AU714404B2 - Creation of Inventions and Patents with Artificial Intelligence

AU714404B2 – Dry foodstuffs containing dipeptide sweetener
– Google Patents

AU714404B2 – Dry foodstuffs containing dipeptide sweetener
– Google Patents
Dry foodstuffs containing dipeptide sweetener

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Publication number
AU714404B2

AU714404B2
AU34648/97A
AU3464897A
AU714404B2
AU 714404 B2
AU714404 B2
AU 714404B2
AU 34648/97 A
AU34648/97 A
AU 34648/97A
AU 3464897 A
AU3464897 A
AU 3464897A
AU 714404 B2
AU714404 B2
AU 714404B2
Authority
AU
Australia
Prior art keywords
acid
sweetener
dry
salt
dipeptide sweetener
Prior art date
1996-07-16
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Application number
AU34648/97A
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AU3464897A
(en

Inventor
John Charles Fry
Annette Catherina Hoek
Leopold Franciscus Wijnandus Vleugels
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Holland Sweetener Co VOF

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Holland Sweetener Co VOF
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.)
1996-07-16
Filing date
1997-07-14
Publication date
2000-01-06

1997-07-14
Application filed by Holland Sweetener Co VOF
filed
Critical
Holland Sweetener Co VOF

1998-02-09
Publication of AU3464897A
publication
Critical
patent/AU3464897A/en

2000-01-06
Application granted
granted
Critical

2000-01-06
Publication of AU714404B2
publication
Critical
patent/AU714404B2/en

2017-07-14
Anticipated expiration
legal-status
Critical

Status
Ceased
legal-status
Critical
Current

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Classifications

A—HUMAN NECESSITIES

A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES

A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF

A23G4/00—Chewing gum

A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds

A23G4/14—Chewing gum characterised by the composition containing organic or inorganic compounds containing peptides or proteins

