MXPA99011680A - Enhanced flavoring compositions containing n-ethyl-p-menthane-3-carboxamide and method of making and using same - Google Patents

Abstract

Enhanced flavoring compositions containing at least one flavoring agent and an effective amount of N-ethyl-p-menthane-3-carboxamide are provided. The N-ethyl-p-menthane-3-carboxamide is present at about 0.04 to about 2.2%by weight of the enhanced flavoring composition. The invention further concerns chewing gums and confectionary compositions containing a flavoring effective amount of the enhanced flavoring compositions.

Description

matrix Greater amounts of flavors are therefore used in the gums to offer a noticeable flavor effect Special attention has been paid to improve the impact of fruit flavors in chewing gums Due to its chemical composition, fruit flavors have a particularly high affinity with gum base. Fruit flavors also have a light flavor quality that provides a low impact U.S. Patent No. 5,158,790, for example, teaches the use of L-carvone with fruit flavors to overcome these difficulties and improve sweetness and taste. U.S. patents 5,415,888 and 5,429,827 teach the use of a polymeric retainer that has a particular solubility parameter relative to the fruity flavor for the release control The synergistic effects provided by the use of substances such as taste enhancements are also well known in food techniques Synergism in flavors is the addition of very small amounts of a non-specific material to accentuate the specific flavoring material. The known synergisms include, example, the use of citric acid in spearmint to accentuate spearmint, vanilla in chocolate to accentuate the chocolate flavor, lemon oil in molasses, spearmint oil in licorice or anise, and "the use of salt in the Most sweets except butter-flavored sweets Cooling agents are compounds used in confectionery compositions and chewing gums for their refreshing sensation and refreshing effects of the breath with or without the presence of flavoring agents. Menthol is perhaps the best known cooling agent but has well-known disadvantages such as high volatility, acidity and a strong mint flavor N-ethyl-p-menthane-3-carboxamide is also known as a refreshing agent. U.S. Patent No. 4,193,939 teaches N-ethyl-p-menthane-3-carboxamide being less volatile than menthol and has little or no aroma. U.S. Patent Nos. 4,060,091, 4,136,163 and 5,405,604 teach the use of N-ethyl-p-menthane-3-carboxamide as a flavoring agent in edible compositions. U.S. Patent No. 5,009,893, U.S. Patent No. 5,244,670, WO 93/23005 and WO 98/25177 all disclose the use of N-ethyl-p-menthane-3-carboxamide as an adjuvant with other cooling agents that include menthol WO 97/06695 teaches, however, that the compounds used as cooling agents all have a negative impact on the flavors, particularly the flavors. fruit trees WO 97/06695 further teaches that to avoid the problem, flavors and cooling agents must be formulated in discrete and distinct regions of the confectionery product.

Thus it is known that the use of N-ethyl-p-menthane-3-carboxamide provides refreshing effects and improves the refreshing effects of flavor, particularly in gum and confectionery products with mint flavor. Food techniques however do not teach the use of N-ethyl-p-menthane-3-carboxamide as an improvement in flavor. More specifically, the technique does not teach the use of N-ethyl-p-menthane-3-carboxamide in combination with flavors, particularly in combination with fruit flavors, in gums and in confectionery products, at levels that produce synergistic effects.

SUMMARY OF THE INVENTION The present invention provides an improved flavor composition comprising at least one flavoring agent and an amount of N-ethyl-p-menthane-3-carboxamide effective to improve the flavoring agent wherein the N-ethyl-p- menthane-3-carboxamide is present at about 0.04 to about 2.2 percent by weight of the improved flavor composition. The invention further relates to a method for improving a flavoring agent comprising adding thereto an effective amount of N-ethyl-p-menthane-3-carboxamide at about 0.04 to about 2.2 percent by weight of the combination . The invention further relates to chewing gums and confectionery compositions that contain an effective flavoring amount of the improved flavoring compositions.

