Taste modifying ingredients

Abstract

To provide a method of providing improved mouthfeel in consumables having a fat content of about 20% or less.SOLUTION: The method includes the step of adding to a consumable composition base from about 0.02 parts per billion to about 25 parts per million based on the total weight of the consumable composition of an Amadori compound, without any subsequent heating. The Amadori compound is a reaction product of glucose with proline.

Description

Technical Field

[0001] Technical Field The present disclosure relates to methods for improving the mouthfeel in consumables using taste modifying components. More specifically, the present disclosure relates to methods for improving the mouthfeel in fatty or low-fat consumables using Amadori compounds, which are reaction products of glucose and amino acids, where the consumables are foods and beverages. Even more specifically, the present disclosure relates to flavor compositions and consumables comprising Amadori taste modifying components, and to the use of Amadori taste modifying components in consumables, for example, to improve the mouthfeel of the consumable.

Background Art

[0002] Background Compounds for modifying the taste of consumable products, i.e., products that are placed in the mouth for either ingestion or expectoration, such as foodstuffs, beverages, confectionery, oral care products, etc., are widely used. They do not add flavor to the consumable per se, but provide desired attendant benefits, such as masking undesirable characteristics of other components, such as an enhanced mouthfeel, or a bitter aftertaste associated with some sweeteners used as a substitute for sugar in diet products. The desired mouthfeel is often represented by smoothness (absence of roughness and friction) and creaminess.

[0003] There remains a need to provide taste modifying components that complement the flavor of the consumables in which they are incorporated, which do not exhibit their own specific taste characteristics, but rather enhance the flavor and mouthfeel of the composition, thus providing a very broad spectrum of use across a wide range of food and beverage categories.

[0004] As a result, there is a need to provide compounds that improve the mouthfeel and at the same time preserve or enhance the desired sensory properties of such edible compositions for use in fatty or low-fat consumables.

Summary of the Invention

[0005] Summary In one exemplary embodiment, a method of providing an improved mouthfeel in a consumable having a fat content of about 20% or less includes adding, based on the total weight of the consumable composition, from about 0.02 parts per billion to about 25 parts per million of an Amadori compound to a consumable composition base, followed by no heating. In another exemplary embodiment, a consumable composition has a consumable base having a fat content of about 20% or less and includes from about 0.02 parts per billion to about 25 parts per million of an Amadori compound, based on the total weight of the consumable composition.

[0006] In another exemplary embodiment, a dairy consumable composition has a consumable base and includes from about 0.02 parts per billion to about 25 parts per million of an Amadori compound, based on the total weight of the consumable composition, where the Amadori compound complements the mouthfeel characteristics of the consumable composition. These and other features, aspects and advantages of particular embodiments will become apparent to those skilled in the art from a reading of the present disclosure.

[0007] Detailed Description The following text presents a broad description of numerous different embodiments of the present disclosure. The description is to be construed as illustrative only and is not intended to recite all possible embodiments, as it is impractical, if not impossible, to recite all possible embodiments. It will be understood that any feature, characteristic, component, composition, ingredient, product, step or methodology described herein may be deleted, combined or substituted, in whole or in part. Numerous alternative embodiments can be implemented using either current technology or technology developed after the filing date of the present application, and they will still fall within the scope of the claims. All publications and patents cited herein are hereby incorporated by reference.

[0008] An undesirable mouthfeel can have a serious disadvantage for otherwise desirably flavored, fat-containing or low-fat consumables. As used herein, "mouthfeel" refers to the physical sensations in the mouth created by a food, beverage or ingredient and includes, but is not limited to, weight, thickness, viscosity, moisture, smoothness, film feel, dryness, and mouth coating. Unfortunately, the desired effects are often characteristics of high-fat foods such as dairy products that should be reduced in consumption for health and dietary reasons for many people. Now, it has been found that undesirable mouthfeel characteristics can be improved by incorporation into a consumable composition of an Amadori compound, where the Amadori compound is present in an amount of from about 0.02 parts per billion to about 25 parts per million, based on the total weight of the consumable composition.

[0009] In one aspect, a method of providing an improved mouthfeel in a consumable having a fat content of about 20% or less, the method comprising adding to a consumable composition base an Amadori compound in an amount of from about 0.02 parts per billion to about 25 parts per million, based on the total weight of the consumable composition, is disclosed. Surprisingly, it has been found that incorporation of the Amadori reaction product of glucose with proline, present at a certain concentration, improves the overall mouthfeel of a consumable having a fat content of about 20% or less.

