Flavor-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 This disclosure relates to methods for improving the mouthfeel of consumer goods using flavor modifiers. More specifically, this disclosure relates to methods for improving the mouthfeel of fat-containing or low-fat consumer goods using Amadori compounds, which are reaction products of glucose and amino acids, wherein the consumer goods are foods and beverages. Even more specifically, this disclosure relates to flavor compositions and consumer goods containing Amadori flavor modifiers, and the use of Amadori flavor modifiers in consumer goods, for example, to improve the mouthfeel of the consumer goods. [Background technology]

[0002] background Compounds used to modify the taste of consumable products—that is, products placed in the mouth either for ingestion or spitting out, such as food, beverages, confectionery, and oral care products—are widely used. While they themselves do not add flavor to the consumable, they provide desired incidental benefits, such as enhanced mouthfeel or masking undesirable characteristics of other ingredients, including the bitter aftertaste associated with certain sweeteners used as sugar substitutes in diet products. Desired mouthfeel is often represented by smoothness (lack of grittiness and friction) and creaminess.

[0003] There remains a need to provide flavor-modifying ingredients that complement the flavors of the consumer products into which they are incorporated, not by exhibiting their own specific flavor characteristics, but by enhancing the flavor and mouthfeel of the composition, thus giving it an extremely broad spectrum of use across a wide range of food and beverage categories.

[0004] Consequently, there is a need to provide compounds that improve palatability for use in fat-containing or low-fat consumer goods, while simultaneously preserving or enhancing the desired functional properties of such edible compositions. [Overview of the project]

[0005] overview In one exemplary embodiment, a method for providing an improved mouthfeel in a consumable having a fat content of about 20% or less comprises the step of adding about 0.02 parts per billion to about 25 parts per million of an Amadori compound to a consumable composition base, based on the total weight of the consumable composition, without subsequent heating. In another exemplary embodiment, the consumable composition comprises a consumable base having a fat content of about 20% or less, and about 0.02 parts per billion to about 25 parts per million of Amadori compounds based on the total weight of the consumable composition.

[0006] In another exemplary embodiment, a dairy-based consumable composition comprises about 0.02 parts per billion to about 25 parts per million of Amadori compounds on a consumable basis and based on the total weight of the consumable composition, where the Amadori compounds complement 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 reading this disclosure.

[0007] Detailed description The following text provides a broad description of the numerous different embodiments of this disclosure. The description is to be interpreted as illustrative only, and it is not possible to describe all possible embodiments, as all possible embodiments would be impractical, if not impossible. It will be understood that any feature, characteristic, component, composition, ingredient, product, step, or methodology described herein may be deleted, combined, or replaced in whole or in part. Numerous alternative embodiments may be carried out using either the current art or art developed after the filing date of this application, and they remain within the scope of the claims. All publications and patents cited herein are incorporated herein by reference.

[0008] Undesirable mouthfeel can pose a serious disadvantage to otherwise desirable, fat-containing or low-fat consumables. As used herein, “mouthfeel” refers to, but is not limited to, the physical sensation in the mouth produced by a food, beverage or ingredient, and includes, but is not limited to, weight, thickness, viscosity, moisture, smoothness, filminess, dryness, and mouth coating. Unfortunately, the desired effect is often a characteristic of fatty foods such as dairy products, whose consumption should be reduced for many people for health and dietary reasons. Now it has been found that undesirable mouthfeel characteristics can be improved by incorporating Amadori compounds into consumable compositions, where Amadori compounds are present in amounts of about 0.02 parts per billion to about 25 parts per million based on the total weight of the consumable composition.

[0009] In one embodiment, a method is disclosed for providing an improved mouthfeel in a consumable having a fat content of about 20% or less, comprising the step of adding about 0.02 parts per billion to about 25 parts per million of an Amadori compound to a consumable composition base, based on the total weight of the consumable composition. Surprisingly, it has been found that the incorporation of an 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 embodiment, it has been found that the Amadori reaction product of glucose with proline, present at a certain concentration, improves the palatability of consumer products with approximately 20% more fat content. It was also found that the Amadori reaction product of glucose with proline, present at a certain concentration, enhances other mouthfeel characteristics such as creaminess, richness, and body. Amadori compounds (also known as Amadori products) are formed via the well-known Amadori rearrangement reaction, in which an aldose sugar is isomerized via an acid or base, then reacted with an amine, and after the rearrangement of a Schiff base intermediate, the Amadori compound is formed (M. Amadori, Atti Accad. Naz. Lincei 2(6), 337 (1925); The Merck Index (14) th See Edition), pg. ONR-3, (2006). The following reaction scheme shows the reaction between hexose sugar and ammonia to form the Amadori compound.