DETAILED DESCRIPTION OF THE INVENTION It has now been surprisingly found that N-ethyl-p-menthane-3-carboxamide can be used per se, as a flavor modifier to improve the taste of a flavoring agent. This synergistic effect is found when N-ethyl-p-menthane-3-carboxamide is used at low levels in combination with the flavoring agent. The character of the flavor is generally more sharp or bright, accentuated, more defined and of longer duration compared to compositions containing the same flavoring agent without N-ethyl-p-menthane-3-carboxamide. The improved flavor composition provides a lasting taste sensation to food compositions such as gums and confectionery, particularly chewing gums with fruit flavors.

The term "flavor" is used in the present with the meaning of the sensation produced by a material introduced into the mouth, particularly by the senses of taste and smell. The flavor is also taken with the meaning of the sum of the characters of the material that produces the sensation. The term "flavoring agent" is used herein to mean the composition of natural or synthetic oils that produces the taste sensation. Flavoring agents are well known in confectionery techniques.

The flavors contemplated in the present include fruit flavors such as blackberry, citrus, tropical fruit flavors and the like; Herbal such as cinnamon, anise, coriander, eucalyptus, ginseng, fennel and the like; sweets such as honey, caramel, caramel sueva, molasses and the like; and species such as nutmeg, pepper, cinnamon, ginger, clover and the like.

The improvement and the perceived prolongation of fruit flavors is a preferred application of the present invention. Fruit flavors can be produced naturally or synthetically and typically contain a combination of aromatic hydrocarbons such as esters, aldehydes and ketones, essential oils of vegetable materials such as lemon oil or other natural oils, and botanical distillates. The fruity flavors include, but are not limited to, lemon, orange, lime, peach, grapefruit, banana, cherry, apple, pineapple, grape, strawberry and mixtures such as tutti fruti and fruit punch and the like.

The amounts of the flavoring agent and the N-ethyl-p-menthane-3-carboxamide in the improved flavor composition will be from about 99.96% to about 97.8% flavoring agent and about 0.04% to about 2.2% N- ethyl-p-menthane-3-carboxamide, with 0.4% to 1.1% of N-ethyl-p-menthane-3-carboxamide being preferred. The amounts will depend a little on factors such as the type of flavor, the end use and the desired effect.

The amount of the improved flavor composition to be used in the final product will also depend on the type of flavor, the final product and the desired effect. In general, the improved flavor composition may be suitable for use in confectionery compositions in a range of about 0.10% to about 1.0% by weight of confectionery with 0.2% to 0.5% being preferred. For chewing gums a larger range of around 0.8 to around 3.5% with 1.0% up to 3.0% is preferred.

The improved flavor compositions of the present invention can be used in edible products such as hard and soft confectionery, and in chewing gums. The preparation of confectionery formulations is historically well known and has changed little over the years. In general a confectionery of boiled solid caramel has a base composed of a mixture of sugar and other carbohydrate volume agents maintained in an amorphous or glassy condition, preferably having from about 0.5% to about 1.5% moisture. The base usually contains up to around 80% sugar and up to 65% corn syrup, with a higher proportion of sucrose - corn syrup. Other ingredients such as flavoring agents, sweetening agents, acidulants, dyes and others can also be added. Solid boiled candies can also be prepared from non-fermentable sugars such as sorbitol, mannitol, silitol, maltitol, erythritol, hydrogenated starch hydrolysates and the like.

Such confectionery can be prepared routinely by conventional methods such as those involving fire burners, vacuum stoves and rough surface stoves also known as high-speed atmospheric stoves. Once the candy dough has been tempered properly, it can be cut into easy-to-work portions or the desirable shapes can be formed. A variety of training techniques can be used depending on the shape and size of the desired end product. A general discussion of the composition and preparation of solid confectionery can be found in E.B. Jackson, Ed. "Maciza Confectionery Manufacturing", 2nd edition, Blackie Academic & Professional Press, Glasgow, United Kingdom, (1990), on pages 129-169.

