US20030003212A1 - Taste modifiers - Google Patents

Taste modifiers Download PDF

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US20030003212A1
US20030003212A1 US09880420 US88042001A US2003003212A1 US 20030003212 A1 US20030003212 A1 US 20030003212A1 US 09880420 US09880420 US 09880420 US 88042001 A US88042001 A US 88042001A US 2003003212 A1 US2003003212 A1 US 2003003212A1
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acid
chlorogenic
acids
consumable
taste
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US09880420
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Mingjien Chien
Hans Leersum
Alex Hausler
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Givaudan SA
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Givaudan SA
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    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12GWINE; OTHER ALCOHOLIC BEVERAGES; PREPARATION THEREOF
    • C12G3/00Preparation of other alcoholic beverages
    • C12G3/04Preparation of other alcoholic beverages by mixing, e.g. liqueurs
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23CDAIRY PRODUCTS, e.g. MILK, BUTTER, CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C11/00Milk substitutes, e.g. coffee whitener compositions
    • A23C11/02Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
    • A23C11/10Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing or not lactose but no other milk components as source of fats, carbohydrates or proteins, e.g. soy milk
    • A23C11/103Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing or not lactose but no other milk components as source of fats, carbohydrates or proteins, e.g. soy milk containing only proteins from pulses, oilseeds or nuts, e.g. soy or nut milk
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23CDAIRY PRODUCTS, e.g. MILK, BUTTER, CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00Milk preparations; Milk powder or milk powder preparations
    • A23C9/12Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1307Milk products or derivatives; Fruit or vegetable juices; Sugars, sugar alcohols, sweeteners; Oligosaccharides; Organic acids or salts thereof or acidifying agents; Flavours, dyes or pigments; Inert or aerosol gases; Carbonation methods
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52Adding ingredients
    • A23L2/56Flavouring or bittering agents
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52Adding ingredients
    • A23L2/60Sweeteners
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • A23L27/202Aliphatic compounds
    • A23L27/2024Aliphatic compounds having oxygen as the only hetero atom
    • A23L27/2026Hydroxy compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • A23L27/204Aromatic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30Artificial sweetening agents
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/84Flavour masking or reducing agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/185Magnoliopsida (dicotyledons)
    • A61K36/74Rubiaceae (Madder family)

Abstract

The present invention discloses a method to modify the taste profile of consumables by adding esters of quinic acid and cinnamic acid derivatives. These esters, which belong to the family of chlorogenic acids, may be synthetic or may be extracted from a natural source such as a botanical. Chlorogenic acid is added to consumables to mask bitter off-tastes or other displeasing tastes imparted by one or more natural, synthetic or semi-synthetic components in the consumable.

Description

    FIELD OF THE INVENTION
  • [0001]
    The invention relates to a process to modify the taste profile of a consumable by adding esters of quinic and cinnamic acid derivatives.
  • BACKGROUND OF THE INVENTION
  • [0002]
    Various consumables, such as food products, beverages, pharmaceuticals, etc. contain substances which provide bitter notes and adversely contribute to the overall flavor of the product. In many instances, the flavor quality of such consumables would be improved by diminishing or removing the bitter notes, while at the same time preserving or enhancing the contribution made to the overall flavor by the non-bitter flavor components.
  • [0003]
    Non-nutritive sweeteners, also called artificial sweeteners, for example, saccharine and aspartame, are only one example of substances that provide bitter notes. Therefore consumables such as beer, coffee, soft drinks, desserts and pharmaceutical products that are sweetened with non-nutritive sweeteners may possess bitter flavors or after-flavors that are generally regarded as undesirable by many consumers.
  • [0004]
    Because of the prevalence and popularity of non-nutritive sweeteners in consumables, several processes have been described for modifying the taste profile of consumables that contain these non-nutritive sweeteners. For example, U.S. Pat. No. 3,296,079 discloses the addition of 0.003% to 160% maltol to edible foodstuffs sweetened with non-nutritive sweetening agents to mask unpleasant aftertastes. U.S. Pat. No. 4,304,794 discloses the addition of aliphatic polyols to minimize the bitter aftertaste of 2,4,6,3′-tetrahydroxy4′-methoxydihydrochalcone. U.S. Pat. Nos. 4,758,438; 3,647,482; and 3,667,969 disclose that the bitter aftertaste of saccharine is diminished by addition of the proteins thaumatin and monellin, by addition of ribonucleosides, ribonucleotides and their deoxy analogs, and by addition of D-galactose, respectively. U.S. Pat. No. 5,336,513 discloses that certain derivatives of cinnamic acid and their salts inhibited the bitterness of consumable materials, such as pharmaceutical preparations, foodstuffs and beverages that were sweetened with the artificial sweeteners saccharine and acesulfame K.
