WO2012107207A1 - Édulcorant et/ou activateur d'édulcorant, compositions d'édulcorant, leurs procédés de fabrication et d'utilisation et produits comestibles en contenant - Google Patents

Édulcorant et/ou activateur d'édulcorant, compositions d'édulcorant, leurs procédés de fabrication et d'utilisation et produits comestibles en contenant Download PDF

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Publication number
WO2012107207A1
WO2012107207A1 PCT/EP2012/000543 EP2012000543W WO2012107207A1 WO 2012107207 A1 WO2012107207 A1 WO 2012107207A1 EP 2012000543 W EP2012000543 W EP 2012000543W WO 2012107207 A1 WO2012107207 A1 WO 2012107207A1
Authority
WO
WIPO (PCT)
Prior art keywords
sweetener
sweetener composition
compound
formula
consumable
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2012/000543
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English (en)
Inventor
Michael Krohn
Simon SEIBERT
Alice Kleber
Johann WONSCHIK
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Celanese Sales Germany GmbH
Original Assignee
Nutrinova Nutrition Specialties and Food Ingredients GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nutrinova Nutrition Specialties and Food Ingredients GmbH filed Critical Nutrinova Nutrition Specialties and Food Ingredients GmbH
Publication of WO2012107207A1 publication Critical patent/WO2012107207A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/18Acyclic radicals, substituted by carbocyclic rings
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52Adding ingredients
    • A23L2/56Flavouring or bittering agents
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52Adding ingredients
    • A23L2/60Sweeteners
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30Artificial sweetening agents
    • A23L27/33Artificial sweetening agents containing sugars or derivatives
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30Artificial sweetening agents
    • A23L27/33Artificial sweetening agents containing sugars or derivatives
    • A23L27/34Sugar alcohols
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88Taste or flavour enhancing agents
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/206Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
    • A23L29/262Cellulose; Derivatives thereof, e.g. ethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses

