AU2012200442B2 - Taste improving substances - Google Patents

Abstract

The present invention relates to a flavour composition comprising: one or more flavouring substances and one or more taste improving substances selected from the 5 group consisting of: substances according to formula (1): CH 2OH-(CHOH) 4-CO-NH CH 2 -X wherein X represents -OH, -O(CO)R, -OP0 3H2, -P0 3H 2, -OSO 3 H or -SO 3H, and R represents a C2 -CIO group comprising at least one carboxylic acid group; and edible salts thereof, wherein, in case the flavour composition contains N-gluconyl ethanolamine or a salt thereof, the weight ratio of the taste improving substances and the flavouring 10 substances is less than 50:1. The invention furthermore concerns substances according to formula (I) wherein X represents -O(CO)R, -OP0 3H2, -P0 3H2, -OSO 3 H or -SO 3 H, and R represents a C2 -CIO group comprising at least one carboxylic acid group; and edible salts thereof

Description

- 1 AUSTRALIA PATENTS ACT 1990 COMPLETE SPECIFICATION FOR A STANDARD PATENT ORIGINAL Name of Applicant: Givaudan Nederland Services B.V. Actual Inventors: Jan Visser and Harry Renes and Chris Winkel and Sylvia Noomen Address for Service is: SHELSTON IP 60 Margaret Street Telephone No: (02) 9777 1111 SYDNEY NSW 2000 Facsimile No. (02) 9241 4666 CCN: 3710000352 Attorney Code: SW Invention Title: TASTE IMPROVING SUBSTANCES Details of Original Application No. 2005264744, dated 6 April 2005 The following statement is a fall description of this invention, including the best method of performing it known to me/us: File: 52984AUP01 -2 TASTE IMPROVING SUBSTANCES Field of the Invention The present invention relates to the field of taste improvement in foodstuffs, 5 beverages, pharmaceutics, tobacco products and oral care products. More particularly, the present invention provides flavour compositions that can be used to confer a fuller and richer taste to foodstuffs, beverages, pharmaceutics, tobacco products and oral care products. The flavour compositions according to the invention are characterised by the presence of one or more substances that are 10 capable of improving and complementing the impact of other flavour imparting substances. The present invention also encompasses the use of the aforementioned taste improving substances for improving the taste of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products, as well as to foodstuffs, 15 beverages, pharmaceutics, tobacco products and oral care products containing these substances. Background of the Invention Any discussion of the prior art throughout the specification should in no 20 way be considered as an admission that such prior art is widely known or forms part of common general knowledge in the field. "Umami" is a term commonly used to describe the taste impact of L glutamate salts and certain nucleotides. Umami is the main taste in the Japanese stock called "dashi", and in bouillon and other stocks. Glutamic acid is an 25 important constituent of food proteins (plant and animal) such as those abundantly found in foods such as meat, poultry, seafood and vegetables. Two nucleotides that contribute most to the umami taste, GMP (guanosine monophosphate) and IMP (inosine monophosphate) are also present in many foods. By themselves these nucleotides do not typically give as powerful a flavour result as MSG (monosodium 30 glutamate). However, due to a synergistic interaction with MSG, a pronounced enhancing effect can be observed if these nucleotides are used in combination with

MSG.

-3 The umami taste has characteristic qualities that differentiate it from other tastes. It has been convincingly shown that umami represents the fifth taste, in addition to the other four basic tastes sweet, acid, salt and bitter. The most common descriptors that are used to describe the umami taste include "savoury", "meaty" 5 and "broth-like". "Umami" is literally translated as "delicious". As alternatives to MSG and 5'-nucleotides, other molecules have been proposed as taste modifying substances: Organic acids like tartaric and succinic acid have been reported to exhibit taste enhancing properties (Ney [1971] Z. Lebensm. Unters. Forsch. 146: 141; 10 Velisek et al. [1978] Nabrung 22: 735). Taste modifying properties have also been attributed to certain di- to octa-peptides (Yamasaki and Maekawa [1978] Agric. Biol. Chem. 42: 1761; Noguchi et al. [1975] J. Agric. Food Chem. 23: 49). WO 97/04667 discloses tripeptides containing a hydrophobic amino acid residue and at least one acidic amino acid residue as well as N-lactoyl-X 15 substances, wherein X represents an amino acid residue, as flavouring ingredients to impart savoury taste and increase the mouthfeel of foodstuffs. It is also disclosed that these peptides and derivatives can partly mimic organoleptic features of MSG. EP-A 1 252 825 discloses flavouring compositions for imparting umami taste to food products comprising substances that are formed by the reaction of the 20 primary or secondary amino group of an amino acid, peptide or protein with the carbonyl group of a reducing sugar. According to this document the most preferred substances are those wherein the amino acid residue is selected from glutamic acid or aspartic acid and the sugar residue is selected from fructose, glucose, maltose, lactose, galactose, rhamnose, xylose and mannose. 25 EP-A 1 356 744 discloses flavouring compositions containing N acetylglycine and the use thereof for imparting umami taste to foodstuffs. As described above umami taste and umami imparting substances contribute to the flavour of foodstuffs, especially in the savoury range. In sweet and beverage products, further examples of the importance of the 30 gustative dimension of flavourings have been reported. These examples include taste attributes such as bitterness, tingling and cooling-freshness.

