WO2013121264A1 - Exhausteur de goût sucré - Google Patents

Exhausteur de goût sucré Download PDF

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Publication number
WO2013121264A1
WO2013121264A1 PCT/IB2013/000177 IB2013000177W WO2013121264A1 WO 2013121264 A1 WO2013121264 A1 WO 2013121264A1 IB 2013000177 W IB2013000177 W IB 2013000177W WO 2013121264 A1 WO2013121264 A1 WO 2013121264A1
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WIPO (PCT)
Prior art keywords
reduced calorie
taste
product
acid
beverage
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PCT/IB2013/000177
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English (en)
Inventor
Hedda Hillmann
Thomas Hofmann
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Frito-Lay Trading Company Gmbh
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Publication of WO2013121264A1 publication Critical patent/WO2013121264A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L21/00—Marmalades, jams, jellies or the like; Products from apiculture; Preparation or treatment thereof

Definitions

  • This disclosure relates generally to sweeteners for reduced-calorie products.
  • balsamic vinegars are made from combinations of Trebbiano and Lambrusco grapes. After cooking the grapes in an open vessel, the reduced must undergoes a spontaneous alcoholic and acetic fermentation in a barrel or "badessa.” Thereafter, the vinegar is matured in a sequence of at least five casks made from different woods such as, e.g. , oak, acacia, chestnut, cherry, mulberry, and ash, respectively. Once a year an aliquot of the aged vinegar is taken from the smallest barrel (“prelivio") and the respective next bigger barrel is sequential refilled
  • balsamic vinegar (“rincalzo”).
  • the vinegar becomes increasingly concentrated by slow evaporation of water.
  • two different varieties of the traditional balsamic vinegar of Modena are available, namely “Affmato” and “Extravecchio” matured for at least 12 and 25 years, respectively, whereas of traditional balsamic vinegar from Reggio Emilia three varieties (aragosta (12 years), argento (18 years) and oro (25 years)) are available (1).
  • balsamic vinegar of Modena is produced on an industrial scale from wine vinegar, coloring and flavoring additives, and greatly differ in price and concentration of monosaccharides, organic acids, amino acids, phenolic acids, and furan-2-aldehydes from the traditional, artisanal-type variety (1 -17).
  • BV balsamic vinegar of Modena
  • FIG. 1 Structures of oak-derived ellagitannins vescalagin (1 ) and castalagin (2),
  • FIGS. 2A-F LC-MS (MRM) analysis.
  • FIG. 2 A vescalagin ( 1 ) and castalagin (2) in balsamic vinegar (BV);
  • FIG. 2B (+)-dihydrorobinetin (3) in BV;
  • FIG. 2C vescalagin (1 ) and castalagin (2) in traditional balsamic vinegar (TBV);
  • FIG. 2D (+)- dihydrorobinetin (3) in TBV;
  • FIG. 2E vescalagin (1) and castalagin (2) in balsamic vinegar (BV) spiked with 1 and 2 prior to analysis;
  • FIG. 2F (+)-dihydrorobinetin (3) in BV spiked with 1 and 2 prior to analysis.
  • TVM-LMW (TBV-LMW, ⁇ 5kDa) isolated from TBVM by means of ultrafiltration.
  • FIG. 4. (A) HILIC-ELSD chromatogram of GAC fraction VII and (B) RP-HPLC- DAD chromatogram of GAC fraction X isolated from the TBV-LMW fraction.
  • FIG. 5 HMBC NMR-spectrum (500 MHz, MeOD) and chemical structure of 5- acetoxymethyl-2-furaldehyde (6) isolated from GAC fraction X-2; s.s. solvent signal.
  • FIG. 6 Influence of maturation on the taste profile of intermediary vinegar samples collected from casks A-H of the "batteria" of TBV manufacturing; data are given as the mean of triplicates.
  • FIGS. 7A-B Sensomics heatmap calculated from quantitative data of selected
  • FIG. 8 Reaction scheme showing the formation of sweet taste modulator 6 via the Maillard reaction product 5-hydroxymethyl-2-furaldehyde and acetic acid generated upon fermentation.
  • This disclosure provides a sweetness-enhancing component consisting essentially of 5-acetoxymethyl-2-furaldehyde, which can be used to enhance sweetness of reduced calorie products comprising a nutritive sweetener.
  • balsamic vinegar of Modena differed significantly by the increased concentration of acetic acid, the significantly lower concentrations of the sweet-modulating 5-acetoxymethyl-2- furaldehyde, the non-volatile organic acids and polyphenols, and the lack of wood- derived ellagitannins.
  • a reduced-calorie product is a product wherein the calorie content has been reduced by at least 25% compared to the full-calorie counterpart.
  • the reduced calorie product is produced, for example, by reducing the amount of nutritive sweetener in the product in order to reduce the calorie content.
  • reducing the amount of nutritive sweetener also reduces the sweetness of the reduced-calorie product compared to the full-calorie counterpart. It was discovered that 5-acetoxymethyl-2- furaldehyde can be added to reduced-calorie products to enhance the sweet taste of the product thus offsetting the effects of reducing the amount of nutritive sweetener.
  • 5-acetoxymethyl-2-furaldehyde is included in a reduced calorie product in an amount sufficient to enhance the sweet taste of the product containing a reduced amount of sweetener compared to compositions that are prepared without 5-acetoxymethyl-2- furaldehyde, as judged by human beings or animals or, in the case of formulations testing, as judged by a majority of a panel of, e.g. , eight human taste testers, via procedures commonly known in the field.
  • the concentration of 5-acetoxymethyl-2-furaldehyde sufficient to enhance sweetness in a reduced calorie product will of course depend on many variables, including the specific type of reduced calorie product and its various other ingredients, as well as natural genetic variability and individual preferences and health conditions of various individuals tasting the reduced calorie product.
  • the concentration of 5-acetoxymethyl-2-furaldehyde sufficient to enhance sweetness in a reduced calorie beverage product is from about 0.1 to 5.0 mmol/L (e.g. , 0.1 , 0.15, 0.2, 0.25, 0.3, 0.35, 0.4, 0.45, 0.5, 0.75, 1.0, 1.5, 2.0, 3.0, 4.0, or 5.0).
  • the ratio of nutritional sweetener to 5-acetoxymethyl-2-furaldehyde on a parts basis is 1 ,170: 1 to 23.4: 1.
  • Similar ratios of nutritional sweetener to 5-acetoxymethyl-2-furaldehyde can also be used in reduced calorie foods, such as those described below.
  • a "comestible reduced calorie product” is a reduced calorie product that can be consumed as food by humans or animals.
  • noncomestible reduced calorie product is a reduced calorie product that is intended to be consumed or used by humans or animals not as food. Both comestible and noncomestible reduced calorie products include solids, gels, pastes, foamy materials, semi-solids, liquids, and mixtures thereof. "Animals” include any non-human animal, such as farm animals and pets.
