WO2001035918A1

WO2001035918A1 - Mint flavor and aroma compositions

Info

Publication number: WO2001035918A1
Application number: PCT/US2000/031266
Authority: WO
Inventors: Lawrence L. Buckholz, Jr.; Brian Byrne
Original assignee: J. Manheimer, Inc.
Priority date: 1999-11-15
Filing date: 2000-11-14
Publication date: 2001-05-25
Also published as: AU1607601A

Abstract

This invention relates to mint flavor and aroma compositions suitable for use in foodstuffs, cosmetics, fragrances, sweeteners and pharmaceuticals. This invention also relates to a process for preparing the inventive compositions.

Description

TITLE OF THE INVENTION

MINT FLAVOR AND AROMA COMPOSITIONS

RELATED APPLICATIONS

This application is related to application USSN 09/438,243, filed November 12, 1999, entitled Citrus Flavor and Aroma Compositions, and to application USSN 09/440,591, filed November 15, 1999, entitled Flavor Freshness Enhancers, both filed concurrently herewith and both of which, as well as all documents cited in those applications and those cited herein are hereby incorporated by reference.

FIELD OF THE INVENTION This invention relates to mint flavor and aroma compositions and coolant compositions suitable for use in foodstuffs, tobacco products, fragrances and pharmaceuticals. This invention also relates to a process for preparing the inventive compositions.

BACKGROUND OF THE INVENTION There is constant interest in improvement of mint flavor. Several approaches have been used to strengthen the flavor and thereby lower the burning and bitterness associated with higher use levels. This has been achieved in part by adding multiple cooling compounds so as to lower the use of menthol and menthol-containing mint oils. By nitrogen sparging peppermint oil to remove the undesirable lower boiling aldehydes and dimethyl sulfide, a smoother, stronger tasting flavor is achieved. Yet another approach has been to encapsulate the mint flavor and cooling agents to reduce the initial bitterness and prolong the effect of cooling, especially in chewing gum applications.

Mint oils and mint flavors are used to flavor confections (sugar candy, breath mints, chewing gum etc.), as well as oral care products ( toothpaste, mouthwash, etc.), tobacco and smoking articles ( snuff, cigarettes, etc.). Mint oils are used to fragrance topically applied materials (perfume, lip balms, lotions, etc.), as well as other fragrance applications (room deodorizers, soaps, cleaning products, etc.). Mint oils and mint flavors are used to deliver topical cooling in the oral cavity (mouthwash, chewing gum etc.) as well as on the skin (colognes, lotions, bandages etc.) SUMMARY OF THE INVENTION

Mint oils, mint flavors and flavors containing chemical components found in mint are used widely in flavoring edible substances and topically applied materials. The present invention provides for the treatment of such oils and flavors with cysteine, its salts, precursors or derivatives thereof. The resultant product possesses properties which include: a) a stronger mint flavor; b) enhanced sweetness; c) more fresh picked flavor; d) a stronger cooling effect; and e) a creamy rich mouthfeel.

The products of this invention allow one to use lower concentrations of mint flavors or oils in products to achieve these effects with the product additionally possessing greater fresh picked character, cooling and creamy mouthfeel. Alternatively, at normal concentrations of mint, a greater flavor strength and impact can be achieved without the bitterness associated with high menthol containing products. When used in chewing gum, a prolongation of the flavor during the chewing process is an added advantage. Moreover, the products of this invention may be used in coolant compositions. The inventive flavor compositions provide for a mint flavor stronger in flavor and enhances the sweetness in edible compositions. Additionally, in edible applications, the mint flavors are fresher (more characteristic of fresh picked mint), with a stronger cooling effect. A secondary characteristic is the development of a creamy rich mouthfeel which compliments the above organoleptic sensations These and other embodiments are disclosed or are obvious from and encompassed by the following Detailed Description.

