WO2010100589A1

WO2010100589A1 - Taste modifying compound

Info

Publication number: WO2010100589A1
Application number: PCT/IB2010/050848
Authority: WO
Inventors: Erik Decorzant; Laetitia Nicolas; Christian Starkenmann; Robert Wagner
Original assignee: Firmenich Sa
Priority date: 2009-03-02
Filing date: 2010-02-26
Publication date: 2010-09-10

Abstract

The present invention relates to the use of a compound of formula (I) wherein A represents a moiety selected from the group consisting of (CH2)nCOOH and CH(R)(CH₂)mCOOH, n is an integer from 1 to 5, m is an integer from 0 to 5, and R is a moiety selected from the group consisting of methyl, ethyl, CH₂SO₂OH and (CH₂) ₃NHC(NH)NH₂ as flavouring ingredient to confer, enhance, improve or modify the taste of a flavoured article.

Description

TASTE MODIFYING COMPOUND

Technical field

The present invention relates to the field of taste. More particularly, it concerns the use of a certain compound as taste-enhancing or taste-modifying ingredient to impart, reinforce or modify tastes such as umami, saltiness, seafood-deliciousness, roundness, creaminess and the like and/or to provide mouthfeel.

The present invention also concerns compositions or articles containing the taste- enhancing or modifying ingredient.

Background and Prior art

In today's world where health issues and their economic impact are studies heavily, the search continues for ingredients which can help satisfy consumers' taste/flavour demands whilst reducing the amount of the taste/flavour ingredient used. For this reason flavour and taste modulation is growing from a small specialist area of interest to one where many companies are involved in the search for new ingredients. Many reviews of taste modifying research are published, one being Magnifying Taste, Melinda Wenner, Scientific American August 2008 p96-98. In this document, it is noted that umami, saltiness and sweetness are all targeted heavily in order to find enhancers that enable reduction of consumer intake of the compounds that may have an adverse impact on consumer health.

Umami applies to the sensation of savoriness, and particularly to the detection of glutamates, which are common in meats, cheese and other protein-rich foods. The behaviour of umami receptors explains why foods containing monosodium glutamate (MSG) often taste "fuller". However, some consumers are apparently sensitive to MSG and may suffer from headaches or other illnesses upon consuming it.

In New Developments in Umami (Enhancing) Molecules, Winkel et al, Chemistry & Biodiversity, VoI 5 (2008), pi 195-1203, a review of known umami modifying compounds is given. However, there is no suggestion of the compounds of the present invention.

Salt ("sodium chloride") is used throughout the food industry to impart a 'salty¹ flavour to foods and beverages. However, sodium chloride is also known to cause an increase in blood pressure in mammals leading to a variety of cardiovascular diseases. To reduce its use, there is a need for compounds that enhance the 'salty' flavour delivered by salt in foods and beverages, thereby enabling a reduced quantity of salt to be present,

Mouthfeel, often associated with fatty ingredients such as butter, provides fuller flavours that can be described as more rounded or creams. Nevertheless, butter-containing foodstuffs are also targeted as products where it would be desirable to be able to reduce the intake of the fatty component without reducing the mouthfeel.

Thus, it would be desirable to provide a flavour or taste modifying ingredient that enhances the umami or saltiness characteristics of a flavour or foodstuff to which it is added. Alternatively or additionally, it would be desirable to provide a compound capable of imparting, enhancing or modifying the mouthfeel of a product that is to be consumed.

Summary of the invention

We have now surprisingly discovered that a certain class of opines can be used as taste enhancing or modifying ingredient, for instance to impart to or reinforce umami, saltiness, seafood-deliciousness, creaminess, roundness or mouthfeel of a flavouring composition or of a flavoured food.

