NZ755861A - Sweetening compositions - Google Patents

Abstract

The invention relates to a sweetening composition comprising a natural sweet-tasting carbohydrate, a stevia compound, rubusoside, and tannin, wherein component d) is present in an amount in the range from 1 mg/l to 400 mg/l. The invention also relates to a sweetening composition comprising a natural sweet-tasting carbohydrate, a stevia compound, rubusoside, tannin and oak extract or pomegranate extract. The invention further relates to a sweetening composition comprising acesulfam or aspartame, sucralose, a stevia compound, saccharin or cyclamate, neohesperidin, and tannin in an amount in the range from 1 mg/l to 400 mg/l. Moreover, the invention relates to a sweetening composition comprising a) 0,1 to 50 g/l of a natural sweet-tasting carbohydrate, b) 40 to 120 g/l of a natural sweet-tasting carbohydrate different from a), and c) 30 to 300 mg/l of rubusoside. And, the invention is about the use of said sweetening compositions for sweetening and preparing beverages. sweet-tasting carbohydrate, a stevia compound, rubusoside, tannin and oak extract or pomegranate extract. The invention further relates to a sweetening composition comprising acesulfam or aspartame, sucralose, a stevia compound, saccharin or cyclamate, neohesperidin, and tannin in an amount in the range from 1 mg/l to 400 mg/l. Moreover, the invention relates to a sweetening composition comprising a) 0,1 to 50 g/l of a natural sweet-tasting carbohydrate, b) 40 to 120 g/l of a natural sweet-tasting carbohydrate different from a), and c) 30 to 300 mg/l of rubusoside. And, the invention is about the use of said sweetening compositions for sweetening and preparing beverages.

Description

WO 2018/122383 PCT/EP2017/084826 Sweetening compositions Description The present invention relates to sweetening compositions, their use for the preparation of sweetening syrups and beverages as well as to the preparation of said beverages.

Common soft drinks usually contain significant amounts of natural sugars such as sucrose, glucose, fructose or mixtures thereof. The caloric content of these natural sugars usually is in the range from 3.6 to 3.9 keal/g. Many attempts have been made to reduce the caloric content of beverages such as soft drinks. In some instances natural sugars have been re» placed by steviol glycosides. Some steviol glycosides have a sweetening power which is about 240 to 400 times that of natural sugar sucrose. Steviol glycosides are derived from extracts of the leaves of the stevia plant (Stevie rebaudicma Ber-tom"). The four major steviol glyeosides found in the leaves of the stevia plant are stevioside (about 5 to 10 wt-%), rebau— (iioside A (about 2 to 4 wt—%), rebaudioside CL (about 1 to 2 wt-»%} and duleoside A (about 0.5 to 1 wt—%). Further steviol glycosides which are found in the extract of the leaves of the stevia plant, however in rather minute quantities, are rebaudioside B, rebaudioside D and rebaudioside E. Tlie common aglycon of all steviol glyeosides is steviol which belongs to the class of cliterpenes.

Unfortunately, beverages sweetened with steviol glyeosides suffer some drawbacks which for many consumers outway the calorie content of conventional beverages. Steviol glyco- sides are known to cause a bitter and/or licoriee—lil<e aftertaste, in some instances also a metallic aftertaste. In addition, the sweet sensation is retarded to some extent, that is, the sweetening exhibit a so—called lingering. In some cases steviol glycosides are also responsi- ble for a blunt or dry mouthfeel.

In El’ 2 519 118 sweetening compositions are disclosed containing a sweetener and at least one sweetness enhancer chosen from terpenes, flavonoids, amino acids, proteins, polyols, other known natural sweeteners, seeowianrmarane glycosides, and analogues thereof. Snit- WO 2018/122383 PCT/EP2017/084826 able sweetening enhancer are reported to include stevia sweeteners, such as stevioside, ste- violbioside, rebaudioside A, rebaudioside B, rebauclioside C, rebandioside D, rebauclioside F, ancl dulcoside A. The at: least one sweetness enhancer has to be present in the composite tion in an amount at or below the sweetness detection threshold level of the at least one sweetness enhancer, and the at least one sweetener and the at least one sweetness enhancer are different.