  • the formulation of a reduced calorie product in accordance with this disclosure can vary to a certain extent, depending upon such factors as the reduced calorie product's intended market segment, its desired nutritional characteristics, flavor profile and the like. For example, it will generally be an option to add further ingredients to the formulation of some embodiments, including any of the reduced calorie product formulations described below. Additional (i.e. , more and/or other) sweeteners may be added, flavorings, electrolytes, vitamins, fruit juices or other fruit reduced calorie products, tastants, masking agents and the like, flavor enhancers, and/or carbonation typically can be added to any such formulations to vary the taste, mouthfeel, nutritional characteristics, etc.
  • Sweeteners may be added, flavorings, electrolytes, vitamins, fruit juices or other fruit reduced calorie products, tastants, masking agents and the like, flavor enhancers, and/or carbonation typically can be added to any such formulations to vary the taste, mouthfeel, nutritional characteristics, etc.
  • additional sweeteners may be included, for example, additional nutritive sweeteners or non-nutritive sweeteners.
  • Non-limiting examples of nutritive sweeteners include sucrose, liquid sucrose,
  • fructose liquid fructose, glucose, liquid glucose, glucose-fructose syrup from natural sources such as apple, chicory, agave, honey, etc., e.g. , high fructose corn syrup, chicory syrup, Agave syrup, invert sugar, medium invert sugar, maple syrup, maple sugar, honey, brown sugar molasses, e.g., cane molasses and sugar beet molasses, sorghum syrup, an mixtures of any of them.
  • natural sources such as apple, chicory, agave, honey, etc., e.g. , high fructose corn syrup, chicory syrup, Agave syrup, invert sugar, medium invert sugar, maple syrup, maple sugar, honey, brown sugar molasses, e.g., cane molasses and sugar beet molasses, sorghum syrup, an mixtures of any of them.
  • Such sweeteners are present in some embodiments in an amount of from about 0.1% to about 20% by weight of the finished food or beverage reduced calorie product, such as from about 6% to about 16% by weight, depending upon the desired level of sweetness for the finished food or beverage reduced calorie product.
  • Nutritive sweeteners may be present in beverage concentrate embodiments up to about 60% by weight of the beverage concentrate.
  • rebaudioside A included in food and beverage reduced calorie products
  • rebaudioside D included in food and beverage reduced calorie products
  • stevioside included in food and beverage reduced calorie products
  • other steviol glycosides included in food and beverage reduced calorie products
  • LHG Lo Han Guo
  • LHG e.g. , LHG juice concentrate or LHG powder
  • thaumatin e.g. , monellin, brazzein, monatin, and mixtures of any of them.
  • LHG if used, may have for example, mogroside V content of from about 2 to about 99%.
  • non-nutritive sweeteners include sorbitol, mannitol, xylitol,
  • the sweetener component can include erythritol, tagatose, an erythritol and tagatose blend, or polydextrose.
  • included in food and beverage reduced calorie products include peptide based sweeteners, e.g. , aspartame, neotame, and alitame, and non-peptide based sweeteners, e.g., sodium saccharin, calcium saccharin, acesulfame (including but not limited to acesulfame potassium), cyclamate (including but not limited to sodium cyclamate and/or calcium cyclamate), neohesperidin dihydrochalcone, sucralose, and mixtures of any of them.
  • peptide based sweeteners e.g. , aspartame, neotame, and alitame
  • non-peptide based sweeteners e.g., sodium saccharin, calcium saccharin, acesulfame (including but not limited to acesulfame potassium), cyclamate (including but not limited to sodium cyclamate and/or calcium cyclamate),
  • Potent non-nutritive sweeteners typically are employed at a level of milligrams per ounce of food or beverage according to their sweetening power, any applicable regulatory provisions of the country where the food or beverage is to be marketed, the desired level of sweetness of the food or beverage, etc. Mixtures of any of the above nutritive and non-nutritive sweeteners are included within the scope of the disclosed invention. It will be within the ability of those skilled in the art, given the benefit of this disclosure, to select suitable additional or alternative sweeteners for use in various embodiments of the food and beverage reduced calorie products disclosed here.
  • beverage concentrates are prepared with an initial volume of water to which the additional ingredients are added.
  • Full strength beverage compositions can be formed from the beverage concentrate by adding further volumes of water to the concentrate.
  • full strength beverages can be prepared from the concentrates by combining approximately 1 part concentrate with between approximately 3 to approximately 7 parts water.
  • the full strength beverage is prepared by combining 1 part concentrate with 5 parts water.
  • the additional water used to form the full strength beverages is carbonated water.
  • a full strength beverage is directly prepared without the formation of a concentrate and subsequent dilution.
  • Water is a basic ingredient in the beverage reduced calorie products disclosed here, typically being the vehicle or primary liquid portion in which the remaining ingredients are dissolved, emulsified, suspended or dispersed.
  • Purified water can be used in the manufacture of certain embodiments of the beverages disclosed here, and water of a standard beverage quality can be employed in order not to adversely affect beverage taste, odor, or appearance.
  • the water typically will be clear, colorless, free from objectionable minerals, tastes and odors, free from organic matter, low in alkalinity and of acceptable microbiological quality based on industry and
  • water is present at a level of from about 80% to about 99.9% by weight of the beverage.
  • treated water refers to water that has been treated to reduce the total dissolved solids of the water prior to optional
  • treated water Methods of producing treated water are known to those of ordinary skill in the art and include deionization, distillation, filtration and reverse osmosis ("r-o"), among others.
  • the terms "treated water,” “purified water,” “demineralized water,” “distilled water,” and “r-o water” are understood to be generally synonymous in this discussion, referring to water from which substantially all mineral content has been removed, typically containing no more than about 500 ppm total dissolved solids, e.g. 250 ppm total dissolved solids.
  • Juices suitable for use in some embodiments of the beverage reduced calorie products disclosed here include, e.g., fruit, vegetable and berry juices.
  • Juices can be employed in the present invention in the form of a single-strength juice, NFC juice, 100% pure juice, juice concentrate, juice puree, or other suitable forms.
  • the term "juice” as used here includes single-strength fruit, berry, or vegetable juice, as well as concentrates, purees, milks, and other forms. Multiple different fruit, vegetable and/or berry juices can be combined, optionally along with other flavorings, to generate a beverage having the desired flavor.
  • suitable juice sources include orange, lemon, lime, tangerine, mandarin orange, tangelo, pomelo, grapefruit, grape, red grape, sweet potato, tomato, celery, beet, lettuce, spinach, cabbage, watercress, rhubarb, carrot, cucumber, raisin, cranberry, pineapple, peach, banana, apple, pear, guava, apricot, watermelon, Saskatoon berry, blueberry, plains berry, prairie berry, mulberry, elderberry, Barbados cherry (acerola cherry), choke cherry, date, coconut, olive, raspberry, strawberry, huckleberry, loganberry, currant, dewberry, boysenberry, kiwi, cherry, blackberry, quince, buckthorn, passion fruit, sloe, rowan, gooseberry, pomegranate, persimmon, mango, rhubarb, papaya, lychee, plum, prune, date, currant, fig, etc. Numero
  • Non-mineral nutritive compounds such as vitamins can be added to the beverage reduced calorie products.
