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WO2006003107A1 - Utilisation de glucosides de l'acide malique comme aromatisants - Google Patents

Utilisation de glucosides de l'acide malique comme aromatisants Download PDF

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Publication number
WO2006003107A1
WO2006003107A1 PCT/EP2005/052933 EP2005052933W WO2006003107A1 WO 2006003107 A1 WO2006003107 A1 WO 2006003107A1 EP 2005052933 W EP2005052933 W EP 2005052933W WO 2006003107 A1 WO2006003107 A1 WO 2006003107A1
Authority
WO
WIPO (PCT)
Prior art keywords
diacid
butane
preparation
glucosyl
oral
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/EP2005/052933
Other languages
German (de)
English (en)
Inventor
Jakob Ley
Günter Kindel
Gerhard Krammer
Sabine Widder
Wilhelm Pickenhagen
Nina Rotzoll
Thomas Hofmann
Andreas Dunkel
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.)
Symrise AG
Original Assignee
Symrise AG
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 Symrise AG filed Critical Symrise AG
Publication of WO2006003107A1 publication Critical patent/WO2006003107A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L27/205—Heterocyclic compounds
    • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/16—Inorganic salts, minerals or trace elements
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the invention relates to the use of malic acid glucosides as flavoring substances, in particular in nutrition, oral hygiene or for pleasure or oral pharmaceutical preparations. Furthermore, the invention relates to corresponding preparations.
  • flavoring also includes taste modulating substances and flavorings.
  • Umami is a term borrowed from the Japanese and is usually described spicy with the term. Substances which show umami taste are above all the various sodium salts of L-glutamic acid, but in particular monosodium glutamate, some other amino acids such as L-aspartic acid, nucleotides such as inosine monophosphate and some peptides.
  • Monosodium glutamate and Other umami-tasting substances are also often referred to as flavor-modulating substances, in particular taste-enhancing substances, since they can enhance and round off the entire flavor and aroma profile of food or beverages and similar products.
  • EP-A 1,356,744 describes N-acetylglycine as a compound which causes umami taste.
  • N- (D-Glucos-1-yl) -L-glutamic acid is described in WO 02087361 -A1 as a umami-tasting compound.
  • the primary object of the present invention was to provide substances which are not based on amino acids and / or nucleotides and nevertheless cause a umami taste impression, are widely applicable, occur in nature and which are therefore used as flavorings in nutrition, oral hygiene or the Consumment serving preparations can be used ver ⁇ .
  • the invention solves the stated primary object by the use of 2- (glucosyl) -butane-1,4-diacid (hereinafter also malic acid glucoside) or a physiologically acceptable salt of 2- (glucosyl) -butane-1,4-diacid as flavoring.
  • Malic acid is 2-hydroxybutane-1,4-diacid and may exist as both (2S) and (2R) -isomer.
  • Glucosides in the context of the invention are all possible D- or L-glucose configuration isomers bound to the malic acid via the 1-hydroxy group.
  • the D-glucose configurational isomers of D-glucopyranose and D-glucofuranose are preferred.
  • the binding of malic acid takes place via the 1-hydroxy function of D-glucose, which may be in the form of an ⁇ or ⁇ anomeric form, or as a mixture of some or all of these forms.
  • the malic acid glucoside is preferably used as a flavoring and component of flavoring preparations which can be used in nutrition, oral hygiene or pleasure or in oral pharmaceutical preparations.
  • a umami taste is enhanced or mediated.
  • the invention also relates to a method for mediating or enhancing a umami flavor in a nutrition, oral or pleasure or oral pharmaceutical preparation, the preparation comprising an effective amount of one or more malic glucosides (2- (glucosyl) - butane-1,4-diacid) or a corresponding physiologically acceptable salt.
  • the sawed material used according to the invention applies correspondingly.
  • the malic acid glucosides to be used according to the invention have an interesting taste with the qualities acidic and, in particular, umami and can therefore be used very well as flavorings.
  • an acetic acid glucoside or a corresponding salt
  • both the flavor profile and the aroma profile of the nutrition or pleasure or oral pharmaceutical preparations are enhanced and a pleasant mouthfeel is caused.