DETAILED DESCRIPTION The cysteine flavor or aroma compositions of the present invention comprise a treated mint oil, flavor or aroma obtained by mixing said mint oil flavor or aroma with cysteine, a salt or ester thereof, a cysteine precursor or a cysteine derivative, optionally in the presence of a solvent. The process by which the treated mint flavors or aromas are obtained vary in time, temperature, solvent and source of cysteine. How this is achieved is limited to the resourcefulness of those skilled in the art and not meant to be the limiting factor of this invention

The temperature for the mixing process may range from low temperatures to high temperatures and the process may be conducted under atmospheric conditions or pressure. In a preferred embodiment, the temperature for the process may range from room temperature (about 20°C) to about 110°C. Depending upon the source of cysteine and contact time needed to complete the process, temperatures above 110°C to about 250°C, with commensurably shorter contact times, may be used. This source of cysteine in the present invention includes cysteine itself, as well as its salts and ester forms. Preferred are the inorganic and organic salts of cysteine, with cysteme hydrochloride being especially preferred. Also preferred are the carboxylic acid alkyl esters of cysteine, with the methyl, ethyl, propyl, isopropyl, butyl and isobutyl ester being most preferred. These sources of cysteine are well known in the art and are obtained either commercially or by processes known in the art.

The source of cysteine may also be precursors of cysteine, such as its amino acid esters. Again, these precursors are well known in the art and are obtained either commercially or by processes known in the art. Derivatives of cysteine include the cysteine adducts obtainable by the reaction of cysteine or an ester or salt thereof with an α,β-unsaturated carbonyl-containing compound. These adducts are described in copending application USSN 09/440,591, entitled Flavor Freshness Enhancers, herein incorporated by reference.

The mint flavor and aroma compounds for the invention and aroma compounds can be, for example, mint oils or flavors made from mint oil. These flavor and aroma compounds can be artificial or derived form natural sources, whether crude, purified or fractionated. The mint oil, refined mint oil, fractionated mint oil or a portion of a mint oil after fractionation, as well as a blend of oils or a compounded mint oil either natural or artificial, for example, natural cornmint oil rectified, plus menthol (artificial). The mint flavor and aroma compositions are well know in the flavor art and may be obtained commercially or through processes known in the art. The ratio of substrate oil or flavor to cysteine can be varied to achieve a particular economic goal, but is not limited to large excesses of one ingredient or the other. It is the preferred embodiment that cysteine be used in parts per million to a one to one weight ratio to the mint oil. When treating distilled whole mint oils it is economically advantageous to treat about 99.9 parts of mint oil with about 0.1 parts cysteine with the product being used directly "as is". In the case of highly purified fractions, nearly one to one ratios of cysteine to the fraction are most effective, with the product being further diluted in other flavors or oils to impart an enhanced sweetness, flavor strength and coolness. A wide range of solvents may be used in the inventive process. The solvents include those which are commonly used in foodstuffs, cosmetics and pharmaceutical preparations. It is also possible to use non-edible solvents, provided that they are removed by a removal step. In a preferred embodiment, ethanol, water or mixtures thereof are used as solvents. Also preferred is the use of no solvent. The pH can be varied depending upon the solvent used, if any, and the cysteine source. Other considerations are conditions necessary to generate cysteine from a precursor or derivative. The preferred embodiment is a pH of about 1 to about 10, although, this is not intended to limit the scope of the invention.

The inventive mint flavor and aroma compositions may also be formulated in coolant compositions where the inventive compositions are combined with other coolant materials. It is well known in the art e.g. U.S. Patent 5,451,404 and references cited therein all herein incorporated by reference, that multiple coolants synergize and amplify the cooling of single coolants. The present compositions also synergize and amplify the effect of single coolants. The coolants, which may be used in these compositions, are well known in the art and may be obtained commercially or through a known process. Suitable coolants include, for example, menthol, N-ethyl-p- methane-3-carboxamide (WS-3), N-2,3-trimethyl-2-isopropyl butamide (WS-23), 1- menthone glycerin ketal, 3-1-menthoxy propane- 1,2-diol or monomenthyl succinate or its salts. Such compositions, as well as the amount of mint flavor or aroma to add to these compositions is well known to one skilled in the art. The mint flavor and aroma compositions may be used in a wide range of products and fragrances such as of foodstuffs, tobacco products, pharmaceuticals, oral care products, and sweeteners. Such products, as well as the amount of flavor or aroma to add to these products, would be well known to one skilled in the art. Especially preferred food products include confectioneries such as chewing gums. Especially preferred oral care products include mouthwashes or toothpastes.