A—HUMAN NECESSITIES

A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES

A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF

A23G4/00—Chewing gum

A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds

A23G4/10—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides

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

A23L27/30—Artificial sweetening agents

A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives

A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives

Description

WO 98/02050 PCT/NL97/00415 1 DRY FOODSTUFFS CONTAINING DIPEPTIDE SWEETENER The invention relates to dry foodstuffs containing dipeptide sweetener. The term “dry foodstuffs” as used in this application includes all possible dry foodstuffs, that is to say foodstuffs with a low moisture content, in particular 10% by wt, which are sweetened with dipeptide sweetener. The dry foodstuffs can be available both in a sugar-free and in a sugarcontaining form. The invention relates more particularly to dry foodstuffs which are produced in substantially solid, dry form using the dipeptide sweetener. The term “dry foodstuffs” also includes chewing gums and all other forms of chewable gum-based products sweetened with dipeptide sweetener. The invention is intended to improve the sweetness stability and the flavour properties of such dry foodstuffs, especially insofar as the stability during storage (storage stability) and the flavour quality are concerned. In particular the invention also relates to dry foodstuff products sweetened with a dipeptide sweetener which contain flavourings based on aldehydes the so-called aldehyde flavour products, or aldehyde flavourings), and also to products in which in addition to the dipeptide sweetener there are also components which can react with the dipeptide sweetener, such as vitamin C ((dehydro)ascorbic acid), uronic acids, strongly reducing sugars, for example Dglucose, D-fructose, D-mannose, D-galactose, D-xylose, L-arabinose and D-ribose, (less) reactive reducing sugars such as lactose, cellobiose, maltose and sucrose, and also products such as sodium bicarbonate, etc. The term “aroma substances” is sometimes used instead of “flavourings”.
WO 98/02050 PCT/NL97/00415 2 Examples of dry foodstuffs as meant in the context of this application are powdered mixtures for instant lemonades or for other drinks based on coffee, tea, cocoa or milk, powdered mixtures for instant desserts based on water or milk, powdered mixtures for making ice cream, powdered mixtures for making dietetic meals, pharmaceutical powdered mixtures and compressed pharmaceutical tablets, hard confectionery such as fruit, menthol and mint pastilles or fruit, menthol and mint sweets and fruit, menthol and mint drops, chocolate, powdered confectionery, effervescent tablets, (effervescent) tablets for making soft drinks, sweetening agents in the form of sweetening tablets, low-calorie sugar cubes or powdered table sweeteners, chewing gums and chewing tablets.
Dry foodstuffs sweetened with dipeptide sweetener are known and described in various patent publications, for example in WO-92/07473. This describes dry foodstuffs, in this case chewing gums, in vhich longer and improved flavour is achieved by using coated synergistic mixtures of the two intense sweeteners aspartame and acesulfame-K; it also reports that there are less marked effects as regards stability problems which can arise with aspartame in the presence of aldehydes, ketones, moisture, etc. Maillard reactions, for example, can occur which can lead to loss of sweet flavour and the development of unwanted off-flavours and/or after-flavours. This is already detrimental during the manufacture of the products, but also detrimental to the storage stability of the products in which the said components are present together, as the sweetening power decreases as a result. Under such circumstances, as a result of unwanted reactions, there may also be discoloration of the (solid) products in which a dipeptide sweetener is incorporated. The reactions in question take place mainly during the manufacture of the foodstuffs and _rsl WO 98/02050 PCT/NL97/00415 3 during the storage thereof if there is increased or relatively high temperature, or increased or relatively high humidity. In addition, in dry foodstuffs containing dipeptide sweetener, regardless of the presence or absence of components that are reactive with a dipeptide sweetener, there often is a need for improved flavour and sweetness and more homogeneous distribution of such improved flavour and sweetness through the foodstuff.
Dry foodstuffs sweetened with dipeptide sweetener are commercially available, in various flavours, including aldehyde flavour, such as chewing gum products from the Wrigley range, e.g. Wrigley’ s Extra PlenTpake with cinnamon flavour. Another example can be found in Sanatogen® vitamin C tablets; these contain inter alia sodium bicarbonate, ascorbic acid and aspartame. A variety of chocolates sweetened with dipeptide sweetener are also known. There are many other examples.
For the purposes of this application “dipeptide sweetener” means products with a sweetening power which is many dozens of times stronger than that of sugar, and which are made up of amino acids or derivatives of amino acids linked via a peptide bond.
The best-known examples of dipeptide sweeteners are aspartame and alitame.
Aspartame (a-L-aspartyl-L-phenylalanine methyl ester), hereinafter also referred to as APM, is a dipeptide sweetener with a sweetening power which is approximately 200x that of sucrose. Aspartame is used as an intense sweetener in many applications because of its good flavour properties and low-calorie characteristics. Aspartame is also widely used in dry foodstuffs.
Alitame (L-a-aspartyl-N-(2,2,4,4-tetramethyl- 3 -thietanyl)-D-alanineamidehydrate), hereinafter also referred to as ALI, is a dipeptide sweetener with a WO 98/02050 PCT/NL97/00415 4 sweetening power which is approximately 2000x that of sucrose.
It is also known that dipeptide sweeteners in dry foodstuffs are used in the form of blends, i.e.