-3a Bitterness is an essential aspect of some food flavours, among which chocolate taste. Purine alkaloids, like theobromine and caffeine, as well as amino acids and peptides have been known for a long time as bitter substances. In British patent no. GB 1420909 it is disclosed that the bitter flavour of cocoa can be 5 reproduced using a combination of a purine alkaloid and an amino acid or an oligopeptide which 'produces a surprisingly more natural simultaneously bitter and astringent flavour note than either of these types of substances alone'. Menthol, an important constituent of peppermint oil, has a strong impact on flavoured products not only because of its mint smell but also because it imparts a 10 cooling and fresh taste. Next to mint flavoured products, it has been suggested to employ menthol in other types of flavour to impart a cool taste. US patent application no. US2005013846 for example discloses how menthol and derivatives thereof can be used as flavouring in water continuous spreadable acidified food products to obtain table spreads exhibiting a fresh, cool taste impression. 15 Similarly, cinnamic aldehyde and eugenol, constituents of cinnamon oil, are used in flavouring composition for confectionary products, not only for their smell but also because they impart a warm and tingling taste. The oral pungency of cinnamic aldehyde was described as burning and tingling by Cliff M and Heymann H [Journal of Sensory Studies 7 (1992)279-290]. According to the same authors 20 eugenol exhibits a long-lasting numbing effect. Cinnamon oil has been proposed as a taste improving flavouring. International patent application no. W09006689 discloses that cinnamon oil, among other spice extracts, added to a minty flavour formulation, can be used to improve the long-lasting flavour of chewing-gum. It is an object of the present invention to overcome or ameliorate at least one 25 of the disadvantages of the prior art, or to provide a useful alternative. Although a lot of work has been focused on finding taste improving substances that are capable of imparting new exciting taste attributes, there remains a general industry desire for new taste improving substances that may be suitable for use in both savoury and non-savoury applications. 30 Unless the context clearly requires otherwise, throughout the description and the claims, the words "comprise", "comprising", and the like are to be construed in an inclusive sense as opposed to an exclusive or exhaustive sense; that is to say, in - 3b the sense of "including, but not limited to". Although the invention will be described with reference to specific examples it will be appreciated by those skilled in the art that the invention may be embodied in many other forms. 5 Summary of the Invention According to a first aspect of the present invention there is provided a flavour composition comprising: a. at least 0.1 wt.% of one or more flavouring substances, optionally 10 including saccharide sweetener in an amount of 0-20% by weight of the composition and/or artificial sweetener in an amount of 0-3 % by weight of the composition; and b. between 0.001 and 95 wt.% of one or more taste improving substances selected from the group consisting of: 15 substances according to formula (I): (I) CH 2

OH-(CHOH)

4

-CO-NH-CH

2

-CH

2 -X wherein X represents -OH, -O(CO)R, -OP0 3

H

2 , -P0 3

H

2 , -OSO 3 H or -SO 3 H, 20 and R represents a C 2

-C

10 group comprising at least one carboxylic acid group; and edible salts thereof wherein, in case the flavour composition contains N-gluconyl ethanolamine or a salt thereof, the weight ratio of the taste improving substances and the flavouring substances is less than 50:1. 25 According to a second aspect, the present invention provides a taste improving substance according to formula (I): (I) CH 2

OH-(CHOH)

4

-CO-NH-CH

2

-CH

2 -X 30 wherein X represents -O(CO)R, -OP0 3

H

2 , -P03H 2 , -OSO 3 H or -SO 3 H, and R represents a C2-Cio group comprising at least one carboxylic acid group; - 3c and edible salts thereof According to a third aspect, the present invention provides use of one or more taste improving substances as defined in the first aspect for improving the 5 taste of foodstuffs, beverages, pharmaceutics, tobacco products or oral care products. According to a fourth aspect, the present invention provides use of one or more taste improving substances as defined in the second aspect for improving the 10 taste of foodstuffs, beverages, pharmaceutics, tobacco products or oral care products. According to a fifth aspect, the present invention provides a process of improving the taste of a foodstuff, a beverage, a pharmaceutical product, a tobacco 15 product or an oral care product, comprising adding to said product one or more taste improving substances selected from the group consisting of substances according to formula (I) and edible salts thereof, in an amount of between 0.1 10,000 ppm. 20 According to a sixth aspect, the present invention provides a product selected from the group consisting of foodstuffs, beverages, pharmaceutics, tobacco products, and oral care products comprising one or more taste improving substances as defined in the first aspect in an amount of between 0.1-10,000 ppm. 25 According to a seventh aspect, the present invention provides a foodstuff, a beverage, a pharmaceutical product, a tobacco product or an oral care product having an improved taste when produced by the process of the fifth aspect. The present inventors have surprisingly found that the substances according 30 to formula (I) and edible salts thereof can be used advantageously to improve the taste of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products: - 3d (I) CH 2

OH-(CHOH)