  • mixtures of the malic acid glucosides to be used according to the invention with other umami-tasting substances, for example monosodium glutamate are used in mixtures. synergistically enhances the umami taste (ie more than the sum), cf. See the examples below.
  • the salt flavor is synergistically enhanced in mixtures of (a) malic acid glucosides to be used according to the invention or their salts, with the proviso that not one of the sodium salts of malic acid glucosides is present, and (b) sodium chloride Reduction of the sodium chloride content in a preparation, eg.
  • the lowering of the sodium salt content in foods is desirable for health reasons.
  • the present invention therefore also relates to the use of an acetic acid glucoside or a physiologically acceptable salt of an acetic acid glucoside for enhancing a salty taste caused by sodium chloride in a preparation.
  • the malic acid glucosides can be used as physiologically acceptable salts in the mono- or dicarboxylate form, with physiologically acceptable cations as counterions.
  • the cations used may be the singly positively charged cations of the first main group and subgroup, ammonium, trialkylammonium, the divalent charged cations of the second main group and subgroup and the trivalent cations of the third main group and subgroup, preferably Na + , K + , NH 4 + , Ca 2+ , Mg 2+ , Al 3+ and Zn 2+ .
  • malic acid glucosides may each be used alone or as mixtures.
  • the malic acid glucosides or their physiologically acceptable salts are dispersed in granules. combination with other flavorings (including flavorings) to obtain flavorings.
  • malic acid glucosides or their physiologically acceptable salts with other umami flavoring agents such as e.g. Sodium salts of glutamic acid or inosine monophosphate.
  • concentration of these other substances causing a umami taste can then be reduced compared to comparative compositions with the same umami taste.
  • the present invention also relates to a dietary, oral or pleasure preparation comprising an effective amount of one or more malic glucosides or a physiologically acceptable salt thereof, wherein the preparation comprises (i) one or more further dietary supplements Oral or nourishing ingredients that are not contained in Synadeni ⁇ m pereskiifolium or in milk and / or (ii) contains one or more other substances that cause a umami taste.
  • the present invention also relates to an oral pharmaceutical preparation comprising an effective amount of one or more malic acid glucosides or a corresponding physiologically acceptable salt, the preparation comprising a pharmaceutically effective amount of one or more ingredients not found in either Synadenium pereskiifolium or milk are included.
  • the preparation is preferably in the form of a semi-finished product and also comprises: one or more (a) further flavorings and, if appropriate, one or more (b) excipients, (c) diluents, (d) solvents and / or (e) dispersant.
  • the preparation is preferably a fragrance, flavor or taste composition or a seasoning mixture.
  • Nutritional or oral pharmaceutical preparations containing nourishment, oral hygiene or pleasure generally contain from 0.000001% by weight to 10% by weight, preferably from 0.00001 to 10% by weight, but in particular 0 , 0001 wt .-% to 1 wt .-%, based on the total weight of the preparation, of one or more malic acid glucosides or their physiologically acceptable salts.
  • Further customary active substances, basic substances, auxiliaries and additives for foodstuffs, oral care or stimulants or oral pharmaceutical preparations can be obtained in quantities of 5 to 99.999999% by weight, preferably 10 to 80% by weight be included on the total weight of the preparation.
  • the preparations may comprise water in an amount of up to 99.999999% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.
  • nutrition or pleasure-serving preparations are, for example, baked goods (eg bread, dry biscuits, cakes, other pastries), confectionery (for example chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (eg coffee, tea, wine, wine-based beverages, beer, beer-based drinks, liqueurs, brandies, brandies, lemonades, isotonic drinks, refreshments, nectars, fruit and vegetable juices, fruit or vegetable juice) preparations), instant drinks (eg instant cocoa drinks, instant tea drinks, instant coffee drinks), meat products (eg ham, fresh sausage or raw sausage preparations, spiced or marinated fresh or salted meat products), eggs or egg products (dry egg , Egg whites, egg yolk), cereal products (eg breakfast cereals, muesli bars, pre-cooked ready-made rice products), dairy products (eg milk drink e, milk ice cream, yoghurt, kefir, cream cheese, soft cheese, hard cheese,
