EP1599103A1 - Derives aminoacides d'acides dicarboxyliques utilises comme aromatisants - Google Patents

Derives aminoacides d'acides dicarboxyliques utilises comme aromatisants

Info

Publication number
EP1599103A1
EP1599103A1 EP04706234A EP04706234A EP1599103A1 EP 1599103 A1 EP1599103 A1 EP 1599103A1 EP 04706234 A EP04706234 A EP 04706234A EP 04706234 A EP04706234 A EP 04706234A EP 1599103 A1 EP1599103 A1 EP 1599103A1
Authority
EP
European Patent Office
Prior art keywords
group
flavoring
formula
flavor
compounds
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.)
Withdrawn
Application number
EP04706234A
Other languages
German (de)
English (en)
Inventor
Eric Frerot
François BENZI
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.)
Firmenich SA
Original Assignee
Firmenich SA
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 Firmenich SA filed Critical Firmenich SA
Publication of EP1599103A1 publication Critical patent/EP1599103A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
    • A23L27/22—Synthetic spices, flavouring agents or condiments containing amino acids containing glutamic acids
    • 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
    • A23L27/203—Alicyclic 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
    • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
    • 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 present invention relates to the field of flavors and in particular it concerns the flavoring of an article upon which it is desired to confer or enhance the fullness and harmony of its taste or aroma, i.e. a mouthfeel.
  • the invention relates more particularly to the use as flavoring ingredient of at least one compound selected from the group consisting of (a) an acid of formula
  • A represents a proteogenic ⁇ -amino acid residue, said residue being bonded to the carbonyl group via the ⁇ -nitrogen atom
  • the invention also relates to the flavoring compositions or the flavored articles containing, as flavoring ingredients, at least one of the invention's compounds.
  • A represents a proteogenic ⁇ -amino acid residue, said residue being bonded to the carbonyl group via the ⁇ -nitrogen atom
  • the edible alkaline or alkaline earth metal salts, and the hydrates, of said compounds of formula (I) is particularly useful to the flavor industry.
  • the use as mouthfeel and/or umami agent and/or as a monosodium glutamate (MSG) partial or total replacer is particularly attractive.
  • Said uses consist, for example, in a method to impart, improve or increase the umami character and/or the mouthfeel of a flavoring composition or a flavored article, which method comprises adding to said composition or article an umami and/or mouthfeel effective amount of at least an invention's compound.
  • mouthfeel agent we mean here a flavoring ingredient capable of modifying, imparting, improving or enhancing the taste properties of flavoring compositions or foodstuffs to which they are added, and this in respect of the "mouth impact" of the aroma of said flavoring compositions or foodstuffs.
  • a “mouthfeel agent” according to the invention provides an effect on the roundness and fullness perception of the aroma or taste of products into which it is added.
  • amami agent we mean here a flavoring ingredient capable of imparting what is commonly defined by a skilled person of the art as the umami taste.
  • ⁇ -amino acid residue has the meaning common in the art, that is an ⁇ -amino acid that lacks a hydrogen atom of the ⁇ -amino group, i.e. the group -(HN-CHR-COOH). These residues will henceforth be represented by the three letter abbreviations shown in brackets hereinbelow, which are of current use for defining the structure of polypeptide chains (see, e.g., Eur. J. Bioch. 1984, 138, 9-37). For the sake of clarity, it has to be mentioned also that by "proteogenic ⁇ -amino acid” we mean here any of the twenty amino acids used in nature for the synthesis of proteins.
  • Said amino acids are: L-glycine (Gly), L-alanine (Ala), L-valine (Val), L-leucine (Leu), L-isoleucine (lie), L-proline (Pro), L-serine (Ser), L-threonine (Thr), L-phenylalanine (Phe), L-tyrosine (Tyr), L-tryptophan (Trp), L-lysine (Lys), L-arginine (Arg), L-histidine (His), L-aspartic acid (Asp), L-glutamic acid (Glu), L-asparagine (Asn), L-glutamine (Gin), L-cysteine (Cys) and L-methionine (Met).
  • the invention is therefore concerned with compounds including a C 3 to C 8 dicarboxylic moiety and a residue of proteogenic amino acids mentioned above.
  • the invention's derivative N-(3-carboxypropionyl)-glutamic acid, or succinoyl-Glu has the following structure:
  • the most interesting organoleptic property of the invention's compounds is their ability to impart highly appreciated umami and/or mouthfeel characteristics to the compositions or foodstuffs to which they are added. More specifically, the mouthfeel or mouth impact provided by the presence of the invention's compounds results in a quite remarkable roundness, fullness and harmony of the whole taste of the flavoring compositions or flavored articles. It has to be said that the overall organoleptic effect is different from the one which could be obtained by compounds consisting of a simple salt between the free diacid and the free amino acid, which have a much sharper taste associated with the acid taste and are not able to impart an umami and mouthfeel character to the food in which they are added.”