4

-CO-NH-CH

2

-CH

2 -O-X It was found that these taste improving substances are particularly useful in a wide variety of applications including savoury food, such as soups and sauces, 5 non-savoury food, such as dairy, beverages and confectionery, as well as pharmaceutics, tobacco products and oral care products. The taste improving substances according to the present invention can be applied advantageously to impart desirable taste attributes to the aforementioned products. In addition, the present taste improving substances are capable of 10 modifying the taste impact of other flavour ingredients contained within these same products, thereby improving the overall flavour quality of these products. WO 92/06601 discloses certain amide based, non-caloric sugar substitutes derived from sugar carboxylic acids and amino alcohols, which possess similar physical rheological and colligative properties to sucrose. These substances may be 15 used as sugar substitutes for formulated foods such as confectioneries, beverages, bakery products and the like, in order to simulate the structure, texture, freezing point depression, moisture retention, density, water solubility, solution viscosity properties, stability, non-reactivity and appearance characteristics of sucrose. Optionally these sugar substitutes may be used in combination with 5 a high potency (artificial) sweetener, typical proportions thereof ranging from about 0.2 to 2.0 parts of sweetener per 100 parts of the sugar substitute. WO 92/06601 discloses a foodstuff (yellow calce) comprising 28.3 wt/o of the sugar substitute. The present invention also relates to flavour compositions, foodstuffs, beverages, pharmaceutics, tobacco products and oral care products comprising one or more substances 10 according to formula (1) and edible salts thereof. Other aspects of the present invention relate to the use of these substances for improving the taste of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products. 15 DETAILED DESCRIPTION OF THE INVENTION Accordingly, a first aspect of the present invention relates to a flavour composition comprising: a, at least 0.1 wt.% of one or more flavouring substances, optionally including saccharide 20 sweetener in an amount of 0-20% by weight of the composition and/or artificial sweetener in an amount of 0-3 % by weight of the composition; and b. between 0.001 and 95 wt.% of one or more taste improving substances selected from the group consisting of: substances according to formula (1): 25 () CH2OH-(CHOH) 4

-CO-NH-CH

2

-CH

2 -X wherein X represents -OH, -O(CO)R, -OPOUz,, -PO 3 H2, -OSOsH or -SO 2 H, and R represents a C 2 -C1 0 group Comprising at least one carboxylic acid group; and edible salts thereof wherein, in case the flavour composition contains N-gluconyl ethanolamine or a salt thereof, 30 the weight ratio of the taste improving substances and the flavouring substances is less than 50:1. Throughout this document the term "flavouring substance" encompasses any substance that is capable of imparting a detectable flavour impact, especially at a 4 concentration below 0.1 wt.%, more preferably below 0.01 wt.%, as well as sweeteners, including saccharide sweeteners and artificial sweeteners. The term "saccharide sweetener" as used in here refers to sweeteners that contain one or more saccharide units and that exhibit a sweetness potency that is of the same order of 5 magnitude as the sweetness potency of sucrose. Typically, the sweetness potency of such saccharide sweeteners is between 20% and 500% the sweetness potency of sucrose. The term "artificial sweetener" is used in here to refer to sweeteners that have a much higher sweetener potency than sucrose, especially a sweetness potency that exceeds the sweetness potency of sucrose by at least a factor 10, preferably by at least- a factor 20. 10 Throughout this document the terms "taste" and "flavour" are used interchangeably to describe the sensory impact that is perceived via the mouth, especially the tongue, and the olfactory epithelium in the nasal cavity. The term "taste modifying" as used herein refers to the capability of a composition or substance to alter the taste impact of other, flavour imparting, substances present within the same product, with the proviso that this change in 15 taste impact is not caused, by the flavour contribution of said composition or substance per se, but instead that it mainly results from the combined effect of on the one hand the taste improving composition or substance and on the other hand the other flavour imparting substances. The present substances combine the capability of modifying the taste of other flavour substances with a taste contribution of their own. The favourable impact of the present 20 taste improving substances is believed to be the result of the combination of these two effects. Preferably, the flavour composition according to the invention contains at least 0.1 wt.% of the taste improving substances as defined above. Typically, the amount of the taste improving substances does not exceed 90 wt.%, preferably it does not exceed 40 wt.%, even more preferably the flavour composition comprises less than 25 wt% of the taste improving 25 substance, most preferably less than 5 wt%. In a preferred embodiment the flavour composition according to the invention comprises flavouring substances in an amount of at least 0.5 wt.%, preferably at least 1 wt.%, based on the total weight of the composition. Preferably, the amount of flavouring substances does not exceed 95 wt%, more preferably it does not exceed 50 wt%. 30 Preferably, in the present flavour composition the taste improving substances and flavouring substances as defined herein before are employed in a weight ratio of less than 50:1, preferably less than 20:1. In a preferred embodiment said weight ratio is within the range of 1:100 to 10:1, more preferably within the range of 1:50 to 5:1. Most preferably, the 5 taste improving substances and flavouring substances are employed in a weight ratio that does not exceed 1:1. In case the flavoring composition comprises N-gluconyl ethanolamine and artificial sweetener, the weight ratio of N-gluconyl ethanolamine and artificial sweetener is preferably 5 less than 50;1, more preferably less than 20:. The flavour composition according to the present invention may suitably be prepared in the form of a liquid, a paste or a powder. In a particularly preferred embodiment the flavour composition is a free flowing powder, In a preferred embodiment, the present flavouring composition is selected from the 10 group consisting of dairy flavourings (e.g. butter and milk flavourings), fruit flavourings (e.g. citrus and red fruit flavourings), savoury flavourings (e.g, meat and cheese flavourings) and bread flavourings. Preferably, in the aforementioned formula (1) X represents a hydroxyl group, a phosphate group, a phosphonate group, a sulfate group or a sulfonate group. Even more 15 preferably, X represents a hydroxyl group, a phosphate group or a phosphonate group. Most preferably, X represents a hydroxyl or a phosphate group. Taste improving substances according to the invention in which X represents a hydroxyl group are particularly suitable for use in dairy flavourings and fruit flavourings as these taste improving substances are particularly effective in improving and complementing aspects of sweet taste. Taste 20 improving substances in which X represents a phosphate group were found to be particularly suitable for use in savoury flavourings and bread flavourings. ' In formula (I) the CH 2

