US2766147A - Tobacco - Google Patents

Description

TOBACCO No Drawing. Application July 26, 1954, Seriai No. 445,893

13 Claims. (til. 131-17) This invention relates to tobacco and has for an object the provision of a smoking tobacco product having improved aroma and flavor characteristics which become apparent during smoking.

Smoking tobacco as now prepared for use in cigarettes comprises essentially a blended mixture of various types of tobaccos which are desired to produce a characteristic flavor and aroma when the tobacco is smoked. Present day cigarette tobaccos normally comprise blends of (1) heat-cured tobaccos, which are sometimes known as fluecured, bright leaf or Virginia tobaccos, (2) air-cured tobaccos, which are sometimes known as burley or Kentucky and Maryland tobaccos, and (3) sun-cured tobaccos, which are known as Turkish or Oriental tobaccos. The relative proportions of these various types blended to produce a desired cigarette tobacco mixture depend in a large measure upon the characteristic flavor or aroma that is desired to be achieved when the tobacco is smoked. Also, it is common practice to add various substances, such as flavoring materials and humectants, in order to provide other desired properties.

A further object of this invention is to provide a smoking tobacco which when smoked will have improved or enhanced flavor and odor characteristics which will be pleasing to the smoker.

A further object of this invention is the provision of a smoking tobacco having added thereto a compound or compounds which, when the tobacco is smoked, will liberate one or more organic acids imparting a selected and desired flavor and aroma to the smoke.

A still further object of this invention is the provision of a tobacco product having added thereto a substantially non-volatile substance which in itself does not substantially change the flavor or aroma of the tobacco but which, when burned on the tobacco, will release to the smoke certain desired flavoror aroma-producing acids.

A still further object of this invention is the provision of a tobacco having added thereto an organic compound which, when the tobacco is smoked or burned, will liberate several types of flavoring acids whereby the desired improvement in the flavor and aroma of the smoke may be achieved.

A still further object of this invention is the provision of additives for tobacco which may be easily and simply prepared and which may be incorporated into the tobacco at any stage during the processing thereof.

Further and additional objects will appear from the following description and the appended claims.

In the copending application of Samuel OBrien Jones, Serial No. 445,891, filed July 26, 1954, it is disclosed that certain esters of flavor-producing acids, when added to tobacco, will, when smoked or burned with the tobacco, release the acid or acids which latter impart a desired characteristic odor and/or flavor to the smoke, thereby contributing to the enjoyment of the smoker.

In accordance with the broad aspects of this invention, a smoking tobacco composition is provided which contains as an additive a small amount of an ester of a polynited States Patent 2,766,47 iatented Got. 9, 1956 hydroxy compound related to the lactones of certain sugar acids, said esters being selected from the group consisting of the monoand polyesters of the lactones of the aldonic and uronic acids. It has been found that these esters, when smoked or burned with the tobacco, will release one or more of the esterifying acids which, to provide the desired flavor and aroma, are those having from 3 to 8 carbon atoms. These acids, when present in the smoke in suitable concentrations, impart characteristic and desirable flavor and aroma to the tobacco smoke, thus contributing to the enjoyment of the smoker. The additives of this invention are substantially nonvolatile under ordinary tobacco storage conditions and will remain dispersed throughout the tobacco until such time as it is smoked and they are sufiiciently nonvolatile so that they Will remain in the burning area of the tobacco to permit the acid release to occur. Obviously, the additive should not volatilize much ahead of the burning Zone or the desired acid release may not occur. The additives herein disclosed are relatively stable under the usual tobacco storage conditions; consequently, the principal release of flavoring acid or acids does not occur until the tobacco is smoked.

The hydroxyl compounds which are esterified to pro duce the additives of this invention are the lactones of the aldonic or the uronic acids. These are polyhydric compounds and one or more of the hydroxyl groups may be esterified with the flavor-producing acid. Suitable lactones of the aldonic acid series are the pentaldonic, hexaldonic or heptaldonic acid, such as arabonic, Xylonic, lyxonic, ribonic, gluconic, galactonic, mannonic, gluonic, talonic, idonic, altronic, or allonic acid. Suitable lactones of the uronic acid series are the penturonic, hexuronic or hepturonic acid, such as araburonic, xyluronic, lyxuronic, riburonic, glucuronic, galacturonic, mannuronic, guluronic, taluronic, iduronic, altruronic or alluronic acid.