physical mixtures, with other sweeteners. See for example Patent WO-92/07473, already mentioned above, in which a (coated) blend of APM and acesulfame-K (the potassium salt of 6-methyl-l,2,3-oxathiazin-4(3H)-one- 2,2-dioxide, hereinafter also referred to as Ace-K) is used.
As will be apparent from the foregoing, the use of dipeptide sweeteners in dry foodstuffs, in particular in dry foodstuffs which contain flavourings based on aldehydes and in other dry foodstuffs in which there are components that are reactive with the dipeptide sweetener, is impeded by problems resulting from the somewhat limited chemical stability of the dipeptide sweeteners. WO-92/07473 and EP-A-0457724, for example, state that aspartame shows instability in the presence of aldehydes, ketones, moisture etc. This is already detrimental during the production of the dry foodstuffs, but also detrimental to the storage stability of the products in which the said components are present together, as the sweetening power decreases as a result and/or part of the desired effect of the other component is lost. Under such circumstances, as a result of unwanted reactions, there may also be discoloration of the (solid) products in which a dipeptide sweetener is incorporated.
For interactions between APM (and Ace-K) and various other substances (such as water-soluble vitamins and food acids, e.g. malic, citric, acetic or tartaric acid) reference is made to: Kroyer et al., ErnAhrung (AUT), 1993, pp. 614-617 (Part II), where stability problems in dry mixtures, in particular, are described, as shown by experiments at increased temperature.
WO 98/02050 PCT/NL97/00415 5 Furthermore, in various dry foodstuffs containing dipeptide sweetener, such as chocolates and hard confectionery, regardless of the presence or absence of components that are reactive with the dipeptide sweetener, distribution of the flavour and sweetness through the foodstuff appears to be nonoptimum and more or less inhomogeneous. In the preparation of hard confectionery (such as drops) using, for example, aspartame as a sweetener, handling using state-of-the-art techniques often is difficult and it is necessary to use a previously prepared dispersion of aspartame in the acid components of the drops. If the acid component is absent or present in insignificant amounts, as in hard confectionary with menthol flavour, homogeneous distribution of the dipeptide sweetener is impossible or hardly possible.
In that case, the dipeptide sweetener has a high tendency to clumping.
In the prior art efforts have been made to find solutions with the aim of improving the sweetness stability and the flavour of dry foodstuffs sweetened with a dipeptide sweetener with particular regard also to combating stability problems due to the presence of dipeptide sweetener in such foodstuffs, for example in chewing gums, by for example providing the dipeptide sweetener with a coating, in an extra process step.
This is described in EP-A-0461197, for example. As described in EP-A-0160607, for example, attempts have also been made to combat stability problems in chewing gums containing aldehydes, for example, by applying the dipeptide sweetener to the surface of the chewing gum.
All this has disadvantages, however, in terms of the complexity of manufacture and requires additional process steps. In addition, so-called “hot spots” may occur in dry foodstuffs which are sweetened with coated sweeteners. In order to improve these various aspects, blends of a dipeptide sweetener and another intense WO 98/02050 PCT/NL97/00415 6 sweetener, such as acesulfame-K or saccharin, are therefore also used in dry foodstuffs. When such blends are used, different peaks may occur in the perception of the sweetness during consumption of the S dry foodstuff because of differences in the sweetening profiles of the various sweeteners, and there is also a risk that a bitter or other off-flavour may be perceived for certain periods during consumption. In addition it should be noted that attempts have also been made to influence the profile of the release of sweetening power in dry foodstuffs, such as chewing gums etc., by varying the particle size of the dipeptide sweetener used in these products (see for example EP-A-0427541), or by appropriate choice of the location of the sweetener in the dry foodstuff product to be sweetened by powdering the outside of the dry foodstuff with sweetener or by providing the dry foodstuff itself with a coating which is also sweetened and optionally contains an aldehyde aroma component, as is described for example in EP-A-0129584).
According to the prior art there is thus still no entirely satisfactory solution for improving the sweetness stability and the flavour of such dry foodstuffs and for limiting the consequences of any discoloration occurring. This is especially the case when there is also reduced storage stability loss of sweetening power during storage).
There is therefore a need to provide dry foodstuffs containing dipeptide sweetener with improved sweetness stability, improved flavour quality and reduced susceptibility to discoloration. There is also a need for a method of producing such dry foodstuffs with improved sweetness stability, improved flavour quality and reduced susceptibility to discoloration in a simple way. In particular there is a need to improve the sweetness stability, the flavour quality and resistance to discoloration of dry foodstuffs sweetened
L
t
A
7 with a dipeptide sweetener which also contain flavourings that are reactive with the dipeptide sweetener such as aldehyde-based flavourings.
Surprisingly, extensive research by the applicant has now yielded dry foodstuffs containing dipeptide sweetener with outstanding sweetness stability and flavour quality and with good resistance to discoloration, where the dipeptide sweetener is a sweetening salt of an aspartic-acid-derived dipeptide sweetener and a derivative of a sweetening acid. It has been found that the dry foodstuffs with such a composition show a surprisingly good sweetness stability during storage as well as good flavour quality and are not susceptible to discoloration.