OH-(CHOH)

4 -CO- moiety preferably represents an aldonic acid residue selected from the group of allonic acid, altronic acid, gluconic acid, mannonic acid, gulonic acid, idonic acid, gulactonic acid and talonic acid. Even more preferably said moiety 25 represents the residue of gluconic acid or mannonic acid. Another aspect of the present invention relates to substances according to aforementioned formula (I), wherein X represents -O(CO)R, -OP0 3

H

2 , -P03H2, -OSO 3 H or SOaH, and R represents a C 2 -CIO group comprising at least one carboxylic acid group, more preferably a C 2 -C7 group comprising one carboxylic acid group; and edible salts thereof. 30 In one embodiment the invention encompasses substances according to formula (I) wherein X represents a hydroxyl group and the CH 2

OH-(COH)

4 -CO- moiety represents a residue of an aldonic acid selected from allonic acid, altronic acid, mannonic acid, gulonic acid, idonic acid, galactonic acid and talonic acid. As explained herein before, the taste 6 improving substances according to this embodiment are particularly suitable for use in dairy flavours and fruit flavours, In another embodiment X presents a phosphate group, a phosphonate group, a sulfate group or a sulfonate group, the CH2OH-(CHOM 4 -CO- moiety preferably representing 5 a residue of an aldonic acid selected from gluconic acid and mannonic acid. The taste improving substances according this particular embodiment are beneficially employed in savoury flavours and bread flavours. In a particularly preferred embodiment the substance according to formula (1) is a gluconic acid derivative of ethanolamine phosphate, which according to RUPAC rules for 10 nomenclature should be referred to as N-gluconyl ethanolamine phosphate, or an edible salt thereof. Yet another aspect of the present invention relates to the use for improving the taste of foodstuffs, beverages, pharmaceutics, tobacco products or oral care products of one or more taste improving substances selected from the group of substances according to formula (1) and 15 edible salts thereof. In a particularly preferred embodiment the present invention relates to the use of one or more substances selected from N-gluconyl ethanolamine, N-gluconyl ethanolamine phosphate and edible salts thereof, for improving the taste of foodstuffs, beverages, pharmaceutics, tobacco products or oral care products. The inventors have found that the present taste improving substances are very useful 20 ingredients. which, in the presence of other flavouring substances, are capable of imparting highly appreciated taste sensations to the products in which they are incorporate, specifically "roundnes", "Ifulness", "substance", "continuity", "ginger-like", "tingling", "fatty", "metallic", "umami" and/or "bitter", Because of this, the present taste improving substances can be employed to improve the taste of foodstuffs, beverages, pharmacentics, tobacco 25 products and oral care products. The taste improving substances of the present invention as such are capable of imparting highly desirable taste attributes. In addition, it has been found that the taste improving substances according to the invention are capable of modifying and complementing the sensory impact of flavouring substances contained in the aforementioned products. The present taste improving substances are particularly effective in improving the 30 taste of products in which they are incorporated if said products comprise one or more other flavouring substances as well as a significant amount of fat, e.g. at least 0.1 wt.% fat or even at least 1 wt.% fat. Because the taste improving substances according to the invention are not particularly volatile, they do not produce a strong aroma impact, even though they can affect the aroma 7 impact of other flavour substances. Here the term "aoma" refers to the aspect of taste that is perceived through the olfactory epithelium. Because of the low volatility of the present taste improving substances it is believed that the advantageous properties of these substances are somehow associated with the impact that these substances have on the sensory receptors 5 located within the mouth. More in particular, the present taste improving substances, especially those that comprise a non-derivatised ethanolamine residue, were found to be useful for improving and complementing taste impact in sweet products, including beverages and dairy products. A suitable example thereof includes "masiing of bitter taste" in said products. The present 10 inventors furthermore found that the present taste improving substances are very useful ingredients for imparting and complementing a tastesensation described as "creamy" and/or "fatty' in products, especially sweetened products, containing a certain minimum amount of fat It is noted that, according to the present use, these effects on creamy and/or fatty taste sensation are not accompanied by a significant effect on the relevant physical parameters, 15 such as viscosity and structure, of the products. Additionally, the present taste improving substances, especially those that contain a phosphate residue, were found to be particularly useful for imparting and complementing 'salty taste impact' in salt containing products. As mentioned herein before, WO 92/06601 describes ingredients that, because of the physical properties thereof, could be used to completely replace sucrose as a stmcturing 20 and/or texturizing agent in sweetened foodstuffs such as confectionery products, bakery products and beverages, One of the substances described in this document is N-gluconyl ethanolamine, In order to fulfil its function the 'structuring agents' have to be used in major amounts in food applications. For example, WO 92/06601 describes a yellow cake comprising 28.3 wt% of said structuring agent. With regard to taste characteristics, WO 92/06601 only 25 mentions that the stimcturing agents disclosed therein, have a sweetness potency corresponding to 0 - 100 % of that of sucrose, and that, in order to accomplish the same final effect as sucrose in formulated foods, an amount of artificial bigh potency sweetener might be included in proportions ranging between 0.2 - 2.0 parts of sweetener per 100 parts of the structuring agent. 30 The use of N-gluconyl etbnolamine according to the present invention differs from this disclosure in that it is used only in minor amounts in order to impart a taste improving effect in combination with other (volatile) flavour substances. As mentioned before, at the levels at which N-gluconyl ethanolamine according to the invention is typically applied in 8 foodstuffs, beverages, pharmaceutics and oral care products, the contribution thereof on structure and texture, i.e. on the physical properties, is essentially insignificant. Yet another aspect of the present invention relates to a product selected from the group consisting of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products, S said product comprising between 0.1 and 10,000 ppm (mg/kg) of one or more taste improving substances selected from the group consisting of substances according to formula (1) and edible salts thereof. More preferably, the product contains at least 1 ppm, most preferably at least 5 ppm of the one or more taste improving substances. Typically, the aforementioned products contain the taste improving substances in a concentration of not more than 5,000 10 ppm, preferably of not more than 2,000 ppm. The present products may further comprise one or more other flavouring substances, typically in amounts of 5-20,000 ppm, more preferably 10-10,000 ppm. The present products comprising N-gluconyl ethanolamine or a salt thereof preferably exhibit a weight ratio of taste improving substances and other flavouring substances of less 15 than 50:1, preferably less than 10:1. In one embodiment, the present product contains no N-gluconyl ethanolamine and/or an edible salt thereof In another embodiment, the present product does not contain added saccharide sweetener or artificial sweetener. 20 In yet another embodiment, the product contains N-gluconyl ethanolamine and/or an edible salt thereof in combination with added sweetener, said product being characterised by the fact that the weight ratio of the taste improving substances and saccharide sweetener does not exceed 1:1, preferably does not exceed 1:2; and by the fact that the weight ratio of the taste improving substances and artificial sweetener is less than 50:1, preferably less than 10:1, 25 even more preferably less than 1:1. Typical examples of foodstuffs according to the present invention include yoghurt, ice cream, desserts, confectioneries, bakery products, sweet snacks, seasonings, sauces, stock, soups and dressings. The benefits of the present invention may also be realised in beverages, in oral care products such as toothpaste and mouthwash, in pharmaceutics such as pills and 30 elixirs and in tobacco products, which includes any type of tobacco product for smoking as well as for non-smoking applications. It is noted that tobacco-like products are available for both smoldng and non-smoking applications. The use of the present taste improving substances in these tobacco substitutes is also encompassed by the present invention. 9 As mentioned herein before, the taste effect of the present taste improving substances is particularly evident in products comprising a certain amount of fat. Therefore, a preferred embodiment relates to products, as described here above, comprising one or more of the present taste improving substances, one or more flavouring substances and additionally at 5 least 0.1 wt.

