WO2012175276A1 - Taste modifying compound including evodiamine - Google Patents

Abstract

The present invention relates to the use of a compound of Formula (I) in the form of one or more of its stereoisomers or mixtures thereof to confer, enhance, improve or modify a spicy and/or peppery note and/or a tingling sensation of an edible composition in which the compound is present. In other words, it concerns the use of evodiamine for this purpose and flavouring compositions comprising evodiamine as a taste modifying ingredient.

Description

TASTE MODIFYING COMPOUND INCLUDING EVODIAMINE Technical field

The present invention relates to the field of taste. More particularly, it concerns the use of evodiamine as a taste-enhancing ingredient to impart or reinforce a pungent, spicy and/or tingling taste sensation.

The present invention also concerns compositions or articles containing at least the aforementioned compound. Back2round and Prior art

Evodiamine is a compound known for acting against obesity. There are numerous publications highlighting this effect. Nevertheless, to the best of our knowledge, there is no disclosure of using evodiamine as a taste or flavor compound to impart, modify or confer spicy peppery notes and/or a tingling sensation.

It is even stated in the literature that the compound has no flavor. For instance in the publication "Capsaicin-like anti-obese activities of evodiamine from fruits of Evodia rutaecarpa, a vanilloid receptor agonist", Kobayashi Y, Nakano Y, Kizaki M, Hoshikuma K, Yokoo Y, Kamiya T, Planta Med. 2001 Oct;67(7):628-33, the abstract states the following:

"Evodiamine, a major alkaloidal principle of Evodia fruits (Evodia rutaecarpa,

Rutaceae), showed vanilloid receptor agonistic activities comparable to capsaicin. The Chinese literature refers to Evodia fruits as a "hot nature" herb. In spite of the similarities in the actions of evodiamine and capsaicin in vitro, evodiamine has no perceptible taste, including a peppery hot taste (emphasis added) .... in conclusion, we have demonstrated that a novel non-pungent (emphasis added) vanilloid receptor agonist, evodiamine, mimics the characteristic anti-obese effects induced by capsaicin.

Description of the invention

Accordingly, we have now surprisingly discovered that a compound having the formula:

(Formula I) in any of its stereoisomeric form or mixtures thereof imparts and/or reinforces a spicy and/or peppery note and/or a tingling sensation of edible compositions in which it is present.

Thus, the present invention provides the use of a compound of formula (I) as defined above in the form of one or more of its stereoisomers or mixtures thereof to confer, enhance, improve or modify a spicy and/or peppery note and/or a tingling sensation of an edible composition in which the compound is present.

According to another aspect, the present invention provides a method of imparting or reinforcing the spicy and/or peppery note and/or a tingling sensation of an edible composition of a flavouring composition or article comprising adding to the composition or article a compound according to Formula (I) as defined herein.

Detailed Description of the Invention

The spicy, peppery, tingling compound according to formula (I) may exist as a mixture of isomers thereof. Preferably, there is an excess of the isomer (5)-(+)- evodiamine. This isomer is found to provide a particularly strong spicy, peppery note and tingling sensation.

Optionally, the compound according to the invention can be used in combination with one or more other spicy, peppery or tingling compounds.

Examples of suitable additional spicy or peppery compounds include piperine, pelargonyl vanillyl amide, vanillyl butyl amide, vanillin butyl ether, eugenol, gingerol, polygodial, shogoal, galangal acetate, capsaicin (N-(4-hydroxy-3-methoxybenzyl)-8- methylnonanamide and/or (6E)-N-(4- hydroxy -3- methoxybenzyl)-8-methyl-6- nonenamide), capsaicin analogues and mixtures comprising two or more of these.

Examples of suitable additional tingling compounds include those selected from the group of spilanthol, sanshool, hydroxy a-sanshool, hydroxy β-sanshool, hydroxy γ-sanshool, sanshool I, sanshool II, sanshoamide, Japanese pepper extract, black pepper extract, chavicine, piperine, echinacea extract, northern prickly ash extract, Nepalese spice timur extract, red pepper oleoresin, 4-(l-menthoxymethyl)-2-phenyl-l,3-dioxolane and jambu oleoresin. Yet more tingling agents can be found in U.S. Pat. No. 5'545'424.

In yet another aspect, the invention provides a flavored article comprising:

i) at least one compound of formula (I), or a flavoring composition as defined above; and

ii) a foodstuff base.

Particularly preferred foodstuffs for use with the compound of formula (I) include savory cubes, instant soups, canned soups, preserved meats, instant noodles, frozen dishes or preparations, sauces, flavored oils and spreads, snacks or biscuits.

Thus, the present invention concerns a method to confer, enhance, improve or modify the taste properties, as indicated above, of a flavoring composition or of a flavored article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I). In the context of the present invention "use of a compound of formula (I)" includes the use of any composition containing compound (I) and which can be advantageously employed in the flavor industry as active ingredient.