  • succinoyl derivatives of Glu, Ala or Leu i.e.
  • N-(3-carboxypropionyl)-glutamic acid succinoyl-Glu
  • N-(3- carboxypropionyl)-alanine succinoyl-Ala
  • N-(3-carboxypropionyl)-leucine succinoyl- Leu
  • MSG replacer and/or as mouthfeel and/or umami agents have shown a very good performance as MSG replacer and/or as mouthfeel and/or umami agents, and are able to provide flavoring compositions and flavored articles with very much appreciated organoleptic characteristics.
  • succinoyl-Glu possesses a slightly acidic note together with a well perceivable umami taste or character having a broth connotation, the overall organoleptic impression being accompanied by a good and long lasting roundness and fullness.
  • the compounds succinoyl-Leu and succinoyl-Ala which have a slightly more acidic and slightly less umami taste than the one of succinoyl-Glu, provide similar organoleptic effects.
  • the organoleptic effect of these compounds has been found to be less sweet than the one provided by MSG, conferring thus an advantage to the invention's compounds for a use in savory application, wherein a sweet note may be undesired.
  • Maleyl-Glu imparts also a slightly more juicy feeling
  • glutaryl-Glu and Glutaryl-Leu imparts also a slightly more fatty feeling.
  • At least one invention's compound as defined above at least one invention's compound as defined above; ii) at least one ingredient selected from the group consisting of a flavor carrier and a flavor base; and iii) optionally at least one flavor adjuvant.
  • An invention's composition consisting of at least one invention's compound and at least one flavor carrier represents a particular embodiment of the invention as well as a flavoring composition comprising at least one invention's compound, at least one flavor carrier, at least one flavor base, and optionally at least one flavor adjuvant.
  • flavor carrier we mean here a material which is practically neutral from a flavor point of view, i.e. which does not alter significantly organoleptic properties of flavoring ingredients. Said carrier maybe a liquid or a solid.
  • liquid carrier one may cite, as non-limiting examples, an emulsifying system or a solvent commonly used in flavors.
  • a skilled person in the art is able to select them on the basis of the nature of the product to be flavored.
  • solvents commonly used in flavors one can cite compounds such as propylene glycol, triacetine, triethyl citrate, benzylic alcohol, ethanol, vegetal oils or terpenes.
  • solid carrier one may cite, as non-limiting examples, absorbing gums or polymers, or yet an encapsulating materials as explained in more details further below.
  • flavor base we mean here a composition comprising at least one flavoring co-ingredient.
  • Said flavoring co-ingredients are not of the formula (I).
  • flavoring co-ingredient it is meant here a compound, which is used in flavoring preparation or composition to impart an hedonic effect.
  • a co-ingredient to be considered as being a flavoring one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the taste of a composition, and not just as having a taste.
  • a flavoring composition comprising at least one compound of formula (I) such as succinoyl-Glu, succinoyl-Ala and succinoyl-Leu, and/or a derivative thereof, is particularly useful from the organoleptic point of view.
  • a flavoring composition wherein the flavor base comprises at least a flavoring co-ingredient selected from the group consisting of an extract derived from a single cell organism, a protein hydrolysate and a fat hydrolysate, has proved to be particularly useful as MSG replacer. Indeed, we have found that the presence of at least one of said flavoring co-ingredients increases or boosts the organoleptic effect provided by the invention's compounds.
  • extract derived from a single cell organism we mean here an extract obtained by degradation, e.g. by autolysis, of a single cell organism such as a yeast.
  • single cell organisms are Saccaromyces cerevisae and Torulla cells.
  • protein hydrolysate we mean here the residue obtained by the degradation, e.g. hydrolysis, of a protein.
  • examples of such material are the product obtained by the hydrolysis of proteins of current use in the flavor industry such as caseine, soya proteins and pea proteins.
  • caseine hydrolysates are very interesting.
  • fat hydrolysate we mean here the residue obtained by the degradation, e.g. by enzymatic hydrolysis, of a fat.
  • examples of such material are hydrolised butter oil.
  • a preferred composition of said invention's embodiments is a flavoring composition wherein the flavor base comprises at least a yeast extract, at least a protein hydrolysate and at least a fat hydrolysate.
  • the unexpected synergies between the co-ingredients has been found to be very profitable for the intended use of said flavoring compositions, e.g. to impart remarkably rich and balanced organoleptic effects, e.g. fullness, volume and perception of the flavor, which are similar to, or more suitable than, those conferred by MSG.
  • the flavoring compositions according to the invention may be in the form of a simple mixture of flavoring ingredients or also in an encapsulated form, i.e. a flavoring composition entrapped into a solid matrix.