Definitions

  • the present invention further relates to a consumable comprising
  • derivative(s) as it relates to a compound of formula (I) or a stereoisomer thereof means organic molecules that are structurally closely related to a compound of formula (I) itself and that have similar characteristics and effects, preferably as sweetener and/or a sweetness enhancer.
  • preferred examples of derivatives of a compound of formula (I) are selected from the group defined below and mixtures thereof.
  • salt(s) as it relates to a compound of formula (I) means the physiologically acceptable acid addition salts and base salts of a compound of formula (I) or its derivatives or its stereoisomers. Suitable acid addition salts are formed from acids which form non-toxic salts.
  • the sweetness and/or sweetness enhancing properties of a compound in some embodiments, can be identified by an in vitro in cell based assay as described in the Examples, in EP 1 865 316 Bl, which is incorporated herein by reference, or by field effector transistor technology of e.g. Alpha MOS.
  • panelists are asked to take a sample of the liquid to be assessed (test substance, e.g. the compound of formula (I)) into the mouth and after some time allowed for taste perception to spit the sample out completely. Subsequently, the panelists are asked to rinse their mouth well with water or black tea to reduce any potential carry over effects. The tasting of a sample can be repeated if required.
  • test substance e.g. the compound of formula (I)
  • the sweetness and/or sweetness enhancing properties of the inventive sweetener composition when dissolved in water, correspond to a particular degrees Brix, a well-known measurement of sugar content in an aqueous solution.
  • the resultant solution has a sweetness that corresponds to a degrees Brix value ranging from 1 to 1000, e.g., from 5 to 500 or from 5 to 100.
  • 1 gram of the sweetener composition contains less calories and carbohydrates than about 1 gram of granulated sugar, e.g., less than about 0.5 grams of granulated sugar.
  • Additional exemplary sweetness enhancers include pine rosin diterpenoids; phloridizin; neoastilbin; dihydroquercetin acetate; glycine; erythritol; cinnamaldehyde; selligueain A; selligueain B; hematoxylin; rebaudioside A; rebaudioside B; rebaudioside C; rebaudioside D; rebaudioside E; dulcoside A; steviolbioside; rubusoside; stevia; stevioside; steviol 13 ⁇ - ⁇ -D-glycoside; mogroside V; Luo Han Guo; siamenoside; siamenoside I; monatin and salts thereof (monatin SS, RR, RS, SR); curculin; glycyrrhizic acid and its salts; thaumatin I; thaumatin II; thaumatin III;
  • US 5,919,486 discloses a "liquid oil and fat ingredient or others" that are carried by pores of a porous carrier composed of porous starch grain obtained by reacting an enzyme having raw starch digestive activity "onto the starch.”
  • sweeteners e.g., non-caloric, high intensity sweeteners, such as acesulfame potassium.
  • sweeteners e.g., non-caloric, high intensity sweeteners, such as acesulfame potassium.
  • sweeteners e.g., non-caloric, high intensity sweeteners, such as acesulfame potassium.
  • the inventive sweetener compositions may further comprise celluloses.
  • cellulose refers to any cellulosic material (other than the pregelatinized starches described herein) known to the skilled person.
  • the pregelatinized starches of utilized in the present invention are different from conventional starches or celluloses and possess particular characteristics that provide for some of the features of the inventive sweetener composition. These characteristics are not present in all starches or cellulosic materials. Thus, it is not expected that conventional starches and/or celluloses would provide for the inventive features demonstrated by the present invention.
  • the cellulose includes polysaccharides having linear chains of at least several hundred beta-linked D-glucose units.
  • the size of the cellulose particles may range from about 1 micron to about 400 microns, e.g., from about 3 microns to about 300 microns, from about 5 microns to about 200 microns, or from about 6 microns to about 100 microns.
  • the insoluble cellulose is a cellulose that if used in amounts exceeding 1% in an aqueous medium can lead to significant viscosity change.
  • tabletop sweetener compositions of the invention contain a plurality of sweetener particles, wherein such particles contain one or more of the ingredients present in the tabletop sweetener composition.
  • the tabletop sweetener composition substantially comprises sweetener particles.
  • the tabletop sweetener composition contains at least about 80 % by weight sweetener particles, or at least about 85 % by weight sweetener particles, or at least about 90 % by weight sweetener particles, based on the total weight of the tabletop sweetener composition.
  • Sweetener compositions of the invention may have any dissolution rate in water that is suitable for their use as sweeteners.
  • the sweetener composition can have a dissolution rate in water at 10°C of between about 100 seconds and about 200 seconds, e.g., between about 125 seconds and about 175 seconds, or between about 140 seconds and 160 seconds, based on the dissolution of about 2 grams of the sweetener composition in 240 ml of water.
  • the invention in another aspect, relates to a method of making a tabletop sweetener composition, comprising the steps of: a) providing a fluid-bed coating apparatus;
  • the consumable product is selected from the group of a dairy product, dairy-derived product and dairy-alternative product, including but not limited to milk, fluid milk, cultured milk product, cultured and noncultured dairy-based drink, cultured milk product cultured with lactobacillus, yoghurt, yoghurt-based beverage, smoothie, lassi, milk shake, acidified milk, acidified milk beverage, butter milk, kefir, milk-based beverages, milk/juice blend, fermented milk beverage, ice cream, dessert, sour cream, dip, salad dressing, cottage cheese, frozen yoghurt, soy milk, rice milk, soy drink, and rice milk drink.
  • dairy product including but not limited to milk, fluid milk, cultured milk product, cultured and noncultured dairy-based drink, cultured milk product cultured with lactobacillus, yoghurt, yoghurt-based beverage, smoothie, lassi, milk shake, acidified milk, acidified milk beverage, butter milk, kefir, milk-based beverages, milk/juice blend,
  • the consumable products are biscuits and the invention relates to biscuits comprising a sweetener composition of the invention or a tabletop sweetener composition of the invention.
  • the biscuits may contain further substances including but not limited to isomalt, powdered isomalt, granulated isomalt, polydextrose, shortening, water, sodium bicarbonate, ammonium bicarbonate, skimmed milk powder, salt, flour, cake flour, flavor, inulin, wheat fiber, shortening, ground raisins, raisin paste, salt, oatrim gel, liquid whole eggs, liquid egg whites, powdered egg whites, egg yolk, vanilla, butter flavor, vanilla flavor, chocolate flavor, cocoa, high fructose corn syrup (HFCS), methocel, baking soda, cinnamon, sodium acid pyrophosphate, margarine spread, margarine, emulsifier, molasses, mono- and diglycerides, powdered cellulose, ground hazelnuts, hazelnuts, sorbi
  • the consumable product is water-based ice and the invention relates to water-based ice comprising a sweetener composition of the invention or a tabletop sweetener composition of the invention, preferably to "ice-pops" and no sugar added strawberry sorbet.
  • the water-based ice may contain further substances including but not limited to acesulfame potassium, aspartame, citric acid, color, fruit concentrate, flavor, isomalt, lemon juice, polydextrose, strawberry puree, sorbitol, thickener and water.
  • the consumable product is ice cream and the invention relates to ice cream comprising a sweetener composition of the invention or a tabletop sweetener composition of the invention.
  • the ice-cream may contain further substances including but not limited to color, emulsifier, flavor, isomalt, milk fat, fat replacer, skim milk powder, palatinit, polydextrose and lactitol.
  • the sweetener composition of any one of items 1 to 10 comprising from 0.0005 wt% to 1.0 wt% of a compound of formula (I) or a derivative or a stereoisomer or a salt or a hydrate thereof, based on the total weight of the sweetener composition.
  • the sweetener composition of any one of items 1 to 11 comprising from 3 wt% to 20 wt% of the sweetener, based on the total weight of the sweetener composition.
  • sweetener composition of any one of items 1 to 12, wherein the sweetener is selected from the group consisting of abiziasaponin, abrusosides, in particular abrusoside A, abrusoside B, abrusoside C, abrusoside D, acesulfame potassium, advantame, albiziasaponin, alitame, aspartame, superaspartame, bayunosides, in particular bayunoside 1 , bayunoside 2, brazzein, bryoside, bryonoside, bryonodulcoside, camosifloside, carrelame, curculin, cyanin, chlorogenic acid, cyclamates and its salts, cyclocaryoside I, dihydroquercetin-3 -acetate, dihydroflavenol, dulcoside, gaudichaudioside, glycyrrhizin, glycyrrhetin acid, gypenoside
  • the tabletop sweetener composition of item 29 or 30 further comprising a sweetness modifier.
  • the tabletop sweetener composition of item 29 or 30 further comprising a mouthfeel enhancer.
  • the tabletop sweetener composition of item 29 or 30 further comprising a flavoring.
  • the sweetener composition of item 62 containing less calories and carbohydrates than about 1 gram of granulated sugar.
  • 66 The sweetener composition of item 62, wherein the sweetener composition comprises sweetener particles.
  • the sweetener composition of item 62, wherein the compound of formula (I) or a derivative or a stereoisomer or a salt or a hydrate thereof is a liquid at ambient conditions.
  • the sweetener composition of item 69 comprising from 80 wt% to 95 wt% of pregelatinized starch based on the total weight of the sweetener composition.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Seasonings (AREA)