In E? 2 386 211 the use of rubusoside for masking, reducing or suppressing a bitter, sour and/or astringent taste impression of a bitter, sour and/or astringent-tasting substance is described. Compositions containing rubusoside shall mask, reduce or suppress in food products and in pharrnaceuticals the bitter, sour and/or astringent taste impression of compouncls such as steviosides and reljaudioside A.

And, W0 2008/049256 addresses a sweetened consumable comprising a) at least 0.0001 % of at least one sweetener, wherein said sweetener includes sucrose, fructose, glucose, high fructose corn syrup, corn syrup, xylose, arabinose, rhamnose, eryfliritol, xylitol, man- nitol, sorbitol, inositol, acesulfame potassium, aspartame, neotarne, sucralose, saccharine, or combinations thereof, wherein said at least one sweetener or sweetener combination is present in a concentration above the sweetness ‘detection threshold in a concentration of at least isosweet to 2% sucrose, and b) at least one sweetness enhancer selected from the group consisting of naringin dihydrochalcone, mogroside V, swingle extract, rubusoside, rubus extract, stevioside, and rebauclioside A. Each sweetness enhancer shall be present in a concentration near its sweetness detection thresholzi. For naringin dihyclrochalcone this concentration shall be from .2 to 60 ppm, for rubusoside from 1.4 ppm to 56 ppm, for rubus extract from 2 ppm to 80 ppm, for mogroside V from 0.4 ppm to 12.5 ppm, for swingle ex— tract from 2 to no ppm, for steviosicle from 2 to 60 ppm, and for rebandioside A from 1 to DPT“- Also many other attempts have been made to overcozrne the afore-mentioned shortcomings of steviol glycoside sweeteners such as a bitter and/ or licorice-like aftertaste, a blunt or dry mouthfeel and/or a sweet aftertaste.

For example, according to W0 2012/073121 A2 the bitter aftertaste of steviol glycosides shall be decreased or eliminated by the reduction or elimination of rebaudioside C or dulcoside A or both from stevia compositions. However, it has been found that the reduc- tion of rebaudioside C and/or dulcoside A as such does not guarantee a reduction in bitter aftertaste. Moreover, even with stevia compositions being void of rebaudioside C or WO 2018/122383 PCT/EP2017/084826 dulcoside A consumers experience a slow onset and sometimes even a longer duration of the sweetness sensation.

In W0 2008/147726 it is described that a more suganlilte flavor profile shall be obtained by sweetener compositions comprising at least a) one sweetness enhancer such as urea or thiourea, b) at least one sweetener comprising a carbohydrate sweetener, a natural high- potency sweetener, a synthetic high-potency sweetener or a combination thereof such as rebaudioside compounds, sucralose, aspartame or acesulfarne potassium, and c) at least one sweet taste improving composition selected from the group consisting of carbohy- drates, polyols, amino acids, or mixtures thereof.

New sweetened beverage formulations which do not exhibit a bitter aftertaste shall be ob- tained according to El’ 2 474 240 A1 by use of rebaudioside D and an acidulant comprising at least lactic acid and one or both of tartaric acid and citric acid, and no phosphoric acid.

From W0 2011/146463 A2 it can be derived that the bitterness in an otherwise sweet com- position containing steviol glycosides shall be masked by incorporating an increased amount, relative to naturally occurring compositions, of rebaudioside D.

EP 2 486 806 A1 discloses a low-calorie orange juice drink which makes use of a mixture of 84. wt—% rebaudioside A and 16 wt—% rehaudioside D. Ditierent from a low»-calorie orange juice having been sweetened with a conventional stevia extract a pleasant taste similar to sucrose, a full mouthfeel, and no bitterness and no aftertaste shall be observed during sen— sory evaluation. A similar outcome was reported for a zero-calorie carbonated beverage.

According to WC) 2008/ 112967 A1 the metallic aftertaste experienced with beverages con- taining conventional steviol glycosides shall be masked by the presence of anisic acid.