In particular it has also been found that dry foodstuffs sweetened with a dipeptide sweetener which also contain aldehyde-based flavourings that are reactive with the dipeptide sweetener or in which there are present other components that can react with the dipeptide sweetener, show a surprisingly good sweetness stability during storage and are highly resistant to discoloration when the dipeptide sweetener is a sweetening salt of an aspartic-acid-derived dipeptide sweetener and a derivative of a sweetening acid. The storage stability of such products is considerably better than that of dry foodstuffs sweetened with a (free or mixed) dipeptide sweetener.
There is provided according to a first embodiment of the invention dry foodstuffs containing dipeptide sweetener, characterized in that the dipeptide sweetener is a 20 sweetening salt of an aspartic acid based dipeptide sweetener and a derivative of an organic acid corresponding to an intense sweetener which is not derived from aspartic acid.
According to a second embodiment of the invention there is provided dry foodstuffs containing dipeptide sweetener and a component that is reactive with it, characterized in that the dipeptide sweetener is a sweetening salt of a dipeptide sweetener 25 derived from aspartic acid and a derivative of an organic acid corresponding to an intense sweetener which is not derived from aspartic acid.
According to a third embodiment of the invention there is provided a process for the preparation of dry foodstuffs containing dipeptide sweetener, which process comprises mixing a dipeptide sweetener into a dry foodstuff base, said dipeptide sweetener being a M sweetening salt in substantially solid form of an aspartic acid based dipeptide sweetener and a derivative of an organic acid corresponding to an intense sweetener which is not derived from aspartic acid.
According to a fourth embodiment of the invention there is provided a process for the preparation of dry foodstuffs containing dipeptide sweetener and a component that is f- 5 tive with it, which process comprises mixing a dipeptide sweetener and a component [R:\LIBFF] 12354.doc:TLT 7a that is reactive with said dipeptide sweetener into a dry foodstuff base, said dipeptide sweetener being a sweetening salt in substantially solid form of an aspartic acid based dipeptide sweetener and a derivative of an organic acid corresponding to an intense sweetener which is not derived from aspartic acid.
Sweetening salts of an aspartic-acid-derived dipeptide sweetener and a derivative of a sweetening acid, as meant here, are described in CA-A-1027113 and ES-A-8604766, and also in Belgian patent application No. 9500836, which had not been pre-published (on the priority date of the present application) and which led to inter alia EP-A-0768041.
Derivatives of sweetening acids as meant here are (derivatives of) organic acids in corresponding to an intense sweetener which is not derived from aspartic acid. From none of the *A *e [R:\LIBFF]12354.doc:TLT WO 98/02050 PCT/NL97/00415 8 aforementioned documents, in which moreover the possibilities of application for the sweetening salts in question are only indicated in very general terms without showing concrete applications, can it be inferred or expected that these sweetening salts, in dry foodstuffs, have such a strong effect on the sweetness stability during storage as well as on the flavour quality and on the resistance to discoloration.
This is relevant not only in comparison with dry foodstuff products in which only a dipeptide sweetener is present as the sweetening component but also in comparison with dry foodstuff products in which the dipeptide sweetener is used in the form of a blend.
Examples of suitable sweetening salts which according to the invention can be used in dry foodstuffs are: salts of aspartame (APM) or alitame (ALI) with acesulphamic acid the acid derived from Ace-K), with saccharic acid (1,2-benz-isothiazol- 3(2H)-one-l,l dioxide) and with cyclohexylsulphamic acid (cyclamate). The most suitable one is the salt of aspartame and acesulphamic acid, hereinafter also referred to as APM-Ace or as the APM-Ace salt; particularly suitable is the exceptionally stable, nonhygroscopic product as obtained in solid form by the process in Belgian non-prepublished patent application No. 9500836. In that process, aspartame and a salt of acesulphamic acid are allowed to react in an aqueous medium in the presence of a strong acid and the APM-Ace formed is isolated from the reaction mixture.
The particle size of the sweetening salts which under this invention are used in the relevant dry foodstuffs, and in particular the particle size of the sweetening salts as present at the time of manufacture of the dry foodstuffs, is not particularly critical, but is generally not more than 1000 pm. The presence of larger particles in the dry foodstuff causes less homogeneous and less balanced release of the sweetening
T-
WO 98/02050 PCT/NL97/00415 9 power during consumption. Use of a sweetening salt with a particle size 350 pm offers advantages in terms of the flavour quality of the dry foodstuffs.
The best flavour quality is achieved if the particle size of the sweetening salt is in the range 100 Pm, but particles in the range from 100-200 pm also give products with excellent sweetness stability and storage stability when used in dry foodstuffs. In a number of cases somewhat better stability of the products is obtained with sweetening salt particles in the range from 100-200 pm. By choosing the particle size of the sweetening salt to be used, the specialist can achieve further fine-tuning of the desired flavour quality and stability.