[0010] In another aspect, it has been found that the Amadori reaction product of glucose with proline, present at a certain concentration, improves the mouthfeel of a consumable having a fat content of more than about 20%. It has also been found that the Amadori reaction product of glucose with proline, present at a certain concentration, also enhances other mouthfeel characteristics such as creaminess, fattiness and body. An Amadori compound (also known as an Amadori product) is formed via the well-known Amadori rearrangement reaction, which isomerizes an aldose sugar via an acid or base and then reacts it with an amine to form the Amadori compound after rearrangement of the Schiff base intermediate (M. Amadori, Atti Accad. Naz. Lincei 2(6), 337 (1925); The Merck Index (14 th Edition), pg. ONR-3, (2006))). The following reaction scheme shows the reaction between a hexose sugar and ammonia to form an Amadori compound.

[0011] [Chemical formula]

[0012] Methods for making Amadori compounds (products) are well known in the art, but their use is less well known in the art. Amadori compounds have no benefit in themselves, but are thought to function as intermediate compounds for the formation of advanced end products (AEPs) that proceed through dehydration, fragmentation or aldol condensation. These AEPs often have benefits as flavorings in the food industry. One such example is the thermal decomposition of an Amadori compound to produce a compound with a caramel odor. Mills et al., “Amadori Compounds as Nonvolatile Flavor Precursors in Processed Foods”, Agric. Food Chem., vol. 17, no. 4, pgs 723-727 (July-August 1969).

[0013] According to one aspect, the Amadori compound is formed by the reaction of glucose with an amino acid, where the amino acid is selected from the group consisting of histidine, isoleucine, methionine, proline, and serine. In one embodiment, the Amadori compound formed by the reaction of glucose and proline can be represented as N-(1-deoxy-D-fructose-1-yl)-L-proline:

[0014]

Chemical formula

[0015] Similarly, the reaction of glucose with other naturally occurring amino acids can be represented as follows: · N-(1-deoxy-D-fructose-1-yl)-L-histidine; · N-(1-deoxy-D-fructose-1-yl)-L-isoleucine; · N-(1-deoxy-D-fructose-1-yl)-L-methionine;

[0016] In another embodiment, the Amadori compound formed by the reaction of glucose and serine can be represented as N-(1-deoxy-D-fructose-1-yl)-L-serine:

[0017]

Chemical formula

[0018] The above structures of the Amadori compounds described in this application are intended to include their salt forms and charged forms. In addition, although the above Amadori compounds depict D-glucose, Amadori compounds from L-glucose are also considered to be part of this disclosure.

[0019] To obtain the excellent beneficial effects resulting from the presence of the Amadori reaction product of glucose with proline, the reaction product should be used at a concentration of 0.02 parts per billion to 25 parts per million, based on the total weight of the consumable composition. Larger amounts can be used, but the beneficial effects are clearly significantly less, and undesirable off-notes become increasingly apparent.

[0020] According to certain embodiments, the amount of the Amadori reaction product of glucose with proline present in the consumable composition may be at a concentration of about 0.02 ppb to about 25 ppm. According to certain embodiments, the amount of the Amadori reaction product of glucose with proline present in the consumable may be at a concentration of about 0.1 ppb to about 10 ppm. According to certain embodiments, the amount of the Amadori reaction product of glucose with proline present in the consumable may be at a concentration of about 0.25 ppb to about 1 ppm. According to certain embodiments, the amount of the Amadori reaction product of glucose with proline present in the consumable may be at a concentration of about 0.5 ppb to about 250 ppb.

[0021] When expressed as "ppb" or "ppm", the concentration is, depending on the situation, parts per billion or parts per million by weight, based on the total weight of the consumable. It should be understood that when ranges of values are recited in this disclosure, it is intended that every value within the range including the endpoints is disclosed. For example, the "range of 100 ppm to 1000 ppm" of the Amadori reaction product of glucose with proline is to be read as indicating every possible numerical value along the continuum between 100 and 1000. The inventors understand and acknowledge that every value within the range is considered to be specified and that the inventors own the entire range and all values within the range.