It is particularly preferred that the compound according to Formula (I) is added in an amount of from 1 to 10 ppm as about 1 ppm appears to correspond to the perception threshold and above 10 ppm, although the spicy effect is still observed the risk of possible off notes or an overpowering spiciness increases.

In another aspect, the invention provides a taste-modifying composition comprising: i) as taste-conferring or modifying ingredient, at least one compound according to formula (I) above;

ii) at least one ingredient selected from the group consisting of a flavor carrier and a flavor base; and

iii) optionally at least one flavor adjuvant.

By "flavor carrier" we mean here a material which is substantially neutral from a flavor point of view, insofar as it does not significantly alter the organoleptic properties of flavoring ingredients. The carrier may be a liquid or a solid. Suitable liquid carriers include, for instance, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in flavors. A detailed description of the nature and type of solvents commonly used in flavor cannot be exhaustive. Suitable solvents include, for instance, propylene glycol, triacetine, triethyl citrate, benzylic alcohol, neobee, ethanol, sucrose esters such as sucrose oleate or sucrose erucate, vegetable oils or terpenes. Of these ethanol and sucrose esters are particularly preferred since they are found to enhance the solubility of the compound according to formula (I).

Suitable solid carriers include, for instance, absorbing gums or polymers, or even encapsulating materials. Examples of such materials may comprise wall-forming and plasticizing materials, such as mono, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as H. Scherz, Hydrokolloids : Stabilisatoren, Dickungs- und Gehermittel in Lebensmittel, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitat, Behr's VerlagGmbH & Co., Hamburg, 1996. Encapsulation is a well known process to a person skilled in the art, and may be performed, for instance, using techniques such as spray-drying, agglomeration, extrusion, coacervation and the like.

By "flavor base" we mean here a composition comprising at least one flavoring ingredient.

Said flavoring ingredient is not a compound of formula (I). Moreover, by "flavoring ingredient" it is meant here a compound, which is used in flavoring preparations or compositions to impart a hedonic effect. In other words such an ingredient, to be considered as being a flavoring one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the taste of a composition, and not just as having a taste.

The nature and type of the flavoring co-ingredients present in the base do not warrant a more detailed description here, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect. In general terms, these flavoring co-ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co- ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of flavor. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of flavoring compounds.

The composition may further comprise a flavor adjuvant. In the context of the present invention, the phrase "flavor adjuvant" denotes an ingredient capable of imparting additional added benefit that is not flavoring. Such additional benefits include, but are not limited to color, light resistance or stability, chemical stability, oxidation resistance and so on. A detailed description of the nature and type of adjuvant commonly used in flavoring bases cannot be exhaustive. Nevertheless, such adjuvants are well known to a person skilled in the art.

A composition consisting of at least one compound of formula (I) and at least one flavor carrier represents an embodiment of the invention as well as a flavoring composition comprising at least one compound of formula (I), at least one flavor carrier, at least one flavor base, and optionally at least one flavor adjuvant.

Moreover, a compound of formula (I) can be advantageously incorporated into flavored articles to positively impart, or modify, the spicy or peppery note or tingling taste of said articles. Thus, in yet another aspect, the present invention provides a flavored article comprising:

i) as taste-conferring or modifying ingredient, at least one compound of formula (I), as defined above, optionally present as part of a flavoring composition; and

ii) a foodstuff base.

Suitable foodstuff bases, e.g. foods or beverages, include compositions for the preparation of carbonated fruit beverages, carbonated cola drinks, wine coolers, cordials, flavored water, powders for drinks, hard candy, soft candy, taffy, chocolates, sugarless candies, chewing gum, bubble gum, condiments, spices and seasonings, dry cereal, oatmeal, cereal bars, alcoholic beverages, energy beverages, juices, teas, coffees, salsa, gel beads, film strips for halitosis, gelatin candies, pectin candies, starch candies, lozenges, cough drops, throat lozenges, throat sprays, toothpastes and mouth rinses.

In the context of the present invention "foodstuff denotes a product that is taken orally and may either swallowed, such as a food or beverage, or spat out, such as a mouthwash or toothpaste. Therefore, a flavored article according to the invention comprises one or more compounds according to formula (I), as well as optional benefit agents, corresponding to taste and flavor profile of the desired edible product, e.g. a chocolate or a toothpaste.

The nature and type of the constituents of the foodstuffs or beverages do not warrant a more detailed description here, the skilled person being able to select them on the basis of his general knowledge and according to the nature of said product.

The proportions in which the compounds according to the invention can be incorporated into the various aforementioned articles or compositions vary within a wide range of values. These values are dependent on the nature of the article to be flavored and on the desired organoleptic effect as well as the nature of the co-ingredients in a given base when the compounds according to the invention are mixed with flavoring co- ingredients, solvents or additives commonly used in the art.

Preferred use levels of the composition according to the invention may range from about 0.0001% or 0.001% to about 0.005%, or from about 0.0005% to about 0.004% , or from about 0.0007% to about 0.0025% , or from about 0.001 % to about 0.002% by weight, based on the total weight of the food or beverage. At these levels the taste is typically tingling.