[0011] [ka]

[0012] While methods for producing Amadori compounds (products) are well known in the art, their applications are not widely known. Amadori compounds themselves are not beneficial, but they are thought to function as intermediates for the formation of advanced end products (AEPs) through dehydration, fragmentation, or aldol condensation. These AEPs are often beneficial in the food industry as flavorings. One such example is the thermal decomposition of Amadori compounds to produce a caramel-scented compound. (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 aspect, 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 aspect, 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 the 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 consumer product 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 consumer product 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 consumer product 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 consumer product. 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 end points 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] In this disclosure, the term “about” as used in relation to a value encompasses the given value and has a meaning determined by the context. For example, it encompasses at least the degree of error associated with measuring a specific value. A person skilled in the art will understand that, as used herein, the term “about” means that an amount “about” of the stated value results in the composition and / or method of this disclosure having the desired degree of effectiveness. A person skilled in the art will further understand that the boundary of “about” with respect to the percentage, amount or quantity of any component in a given aspect can be determined by varying the value and, with respect to each value, determining the effectiveness of the composition or method and determining the range of values ​​that results in a composition or method having the desired degree of effectiveness according to this disclosure.

[0023] As used herein, the articles "a," "an," and "the" refer to one or more (i.e., at least one) grammatical objects. For example, "a compound" refers to one or more compounds.

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

[0025] The consumable composition may include a base. As used herein, the term “base” refers to all the components necessary for the consumable, apart from the Amadori reaction product of glucose with proline for flavor modification. These components, of course, vary in nature and proportion depending on the nature and use of the consumable or additive, but are all 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 merely as an example, suitable bases may include: anti-caking agents, defoaming 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, as examples, water, ethanol, ethylene glycol, propylene glycol, glycerin, and triacetin. Capsule materials and gums include: 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: “Perfume and Flavour Materials of Natural Origin”, S. Arctander, Ed., Elizabeth, NJ, 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”, JM Nikitakis (ed.), 1st ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

[0028] In one embodiment, the Amadori reaction product of glucose with proline may be added to a consumable as part of a flavor-modifying composition, wherein the composition comprises at least one characteristic flavor. The Amadori reaction product of glucose with proline may be added directly to the consumable or pre-mixed with a component of the consumable. Non-limiting examples of characteristic flavors include natural flavors, artificial flavors, spices, seasonings, etc. These include synthetic flavor oils and flavor aromas and / or oils, oleoresins, essences, and distillates, and combinations thereof. The term “characteristic flavor” refers to a flavor that is perceived as dominant at the time of consumption by an individual.

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

[0030] Additional example flavors provided by distinctive flavors include: milk flavors, butter flavors, cheese flavors, cream flavors, and yogurt flavors; vanilla flavors; tea or coffee flavors, such as green tea flavors, oolong tea flavors, tea flavors, cocoa flavors, chocolate flavors, and coffee flavors; mint flavors, such as peppermint flavors, spearmint flavors, and mint flavors; spicy flavors, such as agi flavors, ajwain flavors, anise flavors, angelica flavors, fennel flavors, allspice flavors, cinnamon flavors, chamomile flavors, mustard flavors, cardamom flavors, caraway flavors, cumin flavors, clove flavors, pepper flavors, coriander - Flavors such as sassafras, savory, sansho pepper, perilla, juniper berry, ginger, star anise, horseradish, thyme, tarragon, dill, chili pepper, nutmeg, basil, marjoram, rosemary, bay leaf, and wasabi; nut flavors such as almond, hazelnut, macadamia nut, peanut, pecan, pistachio, and walnut; floral flavors; and vegetable flavors such as onion, garlic, cabbage, carrot, celery, mushroom, and tomato.