  • non-mineral nutritional supplement ingredients are known to those of ordinary skill in the art and include, for example, antioxidants and vitamins, including Vitamins A, D, E (tocopherol), C (ascorbic acid), Bj (thiamine), B 2 (riboflavin), B 6 , B 12, and K, niacin, folic acid, biotin, and combinations thereof.
  • the optional non-mineral nutritional supplements are typically present in amounts generally accepted under good manufacturing practices. In some
  • amounts are between about 1% and about 100% RDV, where such RDV are established.
  • the non-mineral nutritional supplement ingredient(s) are present in an amount of from about 5% to about 20% RDV, where established.
  • Acid used in beverage reduced calorie products disclosed here can serve any one or more of several functions, including, for example, providing antioxidant activity, lending tartness to the taste of the beverage, enhancing palatability, increasing thirst quenching effect, modifying sweetness and acting as a mild preservative by providing microbiological stability.
  • Any suitable edible acidulant may be used, for example citric acid, malic acid, tartaric acid, phosphoric acid, ascorbic acid, lactic acid, formic acid, fumaric acid, gluconic acid, succinic acid, maleic acid, sodium acid sulfate and/or adipic acid.
  • the acid can be used in solution form, for example, and in an amount sufficient to provide the desired pH of the beverage.
  • the one or more acids of the acidulant are used in amount, collectively, of from about 0.01% to about 1.0% by weight of the beverage, e.g., from about 0.05% to about 0.5% by weight of the beverage, such as 0.1% to 0.25% by weight of the beverage, depending upon the acidulant used, desired pH, other ingredients used, etc.
  • a “full-calorie” beverage formulation is one fully sweetened with a nutritive sweetener.
  • nutritive sweetener refers generally to sweeteners which provide significant caloric content in typical usage amounts, e.g., more than about 5 calories per 8 oz. serving of beverage.
  • a “potent sweetener” means a sweetener which is at least twice as sweet as sugar, that is, a sweetener which on a weight basis requires no more than half the weight of sugar to achieve an equivalent sweetness. For example, a potent sweetener may require less than one-half the weight of sugar to achieve an equivalent sweetness in a beverage sweetened to a level of 10 degrees Brix with sugar.
  • Potent sweeteners include both nutritive (e.g., Lo Han Guo juice concentrate) and non-nutritive sweeteners (e.g., typically, Lo Han Guo powder).
  • potent sweeteners include both natural potent sweeteners (e.g., steviol glycosides, Lo Han Guo, etc.) and artificial potent sweeteners (e.g., neotame, etc.).
  • natural potent sweeteners e.g., steviol glycosides, Lo Han Guo, etc.
  • artificial potent sweeteners e.g., neotame, etc.
  • Commonly accepted potency figures for certain potent sweeteners include, for example,
  • Mogroside V 100-300 times as sweet as sugar
  • a "non-nutritive sweetener” is one which does not provide significant caloric content in typical usage amounts, i.e., is one which imparts less than 5 calories per 8 oz. serving of beverage to achieve the sweetness equivalent of 10 Brix of sugar.
  • reduced calorie beverage means a beverage having at least a 25% reduction in calories per 8 oz. serving of beverage as compared to the full calorie version, typically a previously commercialized full-calorie version.
  • a "low-calorie beverage” has fewer than 40 calories per 8 oz. serving of beverage.
  • zero-calorie or “diet” means having less than 5 calories per serving, e.g., per 8 oz. for beverages.
  • Natural embodiments of the beverage reduced calorie products disclosed here are natural in that they do not contain anything artificial or synthetic (including any color additives regardless of source) that would not normally be expected to be in the food.
  • a "natural" beverage composition is defined in accordance with the following guidelines: Raw materials for a natural ingredient exists or originates in nature. Biological synthesis involving fermentation and enzymes can be employed, but synthesis with chemical reagents is not utilized. Artificial colors, preservatives, and flavors are not considered natural ingredients. Ingredients may be processed or purified through certain specified techniques including at least: physical processes, fermentation, and enzymolysis. Appropriate processes and purification techniques include at least: absorption, adsorption, agglomeration, centrifugation, chopping, cooking (baking, frying, boiling, roasting), cooling, cutting,
  • Processing aids are considered incidental additives and may be used if removed appropriately.
  • Sweeteners suitable for use in various embodiments of the beverages disclosed herein include nutritive and non-nutritive, natural and artificial or synthetic sweeteners. Suitable sweeteners and combinations of sweeteners are selected for the desired nutritional characteristics, functional characteristics, taste profile for the beverage, mouthfeel and other organoleptic factors.
  • Non-nutritive artificial sweeteners suitable in some embodiments include, for example, peptide based sweeteners, e.g., aspartame, neotame, and alitame, and non-peptide based sweeteners, for example, sodium saccharin, calcium saccharin, acesulfame (including but not limited to acesulfame potassium), cyclamate (including but not limited to sodium cyclamate and/or calcium cyclamate), neohesperidin dihydrochalcone, and sucralose.
  • Alitame may be less desirable for caramel-containing beverages where it has been known to form a precipitate.
  • the beverage reduced calorie product employs aspartame as the sweetener, either alone or with other sweeteners.
  • the sweetener comprises aspartame and acesulfame potassium.
  • Other non-nutritive sweeteners suitable in some embodiments include, for example, sorbitol, mannitol, xylitol, glycyrrhizin, neohesperidin dihydrochalcone, D-tagatose, erythritol, meso-erythritol, malitol, maltose, lactose, fructo-oligosaccharides, Lo Han Guo powder, steviol glycosides, e.g., rebaudiosides such as Rebaudioside A, stevioside, etc., xylose, arabinose, isomalt, lactitol, maltitol, trehalulose, and ribose, and protein sweeten
  • steviol glycosides e.g., rebaudiosides such as Rebaudioside A, stevioside, etc. and related compounds, as discussed further below, are natural non-nutritive potent sweeteners. It will be within the ability of those skilled in the art, given the benefit of this disclosure, to select suitable non-nutritive sweeteners (e.g., one or combination of non-nutritive sweeteners, either alone or together with nutritive sweetener) for a particular embodiment of the beverage reduced calorie products disclosed here.