In the manufacture of dry foodstuffs according to the invention, use is preferably made of sweetening salts in substantially dry form. “In substantially dry form” means that the salt, as available in dry form with a moisture content of 2% by vt or less), is directly incorporated into the dry foodstuff, for example by mixing the dry ingredients, with or without subsequent compacting, etc. It is also possible to use the sweetening salt in substantially dry form by moistening it to a limited extent, for example in a wet granulation step, or even incorporating it in the form of a wet slurry, in which at least 85% by wt of the original sweetening salt is still present in solid form, and processing the product so obtained into the final product in the usual way, by (spray) drying, agglomeration and, if necessary, grinding, etc.
The content of sweetening salt in the dry foodstuffs according to the invention can vary within a very wide range; for chewing gums it should generally lie within the range from 100 to 6000 ppm (calculated relative to the total mass of the chewing gum); for table sweeteners the content of sweetening salt in the WO 98/02050 PCT/NL97/00415 10 sweetener may be in the range from 10 to 50% by wt (calculated relative to the total sweetener). Other ranges may be applicable for other products. These can easily be determined by the specialist, depending on the desired sweetness etc. of the products. In chocolates and other dry confectionery, for example, the sweetening salt content will usually be from 400 to 3000 ppm. The invention is in addition particularly advantageous in the manufacture of hard confectionery containing no or only little nutritive acid and where the transparency of the confectionery also plays a role. It has been found that when the process of the invention is used for the manufacture of transparent, hard confectionery, such as mint sweets or medicinal mentholyptus sweets, completely clear and transparent sweets can be obtained as a result of the excellent dispersability of the sweetening salts used, the same proving impossible when blends of the individual components of the said salts are used.
Also, the taste and oral sensation of the sweets obtained according to the invention are clearly better and more similar to those of sweets sweetened with sugar than of sweets obtained using blends of the individual components. In the manufacture of sugar-free chocolates, too, the present invention has proved particularly suitable; the chocolates obtained with it have a sweetness resembling that of sugar more closely and a fuller taste than chocolates obtained in like fashion from blends of the individual components.
It will be clear to the specialist that although dry foodstuffs with excellent sweetness stability and storage stability are already produced according to the invention, further adjustments with regard to the flavour profile and other properties of the foodstuffs, such as the said stabilities, can be made by adding additional small quantities of a separate intense sweetener or of a blend of sweeteners, WO 98/02050 PCT/NL97/00415 11 in addition to choosing the particle size of the sweetening salt. Accelerated emergence of the sweet flavour, the so-called “up-front release”, can thus be achieved, for example. In addition, the properties in question can be further influenced by applying all or a proportion of the particles of the sweetening salt in the dry foodstuff in coated form, or by adding the additional small quantity of a separate intense sweetener (if one is used) to the dry foodstuff also partially or entirely in coated form. Application of part or all of the sweetener in coated form ensures an adapted profile of the release of the sweet flavour and can thus be regarded as a form of “controlled release”.
In addition, all the known techniques in relation to the technical shaping of the final products (the dry foodstuffs) and/or the components to be incorporated, such as the sweetening salt, are of course also available to the specialist in order to achieve further desired flavour effects and/or aesthetic effects.
Examples of such techniques in relation to the technical shaping of the components are granulation, grinding, freeze-drying, spray-drying, agglomeration etc. The invention is in no way limited with regard to the place where the sweetening salt used according to the invention is located in or on the dry foodstuff.
Where the dry foodstuff relates to chewing gums, it should be noted that chewing gums, as is known and customary, consist in large part (about 5 to 95% by wt) of a so-called “gum base” and all sorts of additives, such as aroma substances. The gum base generally consists of a combination of natural gums and/or synthetic elastomers and resins, and also contains softeners and (5 to 60% by wt) inorganic fillers. The gum base may also contain other components such as antioxidants, colourants and emulsifiers. Furthermore, chewing gums contain all sorts of flavourings which may originate from natural WO 98/02050 PCT/NL97/00415 12 plant extracts or be obtained synthetically.
Examples of aldehyde flavourings which can be used in dry foodstuffs are acetaldehyde, benzaldehyde, anisaldehyde, cinnamaldehyde, citral, c-citral, 6citral, decanal, ethyl vanillin, heliotropin (piperonal), vanillin, a-amyl-cinnamaldehyde, citronellal, aldehyde C-8, aldehyde C-9, aldehyde C-12, trans-2-hexenal, veratraldehyde, etc.
Examples of ketones which can be used in dry foodstuffs are acetophenone, acetone, methyl-namylketone, p-hydroxyphenyl-2-butanone, a-ionone, pionone, methyl-3-butanone, 2-heptanone, o-hydroxyacetophenone, 2-methyl-2-hepten-6-one, 2-octanone, 2undecanone and 2-pentanone.
Besides the sweetening salts to be used according to the invention, food sugars and/or other sweeteners can also be present in the dry foodstuffs according to the invention. Examples of these are aspartame, alitame, acesulfame-K, saccharinates, tyclanates, glycyrrhizin, thaumatin, monellin, neohesperidin dihydrochalcone (NHDC), sucralose, sorbitol, mannitol, xylitol, lactitol, isomalt, maltitol, hydrogenated starch hydrolysates, dextrins, sucrose, dextrose, glucose syrups, fructose, fructose syrups, etc., or combinations thereof.
The invention will now be clarified by means of some tests and comparative tests, in which chewing gums, chocolates and hard confectionery are used as an example of dry foodstuffs, but is in no respect limited to these.
