Patent Description:
Some flavor molecules are poorly soluble in water. In particular, amides described in Patent Application Number <CIT>, incorporated by reference in its entirety herein, are poorly soluble in water and difficult to solubilize. Hence, it would be advantageous to provide a means for increasing the dissolution rates of these compounds in water.

<CIT> relates to cinnamic acid amides of aromatic amines and their use as flavouring agents in aromatic blends, wherein said amides impart, modify and/or enhance at least one of the taste impressions umami, kokumi and salty.

The present invention relates to a process for increasing the dissolution rate of a sparingly water soluble compound selected from the group consisting of a flavor and a taste modifier in water comprising:.

The present invention also relates to a solid dispersion particle prepared according to the process of the invention.

A compound that is considered sparingly soluble in water is one that is not fully soluble in water above <NUM>% or above <NUM> ppm (by weight), at <NUM>. A water soluble second compound is one that is soluble in water at or above <NUM>% or at or above <NUM> ppm at <NUM>.

In one embodiment, the second compound is a highly water soluble compound that is soluble in water at about ≥ <NUM>% or ≥<NUM> ppm in water at <NUM>.

In one embodiment of the present disclosure, the second compound is selected from the group consisting of ribotides, amino acids and MSG, and ingredients that are sources of amino acids and ribotides like yeast extracts, hydrolyzed proteins or peptides. In the process of the present invention, the second compound is an amino acid and more particularly the second compound may be selected from the group consisting of glycine and betaine.

In one embodiment, the process of the present invention is carried out in the substantial absence of a polymer, particularly less than <NUM>%, <NUM>%, less than <NUM>%, less than <NUM>%, less than <NUM>%; and no polymer by weight, of the dispersion or solution.

In one embodiment of the present disclosure, the water based solution comprises water combined with a volatile water miscible solvent selected from the group consisting of propylene glycol, benzyl alcohol, propanol, ethanol, triacetin, and ethyl citrate.

In the process of the present invention, the water based solution comprises a water ethanol mixture.

In the process of the present invention, the ratio, of the sparingly soluble compound to the second compound, by weight, is from <NUM>:<NUM> to <NUM>:<NUM>, particularly <NUM>:<NUM>.

In one embodiment of the present disclosure, the sparingly soluble compound is provided in an amount of ≥ <NUM>% by weight of the total weight of the solution or dispersion; more particularly in an amount of ><NUM>% by weight of the total weight of the solution or dispersion.

In one embodiment of the present disclosure, a water based solution is used wherein the compound and the second compound are dispersed.

In one embodiment of the present disclosure, a water based solution is used wherein the compound is dispersed and the second compound is dissolved.

In one embodiment of the present disclosure, a water based solution is used wherein the compound and the second compound are dissolved.

In one embodiment of the present disclosure, the water insoluble compound comprises a compound of Formula (I)
<CHM>
in the form of any one of its stereoisomers or a mixture thereof, and wherein n is an integer from <NUM> to <NUM>;the dotted line represents a carbon-carbon single or double bond; and each of R<NUM> to R<NUM>, when taken independently from each other, represents a hydrogen atom or represents a R<NUM> or OR<NUM> group, R<NUM> representing a C<NUM> to C<NUM> alkyl group; and optionally one of the groups R<NUM> to R<NUM> represents -OH; and/or when R<NUM> and R<NUM> are taken together, and/or R<NUM> and R<NUM> are taken together, represent a OCH<NUM>O group, provided said groups taken together are adjacent substituents of the phenyl group.

In the process of the present invention, the sparingly soluble compound is a compound of formula (II)
<CHM>
in the form of any one of its stereoisomers or a mixture thereof, and wherein each of R<NUM> or R<NUM>, taken independently from each other, represents a hydrogen atom or represents a R<NUM> or OR<NUM> group, R<NUM> representing a C<NUM> to C<NUM>, or even a C<NUM> to C<NUM> alkyl group.

In one embodiment of the process according to the present invention, the sparingly soluble compound is selected from the group consisting of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide, (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-ethoxyphenethyl)acrylamide, (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-propoxyphenethyl)acrylamide, (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-isopropoxy-phenethyl)acrylamide, (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-ethylphenethyl)acrylamide (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>,<NUM>-dimethylphenethyl)acrylamide, (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-isopropylphenethyl)acrylamide or (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methylphenethyl)acrylamide, or (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>,<NUM>-dimethoxyphenethyl)acrlyamide.

In one embodiment of the present disclosure, the solution or dispersion is lyophilized to form solid particles.

In the process of the present invention, the solution or dispersion is spray dried to form the solid dispersion as solid particles.

In one embodiment of the present disclosure, the solution or dispersion is dried on a fluidized bed to form solid particles.

In one embodiment of the present disclosure, a particle provided herein dissolves in water at a rate of up to <NUM> ppm/min at a temperature of about <NUM>, particularly at a rate of <NUM> ppm/min at a temperature of about <NUM>. In one aspect, the methods provided herein provide increased dissolution rates of a sparingly soluble compound in water. In another aspect, a method provided herein may further enhance the performance of a sparingly soluble compound as a flavor or taste modulator in food and beverage applications.

The types of end products where particles or dry powders provided herein are useful are:.

Compounds of Formula I and II and dispersions provided herein can be used alone or in mixtures and provide a strong kokumi or umami taste at exceptionally low levels.

Provided herein is the use of powders provided herein as a taste-conferring or enhancing ingredient, and in particular to impart or reinforce kokumi or umami taste.

In a particular embodiment of the present disclosure, said compound (I) and (II) is used to impart or reinforce kokumi or umami taste as well as to enhance the saltiness and/or savory perception of a flavor.