The flavor-producing esterifying acids which are released by the esters upon smoking in accordance with this invention are preferably those flavoring acids which will volatilize and will be carried by the smoke, such acids usually being the organic carboxylic acids having 3, 4, 5, 6, 7 or 8 carbon atoms, herein collectively referred to as those having from 3 to 8 carbon atoms. Representative acids are the saturated aliphatic fatty acids, such as propionic, n-butyric, isobutyric, n-valeric, isovaleric, Z-methylbutyric, n-caproic, 4-methylvaleric, 3- methylvaleric, 2,2-dimethylbutyric, Z-methylisovaleric, straight or branched chain heptoic, or straight or branched chain caprylic acids; the unsaturated aliphatic fatty acids, such as acrylic, crotonic, vinylacetic, 4-methyl-4-hexenoic and S-methylsorbic acids; the cycloalkane or cyeloalkene aliphatic acids, such as cyclopentanecarboxylic, cyclohexanecarboxylic, cyclopentaneacetic or cyclohexaneacetic acids or the corresponding unsaturated cycloalkenes; the aromatic carboxylic acids, such as benzoic or toluic acids; and phenylacetic acid. Also the volatile derivatives of these acids, such as the hydroxy acids or the keto acids may be the acid compounds released to impart the de sired odor or flavor to the smoke. It is preferred that the flavoring acid be an aliphatic or alicyclic saturated monocarboxylic acid of the fatty acid series having 4, 5 or 6 carbon atoms, herein collectively referred to as those having from 4 to 6 carbon atoms.

It will be apparent that the ester additive may be selected or prepared in such a manner that any one of the foregoing acids will be released during smoking. Also a single additive or mixture of additives may be selected and added to the tobacco so that a plurality of desired flavoring acids may be simultaneously liberated if desired, thus effecting a blend of the various types of aromas which has the characteristics of the several flavoring acids. Also, if desired, the several hydroxyl groups in the polyhydroxy lactone compound may be esterified with one or more diflerent flavoring acids or less than all of the hydroxyl groups may be esterified to produce the additive used in accordance with this invention. The specific flavor-producing acid or acids that are combined with the hydroxy compound to form the ester will depend upon the flavor and aroma desired in the tobacco smoke. As indicated above, the particular flavoring acid selected for the preparation of the ester is of consequence only in so far as the particular flavor contributed by that particular acid is important. Any of the flavor-producing acids may be utilized and, as previously indicated, they generally comprise the saturated or unsaturated organic carboxylic acids containing from 3 to 8 carbon atoms, preferably the saturated aliphatic monoearboxylic acids having from 4 to 6 carbon atoms.

The additives contemplated by this invention may be incorporated into the tobacco in any desired manner. For example, solutions of the additive in a suitable solvent, such as alcohol, ethyl ether, acetone or the like, may be applied to the tobacco as by spraying or otherwise, whereafter the solvent is driven off as a vapor leaving the additive thoroughly incorporated with the tobacco. The additive may also be uniformly dispersed in water and applied in a like manner if desired. The incorporation of the additive may take place at any time prior to the final packaging of the tobacco product. In the case of cigarette tobacco, it may be incorporated before or after blending of the various tobaccos if, in fact, blended tobacco is employed, and the additives may be applied to one or all of the blend constituents. Under certain circumstances the additive may be incorporated into the tobacco before aging and curing; however, this would not ordinarily be done if the additive has a tendency to decompose during the aging and curing process. in the case of cigarettes the additive in some instances might be applied to the paper instead of to the tobacco.

The amount of additive in the final tobacco product contemplated by this invention is quite small but will vary widely with the particular additive employed and the amount of acid released upon burning or the flavor or aroma desired in the smoke. Thus an additive that releases only a comparatively small fraction of its total available flavoring acid on burning will be required in higher concentrations than those additives which are more eflicient with respect to the amount of flavoring acid released. Also, it is well known that some of the aliphatic fatty acids having from 4 to 6' carbon atoms have a disagreeable odor per so when vapors of these acids are smelled in certain concentrations. However, in very low concentrations they provide in the tobacco smoke a desirable flavor and aroma, and the amount of additive in the tobacco should be such as not to ex ceed the amount which, when the tobacco is smoked, will release desirable quantities of the acid. This amount in'many cases will be determined by actual experimentation. Generally speaking, however, desirable flavor and aroma are produced if the additives are incorporated into the final tobacco product in amounts between about 0.01 and 1.0 percent by weight (dry basis).