  • [0005]
    Processes have also been described for modifying a foodstuff or beverage by enhancing its sweetness characteristics. For example, U.S. Pat. Nos. 3,867,557 and 3,908,026 disclose that mixing or co-dissolving paramethoxycinnarnaldehyde (PMCA) with other known natural or synthetic sweetening agents results in a composition having enhanced sweetness characteristics. These patents also disclose that PMCA enhances the flavor characteristics of vanillin and instant coffee, while suppressing their associated bitterness.
  • [0006]
    Processes disclosed in U.S. Pat. Nos. 3,924,017 and 3,916,028 show that salts of chlorogenic acid, caffeic acid, cynarine, and their isomers induce sweetness, and impart a very pleasant, sweet character to non-sweet foodstuffs or to foods with very low sweetness, such as water and milk.
  • [0007]
    The above-described references either disclose methods for enhancing or inducing sweetness in consumables, or methods using specific agents to mask unpleasant aftertastes in consumables containing artificial sweeteners. Additional compounds and methods to modify the many types of off-tastes and off-notes in the many varieties of consumables are desired.
  • SUMMARY OF THE INVENTION
  • [0008]
    The invention is directed to a method for modifying an off-taste of a consumable by adding chlorogenic acids to the consumable. The off-taste may be a metallic and/or bitter taste, such as occurs with consumption of products containing artificial sweeteners. The off-taste may be a burning taste, such as occurs with consumption of alcohols and carbonated products. The off-taste may be a beany, and/or aldehydic taste, such as occurs with consumption of products containing soy.
  • [0009]
    As defined herein, chlorogenic acids are esters of trans-cinnamic acids and quinic acid, and may be mixtures in this family. They may be extracted from natural sources such as botanicals, and/or may be synthetic.
  • [0010]
    The amount of chlorogenic acids added to the consumable is sufficient to modify the off-taste, usually at a concentration from about 0.0001%w/v to about 0.1%w/v the consumable.
  • [0011]
    In other embodiments, the invention is directed to a method for modifying a taste of a consumable containing an artificial sweetener by adding chlorogenic acids, a method for modifying a taste of a consumable containing an alcohol by adding chlorogenic acids, a method for modifying a taste of a consumable containing a soy product by adding chlorogenic acids, and a method for modifying a taste of a carbonated consumable by adding chlorogenic acids.
  • [0012]
    In yet another embodiment, the invention is directed to a method for modifying sweetness perception of a consumable by adding chlorogenic acids.
  • [0013]
    The invention is also directed to a consumable containing an ingredient or component that imparts an off-taste to the consumable, and chlorogenic acids in an amount to modify the off-taste. The ingredient or component imparting an the off-taste may be a non-nutritive sweetener, soy or a soy product, alcohol, and/or a carbonated ingredient.
  • [0014]
    The invention is additionally directed to a sweetening composition for consumables, where the sweetening composition contains a non-nutritive sweetener and from about 0.0001%w/v to about 0.1%w/v chlorogenic acids.
  • [0015]
    These and other advantages of the invention will be apparent from the following drawings, description, and examples.
  • BRIEF DESCRIPTION OF DRAWINGS
  • [0016]
    [0016]FIG. 1 shows the structure of quinic acid.
  • [0017]
    [0017]FIG. 2 shows examples of acids belonging to the cinnamic acid family.
  • [0018]
    [0018]FIG. 3 shows the structure of 5-caffeoylquinic acid.
  • DETAILED DESCRIPTION OF THE INVENTION
  • [0019]
    The invention discloses the use of chlorogenic acid, defined herein as esters of quinic acid and cinnamic acid derivatives, to modify or mask an off-taste in a consumable. In the method, the esters of quinic acid and cinnamic acid derivatives are added to consumables to modify or mask bitter off-tastes or other displeasing tastes imparted by one or more natural, synthetic or semi-synthetic components in the consumable.
  • [0020]
    An off-taste may be imparted by a non-nutritive (artificial) sweetener. Off-tastes produced by non-nutritive sweeteners have been described as being metallic and/or bitter. Non-nutritive sweeteners are present in vast categories of consumables including, but not limited to, soft drinks, dairy products, dessert products, savory products, salad dressings, sauces, condiments, alcoholic beverages, confections, gums, and medicaments. Examples of non-nutritive sweeteners include L-aspartyl-L-phenylalanine methyl ester (aspartame), saccharine and salts thereof, acesulfame salts (e.g., acesulfame K), cyclohexylsulfamic acid, dihydrochalcones, xylitol, neotame, sucralose, alitame cyclamates, steviol derivatives, and the like. In the inventive composition, the consumable contains an amount of chlorogenic acids sufficient to modify or mask the off-taste imparted by the artificial sweetener. A sweetening composition of the non-nutritive sweetener and from about 0.0001%w/v about 0.1%w/v chlorogenic acids may also be prepared and added to the consumable. In other embodiments, the concentration of chlorogenic acids in a consumable containing one or more non-nutritive sweeteners is in the range from about 0.001%w/v about 0.01%w/v.