Particular applications provided herein are uses to impart or enhance the kokumi or umami taste in savory flavors, such as beef, chicken, pork, and seafood. Surprisingly, in seafood applications such as surimi, or seafood bouillons or snack flavors, compounds according to formula (I) are also found to enhance the perception of sweetness and longevity of the flavor. By contrast, in beef flavors, the compounds according to formula (I) are found to enhance perception of fattiness and tallow notes. Additionally we found that said compounds can increase juiciness in meat based products.

Suitable foodstuff bases, e.g. foods or beverages, can be fried or not, as well as frozen or not, low fat or not, marinated, battered, chilled, dehydrated, instant, canned, reconstituted, retorted or preserved. Typical examples of said foodstuff bases include:.

Particular foodstuffs in which the compound according to formula (I) or (II) find utility include those having flavors such as seafood, beef, chicken, vegetables, cheese, fat, tallow and/or marrow are important.

In one embodiment of the present disclosure, an end product is useful as dry, powder form of a taste modifier or flavour in the form of a solid dispersion a sparingly soluble compound, which can be used for example in powder and seasoning blends.

For the sake of clarity, it has to be mentioned that, by "foodstuff' we mean here an edible product, e.g. a food or a beverage. Therefore, a flavored article according to the present disclosure 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 savory cube. 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 examples provided below are not limiting and are for illustrative purposes only.

<NUM> of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide and <NUM> glycine were mixed with <NUM> of a mixture of ethanol and water (<NUM>:<NUM> w/w). The dispersion was heated to <NUM> until complete dissolution of the solid material. A clear and transparent solution was obtained. The solution was kept at <NUM>, spray dried, and a fine, white powder was obtained. The loading of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide of <NUM>% (w/w) in the solid dispersion was confirmed by NMR spectroscopy.

<NUM> of the solid dispersion of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide and glycine were dispersed in <NUM> of water at <NUM>, and the solution was stirred at <NUM> rpm. The dissolution process was followed on-line by monitoring the UV signal of dissolved (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide with UV/Vis spectroscopy (measuring absorbance at <NUM>). The dissolution process yielded <NUM>% of the target concentration of <NUM> ppm of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide (<NUM> ppm) after <NUM> minutes, and <NUM>% (<NUM> ppm) after <NUM> minutes.

<NUM> of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide were dispersed in <NUM> of water at <NUM>. The dissolution process yielded <NUM>% of the target concentration of <NUM> ppm (<NUM> ppm) after <NUM> minutes (factor <NUM> slower compared to example <NUM>). <NUM>% (<NUM> ppm) of the target concentration could not be achieved after <NUM> hours. The concentration of dissolved (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide after <NUM> hours was <NUM> ppm (<NUM>% of target).

<NUM> of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide and <NUM> betaine were mixed with <NUM> of a mixture of ethanol and water (<NUM>:<NUM> w/w). The dispersion was heated to <NUM> until complete dissolution of the solid material. The solution was kept at <NUM>, spray dried, and a fine, white powder was obtained.

<NUM> of the solid dispersion of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide and betaine were dispersed in <NUM> of water at <NUM>. The dissolution process yielded <NUM>% of the target concentration of <NUM> ppm of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide (<NUM> ppm) after <NUM> minutes, and <NUM>% (<NUM> ppm) after <NUM> minutes.

Aqueous solutions containing <NUM> ppm of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide and <NUM> ppm of a solid dispersion of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide and glycine according to the invention (<NUM>:<NUM> w/w), respectively, were prepared in hot water. The solutions were presented to <NUM> trained panelists on a blind test basis after <NUM> minutes. They were asked to rate the samples for the umami taste intensity from <NUM> to <NUM> (<NUM> denoted no umami effect, and <NUM> denoted very strong umami taste). The sample according to the invention was rated higher in umami intensity (<NUM>) than the comparative sample (<NUM>).

Aqueous solutions containing <NUM> ppm of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide and <NUM> ppm of a solid dispersion of (E)-<NUM>-(<NUM>,<NUM>-dimethoxyphenyl)-N-(<NUM>-methoxyphenethyl)acrylamide and glycine according to the invention (<NUM>:<NUM> w/w) , respectively, were prepared in cold water (room temperature). The solutions were presented to <NUM> trained panelists on a blind test basis after <NUM> minutes. The sample according to the invention was rated higher in umami intensity (<NUM>) than the comparative sample (<NUM>).

Claim 1:
A process for increasing the dissolution rate of a sparingly water soluble compound selected from the group consisting of a flavor and a taste modifier in water comprising:
a. mixing the compound and a highly water soluble second compound in a water based solution to form a solution or dispersion of the compound; and
b. drying the solution or dispersion to form a solid dispersion of the compound wherein the compound has an increased dissolution rate in water as compared to the compound when dissolved in water alone,
wherein the sparingly soluble compound is a compound of Formula (II):
<CHM>
in the form of any one of its stereoisomers or a mixture thereof, and wherein each of R<NUM> or R<NUM>, taken independently from each other, represents a hydrogen atom or represents a R<NUM> or OR<NUM> group, R<NUM> representing a C<NUM> to C<NUM>, or even a C<NUM> to C<NUM> alkyl group; and
wherein the second compound is an amino acid;
wherein the water based solution comprises a water ethanol mixture;
wherein the ratio of the sparingly soluble compound to the second compound, by weight,
is from <NUM>:<NUM> to <NUM>:<NUM>;
wherein in step b), the solution or dispersion is spray dried to form the solid dispersion as solid particles.