As pointed out in the copending Jones application hereinbefore referred to, a number of methods have been employed for incorporating acid-releasing compounds into cigarette tobacco and evaluating them for acid release. Certain of such methods are suggestive of procedures that may be used in actual commercial practice and include the following:

METHOD 1 One gram of shredded flue-cured tobacco was spread out on a watch glass of 10 cm. diameter. One milliliter of a solution of the additive in a suitable solvent such as ethyl ether was added uniformly to the tobacco from a pipette. The amounts of the additives vary but in general 10 milligrams of additive were applied to the one gram sample. After the other had evaporated, the tobacco was rolled into a cigarette which was stored at 75 F. and about 60% relative humidity.

METHOD 2 A small quantity of liquid additive in the amount of l to S milligrams was streaked longitudinally along the paper of a cigarette by means of a stirring rod.

METHOD 3 The additive was dissolved in a volatile solvent, such as acetone, alcohol or ether, using 2 to 40 milligrams of additive per milliliter of solvent. One-fourth milliliter of the resulting solution was then distributed through a one-inch portion (which was to be burned) of a cigarette by means of a M1 milliliter hypodermic syringe. The volatile solvent Was then blown out of the cigarette with a stream of compressed air, leaving the additive dispersed in the cigarette.

.IETHOD 4 The additive was dissolved in ethyl alcohol or other suitable solvent and sprayed onto shredded flue-cured tobacco spread out on a table. Two hundred milliliters of solution containing 1 to 29 grams of additive were used for each 3 kilograms of tobacco. The tobacco was exposed to the air until substantially all of the solvent had evaporated and then was manufactured into cigarettes in the usual manner having an average weight of one gram each. These were stored for a period of l to 12 months at 75 F. and 60% relative humidity in order to ascertain the stability of the additive when .stored'on tobacco.

METHOD 5 The additive was dissolved in alcohol or other suitable solvent and sprayed onto one of the types of leaf tobacco that is used in a blended cigarette. This leaf tobacco was allowed to dry and was cut on a shredding machine. The shredded tobacco was blended with other types of shredded tobaccos that had not been treated with additive and the blend was made into cigarettes.

The compound or additive under test when applied to a low flavor tobacco or cigarette made therefrom, as indicated in one of the foregoing methods, was evaluated by organoleptic testing. This was carried out by smoking the cigarette and examining the smoke by sensory methods. In each of these tests special efforts were made to determine whether any acid vodor was present in the smoke. This included a careful sensory study of both the main stream and the side stream. If the acid odor was detected in either the side stream or the main stream, it was concluded that the additive released the acid during the smoking or burning of the treated tobacco or cigarette.

In the foregoing, reference has been made to a general class of esters of polyhydroxy lactones of the aldonic and uronic acids which are useful as additives for tobacco in accordance with this invention. Certain of'the specific compounds in this class are new and certain of them are not available commercially. Accordingly, se eral examples will be presented in the following disclosing methods of preparing representative compounds that are useful as additives in accordance with this invention. In each case the compounds which were prepared by the specific procedures given in the examples to follow were tested by one of the methods previously mentioned and each was found to release flavoring acid when smoked with tobacco. It will be understood that in the following, examples are given of preparing esters which will, upon burning or smoking of the tobacco treated therewith, liberate onlyone of the flavor-producing acids contemplated by this invention. However, it will be apparent to one skilled in the art how other esters releasing other particular flavoring acids may be prepared. For example, in the following where there are given examples of processes of preparing esters of one or more specific flavoring acids, it will be understood that essentially the same or similar means known to chemists could be employed for preparing the esters of other flavoring acids of the character hereinabove specified and that all such esters are contemplated as additives within the scope of this invention.

Gluconoltrctone tetraisovalerate To a mixture of 5.9 grams of glucono (delta) lactone (Pfizer), 80 millileters of chloroform and 14 milliliters of pyridine cooled in an ice water bath were added dropwise with stirring over a period of 45 minutes 20 grams of isovaleryl chloride. The solution was allowed to stand for three hours after which it was heated under reflux for two hours. The reaction mixture was diluted with 200 millileters of ether. The ethereal solution was washed successively with 100 milliliters of water, 60 milliliters of cold 2 N sulfuric acid, 60 milliliters of water, two 60- milliliter portions of 5 percent sodium bicarbonate solution and 60 milliliters of ice water After the ethereal solution was dried over calcium chloride, the low-boiling solvents were removed by distillation under reduced pressure. The residue was dissolved in ether and was treated with decolorizing charcoal (Norite). After removal of the Norite and of the ether, the product weighed 13.9 grams (87 percent yield).