  • [0021]
    An off-taste may be imparted by alcohol in the consumable product. Alcohols include both grain alcohols and fermentation products (beer and wine), either alone or in combination with other components. Off-tastes produced by alcohols have been described as imparting a burning taste. In one embodiment, the concentration of chlorogenic acids in a consumable containing alcohol is in the range from about 0.0001%w/v to about 0.1%w/v. In another embodiment, the concentration of chlorogenic acids in a consumable containing alcohol is in the range from about 0.001%w/v to about 0.01%w/v.
  • [0022]
    An off-taste may be imparted by a soy product. As used herein, soy includes all consumables containing soy in any form, including soybean oil used either alone, in combination, as a nutraceutical, or as a medicament; soy bean curd; soy milk, soy butter; soy paste; etc. Off-tastes produced by soy products have been described as imparting a beany, aldehyde-like taste. In one embodiment, the concentration of chlorogenic acids in a consumable containing a soy product is in the range from about 0.0001%w/v to about 0.1%w/v. In another embodiment, the concentration of chlorogenic acids in a consumable containing a soy product is in the range from about 0.01%w/v to about 0.1%w/v.
  • [0023]
    An off-taste may be due to carbonation in the product. Examples of carbonated products include colas, citrus-flavored beverages, ales, beers and other consumables containing these products such as ices and frozen confections. Off-tastes produced by carbonated products have been described as imparting a burning sensation. In one embodiment, the concentration of chlorogenic acids in a carbonated product is in the range from about 0.0001%w/v to about 0.1%w/v. In another embodiment, the concentration of chlorogenic acids in a carbonated product is in the range from about 0.0005%w/v to about 0.005%w/v.
  • [0024]
    Besides modifying an off-taste, the esters of quinic acid and cinnamic acid may also mask an off-taste by reducing its perception and/or enhancing an overall sweetness perception.
  • [0025]
    As used herein, the term consumable broadly includes all products that are ingested. These encompass foods and beverages whether or not they provide nutritive value and in all forms, including forms requiring reconstitution; condiments; sweeteners; nutraceuticals; gelatins; pharmaceutical and non-pharmaceutical gums, tablets, lozenges, drops, emulsions, elixirs, syrups, etc.
  • [0026]
    Specifically, a mixture of esters of quinic acid and various cinnamic acid derivatives encompassing members of the family of chlorogenic acids are added to various consumables to improve the taste or taste perception of the consumable and/or to decrease off-tastes. The quinic and cinnamic acid esters may be naturally occurring, synthetic, or a combination of natural and synthetic.
  • [0027]
    The structure of quinic acid (IR-(1α, 3α, 4α, 5β)-1, 3, 4, 5 tetrahydroxy-cyclohexane carboxylic acid) is shown in FIG. 1. Quinic acid has axial hydroxyl groups (on carbons 1 and 3) and equatorial hydroxyl groups (on carbons 4 and 5). Substitutions on the R groups produce various chlorogenic acids, as derived from Clifford, ASIC, 17 colloque, Nairobi, 1997, pp 79-91 which is expressly incorporated by reference herein in its entirety and listed in Table 1, where CQA is caffeoylquinic acid, FQA is feruloylquinic acid, CoQA is coumaroylquinic acid, and CFQA is caffeoylferuloylquinic acid.
    TABLE 1
    Compound Identity of R3 Identity of R4 Identity of R5
    3-CQA caffeic acid H H
    4-CQA H caffeic acid H
    5-CQA H H caffeic acid
    3-FQA ferulic acid H H
    4-FQA H ferulic acid H
    5-FQA H H ferulic acid
    3-p-CoQA p-coumaric H H
    acid
    4-p-CoQA H p-coumaric H
    acid
    5-p-CoQA H H p-coumaric
    acid
    3, 4-diCQA caffeic acid caffeic acid H
    3, 5-diCQA caffeic acid H caffeic acid
    4, 5-diCQA H caffeic acid caffeic acid
    3, 4-CFQA caffeic acid ferulic acid H
    3, 4-CFQA ferulic acid caffeic acid H
    3, 5-CFQA caffeic acid H ferulic acid
    3, 5-CFQA ferulic acid H caffeic acid
    4, 5-CFQA H caffeic acid ferulic acid
    4, 5-CFQA H ferulic acid caffeic acid
  • [0028]
    The structures of various acids or derivatives belonging to the cinnamic acid family are shown in FIG. 2. Cinnamic acids and their derivatives, used as sweetness enhancers/inducers in various products, encompass a series of trans-3-phenyl-propenoic acids that differ in the chemical groups substituted on the aromatic ring. They are widely distributed as organic conjugates in a variety of plant material, and are rarely found as free acids in unprocessed plant material. Besides cinnamic acid itself, the most common of the cinnamic acids in this family are caffeic acid (3,4-dihydroxycinnamic acid), ferulic acid (3-methoxy-4-hydroxycinnamic acid), sinapic acid (3,5-dimethoxy4-hydroxycinnamic acid), and p-coumaric acid (p-hydroxycinnamic acid).