Abstract

La présente invention concerne l'utilisation d'un composé de formule (I) dans laquelle un ou des atomes d'hydrogène dans le groupe phényle ou le groupe benzyle peut/peuvent être substitué(s) par un alkyle C1-6 ou alcoxy C1-6 et un ou des groupe(s) hydroxyle(s) peut/peuvent être substitué(s) par alcoxy C1-6 ou acyloxy C1-6, ou d'un dérivé ou d'un stéréoisomère ou d'un sel ou d'un hydrate de celui-ci, comme édulcorant et/ou activateur d'édulcorant, des compositions d'édulcorant comportant un composé de formule (I) ou un dérivé ou un stéréoisomère ou un sel ou un hydrate de celui-ci, et, éventuellement, un amidon prégélatinisé, des procédés de fabrication des compositions d'édulcorant et des compositions d'édulcorant de table comportant un composé de formule (I) ou un dérivé ou un stéréoisomère ou un sel ou un hydrate de celui-ci. L'invention concerne également des produits comestibles comportant un produit comestible et un composé de formule (I) ou un dérivé ou un stéréoisomère ou un sel ou un hydrate de celui-ci. Des produits comestibles préférés comprennent des produits comestibles à base d'eau, des produits comestibles secs solides, des produits laitiers, des produits laitiers dérivés et des produits laitiers alternatifs.
PCT/EP2012/000543 2011-02-08 2012-02-07 Édulcorant et/ou activateur d'édulcorant, compositions d'édulcorant, leurs procédés de fabrication et d'utilisation et produits comestibles en contenant Ceased WO2012107207A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201161440815P 2011-02-08 2011-02-08
US61/440,815 2011-02-08
EP11001011 2011-02-08
EP11001011.3 2011-02-08

Publications (1)

Publication Number Publication Date
WO2012107207A1 true WO2012107207A1 (fr) 2012-08-16

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013041236A1 (fr) * 2011-09-22 2013-03-28 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Compositions édulcorantes, procédé de fabrication correspondant, et produits comestibles les contenant
CN109970828A (zh) * 2019-04-25 2019-07-05 天然润宝健康产业有限公司 从橘红中提取柚皮苷的方法
WO2022221250A1 (fr) 2021-04-12 2022-10-20 International Flavors & Fragrances Inc. Nouvelles compositions pour le masquage du goût
EP3915397B1 (fr) 2020-05-25 2024-11-20 BRAIN Biotech AG Utilisation d'une protéine sucrée pour améliorer le goût sucré et/ou la qualité sucrée