Gluconolactone tetracyclopentanecarboxylate To a mixture of 6.0 grams of gluconolactone, 100 milliliters of chloroform and 13 grams of pyridine cooled in an ice bath were added dropwise with stirring over a period of fifteen minutes 21.8 grams of cyclopentanecarboxyl chloride. After one hour, the reaction mixture was heated under reflux and then was allowed to stand at room temperature for sixteen hours. The mixture was diluted with 200 milliliters of ether. The ethereal solution was washed successively with 100 milliliters of water, 100 milliliters of 2 N sulfuric acid, 70 milliliters of water, two SO-milliliter portionss of 5 percent sodium bicarbonate and 50 milliliters of water. After the solution was dried over calcium chloride, the low-boiling solvents were removed by distillation under reduced pressure. The residue was crystallized three times from a liquid hydrocarbon (Skellysolve B), yielding 9.0 grams of solid melting at 99.5l00.5 C.

Gluconolactone tetrabenzoare To a mixture of 70 milliliters of chloroform, 17.7 grams of benzoyl chloride and 9.9 grams of pyridine cooled in a dry ice bath were added 4.5 grams of gluconolactone. The cooling bath was removed and the mixture was stirred for three hours. To the mixture were added 200 milliliters of ether and 100 milliliters of water. The solid material was collected by filtration and was washed with ether. The product weighed 10.2 grams and melted at 159-160 C. Crystallization from toluene did not alter the melting point.

Galactonolactone zetracyclopentanecarboxylate To a chilled mixture of 100 milliliters of chloroform, 19.5 grams of pyridine and 33.1 grams of cyclopentanecarboxyl chloride were added 8.9 grams of galactonolactone. The mixture was allowed to warm to room temperature. After 20 hours, the mixture was heated under reflux for 1.2 hours. The mixture was diluted with 200 milliliters of ether and the ethereal solution was washed successively with 100 milliliters of water, 100 milliliters of 2 N sulfuric acid, 100 milliliters of water, two 100- milliliter portions of 5 percent sodium bicarbonate and 100 milliliters of water. After the ethereal solution was dried over calcium chloride the low-boiling solvents were removed by distillation under reduced pressure. Crystallization of the residue from hexane gave 21.5 grams of solid metling at 77-79 C. Two further recrystallizations from hexane raised the melting point to 79.581 C.

Glucuronolactane triisobuzyrate' To a mixture of 5.8 grams of glucuronolactone, 7.8 grams of pyridine and milliliters of chloroform chilled in a dry ice bath were added dropwise with stirring 11.7 grams of isobutyryl chloride. The mixture was allowed to warm slowly to room temperature after which it was heated under reflux for 1.5 hours. The mixture was diluted with 250 milliliters of ether and the ethereal solution was washed successively with 100 milliliters of water, 100 milliliters of 2 N sulfuric acid, 100 milliliters of water, two 100-milliliter portions of 5 per cent sodium bicarbonate solution and 100 milliliters of water. After the ethereal solution was dried over calcium chloride, the low-boiling solvents were removed by distillation under reduced pressure. The residue, 9.8 grams, was partitioned between 70 percent petroleum ether-30 percent ether and 70 percent methanol30 percent water. The petroleum ether-ether layers yielded 4.4 grams (35 percent) of the product,

Glucuronolactone triisovalerate To a mixture of 8.8 grams glucuronolactone (Corn Products Sales Co.), 16 milliliters of pyridine and 75 milliliters of freshly distilled chloroform chilled in a dry ice bath were added dropwise with stirring over a period of 30 minutes 25 grams 10f isovaleryl chloride. The cooling bath was removed and the mixture was allowed to stand for one hour after which it was heated under reflux for two hours. After twenty hours, the mixture was diluted with 300 milliliters of other. The ethereal solution was washed successively with two l00-milliliter portions of ice water, two 100-milliliter portions of 2 N sulfuric acid, 50 milliliters of water, two 100-milliliter portions of 5 percent sodium bicarbonate solution and 100 milliliters of water, After the ethereal solution was dried over calcium chloride, the ether was removed under reduced pressure. The residue weighed 19.5 grams.