Examples

The invention will now be described in further detail by way of the following example, wherein the abbreviations have the usual meaning in the art, the NMR spectral

13

data, where present, are recorded in CDC1₃, at 125 MHz for C, the chemical displacements, δ, are indicated in ppm with respect to TMS as standard, and the coupling constants, /, are expressed in Hz. Example 1

Sensory Evaluation of the Compound of Formula (I)

Evodiamine (ex Sigma Aldrich) was dissolved in ethanol with the aid of ultrasonic agitation and heated to provide a 0.25% solution ("mother solution"). A 0.2% sugar ester aqueous solution (SE-1670 Ryoto, ex Mitsubishi Kagaku Foods Corp., Japan) was prepared as a base solution. The mother solution was then mixed with the base solution to provide evodiamine in the amounts (ppm) given in the following table. The resulting solutions were used for testing within 30 minutes of preparation. Table 1

A dose response analysis was then performed using the LMS (Labelled Magnitude Scale) with values and outputs as given in the table below:

Table 2

A standard aliquot of each of the samples was provided to 18 panelists. The panelists were instructed to drink the sample without swallowing and hold it in their mouth for around 5 seconds, after which each sample was then spat out. The panelists were then asked to evaluate (i) the time of appearance of a hot/pungent/irritant sensation (T_app), (ii) the perceived maximum intensity of the sample (I_max), (iii) the time at which this occurred (Tim_ax) and (iv) the perceived intensity after 3 minutes ( _mi„), or, if the sensation disappears within 3 minutes, the time of disappearance. Between samples, the panelists rinsed their mouths with water.

The perceived intensity of pungent-hot-irritant, tingling and lingering sensation is given in the following table: Table 3

Example 2

Threshold Evaluation of the Compound of Formula (I)

Evodiamine (ex Sigma Aldrich) was dissolved in ethanol with the aid of ultrasonic agitation and heated to provide a 0.25% solution ("mother solution"). A 0.1% sugar ester aqueous solution (SE-1670 Ryoto, ex Mitsubishi Kagaku Foods Corp., Japan) was prepared as a base solution. The mother solution was then mixed with the base solution to provide evodiamine in the amounts (ppm) given in the following table. The resulting solution was used for testing within 30 minutes of preparation.

Table 4

Sample Concentration (ppm)

Evodiamine 5ppm

7

With ethanol at 0.2%

Blank c Ethanol 0.2%

Evodiamine 2.5ppm

8

With ethanol at 0.1%

Blank d Ethanol 0.1%

Evodiamine 1.25ppm

9

With ethanol at 0.05%

Blank e Ethanol 0.05%

Evodiamine 0.625ppm

10

With ethanol at 0.025%

Blank f Ethanol 0.025% Evodiamine 0.31ppm

11

With ethanol at 0.0125%

Blank g Ethanol 0.0125%

Evodiamine 0.15ppm

12

With ethanol at 0.00625%

Blank h Ethanol 0.00625%

The ASTM E679 method was used for threshold determination, in which a 3 Alternative- Forced-Choice was made, based on two blank samples and one sample containing the compound according to formula (I).

Six sets of 3 samples were chosen from the result of dose-response curve and pre-tasting, with the concentration range of Evodiamine from 5 ppm to 0.16 ppm and a dilution factor of 2.

The sets of 3 samples were presented in ascending order of concentration of evodiamine, and after each tasting the panellists were told to wait at least 30 seconds before rinsing their mouth, take any decision and move on to the next tasting within a set. Between tasting, there was a 3 minute gap and water and crackers were consumed to avoid cross- sample contamination.

The group Best Estimate Threshold of Evodiamine was calculated from the geometric mean of each individual threshold. From the individual threshold of 29 panellists, the group BET of Evodiamine tested was 1.06 ppm. Two repetitions were made for each panellist.

The distribution of the panellists indicating their threshold perception is shown in the table below: Table 5

Sample 12 11 10 9 8 7

Number of panelists 0 2 3 15 9 0

Claims

Claims

1. Use of a compound of Formula (I)

Formula (I) in the form of one or more of its stereoisomers or mixtures thereof to confer, enhance, improve or modify a spicy and/or peppery note and/or a tingling sensation of an edible composition in which the compound is present.

2. Use according to claim 1, wherein the compound according to formula (I) is (5)-(+)-evodiamine

3. Use according to claim 1 or claim 2 in combination with a solvent wherein the solvent is ethanol or a liquid sugar ester.

4. Use according to claim 1, wherein the compound of Formula (I) is present in an amount of from 1 ppm to 50 ppm.

5. A taste-modifying composition comprising:

i) as taste-modifying ingredient, at least one compound according to Formula (I) as defined in any one of the preceding claims;

ii) at least one ingredient selected from the group consisting of a flavor carrier and a flavor base; and

iii) optionally at least one flavor adjuvant.

6. A flavored article comprising:

i) as taste-conferring or modifying ingredient, at least one compound of formula (I), as defined above, optionally present as part of a flavoring composition; and

ii) a foodstuff base.