US20030003212A1 - Taste modifiers - Google Patents

Taste modifiers Download PDF

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Publication number
US20030003212A1
US20030003212A1 US09/880,420 US88042001A US2003003212A1 US 20030003212 A1 US20030003212 A1 US 20030003212A1 US 88042001 A US88042001 A US 88042001A US 2003003212 A1 US2003003212 A1 US 2003003212A1
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United States
Prior art keywords
consumable
chlorogenic acid
taste
chlorogenic
acid
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Abandoned
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US09/880,420
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English (en)
Inventor
Mingjien Chien
Hans Leersum
Alex Hausler
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Givaudan SA
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Givaudan SA
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Priority to US09/880,420 priority Critical patent/US20030003212A1/en
Assigned to GIVAUDAN SA reassignment GIVAUDAN SA ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHIEN, MINGJIEN, HAUSLER, ALEX, VAN LEERSUM, HANS
Priority to EP02734972A priority patent/EP1399034B1/en
Priority to PCT/CH2002/000315 priority patent/WO2002100192A1/en
Priority to US10/480,372 priority patent/US8197875B2/en
Priority to BR0210372-9A priority patent/BR0210372A/pt
Priority to MXPA03011043A priority patent/MXPA03011043A/es
Priority to AT02734972T priority patent/ATE305233T1/de
Priority to CNB028118146A priority patent/CN1253099C/zh
Priority to DE60206378T priority patent/DE60206378T2/de
Priority to JP2003503023A priority patent/JP2004528050A/ja
Priority to CA002446194A priority patent/CA2446194A1/en
Priority to ES02734972T priority patent/ES2247339T3/es
Publication of US20030003212A1 publication Critical patent/US20030003212A1/en
Priority to JP2009244892A priority patent/JP5085632B2/ja
Priority to US13/436,254 priority patent/US20120189750A1/en
Priority to JP2012156122A priority patent/JP5363624B2/ja
Priority to JP2013142246A priority patent/JP5898137B2/ja
Priority to JP2015045789A priority patent/JP6346578B2/ja
Priority to JP2016132082A priority patent/JP6472413B2/ja
Priority to US15/662,950 priority patent/US10597620B2/en
Priority to JP2017245548A priority patent/JP6944744B2/ja
Priority to JP2019082385A priority patent/JP7090966B2/ja
Priority to US16/751,610 priority patent/US20200157480A1/en
Priority to JP2020188190A priority patent/JP2021035389A/ja
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
    • C12G3/00—Preparation of other alcoholic beverages
    • C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C11/00—Milk substitutes, e.g. coffee whitener compositions
    • A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
    • A23C11/10—Milk 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
    • A23C11/103—Milk 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 containing only proteins from pulses, oilseeds or nuts, e.g. nut milk
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1307—Milk 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
    • 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
    • A23L11/00—Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
    • A23L11/60—Drinks from legumes, e.g. lupine drinks
    • A23L11/65—Soy drinks
    • 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
    • A23L2/56—Flavouring or bittering 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
    • 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
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A23L27/2026—Hydroxy compounds
    • 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
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/204—Aromatic compounds
    • 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
    • A23L27/30—Artificial sweetening 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/84—Flavour masking or reducing agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/74—Rubiaceae (Madder family)

Definitions

  • the invention relates to a process to modify the taste profile of a consumable by adding esters of quinic and cinnamic acid derivatives.
  • Non-nutritive sweeteners also called artificial sweeteners, for example, saccharine and aspartame
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • the invention is directed to a method for modifying sweetness perception of a consumable by adding chlorogenic acids.
  • 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.
  • 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.
  • FIG. 1 shows the structure of quinic acid.
  • FIG. 2 shows examples of acids belonging to the cinnamic acid family.
  • FIG. 3 shows the structure of 5-caffeoylquinic acid.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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 .
  • 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.
  • 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 .
  • an off-taste may be imparted by a soy product.
  • 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.
  • 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 .
  • 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 .
  • 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.
  • 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 .
  • esters of quinic acid and cinnamic acid may also mask an off-taste by reducing its perception and/or enhancing an overall sweetness perception.
  • 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.
  • 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.
  • 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.
  • 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).
  • chlorogenic acid is a trivial name used somewhat loosely in the literature to describe a range of phenolic acids found in plant materials.
  • 5-caffeoylquinic acid alone is referred to as “chlorogenic acid”.
  • 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.
  • 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.
  • green coffee beans e.g., Arabica, Robusta and Liberica
  • leaves of Illex paraguariensis e.g., apples and pears
  • stone fruits e.g., cherries and plums
  • berry fruits e.g.
  • 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.
  • 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
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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).
  • 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.
  • 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.
  • 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.