[0031] In general, any distinctive flavor or food additive can be used, such as those listed 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 consumables or additives, and enhanced nutritional value. Non-limiting typical examples of such auxiliary components include: stabilizers, emulsifiers, preservatives, gums, starches, dextrins, vitamins and minerals, functional ingredients, salts, antioxidants, and polyunsaturated fatty acids. Specific examples include emulsifiers and carriers useful in spray-drying processes. These non-limiting examples are found in Capsul TM These include 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 fluidized bed drying.

[0034] Amadori reaction products may be used in a wide variety of consumables or applications and are not limited to any specific physical mode or product form. In accordance with this disclosure, the term “consumable” refers to a product intended to be consumed by a subject typically via the oral cavity (however, consumption may occur via non-oral means such as inhalation) for at least one purpose of enjoyment, nutrition, or health and wellness benefit. Consumables may exist in any form, but are 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, for example, to diets and nutrition, as well as health and wellness supplements. Consumables include compositions that are placed in the oral cavity for a period of time before being discarded but are not swallowed. They may be placed in the oral cavity before consumption and may be held in the oral cavity for a period of time before being discarded. It has been found that the mouthfeel-improving effect of Amadori reaction products is particularly enhanced when used in combination with dairy products and reduced-fat dairy products.

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

[0036] An unrestricted example of a consumable item includes wet / liquid soups, including frozen soups, regardless of their concentration or container. For the purposes of this definition, soup(singular or plural) means a food prepared in liquid from meat, poultry, fish, vegetables, grains, fruits and other ingredients, and this includes any visible piece of some or all of these ingredients.This includes clear (broth) or thick (chowder), smooth, puree or chunky, instant, semi-condensed or concentrated, and can be served hot or cold as the first course or main course of a meal or as a snack between meals (sipped like a drink); soups can be used as ingredients to prepare other meal components and may range from soups (consommé) to sauces (cream or cheese-based soups); dehydrated and cooked foods, which include cooking aid products such as: powders, granules, pastes, concentrated liquid products (including: concentrated bouillon, bouillon and bouillon-like products in compressed cube, tablet or powder or granular form, sold as finished products or as ingredients in products, sauces and recipe mixes (regardless of technology)); meal solution products, e.g., dehydrated and freeze-dried soups, which include: dehydrated soup mixes, dehydrated instant soups, dehydrated cooking soups, cooked dishes, meals, and single-serving entrees (pasta, Dehydrated or room-temperature preparations of potatoes and rice dishes; food decoration products, e.g.: 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 within products; beverages, including beverage mixes and concentrates, which include but are not limited to: ready-to-drink alcoholic and non-alcoholic beverages and dry powdered beverages, carbonated and non-carbonated beverages, e.g., 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, e.g., cakes, cookies, pies, candies, chewing gum, gelatin, ice cream, sorbet, pudding, jam, jelly, salad dressings, and other condiments, cereals, and other breakfast foods, canned fruits and fruit sauces, etc.

[0037] In one embodiment, 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. In another embodiment, 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] The dairy products listed as examples include, but are not limited to, cheese, cheese sauce, cheese-based products, ice cream, impulse ice cream, single serving dairy ice cream, single serving water ice cream, multi-pack dairy ice cream, multi-pack water ice cream, takeaway ice cream, takeaway dairy ice cream, ice cream desserts, large-capacity ice cream, takeaway water ice cream, frozen yogurt, artisan ice cream, milk, fresh / pasteurized milk, whole-fat fresh / pasteurized milk, semi-skimmed fresh / pasteurized milk, long-life / uht milk, whole-fat 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 beverages, dairy-only flavored milk beverages, fruit juice flavored milk beverages, soy milk, soy milk beverages, fermented dairy beverages, coffee whiteners, powdered milk, flavored powdered milk beverages, cream, yogurt, plain / natural yogurt, flavored yogurt, fruit yogurt, probiotic yogurt, drinking yogurt, regular drinking yogurt, probiotic drinking yogurt, refrigerated and room-temperature 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 components (e.g., indigestible fats, proteins, fiber, gums), the fat content in dairy products increases adverse sensory effects (e.g., mouth coating, dryness, lack of crispness, and lack of flavor). Adverse sensory effects result in a less palatable product. In accordance with this 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 given solely for illustrative purposes and should not be construed as limitations of the invention, as many variations of the invention are possible without departing from the spirit and scope of this disclosure.