  • the encapsulation process by which the aroma can be protected may consist of techniques such as spray-drying, agglomeration or yet extrusion; or consists of a coating encapsulation, including coacervation and complex coacervation techniques.
  • Carrier materials used for matrices are wall-forming and plasticizing materials such as mono, di- or trisaccharides, natural or modified starches, hydrocoUoids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins.
  • Example of particularly useful matrix materials include sucrose, glucose, lactose, levulose, fructose, maltose, ribose, dextrose, isomalt, sorbitol, mannitol, xylitol, lactitol, maltitol, pentatol, arabinose, pentose, xylose, galactose, maltodextrin, dextrin, chemically modified starch, hydrogenated starch hydrolysate, succinylated or hydrolysed starch, agar, carrageenan, gum arabic, gum accacia, tragacanth, alginates, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropylmethyl cellulose, derivatives and mixtures thereof.
  • Coating encapsulation is typically based on thin xerogel carrier systems including gelatin, agar and alginate.
  • suitable carrier ingredients are cited in reference texts such as H. Scherz, Hydrokolloids: Stabilisatoren, Dickungs- und Gieherstoff in Struktur, Band 2 der Kunststoffen Herbert Strukturchemie, claritat, Behr's VerlagGmbH & Co., Hamburg, 1996.
  • the cited materials are hereby given by way of example and are not to be interpreted as limiting the invention.
  • flavor adjuvant we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc.
  • flavor adjuvant we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc.
  • a detailed description of the nature and type of adjuvant commonly used in flavoring bases cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art.
  • an invention's compound or composition is a useful flavoring ingredient which can be advantageously incorporated to flavored articles or foodstuffs to improve or enhance their taste. Consequently, a flavored article comprising: i) at least one compound selected from the group consisting of a compound of formula (I), its edible alkaline or alkaline earth salts and the hydrates thereof, or an invention's composition; and ii) a foodstuff base, is also an object of the present invention.
  • a flavored article according to the invention comprises the functional formulation, as well as optionally additional benefit agents, corresponding to an edible product, e.g. a stock, and a flavor effective amount of at least an invention's compound and optionally one or more solvents commonly used in flavors.
  • Suitable foodstuffs base e.g. foods or beverages
  • low fat we mean here a fat content which is 30%, preferably 50%, lower than in the classical article. Indeed, we have found that low fat and classical food products, and in particular the low fat ones, can be improved from the point of view of the umami and/or mouthfeel character using a compound or a flavoring composition according to the invention.
  • Suitable foodstuff bases comprise, for example, all savory foods, such as those of the meaty, poultry, fishy, vegetable, cheese and dairy types.
  • the proportions in which the compounds according to the invention can be incorporated into the various aforementioned articles or compositions vary within a wide range of values. These values are dependent on the nature of the article or product to be flavored and on the desired effect as well as the nature of the co-ingredients in a given composition when the compounds according to the invention are mixed with flavoring co- ingredients, solvents or additives commonly used in the art.
  • concentrations from 0.05% to 0.25%), and preferably from 0.1%) to 0.2%, by weight of these compounds, with respect to the food article in which they are incorporated can be typically used.
  • concentrations than these can be used when these compounds are incorporated into flavoring compositions.
  • the invention's compounds are prepared from commercially available products and using processes which make use of conventional reactions.
  • one of the methods which can be used to synthesize the invention's compounds consists in reacting the starting diacid of formula HOOC-G-COOH, wherein G is as defined in formula (I), with approximately one molar equivalent of a proteogenic ⁇ -amino acid in the presence of carboxylic acid activators such as DCC (N,N'-dicyclohexylcarbodiimide) and N-hydroxysuccinimide.
  • carboxylic acid activators such as DCC (N,N'-dicyclohexylcarbodiimide) and N-hydroxysuccinimide.
  • the resulting mixture was filtered, and the solution evaporated to dryness to obtain the invention's compound in its acidic form.
  • an edible salt is desired, prior the evaporation to dryness it is possible of adding an adequate amount of an adequate base.
  • the product thus obtained had a purity of at least 90%, frequently more than 95%>, the remaining being the dicarboxylic acid obtained by the hydrolysis of the starting anhydride.
  • the water solution thus obtained was lyophilized to afford a crude product.
  • the crude product was purified by preparative HPLC (conditions: Column Microsorb C18, 250*10 mm id. (Rainin), elution with 4 ml/min of an isocratic mixture of water and acetonitrile 8/2 containing
  • Flavor comprising an invention compound