The sweetening salt of aspartame and acesulphamic acid (hereinafter referred to as APM-Ace) used in the investigations was produced by the method in Experiment 4a of Belgian non-prepublished patent application No. 9500836. The procedure was as follows: 608 g of APM and 410 g of AceK (each 2.0 mol) WO 98/02050 PCT/NL97/00415 13 were added consecutively to 2 1 of water at 20°C, after which the resultant slurry was brought to 50 0 C and 370 g of 20% HC1 in water was added, with stirring, over minutes. In this operation the initially rather voluminous slurry changed into a less voluminous slurry. At the end of the addition of HC1 the slurry obtained was cooled to 10 0 C over about 30 minutes via indirect heat exchange with a cooling medium at 0°C and was then filtered off. The crystalline mass obtained was washed with a minimum quantity of chilled water and dried in a vacuum at 40 0 C. This produced in total 820 g a yield of 90%) of a white product which according to ‘H-NMR consisted entirely of the 1:1 salt of APM and acesulphamic acid, with a purity The moisture content was 0.12%. Two fractions were separated from this product by sieving procedures: an initial fraction with particles 100 pm and a fraction with particles of 100-200 pm.
For comparison purposes corresponding particle size fractions were also made from each of the sweeteners aspartame and acesulfame-K separately, and 1:1 blends were made up on a molar basis both for APM and Ace-K with a particle size 100 pm and for APM and Ace-K with a particle size in the range 100-200 pm.
These blends had a composition of approximately 3:2 by weight. When they were used in the comparative experiments, the quantity of the blends taken in each case was such that (allowing for corrections for the potassium content in Ace-K and for the water content, determined by the “loss-on-drying” method, in APM) the same amount of aspartame was used as in the case of addition of the sweetening APM-Ace salt.
As part of the investigation, tests (and comparative tests) were made with chewing gums with cinnamon flavour in order to determine various sensory properties (“attributes”), and in addition analytical tests were made with regard to the storage stability of WO 98/02050 PCT/NL97/00415 14 the chewing gums. All the chewing gums tested were made in accordance with a standard formulation consisting of a sugar-free gum base and sorbitol. The formulations conformed to the following composition: Ingredients w/w): sorbitol powder (P100T, Roquette) 52.4 sugar-free gum base (Valencia-T, Cafosa) 24.6 sorbitol solution (Neosorb 70/70; Roquette) 16.2 glycerine 4.8 cinnamon flavour (17.42.7305, IFF) 100.0 2700 ppm of the sweetener APM-Ace to be used according to the invention was also incorporated in this composition, in two separately tested fractions in terms of particle size, viz. a fraction 100 pm (see tests Kl) and a fraction of 100-200 pm (see tests K2).
For comparison purposes, tests were made with compositions as indicated above in which the 2700 ppm of APM-Ace was replaced by 3000 ppm of a blend of APM and Ace-K (in a 1:1 molar ratio; 3:2 ratio by weight).
In determining the amount of 3000 ppm allowance was made for the correction for the water content of APM (according to the “loss-on-drying” method) and the potassium content of Ace-K. In order to optimize comparability, use was also made of blends in two different fractions in terms of particle size: a fraction with APM and Ace-K particles 100 pm (see comparative tests KIA) and a fraction with APM and Ace- K particles of 100-200 pm (see comparative tests K2A).
The procedure for making the test chewing gums (including that for the comparative test chewing gums KA) was in each case as follows: The gum base was put into a Z-blade mixer and softened in it with heating to a final temperature of WO 98/02050 PCT/NL97/00415 15 to 60°C and stirring. In each formulation the sweetener in the amount indicated (see above) was first dispersed in the sorbitol powder, while the sorbitol solution with the glycerine was also heated, to 60 0
C,
before the sorbitol powder and sorbitol solution were both added to the gum base, with stirring. The whole was mixed for 10 minutes at the above-mentioned temperature, and then for a further 10 minutes with the heating element switched off. The dough obtained was rolled out with a dough roller (“pastry brake”) to a thickness of 1.5 mm. Strips of 73 x 19 mm, which were each packed in foil (as is usual for chewing gum), were cut out of the rolled-out mass.
Part of the chewing gums made in this way was then kept frozen in order that samples which best approximated to the original condition of the relevant chewing gum would be available for comparison at any desired time. Another part of the chewing gums with cinnamon flavour was stored at 20°C (storage-quality tests). Sensory tests were made on these chewing gums after 4 and 12 weeks of storage, with comparisons being made with corresponding chewing gums that had been kept frozen at -18 0 C. Yet another part of the chewing gums with cinnamon flavour was kept at 40 0 C, as an accelerated storage-quality test. The storage stability of these chewing gums was monitored by analysis of the content of APM and Ace-K (or Ace) after 14 and 28 days of storage.
As regards the sensory tests, the chewing gums were evaluated by an experienced panel, with 6 members, for: sweetness intensity, hereinafter referred to as “SI” sweetness quality, hereinafter referred to as particular attention being paid to offflavours such as metallic flavour and bitterness; release of the desired flavour (here mint and WO 98/02050 PCT/NL97/00415 16 cinnamon flavour, respectively), hereinafter referred to as and for overall acceptability of the chewing gum, hereinafter referred to as “OA”, these evaluations in each case being made after seconds, 2 minutes, 6 minutes, 10 minutes and minutes of chewing.