0 /a fat, based on the total weight of the product. Even more preferably, the product contains at least 1 wt.% fat. Typical examples of such products include ice cream, desserts, spreads, snacks, soups, sauces and cheese products. Yet another aspect the present invention relates to a process of improving the taste of a foodstuff, a beverage, a pharmaceutical product, a tobacco product or an oral care product, 10 comprising adding to said product one or more taste improving substances selected from the group consisting of substances according to formula (I) and edible salts thereof. Substances according to formula (I) are suitably produced by reacting an aldonolactone with ethanolamine or a derivative thereof. N-gluconyl ethanolamine is suitably produced by reacting gluconic acid or 15 gluconolactone or a salt thereof with ethanolamine. N-gluconyl ethanolaminephosphate is suitably produced by reacting gluconic acid or gluconolactone or a salt thereof with 2 amineothylmonophosphtate. In the reactions described here above also derivatives of ethanolamine or ethanolamine phosphate with a polyester of the aldonic acid may be formed. Said aldonic acid polyesters 20 may comprise several aldonic acid units, typically 2-5. Another embodiment of the invention relates to these substances and their use as taste improving substances, The invention is further illustrated by means of the following examples EXAMPLES 25 Example 1 175 g of gluconio acid (50 % aqueous solution) was mixed with 25 g of ethanolamine. First the water was removed and subsequently the mixture was reacted at 120 *C for 4 hours. The mixture was washed with isopropyl alcohol (1 x 900 ml, 2 x 600 ml). The residue was diluted 30 with 200 ml of water and the pH was adjusted to 5.5 with 50% NaOH. 400 g of maltodextrin MD1O and 200 g of salt were added and the total mixture was spray-dried. The spray-dried sample was stored as such until tasting 10 Example 2 40 g of gluconolactone and 13.6 g of ethanolamine were mixed with 500 g of methanol and the mixture was heated to reflux during 5 hours. The mixture was left at room temperature overnight. The mixture was then cooled at - 20 *C for three hours. A white precipitate was 5 formed and was isolated by filtration, The solid was dried in vacuo at 60 *C. 34.7 g of product was obtained (yield: 64%). NMR spectroscopy showed that the product contained more than 90 wt.% N-gluconyl ethanolamine. Example 3 10 2-Aminoethyl dihydrogen phosphate (10 g / 0.07 mol), gluconolactone (13.4 g / 0.07 mol) and triethylamine (6.9 g / 0.07 mol) were combined in 50 g of glycerol. The mixture was stirred at 60 *C during approx. 18 hours. The mixture was poured into 150 ml of isopropanol (IPA) and stirred. First a gel like precipitate was formed, after stirring with 150 mal of extra IPA the material became more paste-like. The paste was washed three times with 300 ml of IPA and 15 once with 300 ml of ethyl acetate. The paste was then dissolved in water and all solvents were removed in vacuo at 30 *C. 25 g of product was obtained. NMR spectroscopy showed that the product contained 10 % of the desired product, N-gluconyl ethanolamine phosphate. Example 4 20 Four yoghurt samples were prepared: A: Yoghurt 0% fat + strawberry flavour + sucralose (25%) 300 ppm B: Yoghurt 0% fat + strawberry flavour + sucralose (25%) 300 ppm + 10 ppm N gluconyl ethanolamine (as prepared in Example 2) C: Yoghurt 0% fat + strawberry flavour + 4% sugar 25 D: Yoghurt 00/a fat + strawberry flavour + 4% sugar + 10 ppm N-gluconyl ethanolamine (as prepared in Example 2) The yoghurts were tasted by a professional panel. There was general agreement among the group on the taste descriptions: 30 A: sweet, bitter, metallic, aftertaste. B: fuller more round and natural taste, more sugar sweetness, significantly less bitter metallic aftertaste C: tart, acidic D: fuller more round and natural taste, more intense sweet.