Glucuronolactone tricyclolzexanecarboxylate To a mixture of 5.8 grams of glucuronolactone, 7.8 grams of pyridine and 100 milliliters of chloroform cooled in a dry ice bath were added dropwise with stirring 16.1 grams of cyclohexanecarboxyl chloride. The mixture Was allowed to warm gradually to room temperature and was heated under reflux for 2 hours. The mixture was diluted with 200 milliliters of ether and was washed successively with 100 milliliters of water, 100 milliliters of 2 N sulfuric acid, 100 milliliters of water, two 100-milliliter portions of 5 percent sodium bicarbonate solution and 100 milliliters of water. After the ethereal solution was dried over calcium chloride, the low-boiling solvents were removed by distillation under reduced pressure. The residue, 16.2 grams, was crystallized successively from hexane, from a mixture of hexane and isopropyl ether and fnom methanol, giving 4.3 grams of product (26 percent) melting at 121122.5 C

Glucuronolactone tribenzoate To a mixture of 8.8 grams of glucuronolactone, 100 milliliters of chloroform and 20 grams of pyridine cooled in ice water were added, with stirring, over a period of 0.5 hour 35.1 grams of benzoyl chloride. The mixture was stirred at room temperature for 2 hours after which it was heated under reflux for 2 hours. The reaction mixture was diluted with 250 milliliters of ether and the mixture was washed with 100 milliliters of water. The insoluble solid was collected by filtration and was washed with two SO-milliliter portions of 5 percent sodium bicarbonate. The ethereal filtrate was washed successively with 70 milliliters of 2 N sulfuric acid, 100 milliliters of water, two 60-milliliter portions of 5 percent sodium bicarbonate and 100 milliliters of water. The ethereal solution was decolorized by treatment with decolorizing charcoal after which the low-boiling solvents were re- 7 moved by distillation under reduced pressure. The residue was crystallized from isopropyl alcohol, whereby 4.8 grams of solid, melting at 145 152 C., were obtained. Further crystallization from isopropyl alcohol followed by two recrystaliizations from methyl alcohol raised the melting point to 156.5157.5 C. The precipitate which separated from the dilution of the reaction mixture with ether and water was crystallized twice to give 6.1 grams of solid melting at 192. 93 C.

It will be understood that the foregoing specific examples are only representative of the large number of esters of the polyhydric lactones of the uronic and aldonic acids that may be used to release acid on smoking of the tobacco treated therewith. It will also be understood that these compounds may be prepared by other methods that are well known .to the art generally. The specific examples given are believed to be adequate to show the manner in which a large number of esters of the various hydroxy compounds and the several flavoring acids may be readily prepared.

A specific example of a method for applying an additive to a cigarette tobacco is as follows:

Three kilograms of stemmed, flue-cured tobacco were spread out on a table and were sprayed with a solution of 1.5 grams of gluconolactone tetracyclopentanecarboxylate in 200 milliliters of 95% alcohol. The tobacco was turned from time to time during this operation in order to expose new leaves to the spray. The treated tobacco was shredded on a tobacco-cutting machine and was manufactured into cigarettes that had an average weight of 1 gram each. The cigarettes were stored in a room maintained at 75 Fahrenheit and 60% relative humidity. The cigarettes were examined by a panel of smokers shortly after manufacture, and again at the end of 90 days. The majority of the smokers detected cyclopentanecarboxylic acid in the smoke from the cigarettes.

Studies have been made in order to determine the ex tent to which various compounds will actually release acid when smoked with tobacco. As pointed out in the above-mentioned copending Jones application, an arbitrary scale has been set up for comparing or evaluating the various additives that may be incorporated into to bacco. The additives which liberate the largest amount of acid on an organoleptic test basis during smoking have been arbitrarily assigned a rating of 10. The additives at the bottom of the scale liberating detectable but small quantities of acid on an organoleptic test basis have been assigned a rating of 1. Using this arbitrary scale and evaluating the various additives by a test panel of a number of smokers, the following ratings were arrived at for certain of the compounds contemplated within the scope of this invention: gluconolaotone isovalerate, gluconolactone cyclopentanecarboxylate and gluconolactone benzoate each have an 3 rating, galactonolactone cyclopentanecarboxylate has a 9 rating, and glucuronolactone isobutyrate, glucuronolactone isovalerate, glucuronolactone cyclchexanecarboxylate and glucuronolactone benzoate each have a 10 rating.