And, in WC 2012/109585 A1 it is disclosed that attributes such as bitterness, sweet after- taste and licorice flavor of steviol glycosides may be overcome by sweetening compositions comprising a blend of rebandioside A, rebaudioside B and steviol glycosides, in particular when the ratio of rebaudioside B to total steviol glycosides in the blend ranges from 0.5 % to about 50 % and more preferably from about 5 % to about 40 %.

Sucrose being the standard natural sweetener has a characteristic time and intensity sweet- ness profile. Whereas some artificial sweeteners have a more rapid onset of sweetness than sucrose, most artificial sweeteners such as stevia compounds have not only a significantly slower onset but ai/so exhibit a significantly longer linger than sucrose. The afore~ WO 2018/122383 PCT/EP2017/084826 mentioned drawbacks associated with the use of steviol glycosides are still not overcome to a satisfactory extent. It is therefore desirable to obtain beverages, which contain less or no natural sweeteners, and which have a much improved sweetness and aroma profile.

Accordingiy, there still is a need to provide low-calorie beverages which do not exhibit a delayed onset of the sensation of sweetness and which, optionally, also do not suffer from a bitter or licorice-like aftertaste and / or which do not cause a blunt or dry xnouthfeel. Hence, it has been a major goal of the present invention to attain a temporal sweetening profil sirn~ ilar or even essentially identicai to that of natural sugar, Le. a natural sweetening profile, in particular with respect to both the onset of sweetness and its lingering time.

The problem underlying the present invention has surprisingly been solved by a sweetening composition according to a first embodiment comprising a) at least one natural sweet- tasting carbohydrate, in) at least one stevia compound, c) rubusoside and/or at least one rubusoside derivative and/or neohesperidin and/or thaumatine and/or phloretin and/or trilobatin and/or monatin and/or hesperetin and/or at least one enzyme—1:reated steviol glycoside, in particular rubusoside or at least one rubusoside derivative or neohesperidin or at least one enzyme~treated steviol glycoside or any combination thereof, and d) at least one tannin, in particular tannic acid and/ or at least one tannic acid derivative or a composition or extract containing tannic acid and/or at least one tannic acid derivative in an amount, based on the at least one tannin, in particular tannic acid and the at least one tannic acid derivative.

With said first embodirnentthe at least one tannin, in particular tannic acid and/or at least one tannic acid derivative or a composition or extract containing tannic acid and/ or at least one tannic acid derivative, are to be present in an amount, based on the at least one tannin, in particular tannic acid and the at least one tannic acid derivative, in the range from 1 mg/l to 400 mg/l, preferably in the range from 10 mg/l to 300 mg/l and more preferably in the range from 25 to 250 mg/1, if the composition of said first embodiment is an aqueous corn~ position, in particular in the ‘form of a beverage.

Alternatively or simultaneously, said first embodiment of a sweetening composition can be characterized in that, based on the total weight of component b), component c), in particu- lar the rubusoside and] or at least one rubusoside derivative, and component cl), in particu~ lar tannic acid and/or at least one tannic acid derivative, the component b) is present in an amount in the range from 45 to 75 wt—%, the component c), in particular the rubusoside and/ or at ieast one rubusoside derivative, is present in an amount in the range from 2 to 40 WO 2018/122383 PCT/EP2017/084826 wI:~%, and the component d), in particular tannic acid and/or at least one tannic acid deriv- ative, is present in an amount in the range from 2 to 40 wt~%, wherein in each case the sum of components h), c) and :1) always adds up to 100 wt—%. The weight ranges are in particu- lar applicable for an alternative embodiment in which the composition of said first embod- iment represents a dry mixture, in particular in powder and/or particulate form.