Similar to solid candy confectionery, soft candy confectionery can be used with this invention. Soft candies include sugar pastes, soft candies, candies, marshmallows and the like and may also include jams and jellies. The preparation of soft confectioneries, such as sweets, involves conventional methods, such as the combination of two main components, namely (l) a high-boiling syrup such as corn syrup or similar and (2) a mass of relatively light texture, generally prepared based on egg albumin, gelatin, vegetable proteins, such as soy-derived compounds, milk-derived compounds such as milk proteins and mixtures thereof. Other ingredients such as the improved flavoring agent, flavoring agents, additional volume carbohydrate agents, dyes, preservatives, medicaments, mixtures thereof and the like can also be added afterwards under agitation. A general discussion of the composition and preparation of such confectionery can be found in E.B. Jackson, Ed.

"Maciza Confectionery Manufacturing", 2nd edition, Blackie Academic & Professional Press, Glasgow, United Kingdom, (1990), on pages 236-258.

The improved flavor compositions can be used in chewing gums.

The chewing gum composition generally comprises one or more natural or synthetic elastomers that are supplemented with conventional chewing gum ingredients. These ingredients include one or more solvents, plasticizers, fillers, flavoring agents, coloring agents and / or sweetening agents.

The elastomers that are suitable for use herein include substances of vegetable origin such as chewing gum, jelutong, gutta percha, guyayale and crown gum. Synthetic elastomers such as butadiene-styrene copolymers, isobutylene-isoprene copolymers, polyisobutylene, polyvinylacetate and mixtures thereof are also useful. The elastomer generally comprises from about 14% to about 50% by weight, preferably from about 20% to about 30% by weight, of the chewing gum composition.

The chewing gum composition may contain elastomer solvents to help soften the polymer component. Said elastomer solvents may include methyl, glycerol or pentaerythritol esters of modified rosins or rosins, such as hydrogenated, dimerized or polymerized rosins or mixtures thereof. Examples of suitable elastomeric solvents herein include pentaerythritol ester of partially hydrogenated wood rosin, pentaerythritol ester of wood rosin, partially dimerized glycerol ester of rosin, polymerized rosin glycerol ester, rosin glycerol ester of tallow oil, glycerol ester of wood rosin and partially hydrolysed wood rosin and partially hydrogenated methyl ester of rosin, and mixtures thereof. Terpene resins, including polyterpene and mixtures thereof are also useful. The solvent can be used in an amount ranging from about 10% to 75% and preferably from about 15% to about 50% by weight of the chewing gum composition.

A variety of traditional ingredients used as plasticizers or emulsifiers such as lanolin, lecithin, glycerol monostearate, stearic acid, sodium stearate, potassium stearate, glycerol triacetate, triacetin, glycerin and the like can also be incorporated into the chewing gum composition to obtain a variety of textures and consistency properties. These additional materials can also include waxes such as natural waxes, vaseline waxes and microcrystalline waxes and fats and oils that include animal fats such as lard and tallow, vegetable oils such as soybean oil and soybean oil. cotton, hydrogenated and partially hydrogenated vegetable oil and cocoa butter. These ingredients are generally employed in amounts of up to about 30% by weight, preferably 1% up to 25% by weight and more preferably from about 3% up to about 7% by weight of the final chewing gum composition .

The chewing gum composition may also include coloring agents such as titanium dioxide, in amounts up to 2% and fillers such as phosphate, magnesium carbonate, aluminum hydroxide, alumina, aluminum silicates, talc, carbonate calcium and combinations thereof in amounts of from 5 to about 35% by weight of the final concentration.