  • suitable non-nutritive sweeteners e.g., one or combination of non-nutritive sweeteners, either alone or together with nutritive sweetener
  • the sweetener component can include nutritive, natural crystalline or liquid sweeteners such as sucrose, liquid sucrose, fructose, liquid fructose, glucose, liquid glucose, leucrose, trehalose, glactose, isomaltulose, dextrose, maltodextrin, corn syrup solids, glucooligosaccharides, glucose-fructose syrup from natural sources such as apple, chicory, honey, etc., e.g., high fructose corn syrup, invert sugar, maple syrup, maple sugar, honey, brown sugar molasses, e.g., cane molasses, such as first molasses, second molasses, blackstrap molasses, and sugar beet molasses, sorghum syrup and/or others.
  • nutritive, natural crystalline or liquid sweeteners such as sucrose, liquid sucrose, fructose, liquid fructose, glucose, liquid glucose, leucrose, treha
  • Such sweeteners are present in some embodiments in an amount of from about 0.1% to about 20% by weight of the beverage ⁇ e.g. , from about 1 % to about 4%, 0.1% to about 3%, 2% to about 10% by weight), depending upon the desired level of sweetness for the beverage.
  • standardized liquid sugars as are commonly employed in the beverage industry can be used. Typically such
  • the sweeteners are edible consumables suitable for consumption and for use in beverages.
  • edible consumables is meant a food or beverage or an ingredient of a food or beverage for human or animal consumption.
  • the sweetener or sweetening agent used here and in the claims can be a nutritive or non-nutritive, natural or synthetic beverage ingredient or additive (or mixtures of them) which provides sweetness to the beverage, i.e., which is perceived as sweet by the sense of taste.
  • the perception of flavoring agents and sweetening agents may depend to some extent on the interrelation of elements.
  • Flavor and sweetness may also be perceived separately, i.e., flavor and sweetness perception may be both dependent upon each other and independent of each other. For example, when a large amount of a flavoring agent is used, a small amount of a sweetening agent may be readily perceptible and vice versa. Thus, the oral and olfactory interaction between a flavoring agent and a sweetening agent may involve the interrelationship of elements.
  • Non-nutritive, high potency sweeteners typically are employed at a level of
  • some embodiments of the beverages disclosed here employ steviol glycosides, e.g., rebaudiosides such as Rebaudioside A, stevioside, etc. or related compounds or mixtures of any of them for sweetening. These compounds can be obtained by extraction or the like from the stevia plant.
  • Stevia e.g., Stevia rebaudiana bectoni
  • the leaves contain a complex mixture of natural sweet diterpene glycosides.
  • Steviol glycosides, e.g., rebaudiosides such as Rebaudioside A, stevioside, etc. are components of Stevia that contribute sweetness.
  • these compounds are found to include stevioside (4-13% dry weight), steviolbioside (trace), the rebaudiosides, including rebaudioside A (2-4%), rebaudioside B (trace), rebaudioside C ( 1 -2%), rebaudioside D (trace), and
  • non-nutritive sweeteners steviol glycosides e.g., rebaudiosides such as Rebaudioside A, stevioside, etc. may be included in ready to drink beverage compositions at a weight percent of about 0.1 % to about 10.0%, and preferably between about 0.2% and about 0.75%.
  • the sweetener Lo Han Guo which has various different spellings and pronunciations and is abbreviated here in some instances as LHG, can be obtained from fruit of the plant family Cucurbitaceae, tribe Jollifieae, subtribe Thladianthinae, genus Siraitia. LHG often is obtained from the genus/species S. grosvenorii, S. siamensis, S.
  • Suitable fruit includes that of the genus/species S. grosvenorii, which is often called Lo Han Guo fruit.
  • LHG contains triterpene glycosides or mogrosides, which constituents may be used as LHG sweeteners.
  • Lo Han Guo is a potent sweetener which can be provided as a natural nutritive or natural non-nutritive sweetener.
  • Lo Han Guo juice concentrate may be a nutritive sweetener
  • Lo Han Guo powder may be a non-nutritive sweetener.
  • Lo Han Guo can be used as the juice or juice concentrate, powder, etc.
  • LHG juice contains at least about 0.1 %, e.g., from 0.1% to about 15%.
  • mogrosides preferably mogroside V, mogroside IV, (1 1-oxo-mogroside V), siamenoside and mixtures thereof.
  • LHG can be produced, for example, as discussed in U.S. patent No. 5,41 1 ,755.
  • Sweeteners from other fruits, vegetables or plants also may be used as natural or processed sweeteners or sweetness enhancers in some embodiments of the beverages disclosed here.
  • Preservatives may be used in at least certain embodiments of the beverages disclosed here. That is, some embodiments contain an optional dissolved preservative system. Solutions with a pH below 4 and especially those below 3 typically are "microstable,” i.e., they resist growth of microorganisms, and so are suitable for longer term storage prior to consumption without the need for further preservatives. However, an additional preservative system can be used if desired. If a preservative system is used, it can be added to the beverage reduced calorie product at any suitable time during reduced calorie production, e.g., in some cases prior to the addition of the sweetener.
  • preservation system or “preservatives” include all suitable preservatives approved for use in food and beverage compositions, including, without limitation, such known chemical preservatives as benzoic acid, benzoates, e.g., sodium, calcium, and potassium benzoate, sorbates, e.g., sodium, calcium, and potassium sorbate, citrates, e.g., sodium citrate and potassium citrate, polyphosphates, e.g., sodium hexametaphosphate (SHMP), dimethyl dicarbonate, and mixtures thereof, and antioxidants such as ascorbic acid, EDTA, BHA, BHT, TBHQ, EMIQ, dehydroacetic acid, ethoxyquin, heptylparaben, and combinations thereof.
  • preservatives include all suitable preservatives approved for use in food and beverage compositions, including, without limitation, such known chemical preservatives as benzoic acid, benzoates, e.g., sodium, calcium, and potassium benzoate
  • Preservatives can be used in amounts not exceeding mandated maximum levels under applicable laws and regulations.
  • the level of preservative used typically is adjusted according to the planned final reduced calorie product pH, as well as an evaluation of the microbiological spoilage potential of the particular beverage formulation.
  • the maximum level employed typically is about 0.05% by weight of the beverage. It will be within the ability of those skilled in the art, given the benefit of this disclosure, to select a suitable preservative or combination of preservatives for beverages according to this disclosure.
  • benzoic acid or its salts (benzoates) may be employed as preservatives in the beverage reduced calorie products.
  • beverage reduced calorie products disclosed here include, e.g., aseptic packaging and/or heat treatment or thermal processing steps, such as hot filling and tunnel pasteurization. Such steps can be used to reduce yeast, mold and microbial growth in the beverage reduced calorie products.
  • aseptic packaging and/or heat treatment or thermal processing steps such as hot filling and tunnel pasteurization.
  • thermal processing steps can be used to reduce yeast, mold and microbial growth in the beverage reduced calorie products.
  • U.S. Patent No. 4,830,862 to Braun et al. discloses the use of pasteurization in the reduced calorie production of fruit juice beverages as well as the use of suitable preservatives in carbonated beverages.