  • [0029]
    “Chlorogenic acid” is a trivial name used somewhat loosely in the literature to describe a range of phenolic acids found in plant materials. For example, in some literature references, 5-caffeoylquinic acid alone is referred to as “chlorogenic acid”. As used herein, however, the term chlorogenic acid is used as prescribed in Clifford, J. Sci. Food Agric., 2000, 80, pp. 1033-1043, which is expressly incorporated by reference herein in its entirety, to refer to the family of related quinic acid conjugates. This reference teaches that the term chlorogenic acid comprises a family of esters that form between certain trans-cinnamic acid derivatives and quinic acid. Clifford subdivides chlorogenic acids by the identity, number, and position of the acyl residues on the quinic acid. This reference teaches that the most common individual chlorogenic acid is 5-O-caffeoylquinic acid (5-CQA), whose structure is shown in FIG. 3, and that while 5-CQA is commonly referred to as chlorogenic acid (CGA), that this is a term which should be used only to refer to the family of related quinic acid conjugates.
  • [0030]
    Chlorogenic acids are widely distributed in the plant kingdom and occur in fruits, leaves and other tissues of dicotyledonous plants. They may be extracted from a variety of natural sources such as green coffee beans (e.g., Arabica, Robusta and Liberica); leaves of Illex paraguariensis, pome fruits (e.g., apples and pears); stone fruits (e.g., cherries and plums); berry fruits; citrus fruits; brassica vegetables (e.g., kale, cabbage and brussel sprouts); solanaceae (e.g., potato tubers, tomatoes, and aubergines); asteraceae (e.g., chicoryroot and artichokes); and a variety of other miscellaneous vegetables.
  • [0031]
    They may also be found in cereal grains (e.g., oats, barley, rye, rice, corn and wheat). The amount and types of chlorogenic acids that are present vary depending upon the source.
  • [0032]
    A variety of chlorogenic acids are found in green coffee beans (Clifford, ASIC, 17 colloque, Nairobi, 1997 pp. 79-91). Specifically, green coffee bean extracts contain the following chlorogenic acids: three mono-esters of caffeic and quinic acids, namely, 3-caffeoylquinic acid (3-CQA), 4-caffeoylquinic acid (4-CQA), and 5-caffeoylquinic acid (5-CQA); three mono-esters of p-coumaric and quinic acids: namely, p-coumaroylquinic acids (p CoQA); three mono-esters of ferulic and quinic acids: feruloylquinic acids (FQA); and three di-esters of caffeic and quinic acids: namely, 3,4-dicaffeoylquinic acid (3,4-di CQA), 3,5-dicaffeoylquinic acid (3,5-di CQA), and 4,5-dicaffeoylquinic acid (4,5-di CQA). In addition, there are also six mixed di-esters of caffeic, ferulic, and quinic acids known as the caffeoylferuloylquinic acids (CFQA).
  • [0033]
    The amounts of several of these chlorogenic acids found in extracts of green Robusta coffee beans have been reported. These values, as follows, are expressed as g/kg of dry green coffee bean: 7.32 g 3-CQA, 11.25 g 4-CQA, 49.66 g 5-CQA, 6.04 g 5-FQA, 5.05 g 3,4-di CQA, 4.61 g 3,5-di CQA, and 4.11 g 4,5-di CQA (Trugo and Macrae, Food Chemistry, 1984,15, pp. 219-227, which is expressly incorporated by reference herein in its entirety). While the presence of chlorogenic acids in green coffee bean extracts is known, the use of these chlorogenic acids to decrease off-taste in various types of consumables has not previously been reported.
  • [0034]
    In the inventive method, chlorogenic acids are provided to the consumable. Either chlorogenic acids extracted from one or more botanical sources, and/or synthetic chlorogenic acids may be used. A solution of the chlorogenic acids may be added to the consumable to modify or mask an off-taste imparted by one or more substances, such as an artificial sweetener. Alternatively, chlorogenic acids may be added to the substance(s) imparting an off-taste to form a composition which is added to the consumable. The total concentration of chlorogenic acids in the consumable ranges from about 0.0001%w/v to about 0.1%wv, depending upon the type of consumable, the source of chlorogenic acids, the qualitative and/or quantitative modification desired, the substance(s) imparting an off-taste, and the presence of other desirable or undesirable taste components.