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Seasonings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)

Abstract

L'invention porte sur l'utilisation d'un dérivé aminoacide et d'un diacide utilisé comme aromatisant. Selon ce procédé, un des groupes carboxyliques du diacide est lié au groupe alpha-amino de l'aminoacide afin de former une liaison amide. Lesdits composés sont particulièrement utiles pour les sensations tactiles buccales et/ou comme agent umami et/ou comme substitut partiel ou total du glutamate monosodique (MSG).
EP04706234A 2003-02-26 2004-01-29 Derives aminoacides d'acides dicarboxyliques utilises comme aromatisants Withdrawn EP1599103A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IB0300755 2003-02-26
WOPCT/IB03/00755 2003-02-26
PCT/IB2004/000258 WO2004075663A1 (fr) 2003-02-26 2004-01-29 Derives aminoacides d'acides dicarboxyliques utilises comme aromatisants

Publications (1)

Publication Number Publication Date
EP1599103A1 true EP1599103A1 (fr) 2005-11-30

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EP04706234A Withdrawn EP1599103A1 (fr) 2003-02-26 2004-01-29 Derives aminoacides d'acides dicarboxyliques utilises comme aromatisants

Country Status (3)

Country Link
EP (1) EP1599103A1 (fr)
JP (1) JP2006519289A (fr)
WO (1) WO2004075663A1 (fr)

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ATE444280T1 (de) 2006-05-05 2009-10-15 Givaudan Nederland Services B Zusammensetzung zur verbesserung von geschmack
CN101528060A (zh) 2006-10-18 2009-09-09 西姆莱斯有限责任两合公司 作为食品风味物质的取代双环[4.1.0]庚烷-7-羧酸酰胺及其衍生物
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GB0917325D0 (en) * 2009-10-02 2009-11-18 Givaudan Sa Flavour enhancement
GB201118480D0 (en) * 2011-10-26 2011-12-07 Givaudan Sa Organic compounds
GB201118497D0 (en) * 2011-10-26 2011-12-07 Givaudan Sa Organic compounds
EP2833738B1 (fr) 2012-03-30 2019-10-30 Givaudan S.A. Dérivés n-acylés de méthionine comme composés d'arôme alimentaire
KR102045589B1 (ko) 2012-03-30 2019-11-15 지보당 에스아 식품 향미 화합물로서의 n-아실-아미노산 유도체
BR112014023959B1 (pt) 2012-03-30 2020-10-20 Givaudan Sa composição comestível
CA2867329C (fr) 2012-03-30 2020-03-10 Givaudan S.A. Acides carboxyliques 1-aminocycloalkyles n-acylates comme composes d'aromatisation d'aliments
JP6248091B2 (ja) 2012-03-30 2017-12-13 ジボダン エス エー 食品フレーバー付与化合物としてのガンマアミノ酪酸およびベータアラニンのｎ−アシル誘導体
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Also Published As

Publication number Publication date
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JP2006519289A (ja) 2006-08-24

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