  • U.S. Patent No. 4,925,686 to astin discloses a heat-pasteurized freezable fruit juice composition which contains sodium benzoate and potassium sorbate.
  • heat treatment includes hot fill methods typically using high temperatures for a short time, e.g., about 190° F for 10 seconds, tunnel pasteurization methods typically using lower temperatures for a longer time, e.g., about 160° F for 10-15 minutes, and retort methods typically using, e.g., about 250° F for 3-5 minutes at elevated pressure, i.e., at pressure above 1 atmosphere.
  • the beverage reduced calorie products disclosed here optionally contain a flavor composition, for example, natural and synthetic fruit flavors, botanical flavors, other flavors, and mixtures thereof.
  • the term "fruit flavor” refers generally to those flavors derived from the edible productive part of a seed plant.
  • berry also is used here to include aggregate fruits, i.e., not “true” berries, but that are commonly accepted as a berry.
  • fruit flavor synthetically prepared flavors made to simulate fruit flavors derived from natural sources.
  • suitable fruit or berry sources include whole berries or portions thereof, berry juice, berry juice concentrates, berry purees and blends thereof, dried berry powders, dried berry juice powders, and the like.
  • fruit flavors include the citrus flavors, e.g., orange, lemon, lime and
  • the beverage concentrates and beverages comprise a fruit flavor component, e.g., a juice concentrate or juice.
  • a fruit flavor component e.g., a juice concentrate or juice.
  • botanical flavors can include those flavors derived from essential oils and extracts of nuts, bark, roots and leaves.
  • synthetically prepared flavors made to simulate botanical flavors derived from natural sources. Examples of such flavors include cola flavors, tea flavors, and the like, and mixtures thereof.
  • the flavor component can further comprise a blend of various of the above-mentioned flavors.
  • the particular amount of the flavor component useful for imparting flavor characteristics to the beverages of the present invention will depend upon the flavor(s) selected, the flavor impression desired, and the form of the flavor component. Those skilled in the art, given the benefit of this disclosure, will be readily able to determine the amount of any particular flavor component(s) used to achieve the desired flavor impression.
  • calorie products disclosed here include, e.g., spice flavorings, such as cassia, clove, cinnamon, pepper, ginger, vanilla spice flavorings, cardamom, coriander, root beer, sassafras, ginseng, and others.
  • spice flavorings such as cassia, clove, cinnamon, pepper, ginger
  • vanilla spice flavorings cardamom, coriander, root beer, sassafras, ginseng, and others.
  • Flavorings can be in the form of an extract, oleoresin, juice concentrate, bottler's base, or other forms known in the art.
  • such spice or other flavors complement that of a juice or juice combination.
  • the one or more flavorings can be used in the form of an emulsion.
  • a flavoring can be used in the form of an emulsion.
  • emulsion can be prepared by mixing some or all of the flavorings together, optionally together with other ingredients of the beverage, and an emulsifying agent.
  • the emulsifying agent may be added with or after the flavorings mixed together.
  • the emulsifying agent is water-soluble.
  • suitable emulsifying agents include gum acacia, modified starch, carboxymethylcellulose, gum tragacanth, gum ghatti and other suitable gums. Additional suitable emulsifying agents will be apparent to those skilled in the art of beverage formulations, given the benefit of this disclosure.
  • the emulsifier in some embodiments comprises greater than about 3% of the mixture of flavorings and emulsifier. In some embodiments, the emulsifier is from about 5% to about 30% of the mixture.
  • beverage concentrates and beverages disclosed here may contain additional ingredients, including, generally, any of those typically found in beverage
  • additional ingredients can typically be added to a stabilized beverage concentrate.
  • additional ingredients include, but are not limited to, caffeine, caramel and other coloring agents or dyes, antifoaming agents, gums, emulsifiers, tea solids and cloud components.
  • Reduced calorie food products comprise at least one food component, i.e. , any edible material suitable for human or animal consumption, whether or not fully or partially digestible).
  • food components include proteins,
  • Food reduced calorie products include, e.g. , oatmeal, cereal, baked goods ⁇ e.g. , cookies, crackers, cakes, brownies, breads, etc.); snack foods ⁇ e.g. , potato chips, tortilla chips, popcorn, snack bars, rice cakes, etc.) and other grain-based food reduced calorie products; sauces; candies, confections; desserts; coatings, frostings, or glazes; dairy products ⁇ e.g. , milk, yoghurt and sour milk drinks, ice cream); spreads (e.g. , jams and preserves, honey, chocolate spreads).
  • reduced calorie food products include, e.g. , oatmeal, cereal, baked goods (e.g. , cookies, crackers, cakes, brownies, breads, etc.), snack foods ⁇ e.g. , potato chips, tortilla chips, popcorn, snack bars, rice cakes, etc.), and other grain- based food products.
  • Ultrapure water used for chromatography was purified by means of a MilliQ-water Gradient A 10 system (Millipore, Schwalbach, Germany) and deuterated solvents for NMR spectroscopy were supplied by Euriso-Top (Gif-Sur-Yvette, France).
  • Reference samples of vescalagin (1 ) and castalagin (2) were isolated and purified from Quercus alba L. following the procedure reported earlier (34).
  • the battericT consisted of a sequence of eight casks differing in wood variety and volumes as given in parenthesis: barrel A (acacia, 50 L), B (chestnut, 40 L), C (cherry, 30 L), D (mulberry, 23 L), E (oak, 13 L), F (chestnut, 10 L), G (chestnut, 5 L), and H (chestnut, 5 L). Dry mass (35) and pH value of intermediary vinegar samples A (43.91%, pH 2.65), B (55.23%, pH 2.62), C (63.75%, pH 2.58), D
  • balsamic vinegar of Modena was obtained from another local producer in the region of Modena, Italy. All samples were kept at 4°C (40°F) in the dark until used for analysis.
  • the retentate was suspended with deionized water (200 mL) and filtered again under pressure (4 bar). This procedure was repeated twice, the retentate was then taken up in deionized water (50 mL), and filtrate and retentate were lyophilized to afford the low ( ⁇ 5kDa; TBV-LMW) and the high molecular weight fraction (> 5kDa; TBV-HMW) in yields of 656.3 and 8.7 g/L, respectively.
  • the isolates obtained for both fractions in various separations were pooled accordingly and, then, stored at -20 °C (-4°F) in the dark until further analysis.
  • chromatography was performed using 1 % aqueous acetic acid as solvent A, and acetonitrile containing 1% acetic acid as solvent B. Starting with 5% A and increasing A to 100% within 20 min, the effluent was monitored by means of an evaporative light scattering detector (ELSD) and fractionated into five subfractions, namely VII- 1 to VII-5, which separated from solvent under vacuum and then lyophilized twice.