Accordingly, the present invention provides the use of a compound of formula (I)

wherein

A represents a moiety selected from the group consisting of (CH₂)nCOOH and CH(R)(CH₂)mC00H, n is an integer from 1 to 5, m is an integer from 0 to 5, and

R is a moiety selected from the group consisting of methyl, ethyl, CH₂SO₂OH and

(CH₂) ₃NHC(NH)NH₂ as flavouring ingredient to confer, enhance, improve or modify the taste of a flavoured article. The invention further provides a method to confer, enhance, improve or modify the taste properties, as indicated above, of a flavouring composition or of a flavoured article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I). In the context of the present invention "use of a compound of formula (I)" includes the use of any composition containing compound (I) and which can be advantageously employed in the flavour industry as active ingredient.

The invention also provides a taste-modifying composition comprising: i) as taste-modifying ingredient, at least one compound according to formula (I) above; ii) at least one ingredient selected from the group consisting of a flavour carrier and a flavour base; and iii) optionally at least one flavour adjuvant.

The invention yet further provides a flavoured article comprising: i) as taste-modifying ingredient, at least one compound of formula (I), as defined above, optionally present as part of a flavouring composition; and ii) a foodstuff base.

Detailed Description of the invention

The compound for use as the taste-modifying ingredient has the following structure:

wherein

A represents a moiety selected from the group consisting of (CH₂)nCOOH and CH(R)(CH₂)mCOOH n is an integer from 1 to 5, m is an integer from 0 to 5, and

(CH₂) ₃NHC(NH)NH_2: CH₂COOH and C₂H₅COOH. In a preferred aspect, n is an integer from 1 to 3, more preferably 1 or 2. It is preferred that m is an integer from 0 to 3, more preferably 0 to 2, most preferably 0 or 1, e.g. 0. Specific compounds according to formula (I) for use according to the invention include:

(S)~2-(carboxymethylamino)propanoic acid, (R)-2-(carboxymethylamino)propanoic acid,

(+/-)-N-[- 1 -carboxyethyl]-alanine,

(+)-N-[(l S)-l-carboxyethyI]-L-aIanine,

(+/-)-N-[(lR)-carboxyethyl]-L-arginine,

(R)-2-(2-sulfoethylamino)propanoic acid, and mixtures of 2 or more thereof.

More preferred are

(S)-2-(carboxymethylamino)propanoic acid,

(R)-2-(carboxymethylamino)propanoic acid,

(+/-)-N-[-l-carboxyethyl]-alanine, (+)-N-[(1 S)-I -carboxyethylJ-L-alanine, and mixtures of 2 or more thereof. Most preferred are

(R)-2-(carboxymethylamino)propanoic acid,

(+/-)-N-[- 1 -carboxyethyl] -alanine, (+)-N-[(I S)-l-carboxyethyl]-L-alanine and mixtures of 2 or more thereof.

(R)-2-(carboxymethylamino)propanoic acid is especially preferred since the threshold at which the taste modifying properties can be detected is very low allowing smaller quantities to be used to achieve the desired effect. For the avoidance of doubt, the structures for use according to the invention may alternatively or additionally be present as salts thereof.

Suitable salts include but are not limited to sodium and potassium salts, more preferably sodium salts, most preferably monosodium salts.

As mentioned above, the invention concerns the use of a compound of formula (I) as a flavour-enhancing ingredient, and in particular to impart, reinforce or modify a variety of tastes and/or mouthfeel. According to a particular embodiment of the invention, such use is very much appreciated by flavourists to impart, enhance or modify the taste or mouthfeel in savoury flavours, such as beef, chicken, pork, and seafood.

In a taste-modifying composition according to the present invention, there may be provided a flavour carrier. In the context of the present invention "flavour carrier" means a material which is substantially neutral from a flavour point of view, insofar as it does not significantly alter the organoleptic properties of flavouring ingredients. The carrier may be a liquid or a solid.