  • the preparations according to the invention can also be used as semi-finished goods for the production of further preparations for nutrition or enjoyment.
  • the preparations according to the invention can also be used in the form of capsules, tablets (non-coated and coated tablets, eg enteric coatings), dragees, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, be present as pastes or as other swallowable or chewable preparations as a dietary supplement.
  • Preferred sprinkling seasonings according to the invention contain e.g. synthetic, natural or nature-identical flavorings and carriers such as e.g. Maltodextrin, salts, e.g. Table salt, spices such as e.g. Peppers and peppers, sugar sweeteners, e.g. Saccharin and other flavor enhancers such as e.g. Monosodium glutamate and / or inosine monophosphate.
  • synthetic, natural or nature-identical flavorings and carriers such as e.g. Maltodextrin, salts, e.g. Table salt, spices such as e.g. Peppers and peppers, sugar sweeteners, e.g. Saccharin and other flavor enhancers such as e.g. Monosodium glutamate and / or inosine monophosphate.
  • Oral pharmaceutical preparations according to the invention are preparations which, for example, are in the form of capsules, tablets (uncoated and coated tablets, eg enteric coatings), dragees, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders , as solutions, as pastes or as other swallowable or chewable preparations and are used as prescription, pharmacy or other medicines or as food supplements.
  • Preparations according to the invention can also be used as nutritional supplements in the form of capsules, tablets (non-coated and coated tablets, eg enteric coatings), dragees, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions , as pastes or as other swallowable or chewable preparations.
  • tablets non-coated and coated tablets, eg enteric coatings
  • dragees granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions , as pastes or as other swallowable or chewable preparations.
  • Preparations according to the invention for oral hygiene are in particular dentifrices such as toothpastes, tooth gels, toothpowder, mouthwashes, oral sprays, flavored films or gels, wipers for cleaning the oral cavity, dental floss or chewing gum and other oral care products.
  • dentifrices such as toothpastes, tooth gels, toothpowder, mouthwashes, oral sprays, flavored films or gels, wipers for cleaning the oral cavity, dental floss or chewing gum and other oral care products.
  • Chewing gums containing the malic acid glucosides to be used in accordance with the invention generally consist of a chewing gum base, i. a chewing gum that becomes plastic during chewing, sugars of various types, sugar substitutes, sweeteners, sugar alcohols, humectants, thickeners, emulsifiers, flavors and stabilizers.
  • the preparations according to the invention which comprise one or more malus glucosides can be prepared by mixing the malic acid glucoside (s) as a substance, as a solution or in the form of a mixture with a solid or liquid carrier into one of the diets, oral hygiene or incorporated into the benefit or oral pharmaceutical base preparation.
  • preparations according to the invention which are present as a solution can also be converted into a solid preparation by spray drying.
  • the malic acid glucosides and optionally other constituents of the preparation according to the invention can first be prepared in emulsions, in liposomes, for example starting from phosphatidylcholine, in microspheres, in nanospheres or else in capsules, granules or extrudates of a matrix suitable for food and semi-luxury products, for example starch, starch derivatives, cellulose or cellulose derivatives (eg hydroxypropylcellulose), other polysaccharides (eg alginate), natural fats, natural waxes (eg beeswax, carnauba wax) or of proteins, For example, gelatin, incorporated.
  • a matrix suitable for food and semi-luxury products for example starch, starch derivatives, cellulose or cellulose derivatives (eg hydroxypropylcellulose), other polysaccharides (eg alginate), natural fats, natural waxes (eg beeswax, carnauba wax) or of proteins, For example
  • the malic acid glucosides are first complexed with one or more suitable complexing agents, for example cyclodextrins or cyclodextrin derivatives, preferably ⁇ -cyclodextrin, and used in this complexed form.
  • suitable complexing agents for example cyclodextrins or cyclodextrin derivatives, preferably ⁇ -cyclodextrin, and used in this complexed form.
  • a preparation according to the invention in which the matrix is chosen such that the malic acid glucosides are released from the matrix with a delay, so that a long-lasting flavor effect is obtained.