[0022] As used herein, the term "about" when used in connection with a value encompasses the recited value and has the meaning ascribed by the context. For example, it encompasses at least the degree of error associated with the measurement of a particular value. One of ordinary skill in the art will understand that the term "about" as used herein means that the amount of "about" the recited value results in the desired degree of effectiveness in the compositions and / or methods of the present disclosure. One of ordinary skill in the art will further understand that the bounds of "about" with respect to the value of any component percentage, amount or quantity in a given aspect vary the value and, for each value, determine the range of values that result in a composition or method having the desired degree of effectiveness in accordance with the present disclosure by determining the range of values that result in a composition or method having the desired degree of effectiveness.

[0023] As used herein, the articles "a", "an" and "the" mean one or more than one (i.e., at least one) grammatical object. By way of example, "a compound" means one compound or more than one compound.

[0024] The final form of the flavor modifying ingredient can be selected according to methods well known in the art and depends on the specific food product. For liquid foods, the flavor modifying ingredient can be used in its liquid form without further processing. For dry applications, spray dried concentrated flavor modifying ingredients can be used. The flavor modifying ingredient may be added directly to the food product or provided as part of a flavor composition for flavoring or seasoning foods.

[0025] Consumable compositions may include a base. As used herein, the term "base" refers to all of the ingredients necessary for the consumer product, apart from the flavor-modifying Amadori reaction product of glucose with proline. These will, of course, vary in nature and proportion depending on the nature and use of the consumer product or additive, but all of these are well known to those skilled in the art and may be used in proportions recognized in the art. Formulations of such bases for any conceivable purpose are, therefore, within the scope of ordinary skill in the art.

[0026] Without limitation and by way of mere illustration, suitable bases may include the following: anti-caking agents, anti-foaming agents, antioxidants, binders, colorants, diluents, disintegrants, emulsifiers, encapsulating agents or formulations, enzymes, fats, flavor enhancers, flavoring agents, gums, polysaccharides, preservatives, proteins, solubilizers, solvents, stabilizers, sugar derivatives, surfactants, sweeteners, vitamins, waxes, etc. Solvents that may be used are known to those skilled in the art and include, by way of example, water, ethanol, ethylene glycol, propylene glycol, glycerin and triacetin. Capsule materials and gums include the following: maltodextrin, gum arabic, alginic acid, gelatin, modified starch, other polysaccharides, and proteins.

[0027] Examples of excipients, carriers, diluents or solvents for flavor compounds can be found, for example, in the following: “Perfume and Flavour Materials of Natural Origin”, S. Arctander, Ed., Elizabeth, N.J., 1960; “Perfume and Flavour Chemicals”, S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; “Flavourings”, E. Ziegler and H. Ziegler (ed.), Wiley-VCH Weinheim, 1998, and “CTFA Cosmetic Ingredient Handbook”, J. M. Nikitakis (ed.), 1st ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

[0028] According to certain embodiments, the Amadori reaction product of glucose with proline may be added to a consumable as part of a taste-modifying composition, where the composition includes at least one characteristic flavor. The Amadori reaction product of glucose with proline may be added directly to the consumable or may be premixed with a component of the consumable. Non-limiting examples of characteristic flavors include natural flavors, artificial flavors, spices, seasonings, and the like. These include synthetic flavor oils and flavor aromatics and / or oils, oleoresins, essences, and distillates, and combinations thereof. The term “characteristic flavor” refers to a flavor that is recognized as dominant upon consumption by an individual.

[0029] Flavor oils include the following: spearmint oil, cinnamon oil, wintergreen oil (methyl salicylate), peppermint oil, menthol oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, hinoki oil, kuzu oil, allspice, sage oil, mace, bitter almond oil, and cassia oil; useful flavoring agents include the following: artificial, natural, and synthetic fruit flavors such as vanilla, and citrus oils including lemon, orange, lime, grapefruit, yuzu, sudachi, and fruit essences including apple, pear, peach, grape, strawberry, blackberry, gooseberry, blueberry, raspberry, cherry, plum, raisin, cola, guarana, neroli, pineapple, apricot, banana, melon, apricot, cherry, tropical fruits, mango, mangosteen, pomegranate, papaya, etc.