  • [0035]
    As an example of an extraction procedure, the procedure used for extraction of chlorogenic acids from green coffee beans is described. The procedure may be modified to extract chlorogenic acids from other plant sources, as is known to one skilled in the art. Therefore, while the extraction of chlorogenic acids from green coffee beans is described for illustration, it will be appreciated that the invention is not limited to the use of chlorogenic acids extracted from this source.
  • [0036]
    About 4.0 kg of green Robusta coffee beans were mixed with constant agitation in 16.0 kg of water at 80° C. for at least four hours. The extract was collected by either decanting, centrifuging, or filtering. The beans were then extracted with an additional 6 kg of water at 80° C. for at least another four hours. The extracts were combined and the water was evaporated by vacuum to concentrate the extract to about 5 or 6 kg. An amount of ethanol (95%) equal to one and one-half times the weight of the concentrated extract was added; the amount of ethanol may be increased to about four times the weight of the concentrated extract if a higher content of chlorogenic acids in the final extract is desired. The mixture was stirred for 15 minutes, and the slurry was allowed to stand at ambient temperature for at least one hour.
  • [0037]
    The resulting precipitate was removed by either centrifugation or filtration and was subsequently discarded. The ethanol was evaporated from the supernatant or filtrate under vacuum, and the aqueous solution was dried under vacuum to yield about 460-500 g of a tan-colored powder. Alternatively, the aqueous solution may be concentrated to an appropriate solid content of about 30% to 45% of the total weight, followed by spray-drying the concentrated aqueous solution to a tan colored powder. The powdered extract was soluble in water up to about 5%w/v pH 5.0.
  • [0038]
    The extract was analyzed by high performance liquid chromatography (HPLC) using a Prodigy ODS-3 column (150×4.6 mm, particle size 5 μm) (Phenomenex, Torrance, Calif.) at ambient temperature, interfaced with a mass spectroscopic detector (MSD) to measure the chlorogenic acids. The gradient used for elution of the compounds is given in Table 2.
    TABLE 2
    Acetonitrile/
    Time Flow Rate 0.1% Trifluoroacetic Water/0.1%
    (min) (mL/min) acid Trifluoroacetic acid
     0 0.8 10 90
    18 0.8 10 90
    30 0.8 70 30
    32 0.8 70 30
    33 0.8 10 90
    43 0.8 10 90
  • [0039]
    The conditions for MSD were as follows: atmospheric pressure chemical ionization mode; positive and negative polarity; gas temperature of 350° C.; vaporizer temperature of 450° C.; drying gas flow rate of 6.0 L/min nitrogen; nebulizer pressure of 35 psig; capillary voltage of 2500 V; corona current of 7 μA, and fragmentor voltage of 80 V. A standard curve was prepared using chlorogenic acid with the molecular formula of C16H8O9 (catalog No. C44206, Aldrich, Milwaukee, Wis.).
  • [0040]
    The analysis revealed the presence of several different chlorogenic acids, which amounted to about 51% of the total mass of the extract. The proportions of the various chlorogenic acids separated by HPLC and quantitated as a weight per weight percentage are shown in Table 3.
    TABLE 3
    Chlorogenic Acids %w/w
    5-CQA 16.7
    4-CQA 8.4
    3-CQA 8.6
    FQA (total) 8.9
    diCQA (total) 5.8
    CFQA (total) 3.0
  • [0041]
    Other chlorogenic acids were also likely present but were not detected using the conditions for analysis. It will be appreciated that the HPLC and MSD conditions may be modified to resolve different chlorogenic acids, and that the yield and content of chlorogenic acids may vary with different batches and different types of green coffee beans or different sources. Chlorogenic acids may be further purified, for example, using absorption column chromatography, to remove impurities; with undesired properties (e.g., color, low water solubility) from the extract.
  • [0042]
    Extracts of chlorogenic acids from several batches of green coffee beans were prepared as 2.8%w/v solutions, pH ranging from about pH 4.5 to about pH 6.0, and were added to various consumables based on the weight of powder. These solutions were added to consumables to modify and/or mask off-tastes.
  • [0043]
    The following examples illustrate the inventive method of modifying an off-taste in a consumable. The examples are for illustrative purposes only and are not to be construed as limiting the scope of the invention.
  • EXAMPLE 1
  • [0044]
    Chlorogenic Acids (Synthetic) Added to an Aged Artificially Sweetened Beverage
  • [0045]
    An artificially sweetened beverage was prepared by mixing 1.4 g aspartame, 0.9 g acesulfame K, 6 mL sodium benzoate (25%w/v in water), 1.3 mL phosphoric acid (85%w/v), and 0.5 mL citric acid (50%w/v in water). The volume of the mixture was adjusted to 1000 mL with water. The beverage mixture was aged for three weeks at 93° F.