  • the oral pharmaceutical preparations according to the invention it is possible to use all other active substances, basic substances, auxiliaries and additives for oral pharmaceutical preparations.
  • the active substances, basic substances, auxiliaries and additives can be converted into the oral administration forms in a manner known per se. This is done using inert, non-toxic, pharmaceutically suitable auxiliaries. These include u.a.
  • Carriers eg microcrystalline celluloses
  • solvents eg liquid polyethylene glycols
  • emulsifiers eg sodium dodecylsulfate
  • dispersants eg polyvinylpyrrolidone
  • synthetic and natural biopolymers eg albumin
  • stabilizers eg antioxidants like ascorbic acid
  • dyes eg inorganic pigments such as iron oxides
  • odor remedies and taste corrigents eg inorganic pigments such as iron oxides
  • Preparations according to the invention preferably also contain an aroma composition in order to round off and refine the taste and / or smell of the preparation.
  • Suitable flavor compositions included For example, synthetic, natural or nature-identical flavorings and fragrances.
  • a further aspect of the invention relates to the use of the preparations according to the invention as semi-finished goods, in particular with the aim of aromatizing finished goods manufactured from the semi-finished goods.
  • the preparations according to the invention which are present as semi-finished goods generally contain from 0.0001% by weight to 95% by weight, preferably from 0.001 to 80% by weight, but preferably from 0.01% by weight to 50% by weight. %, based on the total weight of the preparation, malic acid glucosides or their physiologically acceptable salts.
  • they comprise one or more other flavoring and flavoring agents and optionally - as mentioned - carriers and / or auxiliaries and / or solvents or the like.
  • ready-to-use preparations according to the invention for the aromatization of finished goods which contain the apple acid glucosides to be used according to the invention and at least one further nachJmami-tasting material, preferably monosodium glutamate and / or inosine monophosphate, are preferred as semi-finished goods.
  • inventive compounds for the flavoring of finished goods which contain the acetic acid glucosides and common salt to be used according to the invention and optionally also excipients and / or adjuvants.
  • the yellow oil was dissolved in acetone (50 ml), cooled to 0 ° C., admixed with a barium hydroxide solution (250 ml, 0.25 mol / l) and shaken for a few minutes. The solution was allowed to stand at 0 ° C. for 1 h and then admixed with a further 250 ml of barium hydroxide solution. After acidification with dilute hydrochloric acid (3 mol / l, 35 ml), the cold, slightly turbid solution was filtered.
  • the filtrate was added with 500 ml of absolute ethanol to precipitate the (2S) -2- ( ⁇ -D-glucopyranosyloxy) -butane-1,4-diacid barium salt; after 12 h storage at 0 ° C, the precipitate was filtered.
  • An SPE cartridge with weak acid cation exchanger (3 g resin, eg Varian Mega Bond Elut CBA) was mixed with dilute formic acid (10 ml, 1 g / 100 g) and then washed neutral with water (25 ml).
  • 0.3 g of the barium salt was dissolved in 10 ml of water and added to the cartridge, the cation exchanger rinsed with water (10 ml) and the eluates combined.
  • the separation of the barium ions was tested with dilute sulfuric acid. From the eluates, (2S) -2- ( ⁇ -D-glucopyranosyloxy) -butane-1,4-diacid could be obtained by lyophilization.
  • Fig. 1 Sensory profile of a solution of 20 mmol / l (2S) -2- ( ⁇ -D-glucopyranosyloxy) -butane-1,4-diacid (a) compared to a solution of the monoammonium salt of (2S) -2 - ( ⁇ -D-glucopyranosyloxy) -butan-1, 4-diacid (b) and to a 20 mmol / l monosodium glutamate solution (c).
  • Fig. 2 Sensory comparison of a 20 mmol / l (2S) -2- (ß-D-glucopyranosyloxy) -butane-1,4-diacid solution (a) and a 20 mmol / l NaCl solution (d) and their 1: 1 mixture (e) (final concentration of 10 mmol / l).
  • Fig. 3 Sensory comparison of a 20 mmol / l (2S) -2- (ß-D-glucopyranosyloxy) -butan-1,4-diacid (a) and a 20 mmol / l mononatrium glutamate solution (c) as well as their 1: 1 mixture (f) (final concentration of 10 mmol / l).
  • Part A The ingredients of Part A are mixed until homogeneous.
  • the fat from part B is melted and added to the powder mixture of part A. Once the fat has been absorbed by the mass, the powder is stored in the freezer for 3 hours and the product is spread through a sieve.
  • Application Example 3 Sodium chloride-reduced "common salt"