  • ELSD evaporative light scattering detector
  • Acetylchloride (3 mmol) was added dropwise to a solution of 5-hydroxymethyl-2- furaldehyde (4 mmol) in THF/triethylamine (5/1 , v/v; 6 mL). After stirring for 18 h at 20°C, deionized water (1 mL) was added and the title compound was isolated by means of preparative HPLC on a 250 x 21.2 mm i.d., 5 ⁇ , Microsorb RP18 column (Varian, Darmstadt, Germany) using water/methanol (60/40, v/v) as the isocratic eluent. 5-[13C2]-Acetoxymethyl-2-furaldehyde (0.5 mmol) was obtained as a white powder and its structure verified by means of LC-MS/MS and NMR spectroscopy.
  • glycine m/z 76.1 ⁇ 76.0; +31/+10/+5/+6
  • glycine- 13C2-15N m/z 79.0 ⁇ 79.0; +41/+10/+5/+5
  • L-alanine m/z 90.1 ⁇ 90.0; +26/+10/+5/+6
  • L-alanine-13C3 m/z 93.0 ⁇ 93.0;
  • L-serine m/z 106.1 ⁇ 60.0; +26/+10/+17/+4
  • L-serine-13C3 m/z 109.0 ⁇ 62.0; +38/+10/+16/+5)
  • L-proline m/z 1 16.1 ⁇ 70.0; +21/+10/+21/+4
  • L- proline-13C5-15N m/z 122.0 ⁇ 75.0; +73/+10/+25/+5)
  • L-valine m/z 1 18.1 ⁇ 72.1 ; +21/+10/+15/+6)
  • L-valine- 13C5 m/z 124.0 ⁇ 77.0; +64/+ 10/+ 14/+ 10
  • L-threonine m/z 120.1 ⁇ 73.9; +36/10/+17/+6), L-threonine- 13C4-15N (m/z 125.0 ⁇ 78.0;
  • L-leucine/L-isoleucine m/z 132.1 ⁇ 86.0; +41 +10/+15/+6), L- leucine-13C2 (m/z 134.1 ⁇ 87.9; +46/+10/+15/+6), L-isoleucine-13C6 (m/z
  • L-glutamine m/z 147.0 ⁇ 84.0; +46/+10/+23/+6
  • L-glutamine- 13C5 m/z 152.0 ⁇ 88.0; +43/+10/+23/+10)
  • L-glutamic acid m/z 148.1 ⁇ 84.0;
  • L-glutamic acid-13C5-15N m/z 154.0 ⁇ 89.0; +38/+10/+23/+10)
  • L-lysine m/z 147.0 ⁇ 84.0; +46/+10/+23/+6
  • L-lysine-13C6-15N2 m/z
  • L-phenylalanine m/z 166.0 ⁇ 120.0; +51/+10/+19/+10), L- phenylalanine-d5 (m/z 171.0 ⁇ 125.0; +48/+ 10/+ 19/+ 10), L-arginine (m/z
  • L-tyrosine m/z 182.1 ⁇ 136.0; +26/+ 10/+ 19/+ 10
  • L-tyrosine-d4 m/z 186.0- ⁇ 140.0; +38/+ 10/+ 19/+ 10
  • L-tryptophan m/z 205.1 ⁇ 146.0;
  • Phenols and 5-Hydroxymethyl-2-furaldehyde Following a literature procedure with some modifications (22), an aliquot (1 mL) of the vinegar samples was applied onto a Strata C I 8-E Giga Tube, 55 ⁇ , 7 ⁇ , RP- 18 cartridge ( 10g/60 mL, Phenomenex, Aillesburg, Germany), which was equilibrated with methanol, followed by water ( 100 mL, each).
  • the target analytes were eluted with methanol ( 100 mL) and, after removing the solvent in vacuum, the residue was taken up in acetonitrile/water (20/80, v/v; 500 ⁇ ) and an aliquot (15 ⁇ ) was injected into the LC-MS/MS-system 2 equipped with a 150 x 2 mm i.d., 5 ⁇ , Synergy Fusion RP18 column (Phenomenex, Aillesburg, Germany).
  • Phenolic acids and esters were analyzed in the positive electrospray ionization mode (ESI+), using the mass transitions and declustering potential (DP, in V), entrance potential (EP, in V), cell entrance potential (CEP, in V), collision energy (CE, in V), and cell exit potential (CXP, in V) given in parentheses: caffeic acid (m/z 181 .1—+89.0;
  • the target analytes were eluted with methanol (100 mL) and, after removing the solvent in vacuum, the residue was taken up in acetonitrile/water (20/80, v/v; 500 ⁇ ) and an aliquot (15 ⁇ ) was injected into the LC-MS/MS-system 1 equipped with a 150 x 2 mm i.d., 5 ⁇ , Luna Phenylhexyl column (Phenomenex, Aillesburg, Germany).
  • Vescalagin (1), castalagin (2), and (+)- dihydrorobinetin (3) were analyzed in the in the MRM mode by use of negative electrospray ionization using the mass transitions and declustering potential (DP, in V), entrance potential (EP, in V), collision energy (CE, in V), and cell exit potential (CXP, in V) given in parentheses: vescalagin/castalagin (m/z 933.0 ⁇ 301.0; -150/- 10/-70/-7; m/z 933.0 ⁇ 631.0; -150/-10/-40/-29); (+)-dihydrorobinetin (m/z
  • 5-acetoxymethyl-2-furaldehyde and 5-[13C2]-acetoxymethyl-2- furaldehyde were analyzed in the positive electrospray ionization mode (ESI+), using the mass transitions and declustering potential (DP, in V), entrance potential (EP, in V), cell entrance potential (CEP, in V) collision energy (CE, in V), and cell exit potential (CXP, in V) given in parentheses: 5-acetoxymethyl-2-furaldehyde (m/z 168.9 ⁇ 109.0; +16/+7/+14/+17/+4), 5-[13C2]-acetoxymethyl-2-furaldehyde (m/z 171.0 ⁇ 109.0; +1 1/+8/+ 14/+17/+4).
  • DP mass transitions and declustering potential
  • EP entrance potential
  • CEP cell entrance potential
  • CE collision energy
  • CXP cell exit potential
  • the isotope labeled standard and the analyte were mixed in eight molar ratios from 0.1 to 8.0 keeping a constant concentration of the internal standard.
  • triplicate LC-MS/MS analysis calibration curves were prepared by plotting peak area ratios of each analyte to the respective internal standard against concentration ratios of each analyte to the internal standard using linear regression (correlation coefficient > 0.99).
  • 6-O-Acetyl-a/B-D-gIucopyranose (4) and l-O-Acetyl-B-D-fructopyranose (5) The balsamic vinegar samples were diluted with water (1/50; v/v), membrane-filtrated (0.45 ⁇ ), and an aliquot (990 ⁇ ) of the sample was then spiked with an aliquot of an internal standard solution (10 ⁇ ) containing 6-0-acetyl-a/B-[13C6]-D- glucopyranose (50 mg/L).