II

Example 5 Two yogurt samples were prepared; A: Yoghurt 3% fat + strawberry flavour + 4% sugar 5 B3: Yoghurt 30 / fat + strawberry flavour + 4% sugar + 10 ppm N-gluconyl ethanolamine (as prepared in Example 2) The yoghurts were tasted by a professional panel. There was general agreement among the group on the taste descriptions: 10 A: tart, acidic B: much filer, more fatty, more round and natural taste, more intense sweet. Example 6 Two ice cream (8% vegetable fat) samples were prepared: 15 A: Ice cream+ strawberry flavour B: Ice cream + strawberry flavour + 10 ppm N-gluconyl ethanolamine (as prepared in Example 2) The ice creams were tasted by a professional panel. There was general agreement among the 20 group on the taste descriptions: A: sweet, strawberry, creamy aftertaste. B: fuller, more round and natural taste, enhanced sweetness and creaminess Ice cream composition: %4 Hydrogenated coconut fat (CN32) 8.00 Skimmed milkpowder 7.00 Whey protein concentrate 3.00 Sucrose 12.00 Corn syrup solids (DE39) 5.00 Sherex IC 9328 0.50 Flavour + Colour + Water Up to 100 12 Example 7 Three still beverages were prepared: 5 A: Tap water with sucrose (7 brix) and 1.5 g/l of citric acid + lemon flavour B: Tap water with sucrose (6.2 brix) and 1.5 g/l of citric acid + lemon flavour C: Tap water with sucrose (6.2 brix) + lemon flavour + N-gluconyl ethanolamine 30 ppm (as prepared in Example 2) 10 The beverages were tasted by a professionMl panel. There was general agreement among the group on the taste descriptions: A: sweet B: empty, less sweet C: fuller, more round and natural taste, more intense sweet taste than B 15 Example 8 A standard chicken soup was prepared, The quantity was split in two and to one half 7 ppm of N-gluconyl ethanolamine, as prepared in example 2, was added. The soups were tasted by a professional panel. 20 The soup containing the N-gluconyl ethanolanine was unanimously described as more tasteful, more complete, more body, more fatty. Example 9 Three different tomato soup powder compositions were prepared by dry mixing the 25 ingredients as given in table 2. Table 2 A B C Ingredients (Control) (50% Reduced salt) (Improved version) Potato starch 16.9 (g) 16.9 (g) 16.9 (g) Tomato powder 35 (g) 35 (g) 35 (g) Sugar 10 (g) 10 (g) 10(g) Fructose 5 (g) 5 (g) 5 (g) 13 Milk powder 20 (g) 20(g) 20 (g) Onion powder 1.6 (g) 1.6 (g) 1.6 (g) Garlic powder 0.1 (g) 0.1 (g) 0.1 (g) Carrot Powder 0.1 (g) 0.1 (g) 0.1 (g) MSG 3.3 (g) 3.3 (g) 3.3 (g) Yeast Extract 1 (g) 1(g) 1 (g) Salt 7 (g) 3.5 (g) Maltodextrin 3.5(g) Product as prepared in 3.5(g) example 3 (N-gluconyl ethanolamine phosphate) Total 100 (g) 100 (g) 100 (g) 10 gram of each composition was mixed with 100 ml hot water to obtain tomato soups. The different soups were tasted and evaluated by a sensory panel. Product C, comprising N gluconyl ethanolamine phosphate, was clearly preferred over product B (50 % salt reduction). 5 Despite the reduced salt content of product C, the perceived saltiness of the product was comparable to that of product A. Furthermore, the taste of product C was described as having "Mor taste", "more impact", "more umami", "more kokumi" and "salivating". Example 10 10 Six sweet milk samples, containing 6 % sucrose, flavoured with a strawbery flavour were prepared: I. Zero fat containing milk drink 2 Zero fat containing milk drink +10 ppm gluconyl ethanolamine (as prepared in example 2) 3. 1.5 % fat milk 15 4. 1.5 % fat milk +10 ppm gluconyl ethanolamine (as prepared in example 2) 5. Full fat milk 6. Full fat milk + 10 ppm gluconyl ethanolamine (as prepared in example 2) All samples were tasted by a professional panel. There was general agreement about the 20 differences in taste between the samples. Samples 2, 4 and 6 were described as fuller, more round natural taste, more creamy and more sweet than sample 1, 3 and 5 respectively. When 14 samples 2 and 3 and samples 4 and 5 were compared with each other, it was concluded that they tasted quite similar and the main difference was that sample 2 and 4 were slightly more sweet than sample 3 and 5 respectively. 