While the rating given a particular compound is indicative of acid release, it is not necessarily conclusive in evaluating that compound for comercial use as a tobacco additive. For example, some compounds having a high rating may have a tendency to be unstable under tobacco storage conditions, thereby prematurely releasing the acid, it being understood that it is generally desirable for the acid not to be released prior to smoking. Also it is pointed out that the polyhydroxy compounds from which the esters are prepared in accordance with this invention are in certain instances related to compounds naturally occurring in tobacco and the residue after the acid has been released does not introduce any objectionable foreign type of constituent into the tobacco during the smoking procedure.

Also in accordance with this invention, it may in certain instances hedesirable to employ an ester of the polyhydroxy lactone wherein iess than all of the hydroxyl groups are esterifiedwith the flavoring acid. However, at least theoretically, such compounds are capable of releasing fewer molecules of flavoring acid per molecule of the ester. Thus, on a weight for weight basis, the polyesters may be more effective than the corresponding monoesters. Generally, however, the degree of acid release in each instance should be tested by actual trial since the degree of acid :release does not always appear to be directly proportional to the number of esterified groups in the hydroxy compound.

It will be understood that compositions have been prepared in accordance with this invention which have improved or enhanced aroma and flavor to give increased pleasure during smoking. Infinite variations with respect to the kinds and amounts of flavor-producing acids are possible and may be readily controlled. The additives of this invention may be particularly useful with tobaccos which are ordinarily low in the type of flavor imparted by the flavoring acids. While the invention has been specifically described with reference to cigarettes, it will be apparent that it has application in the manufacture of other smoking tobaccos such as used for hand-rolled cigarettes, pipes and cigars.

While several particular embodiments of this invention are shown above, it will be understood, of course, that the invention is not to be limited thereto, since many modifications may be made, and it is contemplated, therefore, by the appended claims, to cover any such modifications as fall within the true spirit and scope of this invention.

I claim:

1. An article of manufacture comprising tobacco and an ester of a volatile organic acid and a lactone of a sugar acid selected from the group consisting of the aldonic acids and the uronic acids.

2. A smoking tobacco having added thereto a small amount of an ester of a volatile organic acid and a polyhydroxy lactone of a sugar acid selected from the group consisting of the aldonic acids and the uronic acids.

3. A smoking tobacco having added thereto a small amount of an ester of a volatile monocarboxylic acid and a lactone of a hexose acid selected from the group consisting of the aldonic acids and the uronic acids.

4. A smoking tobacco having added thereto a small amount of an ester of a monocarboxylic acid having from 3 to 8 carbon atoms and a lactone of a hexaldonic acid.

5. A smoking tobacco having added thereto a small amount of an ester of a monocarboxylic acid having from 3 to 8 carbon atoms and a lactone of a hexuronic acid.

6. A smoking tobacco having added thereto between about 0.01 and 1.0 percent by weight (dry basis) of an ester of a volatile monocarboxylic flavoring acid having from 3 to 8 carbon atoms and a lactone of an acid selected from the group consisting of the hexaldonic acids and the hexuronic acids.

7. The tobacco recited in claim 6 wherein said lactone is gluconolactone.

8. The tobacco recited in claim 6 wherein said lactone is galactonolactonc.

9. The tobacco recited in claim 6 wherein said lactone is glucuronolactone.

10. The tobacco recited in claim 6 wherein said acid has from 4 to 6 carbon atoms.

11. An article of manufacture comprising tobacco and between about 1.0 and about 0.01 percent by Weight (dry basis) of an ester of a volatile organic acid and a lactone of a sugar acid selected from the group consisting of the aldonic acids and the uronic acids.

12. A smoking tobacco having added thereto between about 1.0 and about 0.01 percent by weight (dry basis) of an ester of a volatile organic acid having from 3 to 8 carbon atoms and a polyhydroxy lactone of a sugar acid selected from the group consisting of the aldonic acids References Cited in the file of this patent and the Home aclds' M. B. Jacobs: Synthetic Food Adjuncts. Pages 13. An article of manufacture comprising tobacco and 136442 Published by Van Nostrand Co a derivative of a lactone of a sugar acid, said derivative 1947 upon smoking with tobacco being capable of releasing a 6 volatile organic flavoring acid selected from the group consisting of the aldonic acids and the uronic acids.

Claims (1)

1. AN ARTICLE OF MANUFACTURE COMPRISING TOBACCO AND AN ESTER OF A VOLATILE ORGANIC ACID AND A LACTONE OF A SUGAR ACID SELECTED FROM THE GROUP CONSISTING OF THE ALDONIC ACIDS AND THE URONIC ACIDS.