EXAMPLES

A better understanding of the present invention and of its many advantages will be had from the following examples, given by way of illustration. Example 1

90.0 g Rectified Spearmint Oil

9.9 g Water

0.1 g Cysteine Hydrochloride

The above ingredients were added to a 500 ml round bottom flask equipped with a reflux condenser, mechanical stirrer and pot thermometer. The contents were heated over 20 minutes to a temperature of 104°C and the temperature held for one hour. The contents were cooled to room temperature and the phase separated. The treated spearmint oil was used as is. Example 2

0.1 g Treated Spearmint Oil (Example 1)

9.9 g Ethanol

A solution of treated spearmint oil from Example 1 was made by using 0.1 g treated spearmint oil with 9.9 g ethanol.

A similar solution was made of untreated spearmint oil. To a 10% sugar water solution, 0.1% of each solution was added. This delivered 10 ppm of both treated and untreated spearmint oil. Comparing the taste of both beverages showed that the treated oil was stronger in flavor, more fresh picked in character, and cooler than the control (untreated oil).

Additionally, all panelists remarked on the increase in sweetness intensity.

Example 3 90.0 g Peppermint Oil

9.9 g Water

0.1 g Cysteine Hydrochloride

The above ingredients were treated as in Example 1.

Example 4 Product of Example 3 was compared against the untreated product as in Example 2.

The treated peppermint oil was stronger, sweeter and cooler than untreated oil.

Example 5

90.0 g Carvone Fraction ex caraway oil (60% Carvone)

9.8 g Water 0.2 g Cysteine Hydrochloride

The above ingredients were treated as in Example 1. The product of Example 5 were evaluated as in Example 2. The treated carvone, product of Example 5, was sweeter, stronger in flavor, fresher tasting and surprisingly was cool tasting relative to the untreated material.

Example 6

Toothpaste Example #6

Sodium Fluoride 0.243

Sorbitol 59.202

Silica 20.000

Synthetic Sodium Alkyl 4.000

Sulfate (27.34% aqueous solution)

Buffers 2.040

Monsodium Phosphate 0.590

TiO₂ 0.525

Thickeners 0.775

Coolant lN-2,3-trιmethyl-2-ιsopropyl butamide 0.200

Coolant 2N-ethyl-p-menthane-3-carboxamιde 0.090

Saccharin 0.460

Spearmint Oil, Product of Example 1 1.000

Total 100.000

Toothpaste was cooler, sweeter and stronger in flavor than control toothpaste made with untreated Spearmint Oil.

Example 7

Toothpaste Example #7

Sodium Fluoride 0.243

Sorbitol 24.614

Silica 23.411

Synthetic Sodium Alkyl 4.000

TiO₂ 0.500

Thickeners 0.800

Glycerin 9.000

Tetrapotassium Pyrophosphate 6.382

PEG-6 3.000

Sodium Acid Prophosphate 2.100 Tetrasodium Pyrophosphate 2.050

Dye 0.050

Menthol 0.400

Coolant lN-2,3-tπ___ethyl-2-_sopropyl butamide 0.200

Coolant 2N-ethyl-p-menthane-3-carboxamιde 0.090

Saccharin 0.460

Peppermint Oil, Product of Example 3 0.800

Total 100.000

Toothpaste was cooler, sweeter and stronger m flavor than control toothpaste made with

10 untreated Peppermint Oil.

Examples 8. 9. 10. 11 Chewing gum compositions were prepared using the formulations set forth below. The formulations were prepared by melting the gum base at a temperature of about 85 to 90°C and then adding with mixing the lecithin followed by adding the corn syrup and

15 1/2 of the sugar and again mixing until homogenous mixture was obtained, approximately 5 minutes total time. The flavor and glycerin were then added and mixed for about 2 minutes each followed by the remaining sugar which was mixed until a homogenous mixture was obtained, about 2 minutes. The formulation was cooled to about 40 to 45 °C and the menthol and carboxamide compounds added and mixed into 0 the formulation. The formulations were then cut into slab shapes. These formulations were subjected to sensory evaluation studies to assess the perceived breath freshening of compositions.

Composition

Ingredient Ex.8 Ex.9 Ex.10 Ex.11

Gum Base 21.00 21.00 21.00 21.00

Corn Syrup 16.50 16.50 16.50 16.50

440BE

Sugar 6x 60.60 60.60 60.60 60.60

Lecithin 0.20 0.20 0.20 0.20

Peppermint Oil 1.1438 1.1438 Product of Example 3 — 1.143 1.1438

Glycerin 0.45 0.45 0.45 0.45

Menthol 0.1062 0.075

N-ethyl-p-menthane-3-carboxamide — — 0.1062 0.1062

Product of Example 8 had high up front cooling which dropped off after 2 minutes and bitterness developed.