5 Example 11 Four samples of staxidard instant vegetable soup were prepared: 1. Soup containing 2% fat 2. Soup containing 2 % fat +7 ppm gluconyl ethanolamine (as prepared in example 2) 3. Soip containing 4 % fat 10 4. Soup containing 4 % fat+ 7 ppm gluconiyl ethanolamine (as prepared in example 2) 5. Soup containing 6 % fat 6. Soup containing 6 % fat +7 ppm gluconyl ethanolamine (as prepared in example 2) All samples were tasted by a professional panel. There was general agreement about the 15 differences in taste between the samples, When sample 2, 4 and 6 were compared with sample 1, 3 and 5 respectively they tasted more fatty, more natural, more round and more sweet. When sample 2 and 3 and samples 4 and 5 were compared they tasted quite similar and the main difference was that sample 2 and 4 tasted slightly more sweet. 20 Example 12 The following mixtures were used as casings to improve the tobacco taste and improvement of the body of the smoke: 25 A: Carob extract 20 g Licorice extract 15 g Prmne extract 10 g cocoa extract log 30 water 45 g dosage of this mixture is lg/ kg tobacco B: 15 Carob extract 20 g Licorice extract 15 g Prune tract log cocoa extract log 5 GlMuconyl Ethanolamine (as prepared in example 2) 2 g water 43 g dosage of this mixture is 1 g/kg tobacco 10 Cigarettes were prepared from both types of tobacco, which were evaluated by a professional panel. Cigarettes prepared with casing B differed from those prepared with casing A in that they exhibited significantly more "body" in the smoke and significantly more "expanding" tobacco smoke. 15 Example 13 One sample of potato chips was seasoned with salt ( 0.7 %). Another sample of potato chips was seasoned with salt ( 0.7 %) and flavoured with 100 ppm N-gluconyl ethanolamine (as prepared in example 2). 20 The chips were tasted by a professional panel. The reference chips were described as salty, slightly rancid, oily-greasy and cardboard-like. The chips containing N-gluconyl ethanolamine were described as salty, exhibiting more fatty fullness, and masking of undesired notes of the reference chips. 25 Example 14 Ketchup was prepared using 506 g of water, 150 g of tomato puree (28 - 30 Brix), 30 g of modified starch (Colflo 67 ex National Starch), 22 g of salt, 2 g of stabilizer (Deltagel CE 1364) and 115 g of vinegar (12 % acetic acid in water), by first mixing the dry ingredients, subsequently adding water and stirring until a homogeneous paste was obtained. Tomato 30 puree and vinegar were than added and the mixture was stirred again and heated to a temperature of 95 *C for 1 minute. The mixture was filled off hot and allowed to cool down. The pH was detenrined to be 3.5. Part of the ketchup was mixed with 20 ppm N-gluconyl ethanolamine (as prepared in example 2). 16 The two ketchups were tasted and compared by a professional panel. The ketchup base was described as strongly acidic, acetic acid-lilr, with a flat tomato profile. The ketchup containing 20 ppm N-gluconyl ethanolamine was described as mildly acidic, less acetic acid-like, exhibiting more sun-ripened tomato character, more fullness. 5 Example 15 A vinaigrette was prepared using 815.8 g of water, 100 g of sunflower oil, 12 g of salt, 30 g of sugar, 45 g of vinegar (12 % acetic acid), 4 g of xanthan gum and 0.2 g of turmeric powder by mixing all ingredients intensively to obtain a homogeneous emulsion, 10 To a part of the vinaigrette 30 ppm of N-gluconyl ethanolamine (as prepared in example 2) was added. Both vinaigrettes were tasted by a professional panel. The original vinaigrette was described as strongly acidic, acetic acid-like, thin, peaky. The vinaigrette containing the N-gluconyl ethanolamine was described as acidic, more 15 rounded, more f6l1, more fat impression, more smooth. 17