According to a preferred embodiment the aforementioned alternate forms of the first em~ bodiment of a sweetening composition, based on the total weight of component b), compo- nent C), in particular the rubusoside and/or at least one ruhusosicle derivative, and compo- nent d), in particular tannic acid and / or at least one tannic acid derivative, the component b) is present in an amount in the range from 50 to 70 wt~%, in particular 55 to 65 wt-%, the component c), in particular the ruhusoside and/or at least one rubusoside derivative, is present in an amount in the range from 5 to 35 wt—%, in particular 10 to 30 wt-%, and the component d), in particular tannic acid and / or at least one tannic acid derivative, is present in an amount in the range from 5 to 35 wt~%, in particular 19 to 30 wt—%, wherein in each case the sum of components b), c) and d) always adds up to 100 wt-%.

The at least one natural swe-et—tasting carbohydrate of the first embodiment in particular is sucrose. And, among the at least one stevia compound of the first embodiment those are preferred selected from the group consisting of steviol glycosides, rebaudiosides and mix- tures thereof.

Among the compounds of component c) of the first embodiment of the sweetening compo- sition of the present invention ruhusoside and/or at least one rubusoside derivative are preferred, rubusoside being particularly preferred.

Tannins in the meaning of the present invention shall comprise polyphenols, in particular so—called plant polyphenols, which exhibit an astringent sensation. It is presently believed that said astringent sensation is caused by or associated with a binding reaction of said po-l~ yphenols to proteins. For example, tannic acid coagulates all:-umen and gelatin. Tannins usually have two or three phenolic hydroxyl groups on the phenyl ring. Tannins can, for example, be classified into pyrogallol type tannins and the catechol type tannins. Tannins can also be classified into so-called. hydrolysable tannins, e.g. based on ellagic acid and gal- lic acid, and condensed tannins, e.g. based on catechol. Tannins of the present invention can be derived from any of the aforementioned classified groups.

WO 2018/122383 PCT/EP2017/084826 Suitable tannins encompass for example ellagitannins, such as punicalagin and geranii, and gallotannins which belong to the class of hydrolysable tannins, as well as stilbenoicls such as astringin or resveratrol. Ellagitannins usually contain various numbers of hexahy- droxydiphenoyl (HHDP) units, as well as galloyl units and,’ or sanguisorboyl units bound to sugar moiety. Suitable representatives of tannins also comprise epigallocatechin gallate, epicatechin gallate, and phlorotannins.

Tannins can for example be obtained from extracts of oak or of pomegranates, in particular pomegranate rind. extracts. For example, gallic acid is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, The composition or extract containing at least one tannin, in particular tannic acid and/ or at least one tannic acid derivative, can be derived from seeds, hark, cones, husk, and/or heartwood of oak, pomegranate, chestnut, gallnut or mimosa, in particular from oak or pomegranate.

Tannic acid in the meaning of the present invention in particular comprises ‘polygalloyl glu- coses and polygalloyl qninic acid esters with the number of galloyl moieties per molecule in particular ranging from 2 up to 12, in particular 3 to 12, eg. decagailoyl glucose. According- ly, tannic acid in the meaning of the present invention can be understood to be, for exam- ple, formed of gallic acid molecules and glucose. Tannic acid will usually hydrolyze into glucose and gallic acid and/or ellagic acid units. In general, with the term tannic acid both an individual compound as well as a mixture of two or more compounds is meant.

Enz.yme—treated steviol glycosides include those steviol glycosides having been treated with, for example, cyclomaltodextrin glucanotransferase (CC-Ease).

The compounds of component c) of the first embodiment of the present invention, in par- ticular rubusoside or a rubusoside derivative or neohesperidin or enzyme—treated steviol glycosides, and even more particular rubusosicle, have been found with the compositions of the present invention to assist in improving its sweetening profile at the onset so that the sweetening sensation is shifted towards the actual consumption of the sweetening composi- tion of a product containing said sweetening composition of the first emboditnent of the present invention. Rubusoside (CAS No: 64849339-4) can be found in leaves of Rubus suavissimus S. Lee (Chinese sweet leaf). Rubusosides in the meaning of the present inven-6 tion shall also comprise enzyinatically-treated. rubusosides.

