releases benzaldehyde flavorant as a volatile component of the cigarette smoke.

Smoking compositions containing a tartrate salt flavorant-release

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 2-(3-hexyl-2-hydroxy-4-phenyl-3-buten-1-yl)--3,5,6-trimethylpyrazine releases pyrazine and cinnamaldehyde type of volatile flavorants into the cigarette smoke: ##STR1## A present invention flavorant-release additive is represented by the formula ##STR2## where R is hydrogen or methyl, R.sup.1 is hydrogen or a C.sub.1 -C.sub.10 alkyl substituent; and R.sup.2 is hydrogen or a C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy substituent.

Smoking compositions containing a pyrazineethanol flavorant-release

This invention provides smoking compositions which contain a novel vanillin flavorant-release additive. Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as ethyl 3-(4'-butoxycarbonyloxy-3'-methoxyphenyl)-3-hydroxy-2-phenylpropanoate pyrolyzes into vanillin and ethyl phenylacetate flavorants as volatile components of the cigarette smoke. A present invention flavorant-release additive is represented by the formula: ##STR1## where R is methyl or ethyl; R.sup.1 is hydrogen or a C.sub.1 -C.sub.4 alkyl substituent; R.sup.2 is hydrogen or a C.sub.1 -C.sub.4 alkyl or C.sub.6 -C.sub.10 aromatic substituent; and R.sup.3 is a C.sub.1 -C.sub.4 alkyl or C.sub.6 -C.sub.10 aromatic substituent.

This invention provides tobacco and non-tobacco smoking compositions which contain a heterocyclic-hydroxy-substituted carboxylate compound as a flavorant additive. In one of its embodiments, this invention provides tobacco compositions which contain a heterocyclic-hydroxy-substituted carboxylic acid flavorant additive such as 2-(2-butyl)-3-hydroxy-3-methyl-3-(3-pyridyl)propionic acid: ##STR1## Under smoking conditions the above illustrated heterocyclic-hydroxy-substituted carboxylate additive and its pyrolysis products flavor the mainstream and sidestream smoke.

Smoking compositions

This invention provides novel .beta.-hydroxyesters which have utility as a flavorant-release additive in smoking compositions. Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as ethyl 3-hydroxy-3-(4'-hydroxy-3'-methoxyphenyl)-2-phenylpropanoate pyrolyzes into vanillin and ethyl phenylacetate flavorants as volatile components of the cigarette smoke.

Beta-hydroxyesters for use as vanillin-release additives in smoking

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

This invention privdes novel heteroaromatic compounds, and smoking compositions which contain an invention heteroaromatic compound as a flavorant-release additive as illustrated by the following additive structure: ##STR1## Under typical cigarette smoking conditions, 2-isopropylpyrazine and acetophenone are released as pyrolysis products, and enhance the flavor and aroma of the mainstream and sidestream smoke.

Smoking compositions containing a heteroaromatic flavorant-release

This invention provides novel heterocyclic ester compounds. This invention further provides smoking compositions which contain an invention heterocyclic ester as a flavorant-release additive, as illustrated by the following structure: ##STR1## Under normal cigarette smoking conditions, tetramethylpyrazine and an olefin are released as pyrolysis products, and they enhance the flavor and aroma of the mainstream and sidestream smoke.

Heterocyclic esters and smoking compositions containing a heterocyclic

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 .beta.-hydroxy-.gamma.-ketoester compound as a flavorant-release additive. In one of its embodiments, this invention provides tobacco compositions which contain a flavorant-release additive such as dodecyl 3-hydroxy-2,2,3-trimethyl-4-oxopentanoate: ##STR1## Under cigarette smoking conditions the above illustrated .beta.-hydroxy-.gamma.-keto ester pyrolyzes into 2,3-butanedione and other products which enhance the flavor of the mainstream smoke and the aroma of sidestream smoke.

Growing community of inventors

Richmond, VA, United States of America

Yoram Houminer