The chewing gum composition may also contain crude sweeteners including sugars such as sucrose, dextrose, maltose, fructose and the like or sugar alcohols such as sorbitol, mannitol, xylitol, maltitol, isomalt, erythritol and hydrogenated starch hydrolysates and combinations thereof. The raw sweeteners may be present in amounts of up to 90% by weight of the final composition. High intensity sweeteners such as Aspartame, acesulfame salts, aliatame saccharine and the like may also be present. These sweeteners can be prepared in amounts of up to 1% by weight of the final gum composition.

The chewing gum may contain flavoring agents in addition to the improved flavor compositions of the improved flavoring compositions in amounts up to 3.5%. In general, any food additive such as those described in "Chemicals used in the Food Process", publication 1274, pages 63-258, by the academy of natural sciences, as it is said.

The chewing gum is usually manufactured according to methods known in the art by sequentially adding the components in a commercial mixer or extruder in a batch or science process.

Chewing gum is usually manufactured by methods known in the art when added sequentially. The improved flavor composition of the present invention is added to the chewing gum in the usual manner. After the ingredients have been completely mixed the dough is discharged and cut, rolled or received the desired shape.

The invention is illustrated by the following non-limiting examples EXAMPLES N-ethyl-p-menthane-carboxamide is available as "WS-3" provided by Sterling Organics.

Example 1: Confectionery A caramel base (478.55 g) was prepared by mixing a 55/45 ratio of granulated sugar and corn syrup with 47.9 g of water and cooking the mixture at 145 ° C. The cooked mixture was transferred to a cooling table and 21.25 g of a flavor premix was kneaded into the base while cooling. Flavored candy was formed by rolling through a drop roller. The flavor premix consisted of 20.0 g of bran and 1.25 g of flavor for 0.25% by weight of flavor in the caramel.

To a similarly prepared base (478.55 g) were added 21.45 g of the second flavor premix that also contained 20.0 g of bran, and 1.25 g of flavor, with the addition of 0.20 g of a 5% ethanol solution of N-ethyl-p-menthane-carboxamide (0.1 g) for 0.002% by weight of the N-ethyl-p-menthane-carboxamide in the caramel, and a taste ratio / N-ethyl-p-menthane-carboxamide of 99.2: 0.8.

Caramels flavored with honey, citrus, herbal and apple spices were prepared by the above methods with either and without N-ethyl-p-menthane-carboxamide in the flavor premix. The four pairs of flavors were evaluated as follows: FLAVOR EVALUATION Honey - The carboxamide intensifies the character of honey. It provides a better and more pleasant feeling of totality to the profile of honey flavor. Species - The carboxamide modifies the taste perception of citrus citrus species. Complete the flavor by mixing the various notes in a flavor perception. Herbal - At this level, the carboxamide intensifies the acidic notes which leads to distortion. Less than 0.002% would be preferred for this herbal flavor. Apple - The carboxamide highlights and better defines the apple notes of this flavor.

Nine people, randomly chosen, were asked to evaluate the caramels composed of N-ethyl-p-menthane-carboxamide in comparison with the base caramel without the additive. The evaluators were asked if the pairs of flavors "had different flavor". The following shows the number of people who found a different flavor for the flavored candies as indicated: Citrus species - 6; apple - 5; honey - 5; herbal - 5 Example 2: Chewing gum A. Preparation 1. A citrus flavored chewing gum was prepared by conventional means from 22.0 g of gum base, 69.04 g of sweetener, 0.24 g of high intensity sweetener, 2.97 g of acidulant, 3.85 g of other conventional additives and 1.9 g of citrus flavoring agent. Two additional samples were prepared in which 0.02 g and 0.04 g respectively of the sweetener were replaced with the same amount of N-ethyl-p-menthane-carboxamide for a taste / N-ethyl-p-menthane-carboxamide ratio of 98.96 / 1.04. and 97.94 / 2.06, respectively. The control and the two examples of the invention were compared as described below. 2. A cinnamon flavor chewing gum was prepared by conventional methods from 22.0 g of gum base, 73.29 g of sweetener, 0.81 g of high intensity sweetener, 2.1 g of other conventional additives and 1.8 g of flavor agent to cinnamon. Two additional samples were prepared in which 0.02 g and 0.04 g respectively of the sweetener were replaced with the same amount of N-ethyl-p-menthane-carboxamide at a taste / N-ethyl-p-menthane-carboxamide ratio of 98.90 / 1.10. and 97.83 / 2.17, respectively. The control and the two examples of the invention were compared as described below.