Claims (21)

1. A flavour composition comprising: a. at least 0.1 wt.% of one or more flavouring substances, 5 optionally including saccharide sweetener in an amount of 0-20% by weight of the composition and/or artificial sweetener in an amount of 0-3 % by weight of the composition; and b. between 0.001 and 95 wt.% of one or more taste improving substances selected from the group consisting of: 10 substances according to formula (I): (I) CH 2 OH-(CHOH) 4 -CO-NH-CH 2 -CH 2 -X wherein X represents -OH, -O(CO)R, -OP0 3 H 2 , -PO 3 H2, -OSO 3 H or 15 -SO 3 H, and R represents a C 2 -Ci 0 group comprising at least one carboxylic acid group; and edible salts thereof, wherein, in case the flavour composition contains N-gluconyl ethanolamine or a salt thereof, the weight ratio of the taste improving 20 substances and the flavouring substances is less than 50:1.

2. A flavour composition according to claim 1, wherein the weight ratio of the taste improving substances and the flavouring substances is within the range of 1:100to 10:1. 25

3. A flavour composition according to claim 1 or claim 2, wherein, in the case the composition contains N-gluconyl ethanolamine and artificial sweetener, the weight ratio of N-gluconyl ethanolamine and artificial sweetener is less than 50:1. 30

4. A flavour composition according to claim 3, wherein said weight ratio is less than 20:1. -19

5. A flavour composition according to any one of the preceding claims, comprising the taste improving substances in an amount of 0.01-90 wt.%. 5

6. A flavour composition according to claim 5, wherein said amount is 0.1-25 wt.%.

7. A flavour composition according to any one of the preceding claims, comprising 1-95 wt.% of flavouring substances. 10

8. A flavour composition according to any one of the preceding claims, wherein X represents -OH, -OP0 3 H 2 , -P0 3 H 2 , -OSO 3 H or -SO3H.

9. A taste improving substance according to formula (I): 15 (I) CH 2 OH-(CHOH) 4 -CO-NH-CH 2 -CH 2 -X wherein X represents -O(CO)R, -OP0 3 H 2 , -PO3H 2 , -OSO 3 H or -SO 3 H, and R represents a C 2 -C1O group comprising at least one carboxylic 20 acid group; and edible salts thereof

10. A taste improving substance according to claim 9, wherein X represents -OP0 3 H 2 , -P0 3 H 2 , -OSO 3 Hor -SO3H. 25

11. A taste improving substance according to claim 10, wherein the substance is N-gluconyl ethanolamine phosphate or an edible salt thereof

12. Use of one or more taste improving substances as defined according to claim 30 1, in an amount of between 0.1-10,000 ppm for improving the taste of foodstuffs, beverages, pharmaceutics, tobacco products or oral care products. - 20

13. Use of one or more taste improving substances as defined according to claim 9, for improving the taste of foodstuffs, beverages, pharmaceutics, tobacco products or oral care products. 5

14. A process of improving the taste of a foodstuff; a beverage, a pharmaceutical product, a tobacco product or an oral care product, said process comprising adding to said product one or more taste improving substances selected from the group consisting of substances according to formula (I) as defined according to claim 1, and edible salts thereof, in an amount of between 0.1 10 10,000 ppm.

15. A process according to claim 14, where said amount is between 1-5,000 ppm.

16. A product selected from the group consisting of foodstuffs, beverages, 15 pharmaceutics, tobacco products, and oral care products comprising one or more taste improving substances as defined according to claim 1, in an amount of between 0.1-10,000 ppm.

17. A product according to claim 16, wherein said amount is between 1-5,000 20 ppm.

18. A product according to claim 16 or claim 17, further containing one or more flavouring substances in an amount of 5-20,000 ppm, wherein the weight ratio of the taste improving substance and the flavouring substance is less 25 than 50:1.

19. A product according to any one of claims 16 to 18, containing added sweetener, wherein, in case the product contains N-gluconyl ethanolamine or a salt thereof, the weight ratio of the taste improving substances and 30 saccharide sweetener does not exceed 1:1 and the weight ratio of the taste improving substances and artificial sweetener is less than 50:1. - 21

20. A foodstuff, a beverage, a pharmaceutical product, a tobacco product or an oral care product having an improved taste when produced by a process as defined according to claim 14 or claim 15. 5

21. A flavour composition according to claim 1; a taste improving substance according to claim 9; use according to claim 12 or claim 13; a process according to claim 14; a product according to claim 16; or a foodstuff, a beverage, a pharmaceutical product, a tobacco product or an oral care product of improving the taste of a foodstuff, a beverage, a pharmaceutical product, a 10 tobacco product or an oral care product, substantially as herein described with reference to any one of the embodiments of the invention illustrated in the accompanying examples. 15 Dated this 2 0 th day of June 2014 Shelston IP Attorneys for: Givaudan Nederland Services B.V.