[0030] Additional exemplary flavors imparted by characteristic flavors include the following: milk flavor, butter flavor, cheese flavor, cream flavor, and yogurt flavor, vanilla flavor, tea or coffee flavor, such as green tea flavor, oolong tea flavor, tea flavor, cocoa flavor, chocolate flavor, and coffee flavor; mint flavor, such as peppermint flavor, spearmint flavor, and Japanese mint flavor; spicy flavors, such as ají flavor, ajowan flavor, anise flavor, star anise flavor, perilla flavor, allspice flavor, cinnamon flavor, chamomile flavor, mustard flavor, cardamom flavor, caraway flavor, cumin flavor, clove flavor, pepper flavor, coriander flavor, sassafras flavor, celery flavor, sansho pepper flavor, perilla seed flavor, juniper berry flavor, ginger flavor, star anise flavor, Japanese horseradish flavor, thyme flavor, tarragon flavor, lovage flavor, chili pepper flavor, Sichuan pepper flavor, basil flavor, marjoram flavor, rosemary flavor, bay leaf flavor, and wasabi flavor; nut flavors, such as almond flavor, sesame seed flavor, macadamia nut flavor, peanut flavor, pecan flavor, pistachio flavor, and walnut flavor; floral flavors; and vegetable flavors, such as onion flavor, garlic flavor, cabbage flavor, carrot flavor, celery flavor, mushroom flavor, and tomato flavor.

[0031] Generally, any characteristic flavor or food additive can be used, such as those described in “Chemicals Used in Food Processing”, Publication No 1274, pages 63 - 258, the National Academy of Sciences.

[0032] Auxiliary components may be present to provide other benefits such as enhanced stability, ease of incorporation into consumer products or additives, and enhanced nutritional value. Non-limiting exemplary instances of such auxiliary components include: stabilizers, emulsifiers, preservatives, gums, starches, dextrins, vitamins and minerals, functional ingredients, salts, antioxidants, and polyunsaturated fatty acids. Specific examples are emulsifiers and carriers useful in spray drying processes. These non-limiting examples are Capsul TM such as modified starches and maltodextrins.

[0033] The additive may be a single component, a blend of components, or encapsulated in any suitable capsule material such as those mentioned above. The additive may be prepared by any suitable method such as spray drying, extrusion, and fluid bed drying.

[0034] The Amadori reaction products may be used in a wide variety of consumer products or applications and are not limited to any specific physical mode or product form. According to the present disclosure, the term "consumer product / consumable" typically refers to a product for consumption by a subject for at least one purpose of enjoyment, nutrition, or health and wellness benefits, typically via the oral cavity (although consumption may occur via non-oral means such as inhalation). Consumer products may exist in any form, including but not limited to: liquids, solids, semi-solids, tablets, capsules, lozenges, strips, powders, gels, gums, pastes, slurries, solutions, suspensions, syrups, aerosols, and sprays. The term also refers to, for example, food and nutrition, as well as health and wellness supplements. Consumer products include compositions that are placed in the oral cavity for a period of time before being discarded but not swallowed. They may be placed in the oral cavity before consumption or held in the oral cavity for a period of time before being discarded. It has been found that the mouthfeel improving effect of the Amadori reaction products is particularly enhanced when used in combination with dairy products and reduced-fat dairy products.

[0035] Broadly, consumer goods, but not limited to these, include: all kinds of confectionery, bakery products, baked goods, sweet products, savory products, fermented products, dairy products, non-dairy products, beverages, dietary supplements and pharmaceuticals.