As a liquid carrier, non-limiting examples include an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in flavours. A detailed description of the nature and type of solvents commonly used in flavour cannot be exhaustive. However, non-limiting examples of suitable solvents include propylene glycol, triacetine, triethyl citrate, benzylic alcohol, ethanol, vegetable oils or terpenes,

As a solid carrier, non-limiting examples include absorbing gums or polymers, or even encapsulating materials. Examples of such materials may comprise wall-forming and plasticizing materials, such as mono, di- or tri saccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or the materials cited in reference texts such as H. Scherz, Hydrokolloids : Stabilisatoren, Dickungs- und Gehermittel in Lebensmittel, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitat, Behr's VerlagGmbH & Co., Hamburg, 1996. Encapsulation is a well known process to a person skilled in the art, and may be performed, for instance, using techniques such as spray-drying, agglomeration, extrusion, coacervation and the like. Spray-dried or extruded solid carriers are preferred.

In a taste-modifying composition according to the present invention, there may be provided a flavour base. In the context of the present invention, "flavour base" means a composition comprising at least one flavouring ingredient.

The flavouring ingredient is not a compound having a structure according to formula (I). In the context of the present invention, "flavouring ingredient" means a compound, which is used in flavouring preparations or compositions to impart a hedonic effect. In other words such an ingredient, to be considered as being a flavouring ingredient, 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.

The nature and type of the flavouring ingredients that may be present do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect. In general terms, these flavouring ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and can be of natural or synthetic origin. Many of these flavouring ingredients are listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals,

1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of flavour. It is also understood that the flavouring ingredients may also be compounds known to release in a controlled manner various types of flavouring compounds. For instance, suitable flavouring compounds for use in combination with the compound of the invention include monosodium glutamate, ribotides, table salt, sucrose, acids, yeast extracts and reaction flavours.

However, according to a particular embodiment of the invention, the flavouring base preferably comprises one or more amino acids. For instance, glycine and/or alanine are particularly preferred.

Thus, a preferred composition according to the invention comprises a compound having a structure according to formula (I) in combination with glycine and/or alanine.

A suitable composition may comprise a flavour adjuvant in combination with the compound according to formula (I). In the context of the present invention, "flavour adjuvant" means an ingredient capable of imparting an additional added benefit such as color, a particular light resistance, chemical stability, and so on. A detailed description of the nature and type of adjuvant commonly used in flavouring bases cannot be exhaustive, though such ingredients are well known to a person skilled in the art.

A composition consisting of at least one compound of formula (I) and at least one flavour carrier represents a particular embodiment of the invention as well as a flavouring composition comprising at least one compound of formula (I)₅ at least one flavour carrier, at least one flavour base, and optionally at least one flavour adjuvant.

In a highly preferred embodiment, more than one compound of formula (I) is used in combination since it is found that a synergistic enhancement of the umami or saltiness taste can be achieved in this way.

Moreover, a compound of formula (I) can be advantageously incorporated into flavoured articles to positively impart, or modify, the taste of said articles. The flavoured articles comprise a foodstuff base. In the context of the present invention, the phrase "foodstuff base" means an edible product, e.g. a food or a beverage. Suitable foodstuff bases include stock cubes, bouillons, instant soups, canned soups, preserved meat, instant noodles, frozen dishes and preparations, sauces, dressings, flavoured oils and spreads, battered fried products, snacks and biscuits. Particularly preferred foodstuffs in which the compound according to formula (I) can be used include those surimi, surimi-based foods, seafood-based foods, seafood-based sauces, seafood-based soups, seafood-based bouillons and seafood- based dressings. Seafood includes, for example, preparations where the primary flavour is fish, crab, shrimp, prawn and the like.

The nature and type of the constituents of the foodstuffs or beverages do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the nature of said product.

In a foodstuff, the taste modifying compound according to the invention is found to be highly effective when the pH of the foodstuff is between 5 and 8, more preferably between 6.5 to 7.0. Thus, it may be preferably to add pH-modifying ingredient to the foodstuff containing the taste-modifying compound of the invention. The proportions in which the compound having the structure according to formula (I) 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 to be flavoured and on the desired organoleptic effect as well as the nature of the co-ingredients in a given base when the compounds according to the invention are mixed with flavouring co- ingredients, solvents or additives commonly used in the art. In the case of flavouring compositions, typical concentrations are in the order of 200ppm to 2000ppm, more preferably 300ppm to 1500ppm, most preferably 400 to 1200ppm of the compounds of the invention based on the weight of the consumer product into which they are incorporated. At these levels the taste is typically described as delivering umaminess, saltiness, seafood-deliciousness, roundness, creaminess or mouthfeel.