  • [0046]
    A 2.8%w/w solution of a commercially available synthetic chlorogenic acid (>95% pure (1,3,4,5-tetrahydroxy-cyclohexanecarboxylic acid 3-[3,4-dihydroxycininamate]), Sigma Chemical Co., St. Louis, Mo.), in water, pH 5.6, was added to a portion of the aged beverage to a final concentration of 0.003%w/v. The beverage containing chlorogenic acid was evaluated and compared to the untreated beverage by a six member panel of trained flavorists. The beverage containing the commercial chlorogenic acid was judged by the panel to display markedly less of the metallic, slightly bitter aftertaste found in the aged artificially sweetened beverage.
  • EXAMPLE 2
  • [0047]
    Chlorogenic Acids (Extracted) Added to an Aged Artificially Sweetened Beverage
  • [0048]
    To another portion of the artificially sweetened beverage prepared as described in the first paragraph of Example 1, an aqueous solution of chlorogenic acids from the powdered extract of green coffee beans was added to a final concentration of 0.003%w/v chlorogenic acid. This beverage was evaluated by the same flavorist panel as described in Example 1. The beverage containing the chlorogenic acids extracted from green coffee beans was also judged to display markedly less of the metallic, slightly bitter aftertaste found in the aged artificially sweetened beverage.
  • EXAMPLE 3
  • [0049]
    Chlorogenic Acids Added to an Unflavored Alcoholic Beverage
  • [0050]
    A 10 proof (5% alcohol) unflavored beverage was prepared by mixing 5.26 mL Grain Neutral Spirits (95% alcohol), 92.24 mL water, 2.0 mL high fructose corn syrup, 0.25 mL sodium benzoate (10%w/v in water), and 0.25 mL potassium sorbate (10%w/v in water).
  • [0051]
    A solution of chlorogenic acids from a green coffee bean extract, prepared as previously described, was added to a portion of the alcoholic beverage to a final concentration of 0.0035%w/v chlorogenic acids. The beverage containing chlorogenic acids was evaluated by a six member panel of trained flavorists. The beverage was judged to display significantly less of the alcohol-burn taste than that observed in the untreated beverage.
  • EXAMPLE 4
  • [0052]
    Chlorogenic Acids Added to a Soy Product
  • [0053]
    A solution of chlorogenic acids from a green coffee bean extract, prepared as previously described, was added to a commercial soy milk product (White Wave, Silk Chocolate) to final concentration of 0.04%w/v chlorogenic acids. After evaluation by a six member panel of trained flavorists, it was judged that the product containing the chlorogenic acids masked the soy milk product's beany, aldehydic, soy off-notes and off-tastes, and that the product was perceived as smoother and creamier than the untreated soy milk product.
  • EXAMPLE 5
  • [0054]
    Chlorogenic Acids; Added to a Flavored Carbonated Beverage
  • [0055]
    A solution of chlorogenic acids from a green coffee bean extract, prepared as previously described, was added to a standard carbonated orange flavored beverage (flavor level 0.2%) to final concentration of 0.001%w/v chlorogenic acids. A six member panel of trained flavorists compared the treated and untreated carbonated beverages. The panel judged that the beverage containing chlorogenic acids significantly lowered the impact of the sharp, slightly burning sensation of the carbonation when compared to the untreated beverage.
  • EXAMPLE 6
  • [0056]
    Chlorogenic Acids Added to Aspartame Sweetened Yogurt
  • [0057]
    A solution of chlorogenic acids from a green coffee bean extract, prepared as previously described, was added to a commercial non-fat yogurt (Dannon, Light'n Fit Vanilla Yogurt, with Aspartame & fructose added) to a final concentration of 0.005%w/v chlorogenic acids. A panel of six trained flavorists compared the treated and untreated yogurts. The panel judged that the product containing the extract of chlorogenic acids displayed an improved body and texture in the mouth, and that the overall sweetness perception was fuller and more rounded than the untreated yogurt.
  • [0058]
    Each of the references previously disclosed is expressly incorporated by reference herein in its entirety. It should also be understood that the embodiments of the present invention shown and described in the specification are only preferred embodiments of the inventor who is skilled in the art and are not limiting in any way. Therefore, various changes, modifications or alterations to these embodiments may be made or resorted to without departing from the spirit of the invention and the scope of the following claims.

Claims (46)

    What is claimed is:
  1. 1. A method for modifying an off-taste of a consumable comprising adding a chlorogenic acid to the consumable in an effective amount to modify the off-taste.