[0036] Non-limiting examples of consumer goods include wet / liquid soups, including frozen soups, regardless of concentration or container. For the purposes of this definition, soup(s) means a food product that is cooked in liquid and prepared from meat, poultry, fish, vegetables, grains, fruits and other ingredients, which includes visible pieces of some or all of these ingredients.This is a transparent (broth) or thick (chowder), smooth, purée or lumpy, instant, semi - condensed or concentrated product, warm or cold, which can be provided as the first course or main course of a meal, or as a snack between meals (sipping like a beverage). The soup can be used as an ingredient for preparing other meal components and can range from soup (consommé) to sauce (cream or cheese - based soup). Dehydrated and cooked food products, which include cooking aids such as: powders, granules, pastes, concentrated liquid products (including: compressed cubes, tablets or concentrated bouillon in powder or granular form, bouillon and bouillon - like products, sold as finished products or as ingredients in products, sauces and recipe mixes regardless of technology); meal solution products, such as dehydrated and freeze - dried soups, which include: dehydrated soup mixes, dehydrated instant soups, dehydrated cooking soups, cooked dishes, meals, and dehydrated or ready - to - serve entrees (pasta, potato, and rice dishes) provided singly; meal decoration products, such as: condiments, marinades, salad dressings, salad toppings, dips, breadcrumbs, batter mixes, shelf - stable spreads, barbecue sauces, liquid recipe mixes, concentrates, sauces or sauce mixes (including salad recipe mixes), which are sold dehydrated, liquid or frozen, as finished products or as ingredients in products; beverages including beverage mixes and concentrates, which include, but are not limited to: alcoholic and non - alcoholic ready - to - drink beverages and dry powder beverages, carbonated and non - carbonated beverages, examples being soda, fruit or vegetable juices, alcoholic and non - alcoholic beverages, teas such as green tea and black tea, wines such as red wine; confectionery products, such as: cakes, cookies, pies, candies, chewing gums, gelatins, ice creams, sorbets, puddings, jams, jelly salad dressings, and other condiments, cereals, and other breakfast foods, canned fruits and fruit sauces etc.

[0037] According to certain aspects, the Amadori reaction product of glucose with an amino acid is used to improve the mouthfeel of low-fat dairy products such as milk or yogurt. According to certain aspects, the Amadori reaction product of glucose with proline is used to improve the mouthfeel of low-fat dairy products such as milk or yogurt.

[0038] Exemplary dairy products include, but are not limited to: cheese, cheese sauce, cheese-based products, ice cream, impulse ice cream, single-serve dairy ice cream, single-serve water ice cream, multi-pack dairy ice cream, multi-pack water ice cream, take-home ice cream, take-home dairy ice cream, ice cream desserts, bulk ice cream, take-home water ice cream, frozen yogurt, artisanal ice cream, milk, fresh / pasteurized milk, whole fresh / pasteurized milk, semi-skimmed fresh / pasteurized milk, long-life / UHT milk, whole long-life / UHT milk, semi-skimmed long-life / UHT milk, fat-free long-life / UHT milk, goat's milk, condensed / evaporated milk, plain condensed / evaporated milk, flavored, functional and other condensed milk, flavored milk drinks, milk drinks flavored with only dairy products, milk drinks flavored with fruit juice, soy milk, soy milk drinks, fermented dairy drinks, coffee whiteners, powdered milk, flavored powdered milk drinks, cream, yogurt, plain / natural yogurt, flavored yogurt, fruit yogurt, probiotic yogurt, drinkable yogurt, regular drinkable yogurt, probiotic drinkable yogurt, refrigerated and ambient-stable desserts, dairy-based desserts, and bean-based desserts.

[0039] The problem with reducing fat in dairy products is the loss of taste and texture. When the fat content in dairy products is reduced or replaced with other ingredients (such as indigestible fats, proteins, fibers, gums), the fat content in dairy products results in increased adverse sensory effects (such as lack of mouthcoating, dryness, lack of crispness, and lack of flavor). The adverse sensory effects result in products with reduced palatability. In accordance with the present disclosure, dairy products have a fat content of about 40% by weight or less, more specifically about 20% or less, even more specifically 15% or less, in another embodiment 10% or less, and in another embodiment 5% or less, based on the total weight of the consumer product.

[0040] Example The following examples are provided for illustrative purposes only and should not be construed as limitations of the present invention, as many variations of the present invention are possible without departing from the spirit and scope of the present disclosure.

[0041] Example 1 In this example, N-(1-deoxy-D-fructose-1-yl)-L-proline (Fru-Pro), an Amadori compound from the reaction of glucose with proline, was prepared. A mixture of 5 g of sugar (27.8 mmol) and 5 g of proline (38.1 mmol) was added to a solution of 1:1 MeOH:DMF (100 ml:100 ml) at room temperature. The mixture was stirred at 85 °C for 3 hours. Then 1.15 g of malonic acid (11.05 mmol) was added to the mixture and the resulting mixture was heated to 90 °C for 2 hours until the color of the reaction became light brown. The light brown mixture was filtered to remove undissolved components and concentrated under vacuum to remove most of the solvent. The Amadori compound was precipitated by adding cold acetone at ~30 °C. 4.14 g (92% pure) of a white solid was obtained after centrifugation and C18 flash column purification. Similarly, Fru-Met can be prepared as described above using methionine instead of proline; Fru-Ileu can be prepared as described above using isoleucine instead of proline; and Fru-His can be prepared as described above using histidine instead of proline.