Product of Example 9 had high up front cooling which maintained for 15 minutes without bitterness development. Flavor was also stronger than Example 8 with a lingering sweetness for 12 minutes.

Product of Example 10 had no up front cooling, however, cooling gradually developed after about 2 minutes.

Product of Example 11 had high up front cooling which maintained for 15 minutes without bitterness development. Flavor was also stronger than Example 10 with a lingering sweetness for 12 minutes. Example 12

90.0 g Fennel Oil

9.9 g Water

0.1 g Cysteine (free base)

The above ingredients were treated as in Example 1 and evaluated as in Example 2. The treated Fennel Oil was stronger in anethol notes, was sweeter and more cooling than the untreated material. Example 13

90.00 g Peppermint Oil

9.95 g Water 0.05 g Cysteine Methyl Ester The above ingredients were treated as in Example 1 and evaluated as in Example 2.

The treated peppermint oil was stronger in peppermint flavor, sweetness and coolness than untreated peppermint oil.

Example 14 90.00 g Rectified Spearmint Oil

0.10 g Cysteine

9.90 g Water

The above ingredients were treated as in Example 1 and the product evaluated as in Example 2. The product of Example 14 was stronger, sweeter and cooler than the untreated oil and was similar in character and strength to the product of Example 1.

The above description of the invention is intended to be illustrative and not limiting. Various changes or modifications in the embodiment described may occur to those skilled in the art. These can be made without departing from the scope and spirit of the invention.

Claims

What is claimed is:

1. A mint flavor or aroma composition comprising a treated mint oil, flavor or aroma obtained by mixing a mint oil, flavor or aroma with a cysteine source selected from the group consisting of cysteine, a salt or ester thereof, a cysteine precursor and a cysteine derivative and, optionally, a solvent.

2. The composition according to claim 1 where in the treated oil is peppermint oil.

3. The composition according to claim 1, wherein the treated oil is spearmint oil.

4. The composition according to claim 1, wherein the mint flavor is a natural flavor.

5. The composition according to claim 1, wherein the 1 mint flavor is an artificial flavor

6. The composition according to claim 1, wherein the source of cysteine is cysteine or cysteine hydrochloride.

7. The composition according to claim 1, wherein the treated oil is rectified spearmint oil, the source of cysteine is cysteine hydrochloride and the solvent is water.

8. The composition according to claim 1, wherein the treated oil is peppermint oil extract, source of cysteine is cysteine hydrochloride, and the solvent is water.

9. A coolant composition comprising the composition according to claim 1 , and at least one cooling material.

10. The coolant composition according to claim 9, wherein the cooling compound is selected form the group consisting of menthol,

N-ethyl-p-methane-3-carboxamide (WS-3), N-2,3-trimethyl-2-isopropyl butamide

(WS-23), 1-menthone glycerin ketal, 3-1-menthoxy propane- 1,2-diol and monomenthyl succinate or its salts.

11. A food product, a tobacco product, or confectionery which comprises a composition according to claim 1.

12. The food product according to claim 11, wherein the confectionery product is a chewing gum.

13. An oral care product comprising a composition according to claim 1.

14. The oral care product according to claim 13, wherein the oral care product is a mouthwash or a toothpaste.

15. A pharmaceutical which comprises a composition according to claim 1, and a medicament.

16. A topically applied pharmaceutical which comprises a composition according to claim 9, and a medicament.

17. A sweetener which comprises a composition according to claim 1.

18. A fragrance which comprises a composition according to claim 1.

19. A fragrance which comprises a composition according to claim 9.

20. The composition according to claim 1 wherein the composition is encapsulated.

21. A process for preparing a treated mint oil, flavor or aroma which comprises which comprises mixing a mint oil, flavor or aroma with a cysteine source selected from the group consisting of cysteine, a salt or ester thereof, a cysteine precursor and a cysteine derivative and, optionally, a solvent.

22. The process according to claim 21, wherein the mixing occurs at a temperature from about 20°C to about 250°C.