B. Comparisons: At a level of use of N-ethyl-p-menthane-carboxamide of 0.02% the release of N-ethyl-p-menthane-carboxamide was expected around 50 ppm and at a use level of 0.04% the release was I expected around lOOppm. The gum-flavored products were compared with the corresponding control samples by a panel of six people who were asked to evaluate the samples by commenting on the differences in perceived taste and flavor taste. Four of the six panelists noted the differences in the samples, which is summarized as follows: For both citric and cinnamon flavors, 0.02 g of N-ethyl-O-menthane-carboxamide provide a preferred flavor enhancement. At 0.04 g, while the flavors are improved, less desirable notes are also described.

Claims (18)

1. CLAIMS: 1. An improved flavor composition comprising at least one flavoring agent and an amount of N-ethyl-O-menthane-carboxamide effective to improve said flavoring agent wherein said N-ethyl-O-menthane-carboxamide is present in about from 0.04 to about 2.2% by weight of said improved flavor composition.
2. 2. The improved flavor composition according to Claim 1 wherein said flavoring agent is selected from the group consisting of fruit, herbal, sweet and species.
3. 3. The improved flavor composition according to Claim 2 wherein said flavoring agent is fruity.
4. 4. The improved flavor composition according to Claim 1 wherein said N-ethyl-p-menthane carboxamide is present at 0.4% up to 1.1%.
5. 5. A method for improving a flavoring agent comprising the addition thereto of an amount of N-ethyl-p-menthane-carboxamide effective to improve said flavoring agent wherein said N-ethyl-p-menthane-carboxamide is present at about 0.04. up to about 2.2% by weight of the combination.
6. 6. The method according to Claim 5 in said flavoring agent is selected from the group consisting of fruit, herbal, sweet and species.
7. 7. The method according to Claim 6 wherein said flavoring agent is fruity.
8. 8. The method according to Claim 5 wherein said N-ethyl-p-menthane-carboxamide is present at 0.04 to 1.1%.
9. 9. A confectionery composition containing an effective flavoring amount of the improved flavor composition of Claim 1.
10. 10. The confectionery composition according to claim 9 wherein said flavoring agent is selected from the group consisting of fruit, herbal, sweet and species.
11. 11. The confectionery composition according to Claim 10 wherein said flavoring agent is fruity.
12. 12. The confectionery composition according to Claim 9 wherein said improved flavoring composition is present at about 0.10% up to about 1.0% by weight of said confectionery composition.
13. 13. The confectionery composition according to Claim 12 wherein said improved flavoring composition is present in 0.2% up to 0.5%.
14. 14. A chewing gum containing an effective flavoring amount of the improved flavor composition of Claim 1.
15. 15. The chewing gum according to claim 14 wherein said flavoring agent is selected from the group consisting of fruit, herbal, sweet and species.
16. 16. The chewing gum according to claim 15 wherein said flavoring agent is fruity.
17. 17. The chewing gum according to claim 14 wherein said improved flavoring composition is present at about 0.8% up to about 3.5%.
18. 18. The chewing gum according to claim 17 wherein said improved flavoring composition is present at 1.0% up to 3.0%. EXTRACT OF THE INVENTION Improved flavor compositions containing at least one flavoring agent and an effective amount of N-ethyl-p-menthane-3-carboxamide are provided. The N-ethyl-p-menthane-3-carboxamide is present at about 0.04 to about 2.2 percent by weight of the improved flavor composition. The invention further relates to chewing gums and confectionery compositions containing an effective flavoring amount of the improved flavoring compositions.