[0041] Example 1 In this example, N-(1-deoxy-D-fructose-1-yl)-L-proline (Fru-Pro), an Amadori compound, was prepared from the reaction of glucose with proline. A mixture of 5 g of sugar (27.8 mmol) and 5 g of proline (38.1 mmol) was added to a 1:1 MeOH:DMF (100 ml:100 ml) solution 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 at 90°C for 2 hours until the reactants turned 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 using methionine instead of proline as described above; Fru-Ileu can be prepared using isoleucine instead of proline as described above; and Fru-His can be prepared using histidine instead of proline as described above.

[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): 6.64 g of oxyal chloride (52.3 mmol) in 200 ml of dichloromethane was cooled to -78°C (acetone / dry ice). To this stirred solution, 12 ml (77 mmol) of DMSO in 20 ml of dichloromethane was added dropwise through a pressurized dropping funnel. Once complete, the mixture was stirred at -78°C for 15 min, then 20 g of acetyl-protected sugar (77 mmol) in 80 ml of dichloromethane was added dropwise again using a pressurized dropping funnel. The mixture was stirred at -78°C for 17 min, then 53.6 ml of triethylamine (77 mmol) was added dropwise using a pressurized dropping funnel, and the mixture was continuously stirred at -78°C for 17 min. The mixture was then warmed to room temperature, water was added, and the mixture was extracted three times with dichloromethane. The organic layers were combined and washed twice with 1N HCl, twice with 5% Na2CO3, twice with water, and with saturated NaCl. The mixture was dried over sodium sulfate, filtered, and the filtrate was concentrated. Using a silica gel column, the mixture was purified by flash chromatography with toluene / hexane gradients of 5%, 10%, 15%, 20% to 100% toluene in hexane to obtain 10 g of clear oil compound A. This compound was used directly.

[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, 1 M sodium borohydride cyanohydride (10 ml, 9.0 mmol) was added at room temperature. The mixture was stirred at the same temperature for 2 hours, and most of the MeOH was removed using a rotary evaporator. Saturated NaCl was added to this mixture, and it was extracted three times with ELISA. The organic layers were combined, concentrated under vacuum, and dried on sodium sulfate. Silica chromatography using 5% MeOH in CH2Cl2 yielded 3 g of compound B as a white solid.

[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] Pd / C was added to a solution of B (3 g, 6.86 mmol) in methanol (50 ml) at room temperature, the solution was degassed, and the mixture was stirred under a hydrogen balloon for 4 days. The solid was filtered, and the solvent was removed under vacuum. 1.15 g of compound B was obtained by silica chromatography using 5% MeOH in CH2Cl2, and this was dissolved in 2N HCl (2 ml). The round-bottom flask was placed on a rotary evaporator, and the solution was concentrated under vacuum (~30 mmHg) at room temperature. The resulting oily residue was dissolved in water and concentrated under vacuum. This procedure was repeated twice to obtain crude amadricerin compound C. This crude material was purified by C18 column chromatography to obtain 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 the Amadori compound, and tasted and compared by professional tasters (5-7 people). The Amadori compound was added to the product without any further heating.

[0052] Vanilla-flavored milk Base: Half-full milk; 5% sugar; 0.1% vanillin; 20ppm Fru-Pro: Slightly richer, more concentrated than the base, richer in fat, sweeter. Base: 2% milk fat; 4% sugar; 0.2% vanilla extract; 0.1 ppb Fru-Pro: Long-lasting sweetness, 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, richer, creamier texture, more dairy-like, with a slight waxy mouthfeel. Base: 2% Fat Milk; 4% Sugar; 0.15% Vanilla Flavor; 6ppm Fru-Pro: Sweeter, richer and creamier, slightly sweeter, juicier, slightly metallic and dry in the mouth.