[0042] NMR Data Fru-Pro 1 H NMR (300 MHz, D2O) δ ppm 1.86-2.13 (m, 3H), 2.14-2.39 (m, 1H), 3.18-4.08 (m, 10H). 13 C NMR (75 MHz, D2O, major isomer) δ ppm 23.35, 28.27, 46.08, 57.36, 63.74, 68.90, 69.90, 69.97, 71.44, 95.64, 173.84.

[0043] Fru-Met 1 H NMR (600 MHz, D2O) δ ppm 2.09 - 2.16 (m, 1 H), 2.18 - 2.30 (m, 2 H), 2.58 - 2.74 (m, 1 H), 3.28 - 3.44 (m, 1 H), 3.74 - 3.81 (m, 1 H), 3.81 - 3.94 (m, 1 H), 3.98 - 4.08 (m, 1 H). 13 C NMR (151 MHz, D2O) δ ppm 16.95, 31.63, 31.90, 55.53, 62.28, 66.76, 71.78, 72.20, 72.76, 98.21, 175.78.

[0044] Fru-Ileu 11H NMR (300 MHz, D2O) δ ppm 0.81 - 0.92 (m, 6H), 1.19 - 1.29 (m, 1H), 1.39 - 1.50 (m, 1H), 1.91 (br m, 1H), 3.20 - 3.22 (m, 2H), 3.56 - 3.95 (m, 6H). 13 13C NMR (75 MHz, D2O, major isomer) δ ppm 11.21, 14.07, 25.86, 25.99, 35.79, 52.35, 63.87, 67.76, 68.89, 69.34, 70.12, 95.26, 172.08.

[0045] Fru-His 1 1H NMR (600 MHz, D2O) δ ppm 3.00 - 3.36 (m, 3 H), 3.46 - 4.03 (m, 5 H), 4.77 - 4.82 (m, 1 H), 4.87 - 5.05 (m, 1 H), 7.10 - 7.23 (m, 1 H), 8.06 (s, 1 H). 13 13C NMR (151 MHz, D2O) δ ppm 30.20, 55.45, 65.35, 65.86, 71.83, 72.31, 72.71, 98.96, 119.42, 134.29, 137.99, 178.04.

[0046] In another example, the Amadori compound formed by the reaction of glucose and serine can be represented as N-(1-deoxy-D-fructose-1-yl)-L-serine (Fru-Ser): Oxalyl chloride (6.64 g, 52.3 mmol) in 200 ml of dichloromethane was cooled to -78 °C (acetone / dry ice), and 12 ml (77 mmol) of DMSO in 20 ml of dichloromethane was added dropwise to this stirred solution via a pressure dropping funnel. When complete, the mixture was stirred at -78 °C for 15 min, then the acetyl-protected sugar (20 g, 77 mmol) in 80 ml of dichloromethane was added dropwise again using a pressure dropping funnel, the mixture was stirred at -78 °C for 17 min, then triethylamine (53.6 ml, 77 mmol) was added dropwise using a pressure dropping funnel, stirring was continued at -78 °C for 17 min, then the mixture was warmed to room temperature, water was added, and the mixture was extracted 3 times with dichloromethane. The organic layers were combined and washed twice with 1N HCl, twice with 5% Na2CO3, twice with water, and once with saturated NaCl. Dried over sodium sulfate, filtered, and the filtrate was concentrated. Purified by flash chromatography using a silica gel column with an EtOAc / hexane gradient of 5%, 10%, 15%, 20% EtOAc in hexane to 100% EtOAc, and 10 g of a clear oil, Compound A, was obtained. Used as is.

[0047] To a solution of A (2.55 g, 9.88 mmol) and benzyl-protected serine (1.76 g, 9.0 mmol) in 50 ml of MeOH, a 1 M solution of sodium cyanoborohydride (10 ml, 9.0 mmol) was added at room temperature, and the mixture was stirred at the same temperature for 2 h. Most of the MeOH was removed on a rotary evaporator. Saturated NaCl was added to this mixture, and it was extracted 3 times with EtOAc. The organic layers were combined, concentrated under vacuum, and dried over sodium sulfate. 3 g of a white solid, Compound B, was obtained by silica chromatography with 5% MeOH in CH2Cl2.