In the sensory tests with the cinnamon flavour chewing gums, the products according to the invention scored better in all cases than the corresponding comparison products. Both in the comparison products and in the products according to the invention, however, a deterioration of attributes as a result of storage at 20 0 C was observed. In all the products there was slight discoloration relative to the products which had been kept under deep-freeze conditions. When the cinnamon chewing gum products sweetened with the sweeteners 100 pm and 100-200 pm were compared with each other, the former products were found to deteriorate somewhat more in terms of sweetness than the latter, but in both types of product there was perceptible sweetness and flavour throughout the 15 minutes of the sensory tests. The overall flavour score for the products which were sweetened with the smaller particles was somewhat higher than for the products which were sweetened with the larger particles. In the comparison chewing gums with cinnamon flavour (in the samples tested after 4 weeks) there was no longer any perceptible sweetness or flavour after about 6-8 minutes.
The sensory findings for the cinnamon flavour products, as evaluated after 4 and 12 weeks of storage, are summarized in Tables I and II below. The bottom row in these tables shows the differences from the frozen chewing gums.
WO 98/02050 PCT/NL97/00415 17 TABLE I me 4 wee Storage ti :ks at 200C TEST K1 COMP. TEST TEST K2 COMP. TEST SI faster start slow but slow start; faster than K1A; good in slow build- build-up of good build-up terms of up of sweetness of sweetness; build-up; sweetness; than K1A; peak after 2 peak after 2 peak after 2 somewhat minutes; minutes; minutes; hotter then decrease then marked decrease in taste than in sweetness; decrease in sweetness KI or K1A; sweetness sweetness; but less fast remains still than K2A decrease; clearly slightly (and than K1 scarcely perceptible sweet after and K1A); any for more than 6 minutes; lengthened sweetness minutes flat flavour sweetness left at 4 after 10 and flavour minutes; minutes profile for scarcely more than 15 any flavour minutes left after 8 minutes SQ good quality good, but good; no good, but and good perceptible off-taste perceptible persistence; for too perceptible; for too no off-taste, short a not bitter short a not bitter; time; no time; no better than off-taste, off-taste; K1A not bitter not bitter WO 98/02050 PCT/NL97/00415 18 FR good; sweet- good, but as good; reten- good, but ness and fla- short as tion of fla- somewhat vour remain sweetness vour because sharper than clearly per- of K1A; as ceptible continuing short as sweetness sweetness OA markedly bet- reasonable markedly reasonable ter than K1A; better than somewhat bet- K2A ter than K2 as sweet less intens- slower start slower start after 2 min- ely sweet to sweetness to sweetness utes; some- and less build-up; build-up what faster flavour than somewhat decrease in REF later but sweetness equally relative to strong peak
REF
relative to product stored at -180C (REF) WO 98/02050 PCT/NL97/00415 19 TABLE II Storage time 12 weeks at 20 0
C
TEST KI COMP. TEST TEST K2 COMP. TEST _K1A K2A rather slow start; good build-up from 40 sec onwards; peak after 2 minutes; rather less than for K1A; then decrease in sweetness but not as fast as K1A; sweetness and flavour remain for more than 15 minutes slow but build-up after 30 sec; peak after 2 minutes; then marked decrease in sweetness; still slightly sweet after 4 minutes; very flat flavour after 6 minutes; an effort to continue chewing slower start than K2A; slow buildup of sweetness; peak after 2.5 minutes; decrease in sweetness, but less than K2A; lengthened flavour and sweetness profile for more than 15 minutes slow start; build-up of sweetness to peak after 2 minutes; rapid decrease; scarcely any sweetness left at 3.5 minutes; scarcely any flavour left after 6 minutes; no sweetness or flavour perceptible after minutes SQ reasonable reasonable, reasonable; reasonable quality and but very not bitter beginning, good sharp but perceppersistence; refreshing tible for not bitter; taste at too short a better than the back of time; not KIA the tongue; bitter not bitter
~L_
WO 98/02050 PCT/NL97/00415 20 flavour peak after 2 minutes; reasonable; sweetness and flavour remain clearly perceptible moderate with dull flavour, but as short as sweetness reasonable; retention of flavour because of continuing sweetness; somewhat flatter than K2A reasonable, but sharp burnt flavour at beginning; flavour and sweetness present for too short a time OA markedly bet- reasonable remains reasonable ter than K1A sweet and tasty for min rather more rather more rather more rather more discoloured; discoloured; discoloured; discolsweetness more refres- slower oured; sweprofile iden- hing; build-up of etness tical but sweetness sweetness intensity rather lower profile ide- and rather much less, intensity and ntical but less faster after 10 min- intensity intensely decrease in utes rather much lower; sweet; sweetness less flavour flavour less rather less and flavour fresh flavour, but better than K2A relative to product stored at -18 0 C (REF) ”I1 21 The results of the sensory tests made with the cinnamon (aldehyde) flavour test chewing gums and comparison chewing gums were also confirmed by accelerated aging tests (at 40 0 in which the concents of APM and Ace-K (or Ace) were determined by EPLC (high-pressure liquid chromatography). An overview of the relevant HPLC analysis results is given in Table III below: TABLE III Relative decrease in contents of APM and Ace-K or Ace during storage at 40 0 C for: 0 days 14 days 28 days (%)content content <0p Kl API4 100 47 36 Ace *XIA 10 0 fe:Ace-K 94 20 100-200 pm K 2 APM 45 44 *Ace 83 84 K2A 16 Ace-K 96 In the framework of examination, tests (and comparative tests) were also conducted on sugar-free chocolates and hard confectionery for purpose establishing various sensory properties (attributes). 30 The preparation started from unsweetened made basis palatinite without addition an intense sweetener. chocolate in question was included as a WO 98>,-suitable places in it or due to the technical shape of the dry foodstuff having been suitably [R:\LIBFF] 12354.doc:TLT C_