  • a basic taste recombinant (rTBVI-VI) was prepared by dissolving the tastants of TBV summarized in groups I- VI (Table 2) in their "natural” concentrations in bottled water and adjusting the pH-value of this solution to 3.0 with trace amounts of hydrochloric acid (0.1 M).
  • an extended taste recombinant (rTBVI-VII) with the taste compounds given in groups I-VI (Table 2) and the TBV-HMW fraction (group VII in Table 2), each in its "natural” concentration, and a total taste recombinant (rTBVtotal) containing all tastants from groups I-VIII of TBV were prepared.
  • rBVtotal a total taste recombinant (rBVtotal) was prepared containing the individual taste compounds of BV, each in its "natural" concentration (Table 2). After equilibration for 12 h, the overall taste profiles of rTBVI-VI, rTBVI-VII, rTBVtotal, and rBVtotal were evaluated by means of taste profile analysis.
  • Threshold concentrations of sour sweet, bitter, salty, or umami tasting compounds were determined in bottled water adjusted to pH 3.0 with trace amounts of hydrochloric acid (0.1 M), using triangle tests with ascending concentrations of the stimulus following the procedure reported in the literature (23). To overcome carry-over effects, astringent tasting compounds were evaluated by use of the already reported half tongue test (36). Values between individuals and separate sessions did not differ more than plus or minus one dilution step; as a result, a threshold value of e.g. 900 ⁇ /L for gluconic acid represents a range of 450- 1800 ⁇ /L.
  • TDA taste Dilution Analysis
  • Concentrations of the stimuli ranged from 0.2 to 10.0 mmol/L for 5-hydroxymethyl-2- furaldehyde and from 0.2 to 2.0 mmol/L for 5-acetoxymethyl-2-furaldehyde (6).
  • HPLC High Performance Liquid Chromatography
  • LC-MS/MS-system 1 a API 4000 Q-Trap LC-MS/MS system (Applied Biosystems Sciex Instruments, Darmstadt, Germany) connected to a 1200 HPLC-system (Agilent, Waldbronn, Germany);
  • LC- MS/MS-system 2 a API 3200 LC-MS/MS system (Applied Biosystems) connected to a 1 100 HPLC-system (Agilent, Waldbronn, Germany).
  • Ion spray voltage was set at 5500 V in the ESI+ mode and at -4500 V in the ESI- mode, source temperature was set at 425 °C, nitrogen was served as curtain gas (20 psi) and declustering potential was set at +/-25 V, respectively. Both mass spectrometers were operated in the full scan mode for monitoring of positive or negative ions. Fragmentation of [M+H]+ or [M-H]- pseudo molecular ions into specific reduced calorie product ions was induced by collision with nitrogen (4x10-5 Torr) and a collision energy of +/-25 V.
  • Declustering potential (DP), entrance potential (EP), collision cell entrance potential (CEP), collision energy (CE), and cell exit potential (CXP) were tuned for each individual compound by flow injection (10 ⁇ ) via syringe pump injection, detecting the fragmentation of the [M+H]+ or [M-H]- pseudomolecular ions into specific reduced calorie product ions after collision with nitrogen (4.5x10-5 Torr).
  • TMSP trimethylsilylpropionic acid-d4
  • Topspin software version 2.1 ; Bruker
  • Mestre-C software version 4.8.6; Mestrelab Research, Santiago de Compostella, Spain
  • the dendrogram was constructed by means of an agglomerative average linkage algorithm (39), whereas the distance between two clusters is defined as the average of distances between all pairs of objects and each pair is made up of one object from each group.
  • the BV sample exhibited a significantly more sour (4.3) and less sweet ( 1.5) taste profile with also lower scores judged for mouthfulness (1.0).
  • umami and salty taste were hardly perceived with an average intensity of 0.2.
  • the mean values obtained for each orosensory impression in triplicate analysis was used to calibrate the sensory panel for the precise sensory evaluation of TBV and the fractions isolated therefrom in the following.
  • TBV was separated by means of ultrafiltration using a polyethersulfone membrane with a 5 kDa cut-off to obtain the low molecular weight (TBV-LMW, ⁇ 5kDa) and the high molecular weight fraction (TBV-HMW, > 5kDa) after freeze- drying as amorphous powders.
  • TBV-LMW low molecular weight
  • TBV-HMW high molecular weight fraction
  • both fractions were taken up in bottled water in their "natural" concentrations, 1+2 diluted with table water, and, after adjusting the pH to 3.0, were analyzed by means of a comparative taste profile analysis using the 1+2 diluted TBVM as reference (Table 1 ).
  • Table 1 The intensities of the orosensory descriptors sweet, bitter, salty, and umami judged for the TBV-LMW fraction were rather close to those of the TBV sample, thus
  • dihydroflavonol (+)-dihydrorobinetin (3) was analyzed in TBV as it is reported as a marker molecule for storage of vinegars in Acacia barrels (40).
  • compounds 1-3 were analyzed by means of RP-HPLC-MS/MS in TBV and for comparison also in the BV sample, the latter of which is not matured in wooden barrels.
  • recording the characteristic mass transitions of vescalagin (1), castalagin (2) and (+)-dihydrorobinetin (3) in the BV sample did not show any signal (A/B; Figure 2).
  • the analysis of the TBV sample clearly demonstrated the presence of the wood-derived polyphenols 1 -3 (C/D; Figure 2).
  • DoT dose-over-threshold
  • group V the cations sodium and potassium and the anions chloride and phosphate were judged with DoT-factors between 1.5 and 3.1 in TBV, whereas none of the amino acids in group VI exceeded their recognition threshold for umami taste.
  • rTBVI-VII recombinant recombinant
  • Comparative taste profile analysis of rTBVI- VII revealed an increase in mouthfulness from 1.1 to 1.6, thus demonstrating the macromolecular components to play an important role in mouthfulness perception.
  • the recombinant rTBVI-VII induced a less long-lasting sweetness perception when compared to the authentic TBV or the TBV-LMF fraction, respectively, thus indicating that the basic taste recombinant is lacking compounds modulating the sweetness perception.
  • the TBV-LMW fraction was fractioned by means of gel absorption chromatography (GAC) on Sephadex LH-20 material using a methanol/water gradient. Monitoring the effluent by means of UV/Vis detection, the TBV-LMW fraction was separated into ten fractions, namely I-X ( Figure 3), which were individually collected and freeze-dried twice.
  • GAC gel absorption chromatography
  • the proton signals H-C(3), H- C(5), H-C(6), and H-C(8) resonating at 5.17, 6.71 , 7.39, and 9.59 ppm were assigned as the protons of the 5-hydroxymethyl-2-furaldehyde moiety.
  • the singlet signal resonating at 2.02 ppm and integrating for three protons indicated the presence of a methyl group.
  • the 13C NMR spectrum exhibited the resonance signal at 178.2 ppm as expected for the aldehyde carbonyl atom C8 and, in addition, another carbon signal C(2) at 170.5 ppm, thus suggesting the presence of an acetyl ester moiety.