[0048] Compound B: 1H NMR (300 MHz, CD3OD-d6, δ ppm) 1.32 (s, 3H), 1.36 (s, 3H), 1.42 (s, 3H), 1.53 (s, 3H), 3.35 (s, 2H), 3.44 (s, 2H), 3.72 - 3.76 (d, d, J = 12.9, Hz, 1H), 3.87 - 4.06 (m, 4H), 4.25 - 4.27 (d, J = 6.2 Hz, 1H), 4.31 - 4.32 (d, J = 2.4Hz, 1H), 4.58 (s, 2H), 4.63 - 4.66 (d, d, J = 2.7, 8.1 Hz, 1H), 7.27 - 7.39 (m, 5H).

[0049] To a solution of B (3 g, 6.86 mmol) in methanol (50 mL) was added Pd / C at room temperature. The solution was degassed and stirred under a hydrogen balloon for 4 days. The solid was filtered off; the solvent was removed under vacuum. Silica chromatography with 5% MeOH in CH2Cl2 gave 1.15 g of white solid Compound B, which was dissolved in 2N HCl (2 mL). The round-bottom flask was placed on a rotary evaporator, and the solution was concentrated at room temperature under vacuum (~30 mmHg). The resulting oily residue was dissolved in water and concentrated under vacuum. This operation was repeated twice to obtain crude Amadori Serine Compound C. This crude material was purified on a C18 column to give 0.32 g of white solid Compound C.

[0050] Fru-Ser 1H NMR (300 MHz, D2O) δ ppm 3.20 - 3.37 (m, 2H), 3.63 - 4.00 (m, 8H). 13C NMR (75 MHz, D2O, major isomer) δ ppm 52.39, 59.04, 63.89, 68.88, 69.33, 70.32, 95.26, 171.14.

[0051] The following formulations were prepared with and without Amadori compounds, tasted by professional tasters (5 - 7 people), and compared. The Amadori compounds were added to the consumables without additional heating.

[0052] Milk with vanilla flavor Base: Half - full milk; 5% sugar; 0.1% vanilla; 20 ppm Fru - Pro: Slightly richer, more robust than the base, richer like fat, sweeter. Base: 2% milk fat; 4% sugar; 0.2% vanilla extract; 0.1 ppb Fru - Pro: The sweetness continues, more powdery, more fatty body, rich and creamy, more dairy impact, creamier mouthfeel, slightly waxy mouthfeel. Base: 2% milk fat; 4% sugar; 0.2% vanilla extract; 1 ppb Fru - Pro: Sweeter, improvement in richness, creamier mouthfeel, more dairy - like, slightly waxy mouthfeel. Base: 2% fat milk; 4% sugar; 0.15% vanilla flavor; 6 ppm Fru - Pro: Sweeter, richer and creamier, slightly sweeter, juicy, slightly metallic and dry mouth.

[0053] Milk with chocolate flavor Base: 2% milk fat; 5% sugar; 2% cocoa powder; 0.05% carrageenan; 0.1 ppb Fru - Pro: Creamy, rich, more robust chocolate, slightly waxy, more cocoa impact. Base: 2% milk fat; 5% sugar; 2% cocoa powder; 0.05% carrageenan; 1 ppb Fru - Pro: More chocolatey, more chocolate, more complex, rich mouthfeel, sweeter impression, darker, waxy, slightly tingly feeling. Base: 2% fat milk; 5% sugar; 2% cocoa powder; 0.05% carrageenan; 10 ppm Fru-Pro: Richer, more body, more authentic chocolate profile, slight increase in bitterness.

[0054] Almond milk Base: Commercially available sweetened vanilla almond milk; 2 ppb Fru-Pro: Creamier, stronger vanilla flavor, more body, creamier mouthfeel; sweeter and saltier.

[0055] Yogurt with strawberry flavor Base: 1.7% fat; 4% sugar; 0.1% strawberry flavor; 1 ppb Fru-Pro: Little effect felt. Base: 1.7% fat; 4% sugar; 0.1% strawberry flavor; 10 ppb Fru-Pro: Sweeter, creamier, more substantial mouthfeel, more fruity. Base: 1.7% fat; 4% sugar; 0.1% strawberry flavor; 100 ppb Fru-Pro: Similar to 10 ppb.