  2. 2. The method of claim 1 wherein the off-taste is selected from the group consisting of a metallic aftertaste, a bitter aftertaste, an alcoholic burn taste, a beany taste, an aldehydic taste, a carbonation burning sensation, and combinations thereof.
  3. 3. The method of claim 1 wherein the off-taste is attributable to a component selected from the group consisting of an artificial sweetener, alcohol, soy, carbon dioxide, and combinations thereof.
  4. 4. The method of claim 3 wherein the artificial sweetener is selected from the group consisting of saccharine, aspartame, acesulfame salts, cyclohexylsulfamic acid, dihydrochalcones, xylitol, neotame, sucralose, alitame cyclamates, stevio derivatives, and combinations thereof.
  5. 5. The method of claim 1 wherein the chlorogenic acid is selected from the group consisting of a natural extract, a synthetic compound, and combinations thereof.
  6. 6. The method of claim 5 wherein the natural extract is a green coffee bean extract.
  7. 7. The method of claim 1 wherein the chlorogenic acid in the consumable is a mixture of chlorogenic acids.
  8. 8. The method of claim 1 wherein the chlorogenic acid is at least one of the chlorogenic acids of Table 1.
  9. 9. The method of claim 1 wherein the chlorogenic acid is present at a final concentration from about 0.0001%w/v to about 0.1%w/v in the consumable.
  10. 10. A method for modifying a taste of a consumable containing an artificial sweetener comprising adding a chlorogenic acid to the consumable in an effective amount to modify the taste.
  11. 11. The method of claim 10 wherein the chlorogenic acid is added in an amount to achieve a final concentration in the range from about 0.0001%w/v to about 0.1%w/v in the consumable.
  12. 12. The method of claim 10 wherein the chlorogenic acid is added in an amount to achieve a final concentration in the range from about 0.001%w/v to about 0.01%w/v in the consumable.
  13. 13. The method of claim 10 wherein a source of the chlorogenic acid is selected from the group consisting of a natural extract, a synthetic compound, and combinations thereof.
  14. 14. The method of claim 10 wherein the chlorogenic acid is at least one of the chlorogenic acids of Table 1.
  15. 15. A method for modifying a burning taste of a consumable containing an alcohol comprising adding a chlorogenic acid to the consumable in an effective amount to modify the taste.
  16. 16. The method of claim 15 wherein the chlorogenic acid is added in an amount to achieve a final concentration in the range from about 0.0001%w/v to about 0.1%w/v in the consumable.
  17. 17. The method of claim 15 wherein the chlorogenic acid is added in an amount to achieve a final concentration in the range from about 0.001%w/v to about 0.01%w/v in the consumable.
  18. 18. The method of claim 15 wherein the chlorogenic acid is selected from the group consisting of a natural extract, a synthetic compound, and combinations thereof.
  19. 19. The method of claim 15 wherein the chlorogenic acid is any one of the chlorogenic acids of Table 1.
  20. 20. A method for modifying a beany taste of a consumable containing soy comprising adding a chlorogenic acid to the consumable in an effective amount to modify the taste.
  21. 21. The method of claim 20 wherein the chlorogenic acid is added in an amount to achieve a final concentration in the range from about 0.0001%w/v to about 0.1%w/v in the consumable.
  22. 22. The method of claim 20 wherein the chlorogenic acid is added in an amount to achieve a final concentration in the range from about 0.01%w/v to about 0.1%w/v in the consumable.
  23. 23. The method of claim 20 wherein the chlorogenic acid is selected from the group consisting of a natural extract, a synthetic compound, and combinations thereof.
  24. 24. The method of claim 20 wherein the chlorogenic acid is at least one of the chlorogenic acids of Table 1.
  25. 25. A method for modifying a sharp taste of a carbonated consumable comprising adding a chlorogenic acid to the consumable in an effective amount to modify the taste.
  26. 26. The method of claim 25 wherein the chlorogenic acid is added in an amount to achieve a final concentration in the range from about 0.0001%w/v to about 0.1%w/v in the consumable.
  27. 27. The method of claim 25 wherein the chlorogenic acid is added in an amount to achieve a final concentration in the range from about 0.0005%w/v to about 0.005%w/v in the consumable.
  28. 28. The method of claim 25 wherein the chlorogenic acid is selected from the group consisting of a natural extract, a synthetic compound, and combinations thereof.
  29. 29. The method of claim 25 wherein the chlorogenic acid is at least one of the chlorogenic acids of Table 1.
  30. 30. A method for modifying a sweetness perception of a consumable comprising adding a chlorogenic acid to the consumable in an effective amount to modify the sweetness perception.
  31. 31. The method of claim 30 wherein the chlorogenic acid is selected from the group consisting of a natural extract, a synthetic compound, and combinations thereof.