[0053] Chocolate-flavored milk Base: 2% milk fat; 5% sugar; 2% cocoa powder; 0.05% carrageenan; 0.1 ppb Fru-Pro: Creamy, rich, more intense chocolate, with a slight waxy, more cocoa impact. Base: 2% milk fat; 5% sugar; 2% cocoa powder; 0.05% carrageenan; 1 ppb Fru-Pro: Longer chocolatey, more chocolatey, more complex, richer mouthfeel, sweeter impression, darker, waxy, slight tingling sensation. Base: 2% Fat Milk; 5% Sugar; 2% Cocoa Powder; 0.05% Carrageenan; 10ppm 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] Strawberry-flavored yogurt Base: 1.7% fat; 4% sugar; 0.1% strawberry flavor; 1 ppb. Fru-Pro: Almost no effect felt. Base: 1.7% fat; 4% sugar; Strawberry flavor 0.1%; 10 ppb. Fru-Pro: Sweeter, creamier, richer mouthfeel, and fruitier. Base: 1.7% fat; 4% sugar; 0.1% strawberry flavor; 100 ppb. Fru-Pro: 10 ppb (same).

[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 sweetness increase, less acidity. Base: 1.5% fat; 5% sugar; 25 ppm Fru-Pro: Increased overall and initial sweetness with a lingering metallic taste.

[0057] ice cream Base: 14.31% heavy whipped cream; 77.60% whole milk; 8% sucrose; 0.009% vanillin; 10ppb Fru-Pro: Creamier, sweeter, slightly rounder in body and 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: A richer, creamier, sweeter, and saltier profile.

[0059] Cheese sauce Base: 33.46% Maltodextrin 10DE; 29.00% Ultrasphere 2000 Starch; 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. 10ppm Fru-Pro: Richer, more cheesy, smoother, saltier, creamier mouthfeel, fresher dairy notes, full-bodied, with a slight metallic and astringent finish. 10ppm Fru-Met: Richer, more cheesy, umami, astringency, sharper cheese notes, saltiness. 10ppm Fru-Ser: Cheesy, creamy, rich, pungent, metallic, dense, smooth. 10ppm Fru-Ileu: Slightly acidic, bitter, creamier, and saltier. 10ppm Fru-His: More cheesy, slightly acidic, aged, meaty, pungent, chalky, increased mouthfeel, creamier.

[0060] While specific embodiments of the present invention have been illustrated and described, it will be obvious 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, all such changes and modifications within the scope of the invention are intended to be covered in all appended claims.

Claims

1. A method for providing enhanced creaminess, fatiness and / or bodyiness in a dairy consumer product having a fat content of 20% or less, comprising the step of adding 10 parts per billion to 25 parts per million of an Amadori compound to a consumer composition base, based on the total weight of the consumer composition, without subsequent heating, wherein the Amadori compound is N-(1-deoxy-D-fructose-1-yl)-L-proline.

2. The method according to claim 1, wherein the amount of Amadori compound in the consumable is 10 parts per billion to 10 parts per million.

3. The method according to claim 1, wherein the fat content is 10% or less.

4. The method according to claim 1, wherein the fat content is 5% or less.

5. The method according to claim 1, wherein the Amadori compound is in powder form.

6. The method according to claim 1, wherein the consuming product is a beverage.

7. The method according to claim 1, wherein the consumer product is yogurt.

8. A dairy-based consumable composition comprising a consumable base having a fat content of 20% or less, and 10 parts per billion to 25 parts per million of an Amadori compound based on the total weight of the consumable composition, wherein the Amadori compound is N-(1-deoxy-D-fructose-1-yl)-L-proline.

9. The consumable composition according to claim 8, wherein the amount of Amadori compound in the consumable is 10 parts per billion to 10 parts per million.

10. The consumable composition according to claim 8, wherein the fat content is 10% or less.

11. The consumable composition according to claim 8, wherein the fat content is 5% or less.

12. The consumable composition according to claim 8, wherein the Amadori compound is in powder form.

13. The consumable composition according to claim 8, wherein the consumable is a beverage.

14. The consumable composition according to claim 8, wherein the consumable is yogurt.

15. An agent for enhancing the creaminess, fatiness and / or bodyiness of a dairy-based consumable composition, Contains N-(1-deoxy-D-fructose-1-yl)-L-proline, It is used to contain 10 parts per billion to 25 parts per million of N-(1-deoxy-D-fructose-1-yl)-L-proline based on the total weight of the consumable composition. The aforementioned agent.

Images