[0056] Plain low-fat yogurt Base: 1.5% fat; 5% sugar; 5 ppm Fru-Pro: Less acidity, sweeter, creamier. Base: 1.5% fat; 5% sugar; 10 ppm Fru-Pro: Initial increase in sweetness, less acidity. Base: 1.5% fat; 5% sugar; 25 ppm Fru-Pro: Persistent metallic taste, overall and initial increase in sweetness.

[0057] Ice cream Base: 14.31% heavy whipping cream; 77.60% whole milk; 8% sucrose; 0.009% vanilla; 10 ppb Fru-Pro: Creamier, sweeter, slightly more body and rounding effect on mouthfeel, slightly stronger milk fat flavor.

[0058] Cream filling Base: 66.4% sucrose; 32% palm oil; 0.2% salt; 0.4% vanilla extract; 1% water; 10 ppb Fru-Pro: More fatty, creamy, sweeter and saltier, more buttery profile.

[0059] Cheese sauce Base: 33.46% maltodextrin 10DE; 29.00% starch Ultrasphere 2000; 10.00% cheddar cheese (white); 9.00% non-fat milk powder; 6.20% whey; 5.00% canola shortening powder; 4.25% salt, mesh; 0.35% yeast extract powder; 0.10% citric acid; 0.10% lactic acid; 2.54% cheese flavor. 10 ppm Fru-Pro: Richer, cheesier, smooth, saltier, creamier mouthfeel, fresher dairy notes, rich, slight metallic and astringency. 10 ppm Fru-Met: Richer, cheesier, umami, astringency, sharper cheese notes, saltiness. 10 ppm Fru-Ser: Cheesier, creamy, rich, pungent, metallic, thick, smooth. 10 ppm Fru-Ileu: Slightly acidic, bitter, creamier, increased saltiness. 10 ppm Fru-His: Cheesier, slightly acidic, aged, meaty, pungent, chalky, increased mouthfeel, creamier.

[0060] Specific embodiments of the invention have been illustrated and described, but it will be apparent to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. Accordingly, it is intended that all such changes and modifications that fall within the scope of the invention be covered in all of the appended claims.

Claims

**Claim 1** A method of providing an improved mouthfeel in a consumable having a fat content of about 20% or less, the method comprising adding, to a consumable composition base, from about 0.02 parts per billion to about 25 parts per million of an Amadori compound, based on the total weight of the consumable composition, followed by no heating, wherein the Amadori compound is a reaction product of glucose with proline. **Claim 2** The method of claim 1, wherein the amount of Amadori compound in the consumable is from about 0.1 parts per billion to 10 parts per million. **Claim 3** The method of claim 1, wherein the fat content is about 10% or less. **Claim 4** The method of claim 1, wherein the fat content is about 5% or less. **Claim 5** The method of claim 1, wherein the Amadori compound is in powder form. **Claim 6** The method of claim 1, wherein the consumable is a beverage. **Claim 7** The method of claim 1, wherein the consumable is yogurt. **Claim 8** A consumable composition base having a fat content of about 20% or less and a consumable composition comprising from about 0.02 parts per billion to about 25 parts per million of an Amadori compound, based on the total weight of the consumable composition, wherein the Amadori compound is a reaction product of glucose with proline and the Amadori compound complements the mouthfeel characteristics of the consumable composition. **Claim 9** The consumable composition of claim 8, wherein the amount of Amadori compound in the consumable is from about 0.1 parts per billion to 10 parts per million. **Claim 10** The consumable composition of claim 8, wherein the fat content is about 10% or less. **Claim 11** The consumable composition of claim 8, wherein the fat content is about 5% or less. **Claim 12** The consumable composition of claim 8, wherein the Amadori compound is in powder form. **Claim 13** The consumable composition of claim 8, wherein the consumable is a beverage. **Claim 14** The consumable composition of claim 8, wherein the consumable is yogurt. **Claim 15** The consumable composition of claim 8, further comprising a characteristic flavor. **Claim 16** A consumable dairy composition comprising from about 0.02 parts per billion to about 25 parts per million of an Amadori compound, based on the weight of the consumer product base and the total weight of the consumable composition, wherein the Amadori compound is a reaction product of glucose with proline, and wherein the Amadori compound complements the mouthfeel characteristics of the consumable composition.

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