Examples

The invention will now be described in further detail by way of the following example, wherein the abbreviations have the usual meaning in the art, the NMR spectral data were recorded in CDCL₃, with a 400MHz machine for C, the chemical displacements, δ, are indicated in ppm with respect to TMS as standard, and the coupling constants, J, are expressed in Hz.

Example 1

Preparation of (R)-2-(carboxymethylamino^')propanoic acid - "R-strombine" (R)-Alanine (15 g, 168 mmole) and glyoxylic acid monohydrate (31 g, 337 mmole) in anhydrous methanol (650 mL) were added to Pd/C 10% (750 mg) suspended in anhydrous ethanol (100 mL). Hydrogenation was performed at atmospheric pressure, at 24°C for 18 hours. The crude product was filtered on Celite and rinsed with methanol (100 mL). The filtrate was discarded. The Ceiite was then washed with water (300 mL), and the water was removed by evaporation under reduced pressure to give 30 g of a viscous liquid (30 g). The crude product was then rediluted in about 100 mL of water, and purified on Dowex 50WX8-400 H⁺ form, (220 g, column 45 mm internal diameter). The elution was performed by portions of 200 mL of water containing an increasing concentration of NH4OH 30%: 200 mLwater, 200 mL water plus 4 mL NH₄OH 30%, then 6 mL₅ 2 x 8 mL, 10 mL 12 mL. The product was eluted with 8 mL Of NH₄OH 30%. After lyophylisation 13 g of pure end product was obtained (non optimized yield of 52%), 1H-NMR: 1.51 (d, J = 7 Hz, 3H), 3.62 (s, 3H), 3.73 (q, J = 7 Hz, IH). 13C-NMR: 377.6 (s), 174.2 (s), 60.3 (d), 50.4 (t), 17.5 (q). [α]²⁰ _D (pH 6, C = 5) - 9.0, [α]20D (pH 1, C = 5) - 5.6. The optical purity was determined after derivatisation of 12 mg of strombine, in MeOH/HCl 1.25 M (2 mL), heated 1 hour in a sealed vial at 100⁰C, After cooling, ethyl acetate (2 mL) and 0.5 mL of NaOH 1 M were added and the organic phase was injected on Chiral column; GC(Chirasil column)-MS: retention time = 21.79 min. MS: 116 (100, M+), 100 (2), 88 (10), 56 (50) (98.8%), S-strombine 21.90 min. (1.2%).

Example 2

Preparation of (S)-2-(carboxymethylamino)propanoic acid - "S-strombine" The preparation conditions as set out in example 1 were used except that (S)-Alanine (GC chira! = 99.6 %), [α]²⁰ _D (pH 6, C = 5) + 9.0, [α]²⁰ _D (pH 1, C = 5) + 5.4 was used as the starting material.

Quantification of (R)-strombine was made after derivatisation of 10 mg of each in three replicates in MeOH/HCl 1.25 M (2 mL), heated 1 hour in a sealed vial at 100⁰C. The solvent was removed under vacuum and trichloroacetic anhydride (0.5 mL) was added and the sample was heated again at 1 hour at 95 ⁰C. The solvent was removed under vacuum and ethylacetate (1 mL) was added. The samples were injected in various dilutions (0.125, 0.25, 0.5, 1 mg), to establish a calibration curve: and injected (1 μL, split 10: 1) on SPB-I column (R² = 0.998). 1H-NMR: 1.51 (d, J = 7 Hz, 3H), 3.62 (s, 3H)₁ 3.73 (q, J = 7 Hz₃ IH). 13C-NMR: 177.6 (s), 174.2 (s), 60.3 (d), 50.4 (t), 17.5 (q)

Example 3

Preparation of (+-)-N-[-l-carboxyethyl^~|-alanine - "meso-alanopine"