  32. 32. The method of claim 31 wherein the natural extract is a green coffee bean extract.
  33. 33. The method of claim 30 wherein the added chlorogenic acid is a mixture of chlorogenic acids.
  34. 34. The method of claim 30 wherein the chlorogenic acid is at least one of the chlorogenic acids of Table 1.
  35. 35. The method of claim 30 wherein the chlorogenic acid is added in an amount to achieve a final concentration in the range from about 0.0001%w/v to about 0.1%w/v in the consumable.
  36. 36. The method of claim 30 wherein the consumable is a dairy product.
  37. 37. A consumable containing a compound imparting an off-taste and a chlorogenic acid in an effective amount to modify or mask the off-taste.
  38. 38. The consumable of claim 37 wherein the amount of chlorogenic acid is added to achieve a final concentration in the range from about 0.0001%w/v to about 0.1%w/v in the consumable.
  39. 39. The consumable of claim 37 wherein the amount of chlorogenic acid is added to achieve a final concentration in the range from about 0.001%w/v to about 0.01%w/v in the consumable.
  40. 40. The consumable of claim 37 wherein the chlorogenic acid is at least one of the chlorogenic acids of Table 1.
  41. 41. The consumable of claim 37 selected from the group consisting of a soft drink, a dairy product, a soy product, a dessert product, a savory product, an alcoholic beverage, a confection, a gum, a medicament, and combinations thereof.
  42. 42. A sweetening composition for consumables comprising an artificial sweetener and from about 0.0001%w/v to about 0.1%w/v chlorogenic acids.
  43. 43. The composition of claim 42 wherein said artificial sweetener is selected from the group consisting of L-aspartyl-L-phenylalanine methyl ester (aspartame), saccharine and salts thereof, acesulfame salts (e.g., acesulfame K), cyclohexylsulfamic acid, dihydrochalcones, xylitol, neotame, sucralose, alitame cyclamates, stevio derivatives, and combinations thereof.
  44. 44. The composition of claim 42 containing from about 0.001%w/v to about 0.01%w/v chlorogenic acid.
  45. 45. The composition of claim 42 wherein the chlorogenic acid is at least one of the chlorogenic acids of Table 1.
  46. 46. A consumable sweetened with the composition of claim 42.
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US09880420 US20030003212A1 (en) 2001-06-13 2001-06-13 Taste modifiers
ES02734972T ES2247339T3 (en) 2001-06-13 2002-06-12 Flavor modifiers comprising chlorogenic acid.
US10480372 US8197875B2 (en) 2001-06-13 2002-06-12 Taste modifiers comprising a chlorogenic acid
CA 2446194 CA2446194A1 (en) 2001-06-13 2002-06-12 Taste modifiers comprising a chlorogenic acid
DE2002606378 DE60206378D1 (en) 2001-06-13 2002-06-12 Chlorogenic acid-containing material geschmacksmodifizierender
DE2002606378 DE60206378T2 (en) 2001-06-13 2002-06-12 Chlorogenic acid-containing material geschmacksmodifizierender
CN 02811814 CN1253099C (en) 2001-06-13 2002-06-12 Taste modifiers comprising chlorogenic acid
EP20020734972 EP1399034B1 (en) 2001-06-13 2002-06-12 Taste modifiers comprising a chlorogenic acid
PCT/CH2002/000315 WO2002100192A1 (en) 2001-06-13 2002-06-12 Taste modifiers comprising a chlorogenic acid
JP2003503023A JP2004528050A (en) 2001-06-13 2002-06-12 Taste-modifying agents, including chlorogenic acid
JP2009244892A JP5085632B2 (en) 2001-06-13 2009-10-23 Taste-modifying agents, including chlorogenic acid
US13436254 US20120189750A1 (en) 2001-06-13 2012-03-30 Taste Modifiers Comprising a Chlorogenic Acid
JP2012156122A JP5363624B2 (en) 2001-06-13 2012-07-12 Taste-modifying agents, including chlorogenic acid
JP2013142246A JP5898137B2 (en) 2001-06-13 2013-07-08 Taste-modifying agents, including chlorogenic acid
JP2015045789A JP2015164422A (en) 2001-06-13 2015-03-09 Taste modifiers comprising chlorogenic acid
JP2016132082A JP2017000146A (en) 2001-06-13 2016-07-01 Taste modifiers comprising chlorogenic acid
US15662950 US20170327776A1 (en) 2001-06-13 2017-07-28 Taste modifiers comprising a chlorogenic acid

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US13436254 Pending US20120189750A1 (en) 2001-06-13 2012-03-30 Taste Modifiers Comprising a Chlorogenic Acid
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US15662950 Pending US20170327776A1 (en) 2001-06-13 2017-07-28 Taste modifiers comprising a chlorogenic acid

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