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Mycology (AREA)
  • Seasonings (AREA)

Abstract

L'invention concerne l'utilisation d'un glucoside de l'acide malique [2-(glucosyl)-butane-1,4-diacide] ou d'un sel physiologiquement acceptable d'un glucoside de l'acide malique en tant qu'aromatisant, notamment en tant qu'aromatisant umami et en tant qu'exhausteur de goût.
PCT/EP2005/052933 2004-06-30 2005-06-23 Utilisation de glucosides de l'acide malique comme aromatisants Ceased WO2006003107A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004031588.4 2004-06-30
DE102004031588A DE102004031588A1 (de) 2004-06-30 2004-06-30 Verwendung von Äpfelsäureglucosiden als Geschmacksstoffe

Publications (1)

Publication Number Publication Date
WO2006003107A1 true WO2006003107A1 (fr) 2006-01-12

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PCT/EP2005/052933 Ceased WO2006003107A1 (fr) 2004-06-30 2005-06-23 Utilisation de glucosides de l'acide malique comme aromatisants

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DE (1) DE102004031588A1 (fr)
WO (1) WO2006003107A1 (fr)

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EP1977655A1 (fr) 2007-03-29 2008-10-08 Symrise GmbH & Co. KG Compositions d'aromes d'alcamides comprenant de l'hespérétine et/ou des 4-hydroxydihydrochalcones et leurs sels destinées à renforcer les impressions sensorielles sucrées
EP2022503A1 (fr) 2007-08-07 2009-02-11 Symrise GmbH & Co. KG Extraits de vaccin encapsulés ayant une libération équilibrée dans l'estomac-intestin
EP2135616A1 (fr) 2008-06-19 2009-12-23 Symrise GmbH & Co. KG Fruit d'airelle séché destiné à influencer l'état de l'intestin
DE102008044126A1 (de) 2008-11-27 2010-06-02 Symrise Gmbh & Co. Kg Aromastoffinklusionscellulose
EP2298084A1 (fr) 2009-08-28 2011-03-23 Symrise AG Produits réduits en saccharine, mélanges d'arômes correspondant et procédé de fabrication de tels produits
EP2305742A1 (fr) 2009-10-01 2011-04-06 Symrise AG Particule cýur/enveloppe sphérique
WO2011039340A2 (fr) 2009-10-02 2011-04-07 Givaudan Sa Renforcement de goût
WO2011095533A1 (fr) 2010-02-04 2011-08-11 Givaudan Sa Dérivé d'oxalamide à titre d'agent de saveur umami
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EP2529632A1 (fr) 2011-05-31 2012-12-05 Symrise AG Acide aminé cinnamique comme arômes épicés
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EP2990036A1 (fr) 2014-07-30 2016-03-02 Symrise AG Hydroxyflavones pour stimulation d'appétit
EP3078273A1 (fr) 2015-04-08 2016-10-12 DMK Deutsches Milchkontor GmbH Produits du lait acidulé comme base pour deserts cocktail
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WO2018096123A1 (fr) 2016-11-25 2018-05-31 Symrise Ag Mélanges ayant des propriétés stabilisantes
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US10301275B2 (en) 2017-03-17 2019-05-28 Altria Client Services Llc Sweet taste modulators
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US10624372B2 (en) 2009-08-28 2020-04-21 Symrise Ag Reduced-sweetener products, flavoring mixtures for said reduced-sweetener products and process for the production of products of this type
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WO2021063942A1 (fr) 2019-09-30 2021-04-08 Givaudan Sa Perfectionnements apportés ou associés à des composés organiques
EP3864966A1 (fr) 2020-02-12 2021-08-18 Savanna Ingredients GmbH Compositiones orales contenant crystals d'allulose
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US20230357301A1 (en) * 2014-03-14 2023-11-09 Faculdade De Ciencias Da Universidade De Lisboa Hexose derivatives, preparation and uses thereof
WO2024240579A1 (fr) 2023-05-22 2024-11-28 Givaudan Sa Perfectionnements apportés ou se rapportant à des composés organiques

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