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WO1989004842A1 (fr) 1987-11-20 1989-06-01 Whistler Roy L Composition en amidon granulaire pour matrices microporeuses
US5919486A (en) 1993-12-27 1999-07-06 San-Ei Sucrochemical Co., Ltd. Powder preparation and a process for preparing the same
WO2000030477A1 (fr) * 1998-11-19 2000-06-02 Norbert Fuchs Boisson pour augmenter la capacite a degrader l'alcool
US6818234B1 (en) * 1999-08-27 2004-11-16 Access Business Group International Llc Dietary food supplement containing natural cyclooxygenase inhibitors and methods for inhibiting pain and inflammation
WO2007110645A1 (fr) 2006-03-28 2007-10-04 Tate & Lyle Public Limited Company Produit de sucre granule
EP1955601A1 (fr) * 2007-01-25 2008-08-13 Symrise GmbH & Co. KG Utilisation de propenylphenylglucosides afin de renforcer les impressions sensorielles de la douceur
WO2009023975A2 (fr) 2007-08-17 2009-02-26 Givaudan Sa Compositions et leur utilisation
WO2009103514A1 (fr) 2008-02-22 2009-08-27 Cargill, Incorporated Amidons prégélatinisés servant de matériaux de support pour composants liquides
EP1865316B1 (fr) 2006-06-07 2010-02-24 Nutrinova Nutrition Specialties & Food Ingredients GmbH Procédé de criblage de composés qui modulent l'activité de gpcrs
WO2010025158A1 (fr) 2008-08-26 2010-03-04 Merisant Company Compositions d’édulcorant comprenant du rebaudioside a, de l’érythritol, un hydrate de carbone de disaccharide ou du fructose et une quantité de cellulose pour améliorer le goût, ainsi que leurs procédés de fabrication

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WO1989004842A1 (fr) 1987-11-20 1989-06-01 Whistler Roy L Composition en amidon granulaire pour matrices microporeuses
US5919486A (en) 1993-12-27 1999-07-06 San-Ei Sucrochemical Co., Ltd. Powder preparation and a process for preparing the same
WO2000030477A1 (fr) * 1998-11-19 2000-06-02 Norbert Fuchs Boisson pour augmenter la capacite a degrader l'alcool
US6818234B1 (en) * 1999-08-27 2004-11-16 Access Business Group International Llc Dietary food supplement containing natural cyclooxygenase inhibitors and methods for inhibiting pain and inflammation
WO2007110645A1 (fr) 2006-03-28 2007-10-04 Tate & Lyle Public Limited Company Produit de sucre granule
EP1865316B1 (fr) 2006-06-07 2010-02-24 Nutrinova Nutrition Specialties & Food Ingredients GmbH Procédé de criblage de composés qui modulent l'activité de gpcrs
EP1955601A1 (fr) * 2007-01-25 2008-08-13 Symrise GmbH & Co. KG Utilisation de propenylphenylglucosides afin de renforcer les impressions sensorielles de la douceur
WO2009023975A2 (fr) 2007-08-17 2009-02-26 Givaudan Sa Compositions et leur utilisation
WO2009103514A1 (fr) 2008-02-22 2009-08-27 Cargill, Incorporated Amidons prégélatinisés servant de matériaux de support pour composants liquides
WO2010025158A1 (fr) 2008-08-26 2010-03-04 Merisant Company Compositions d’édulcorant comprenant du rebaudioside a, de l’érythritol, un hydrate de carbone de disaccharide ou du fructose et une quantité de cellulose pour améliorer le goût, ainsi que leurs procédés de fabrication

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013041236A1 (fr) * 2011-09-22 2013-03-28 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Compositions édulcorantes, procédé de fabrication correspondant, et produits comestibles les contenant
CN109970828A (zh) * 2019-04-25 2019-07-05 天然润宝健康产业有限公司 从橘红中提取柚皮苷的方法
CN109970828B (zh) * 2019-04-25 2022-03-11 天然润宝健康产业有限公司 从橘红中提取柚皮苷的方法
EP3915397B1 (fr) 2020-05-25 2024-11-20 BRAIN Biotech AG Utilisation d'une protéine sucrée pour améliorer le goût sucré et/ou la qualité sucrée
WO2022221250A1 (fr) 2021-04-12 2022-10-20 International Flavors & Fragrances Inc. Nouvelles compositions pour le masquage du goût

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