12. A dry foodstuff containing dipeptide sweetener, which foodstuff is substantially as herein described with reference to test compositions K1 and K2.

13. Process for the preparation of dry foodstuffs containing dipeptide sweetener, which process comprises mixing a dipeptide sweetener into a dry foodstuff base, said dipeptide sweetener being a sweetening salt in substantially solid form of an aspartic acid based dipeptide sweetener and a derivative of an organic acid corresponding to an intense sweetener which is not derived from aspartic acid.

14. Process for the preparation of dry foodstuffs containing dipeptide sweetener and a component that is reactive with it, which process comprises mixing a I0 dipeptide sweetener and a component that is reactive with said dipeptide sweetener into a dry foodstuff base, said dipeptide sweetener being a sweetening salt in substantially solid form of an aspartic acid based dipeptide sweetener and a derivative of an organic acid corresponding to an intense sweetener which is not derived from aspartic acid.

Process according to claim 14, characterized in that the dry foodstuff containing dipeptide sweetener also contains an aldehyde flavouring substance.

16. Process according to any one of claims 13 to 15, characterized in that the sweetening salt used is chosen from the salts of aspartame with acesulphamic acid, saccharinic acid or cyclohexylsulphamic acid and from the salts of alitame with acesulphamic acid, saccharinic acid or cyclohexyl sulphamic acid. 20

17. Process according to claim 16, characterized in that the sweetening salt used is the salt of aspartame and acesulphamic acid.

18. Process according to claim 17, wherein a salt of aspartame and acesulphamic acid in solid form is used which has been obtained by allowing aspartame and a salt of acesulphamic acid to react in an aqueous medium in the presence of a strong acid 25 and isolating the salt formed from the reaction mixture.

19. Process according to any one of claims 13 to 18, characterized in that the particle size of the sweetening salt is smaller than 1000 ptm.

20. Process according to claim 19 characterized in that the particle size is smaller than 350 pm. 30

21. Process according to claim 20 characterized in that the particle size is smaller than 200 pm.

22. Process according to claim 21 characterized in that the particle size is in the range below 100 utm. SRA I

23. Process according to any one of claims 13 to 22 characterized in that at least rt of the sweetening salt used as been applied in coated form or in an appropriate [R:\LIBFF] 2354.doc:TLT _Cq~ ~2 I 27 technical shape or with further amounts of a sweetener being added to the dry foodstuff or with the technical shape of the dry foodstuff being suitably adapted.

24. Process for the preparation of dry foodstuffs containing dipeptide sweeteners which process is substantially as herein described with reference to the process for preparing test compositions K1 and K2. Dated 2 November, 1999 Holland Sweetener Company V.o.F. Patent Attorneys for the Applicant/Nominated Person SPRUSON FERGUSON oi o e9 *9 *9 9 rR:\LIBFF] I 2354.doc:TLT

AU34648/97A
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Dry foodstuffs containing dipeptide sweetener

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Dipeptide sweetener and a reactive component containing dry foods with improved taste.

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PCT/NL1997/000415

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Dry foodstuffs containing dipeptide sweetener

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Nutrinova Nutrition Specialties & Food Ingredients Gmbh

Process for the preparation of a sweetener salt based on aspartame and acesulfame

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2005-11-23
2015-08-11
The Coca-Cola Company
Condiments with high-potency sweetener

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2007-11-29
Pokka Corp
Brain function improver and brain function-improving composition containing the same

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2006-09-18
2008-03-20
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2006-09-18
2008-03-20
ISON Renny
Cohesive non-free flowing sweetener compositions including low-calorie ingredients

US8017168B2
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2006-11-02
2011-09-13
The Coca-Cola Company
High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith

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Sweetener solution containing saccharin and aspartane

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1985-12-31
Wm. Wrigley Jr. Company
Chewing gum with coating of thaumatin or monellin and method

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1985-09-20
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1989-03-28
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Wm. Wrigley Jr. Company
Improved alitame stability in chewing gum by encapsulation

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1990-10-31
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2000-10-03
味の素株式会社

Method for producing dipeptide sweetener granules

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