(-)-S-ethyl-L-lactate (12.5 g, 106 mmol) and pyridine (8.37 g, 106 mmole) in CH₂Cl₂ (100 mL) were added to trifluoromethanesulfonic anhydride (30 g, 106 mmole) in CH₂Cl₂ (100 mL) at 0 ⁰C₃ stirring for I h at 5 ⁰C. Then pentane (150 mL) was added, the precipitate was removed by filtration on filter paper. After distillation: bp 0.5 mbar 35°C, triflate of (-)-S- ethyl-L-lactate was obtained (22.7 g, 85%).

L-alanine ethyl ester (1.16 g, 10 mmole) in CH₂Cl₂ (20 mL) was treated with the triflate (2.5 g, 10 mmole) at O ⁰C, then the reaction was stirred at room temperature overnight. The crude mixture was then treated with brine, the aqueous phase extracted with CH₂Cl₂ and washed with NaHCO₃. The solvent was removed under vacuum, giving 2.2 g of solid (yield 100%). This product (1 g, 4.5 mmole) was then hydrolysed with KOH (1 g, 15 mmole), in water (10 niL) and EtOH (20 mL) under reflux for 6 hours. The crude mixture was then poured on ice HCl 5 M and the solvent was removed by distillation under vacuum on a rotary evaporator. The resulting syrup was diluted with a small amount of water and added to a column (i. d. 4.5 cm) DOWEX 50WX8-400 (150 g), H⁺ form. The product was eluted by passing through the column: water, water with 2% NH40H 30%, 3%, 4%, 5%, 6%, 7%, 8%. The alanopine was in 6-7% fractions. The solvent was removed first on the rotary evaporator under vacuum, then rediluted in water and lyophylised (highly hygroscopic powder, then resuspended in MeOH and re-concentrated under vacuum. Meso-alanopine was obtained 0.69 g (yield 92%).

The stereo-purity was checked on the methyl ester (treatment with MeOH/HCl 1.25 M, 2.5 hours at 95 ⁰C), Col. _SPB-_I meso-alanopine 13.64 min > 98%), anti-alanopine 13.76 min. LC-MS ESI pos: xxx. ¹H-NMR: 1.50 (m, 6H), 3.71-3.78 (m, 2xlH),. ¹³C-NMR: 177.8 (s), 59.3 (d), 17.8 (q).

Example 4

Preparation; (+)-N-[^"(l S)-l-carboxyethyl]-L-arginine, - "S-octopine" L-Arginine (10.5 g, 50 mmole) was stirred 48 hours at 45 ⁰C in presence of S-bromopropionic acid (15.3 g, 100 mmole, ACROS e.e. 85%) and barium hydroxide octahydrate (31 g, 100 mmole) in water 200 mL. The milky solution was acidified to pH 6 with H₂SO₄ and purified on column i.d. 6 cm: DOWEX 50WX8-400 (200 g), H⁺ form. The product was eluted by passing through the column: water, water (1 L) with water 400 mL containing 10 mL of NH₄OH₅ water 400 mL containing 15 mL of NH₄OH, 400 mL containing 20 mL of NH₄OH, 400 mL containing 25 mL of NH₄OH. The octopine was in fractions 2 and 3. Lyophylisation yield a crude product 10.4 g (yield 84%). Re-crystallisation,

[α]D 20 +19.5 c = 2.5 in H₂O pH 6; GC _SPB-_I methylated: 32.32 min d.e. > 96%.