  • HMBC Heteronuclear couplings
  • the TBV sample contained 13823 and 8329 ⁇ ⁇ 1 -O-acetyl-P-D-fructopyranose (5) and 6-0- acetyl-a/p-D-glucopyranose (4) as well as 315 ⁇ ⁇ . of 5-acetoxymethyl-2- furaldehyde (6) (Table 2).
  • Calculation of DoT-factors revealed values of 0.7 and 0.8 for the intrinsic sweetness of the hexose acetates 5 and 4, respectively, and a value of 0.2 for 5-acetoxymethyl-2-furaldehyde based on its threshold concentration in a 4% sucrose solution (Table 2).
  • BV showed significantly lower DoT- factors for the minerals as well as the polyphenolic acids, and the wood-derived ellagitannins 1 and 2 as well as (+)-dihydrorobinetin (3) were not detectable at all in BV, thus indicating the lack of any wood maturation in industrial BV manufacturing.
  • sensometabolites ( Figure 7).
  • concentrations used for these calculations are based on fresh weight (A; Figure 7) and dry matter (B), respectively.
  • the cluster analysis quantifies the degree of similarity between the sensometabolites by calculating the distance between all possible pairs of molecules. The two most similar sensometabolites were then grouped together and the distance measure recalculated. This iterative process was continued until all sensometabolites were members of a single cluster. This resulting hierarchical clustering is visually displayed as a dendrogram ( Figure 7A, B). The closer the sensometabolites are to each other in the dendrogram, the smaller the differences in their concentration patterns throughout the entire TBVM manufacturing process.
  • Cluster l a ( Figure 7A) consisted of vescalagin ( 1 ), glycolic acid, quinic acid, and gluconic acid, following a mixed trend throughout the maturation procedure. For example, gluconic acid went through a maximum in barrel E fitting well to decreasing microbial activity with increasing age (/, 6). In comparison, highest levels of vescalagin were observed in barrel H made from fresh chestnut collaborating well with its release from chestnut (41).
  • Cluster l b ( Figure 7A) comprised the sensometabolites increasing in concentration upon maturation, among them the sweet tasting fructose, glucose, 1 -O-acetyl-P-D- fructopyranose, 6-0-acetyl-a/p-D-glucopyranose, glycerol, sorbitol, xylitol, erythritol, mannitol, and the sweetness modulating 5-acetoxymethyl-2-furaldehyde (6), being well in line with the increased sweetness impact developing from sample A to H.
  • the sour tasting organic acids malic acid, citric acid, lactic acid, tartaric acid, and the astringent compounds gallic acid and 5-hydroxymethylfurfural increased with maturation age.
  • Cluster l a ( Figure 7B) comprises the sensometabolites which are partially degraded with increasing degree of maturation, namely the astringent phenolic compounds, the sour tasting acetic acid, gluconic acid, malic acid, and lactic acid, as well as mannitol.
  • Cluster l b contained sensometabolites which were detected in highest concentrations in barrel sample A and dropped drastically already in barrel B such as, e.g. (+)-dihydrorobinetin (3).
  • cluster 2 (Figure 7B) summarized the sensometabolites which are
  • (+)-Dihydrorobinetin a Marker of Vinegar Aging in Acacia (Robinia pseudiacacia) Wood. J. Agric. Food Chem. 2009, 57, 9551-9554.
  • L-leucine 1 1000 6 143 ( ⁇ 7.3) 531 ( ⁇ 2.3) ⁇ 0.1 ⁇ 0. 1
  • Dose- over-threshold (DoT) factor is calculated as the ratio of
  • rTBV[.vi contained the tastants in groups I-VI in concentrations given in Table 2 in water (pH 3.0); rTBVj.vi was prepared by dissolving the HMW fraction (8.7 g/L) in rTBV I-V i; rTBV, 0 , a i was prepared by spiking rTBV
  • V u w tastant group VIII (compounds 4-6) in concentrations given in Table 2; rBV, ota i contained the tastants in groups I-VIII in concentrations given in Table 2 in water (pH 3.0).
  • TDA taste Dilution Analysis
  • cTPA Comparative Taste Profile Analysis
  • a Numbering of GAC fractions corresponds to Figure 3.
  • Taste dilution analysis was carried out after dissolving the individual GAC fractions in bottled water (pH 3.0) in their "natural" concentration ratios.
  • the individual GAC fractions were dissolved in a 1 -2 dilution of the basic taste recombinant solution rTBV
  • V i (pH 3.0) containing all tastant groups I-VI given in Table 2.
  • the descriptors given by each panellist were collected and those given by at least nine out of the twelve panellists are given.
  • the rTBVi.vi solution lacking any GAC fractions was used as control, n.d. no difference detectable.

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Abstract

Cette invention concerne un composant exhausteur de goût sucré comprenant principalement 5-acétoxyméthyl-2-furaldéhyde qui peut être utilisé pour renforcer le goût sucré de produits à teneur réduite en calories comprenant un édulcorant nutritif.
PCT/IB2013/000177 2012-02-13 2013-02-12 Exhausteur de goût sucré WO2013121264A1 (fr)

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Cited By (5)

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Publication number Priority date Publication date Assignee Title
US10301275B2 (en) 2017-03-17 2019-05-28 Altria Client Services Llc Sweet taste modulators
CN111599416A (zh) * 2020-06-04 2020-08-28 广东省生物工程研究所（广州甘蔗糖业研究所） 一种快速确定甜味剂配方及使用量的方法及其应用
WO2020183404A1 (fr) * 2019-03-12 2020-09-17 Monari Federzoni S.P.A. Boisson alimentaire
CN113686986A (zh) * 2021-08-19 2021-11-23 北京工业大学 超声-固相萃取-液质联用同时检测市政污泥中6种人工甜味剂的方法
WO2023166503A1 (fr) 2022-03-01 2023-09-07 Celluflux Ltd. Synthèse de 5-acétoxyméthylfurfural en présence de catalyseurs salins recyclables

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10301275B2 (en) 2017-03-17 2019-05-28 Altria Client Services Llc Sweet taste modulators
WO2020183404A1 (fr) * 2019-03-12 2020-09-17 Monari Federzoni S.P.A. Boisson alimentaire
CN111599416A (zh) * 2020-06-04 2020-08-28 广东省生物工程研究所（广州甘蔗糖业研究所） 一种快速确定甜味剂配方及使用量的方法及其应用
CN113686986A (zh) * 2021-08-19 2021-11-23 北京工业大学 超声-固相萃取-液质联用同时检测市政污泥中6种人工甜味剂的方法
WO2023166503A1 (fr) 2022-03-01 2023-09-07 Celluflux Ltd. Synthèse de 5-acétoxyméthylfurfural en présence de catalyseurs salins recyclables

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