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US09/880,420 2001-06-13 2001-06-13 Taste modifiers Abandoned US20030003212A1 (en)

Priority Applications (23)

Application Number Priority Date Filing Date Title
US09/880,420 US20030003212A1 (en) 2001-06-13 2001-06-13 Taste modifiers
ES02734972T ES2247339T3 (es) 2001-06-13 2002-06-12 Modificadores de sabor que comprenden acido clorogenico.
JP2003503023A JP2004528050A (ja) 2001-06-13 2002-06-12 クロロゲン酸を含む味覚改変剤
CA002446194A CA2446194A1 (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
US10/480,372 US8197875B2 (en) 2001-06-13 2002-06-12 Taste modifiers comprising a chlorogenic acid
BR0210372-9A BR0210372A (pt) 2001-06-13 2002-06-12 Produto consumìvel, composição e métodos para miodificar sabor, método de formação de um extrato de ácido clorogênico e seu uso
MXPA03011043A MXPA03011043A (es) 2001-06-13 2002-06-12 Modificadores de sabor los cuales comprenden acido clorogenico.
AT02734972T ATE305233T1 (de) 2001-06-13 2002-06-12 Chlorogensäure enthaltender geschmacksmodifizierender stoff
CNB028118146A CN1253099C (zh) 2001-06-13 2002-06-12 含绿原酸的味道改良剂
DE60206378T DE60206378T2 (de) 2001-06-13 2002-06-12 Chlorogensäure enthaltender geschmacksmodifizierender stoff
EP02734972A EP1399034B1 (en) 2001-06-13 2002-06-12 Taste modifiers comprising a chlorogenic acid
JP2009244892A JP5085632B2 (ja) 2001-06-13 2009-10-23 クロロゲン酸を含む味覚改変剤
US13/436,254 US20120189750A1 (en) 2001-06-13 2012-03-30 Taste Modifiers Comprising a Chlorogenic Acid
JP2012156122A JP5363624B2 (ja) 2001-06-13 2012-07-12 クロロゲン酸を含む味覚改変剤
JP2013142246A JP5898137B2 (ja) 2001-06-13 2013-07-08 クロロゲン酸を含む味覚改変剤
JP2015045789A JP6346578B2 (ja) 2001-06-13 2015-03-09 クロロゲン酸を含む味覚改変剤
JP2016132082A JP6472413B2 (ja) 2001-06-13 2016-07-01 クロロゲン酸を含む味覚改変剤
US15/662,950 US10597620B2 (en) 2001-06-13 2017-07-28 Taste modifiers comprising a chlorogenic acid
JP2017245548A JP6944744B2 (ja) 2001-06-13 2017-12-21 クロロゲン酸を含む味覚改変剤
JP2019082385A JP7090966B2 (ja) 2001-06-13 2019-04-24 クロロゲン酸を含む味覚改変剤
US16/751,610 US20200157480A1 (en) 2001-06-13 2020-01-24 Taste modifiers comprising a chlorogenic acid
JP2020188190A JP2021035389A (ja) 2001-06-13 2020-11-11 クロロゲン酸を含む味覚改変剤

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US20040213881A1 (en) 2004-10-28
US8197875B2 (en) 2012-06-12
MXPA03011043A (es) 2004-03-19
CN1516553A (zh) 2004-07-28
CN1253099C (zh) 2006-04-26
US20120189750A1 (en) 2012-07-26
ATE305233T1 (de) 2005-10-15
JP7090966B2 (ja) 2022-06-27
JP2004528050A (ja) 2004-09-16
US20170327776A1 (en) 2017-11-16
WO2002100192A1 (en) 2002-12-19
JP6346578B2 (ja) 2018-06-20
EP1399034A1 (en) 2004-03-24

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