LC-MS ESI pos: xxx. ¹H-NMR: 1.50 (d, J = 7 Hz, 3H), 1.60-1.71 (m, 2H)₃ 1.89-2.0 0 (m,

2H), 3.24-3.38 (t, J = 7 Hz, 2H), 3.71-3.76 (m, 2x I H). 13C-NMR: 177.8 (s), 176.7 (s), 159.6 (s), 62.9 (t), 59.7 (d), 43.3 (t), 29.8 (t), 27.0 (t), 17.2 (q). Example 5

Preparation of (R)-2-(2-sulfoethylamino)propanoic acid - "tauropine" Taurine (6.25 g, 50 mmole), S-bromopropionic acid (25 g, 163 mmole) and NaOH IM (350 mL) were heated for 4 hours at 100 ⁰C. The crude product was purified on column (i.d. 6 cm): DOWEX 1X2 (200 g), OH^" form. The product was eluted by passing through the column: water, water (0.8 L) with acetic acid IM 250 mL, then HCl IM. A crude brown solid was obtained, 4.75 g (yield 48%).

LC-MS ESI pos: 394.8. ¹H-NMR: 1.51 (d, J = 7 Hz, 3H), 3.30-3.34 (m, 2H), 3.50-3.54 (m, 2H), 4.12 (q, J = 7 Hz, IH). 13C-NMR: 175.0 (s), 59.0 (d), 49.5 (t), 44.5 (t), 16.9 (q).

Example 6

Taste Analysis of Compounds of Examples 1 and 2

According to the ASTM E679 Ascending Concentration Series Method of Limits, 7 different concentrations of the taste modifying compounds of examples 1 and 2 were chosen for each triangle test (one sample containing the taste modifying compound and the two others containing water). The panelists started with the weakest concentration of the taste modifying compound to the strongest. The presentation order of each triangle test was randomized. The compositions tested are given in the following tables:

Taste Modifying Compound of Example 1

Taste Modifying Compound of Example 2

The sensory characterization was realized together with threshold measurement in one session, with choices of sensory attribute after each triangle. The panelists were asked to choose among sweet, salty, bitter, umami, acid, mouthfeel and metallic or "by chance". Two repetitions were performed for each taste modifying compound. 10 ml or 20ml was presented to the panelists for the session with the taste modifying compound of example 1. 10ml sample was presented for the session with the taste modifying compound of example 2. Sip and spit out procedure was used.

Taste analysis was performed by 47 trained panelists in two sessions, of whom 13 performed replicates. 60 responses were obtained and 55 of them were used to evaluate the threshold value, except for 5 responses, for which the individual threshold was above 4 g/L. For the compound of example 1, some panelists detected a taste modifying effect, such as salty, umami and mouthfeel, at very low levels. A significant number detected a taste modifying effect at 0.5 g/L.

For the compound of example 2, some panelists detected a taste modifying effect, such as salty, umami and mouthfeel, at very low levels. A significant number detected a taste modifying effect at 0.74 g/L. Example 7

Taste Analysis of Alanopine and Octopine

15 trained subjects evaluated the saltiness intensity of 3 salty solutions, shown in the following table, with and without nose-clips on a linear scale of 0 (no taste) to 10 (very intense taste).

Henniez (Switzerland)

The saltiness of samples 1 and 2 was compared to the reference using the student t-test for the both evaluations with and without nose-clips.

The mean score for the 15 panelists' results are given in the following table:

It can be seen that sample 1 was perceived as significantly more salty than the reference (at a level of 95%) with and without nose-clips. Sample 2 was perceived significantly more salty than the reference (at a level of 95%) with the nose-clip. These results demonstrate clearly a saltiness enhancing effect for both compounds.

Example 8

Instant Soup Preparation

An instant vegetable soup (Reference) was prepared by thoroughly mixing the following ingredients together with boiling water (IL):

(l) Prjel VA70T aggl

The reference sample was allowed to stand for 1 to 2 minutes prior to tasting. Various quantities of a racemic mixture of (R) and (S) strombine were added to aliquots of the reference sample. The pH of the resulting mixtures was adjusted to about 7 using a solution of tripotassium phosphate. A team of 5 trained panelists were then asked to judge the increase in mouthfeel (creaminess) and fat enhancement on a scale of 0 (no enhancement) to 5 (very strong enhancement).

*% by weight of the ingredient in the product as consumed Example 9

White Sauce for Ready Meals

A white sauce for seafood ready meals was prepared by firstly mixing together the following ingredients:

The mixture was then heated until boiling and allowed to simmer under stirring for 10 to 35 minutes. 150 g of modified starch (COL FLO 67) was dissolved in cold water and then added to the sauce. The resulting product was heated to 85°C for 2 to 3 minutes and then filled into cans and retorted at 110⁰C for 5 minutes.

Various aliquots of a racemic mixture of (R) and (S) strombine, and in sample 2 certain amino acids, were added to the white sauce preparation and stirred. The pH of the resulting mixtures was then adjusted to about 7 using a solution of tripotassium phosphate. A team of trained 5 panelists were then asked to judge the increase in creamy mouthfeel and fat enhancement on a scale of 0 (no enhancement) to 5 (very strong enhancement).

Example 10 Chicken Burger

Chicken (82g) was ground in a mincer. A marinade was prepared by mixing water (14.9g), Satagiel Adg38 (0.2g), salt (0.6g) and starch (2.3g). The chicken was then introduced into the marinade and 8Og of the resulting product was formed into a burger and frozen. A batter was prepared by mixing Adhesion Batter BPF 069 (50g) and water (9Og). The burger was divided into 2 portions and passed through the batter. The battered chicken was then coated with commercially available breadcrumbs (5g), par-fried at 180⁰C for 30 seconds and then frozen. Finally the par-fried breaded chicken was fried for 2.5 minutes at 190°C to provide the reference sample.

For samples 1 and 2, the preparation was the same as for the Reference sample except that various quantities of a racemic mixture of (R) and (S) strombine, and in sample 2 certain amino acids, were added to the marinade prior to mixing with the chicken. A team of 5 trained panelists was asked to judge the increase in mouthfeel and fat enhancement of samples 1 and 2 over the reference sample on a scale of 0 (no enhancement) to 5 (very strong enhancement).

Claims

1. Use of a compound of formula (I)

wherein

A represents a moiety selected from the group consisting of (CH₂)nC00H and CH(R)(CH₂)mCOOH, n is an integer from 1 to 5, m is an integer from 0 to 5, and

R is a moiety selected from the group consisting of methy!, ethyl, CH₂SO2OH and

(CH₂) ₃NHC(NH)NH₂ as flavouring ingredient to confer, enhance, improve or modify the taste of a flavoured article.

2. Use as defined in claim 1 wherein n is an integer from 1 to 3 and m is an integer from O to 3.

3. Use as defined in claim 1 wherein n 1 or 2 and m is 0 or 1.

4. Use as defined in claim 3 wherein the compound according to formula (I) is selected from the group consisting of (S)-2-(carboxymethylamino)propanoic acid, (R)-2-(carboxymethylamino)propanoic acid, (+-)-N-[-l-carboxyethyl]-alanine, (+)-N-[(l S)-l-carboxyethyl]-L-aIanine, (+/-)-N-[(lR)-carboxyethyl]-L-arginine, (R)-2-(2- sulfoethylamino)propanoic acid, and mixtures thereof.

5. A method to confer, enhance, improve or modify the taste properties of a flavouring composition or of a flavoured article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I), as defined in claim 1.

6. A taste-modifying composition comprising: i) as taste-modifying ingredient, at least one compound according to formula (I), as defined claim 1; ii) at least one ingredient selected from the group consisting of a flavour carrier and a flavour base; and iii) optionally at least one flavour adjuvant.

7. A taste-modifying composition according to claim 6 further comprising an amino acid.

8. A taste-modifying composition according to claim 7 wherein the amino acid is selected from the group consisting of glycine, alanine and mixtures thereof.

9. A flavoured article comprising: i) as taste-modifying ingredient, at least one compound of formula (I), as defined in any one of claims 1 to 4, optionally present as part of a flavouring composition; and ii) a foodstuff base.

10. A flavoured article according to claim 9 wherein the foodstuff base is selected from the group consisting of stock cubes, bouillons, instant soups, canned soups, preserved meat, instant noodles, frozen dishes and preparations, sauces, dressings, flavoured oils and spreads, battered fried products, snacks and biscuits.