WO 2018/122383 PCT/EP2017/084826 With the sweetening cotnpositions according to said first embodiment it is preferred that the at least one natural sweet-tasting carbohydrate, in particular sucrose, is present in an amount in the range from 5 to 80 g/l, preferably in the range from 15 g/l to 70 g/l and more preferably in the range from 25 to 55 g/3. Alternatively or in addition in said sweetening compositions of the first embodiment rubusoside and / or at least one rubusoside derivative preferably is present in an amount in the range from 20 to 200 mg/1, more preferably in the range from 20 mg/l to 150 mg/l and in particular in the range from 30 to 125 mg/l.

The problem underlying the present invention has also been solved by a sweetening compo- sition, also referred to as second embodiment of a sweetening composition of the present invention, comprising a) at least one natural ewe-et—tasting carbohydrate, in particular su- crose, lo) at least one stevia compound, in particular selected from the group consisting of stcviol glycosides, rebaudiosides and mixtures thereof, cl rubusoside and/’ or at least one rubusoside derivative and/or neohesperidin and/or thaumatine and/or phloretin and/or trilobatin and/or monatin and/or hesperetin and/or at least one enzyme~treated steviol glycoside, in particular rubusoside or at least one rubusoside derivative or neohesperidin or at least one enzyme-treated steviol glycoside or any combination thereof, d) tannic acid and/ or at least one tannic acid derivative and e) oak extract and/or pomegranate extract.

Among the compounds of component c) of the second embodiment of the sweetening co1n~ position of the present invention ruhusoside and/ or at least one ruhusoside derivative are preferred, rubusoside being particularly preferred.

In said second embodimentof the sweetening composition of the present invention the at least one natural sweet—tasting carbohydrate, in particular sucrose, is preferably present in an amount in the range from 5 to 80 g/l, more preferably in the range from 15 g/i to 7o g/l and in particular in the range from 25 to 55 g/l. Alternatively or in addition in said sweete:n— ing compositions of the second embodiment rubusoside and/or at least one rubusoside derivative is preferably present in an amount in the range from 2o to 20:) mg/l, more pref?» erably in the range from 20 mg/l to 150 mg/l and in particular in the range from 30 to 125 mg/l. And, again, alternatively or in addition in said second embodiment of the sweetening composition of the present invention the total amount of tannic acid and/ or at least one tannic acid derivative is preferably present in an amount in the range from 1 mg/l to 4oo mag/1, more preferably in the range from 10 mg/l to 300 mg/l and in particular in the range from 25 to 250 mg/l.

WO 2018/122383 PCT/EP2017/084826 The problem underlying the present invention has also been solved by a sweetening compo- sition, also referred to as third embodiment of a sweetening composition of the present in- vention, comprising a) acesulfam and/or aspartam, in particular acesulfarn, bl sucralose and/or at least one stevia compound, in particular selected from the group consisting of steviol glycosides, rebaudiosides and mixtures thereof, and/or saccharin and/or cyclarnate, C) ncohesperidin and/or thaumatine and/or rubusoside and/or at least one rubusoside de- rivative and./or phloretin and/or trilohatin and/ or monatin and/or hesperetin, cl) at least one tannin, in particular tannic acid and/ or at least one tannic acid derivative or a composi- tion or extract containing tannic acid and/or at least one tannic acid derivative.

Among the compounds of component c) of the third embodiment of the sweetening compo- sition of the present invention neohesperidine and ruhusoside are preferred, neohesperi- dine being particularly preferred. in this third embodiment component d), based on the at least one tannin, in particular tan- nic acid and the at icast one tannic acid derivative, is present in an amount in the range from 1 mg/l to 400 mg/l, preferably in the range from 10 mg/l to 300 mg/l and more pref- erably in the range from 25 to 250 mg/l.

Such a sweetening composition according to the third embodiment of the invention is par- ticularly preferred which comprises a) acesulfam and/ or aspartame, in particular acesul- fam, h) sucralose or saccharin or at least one ate-via compound, in particular selected from the group consisting of steviol glycosides, rehaudiosides and mixtures thereof, c) neohe- speridin, and d) at least one tannin, in particular tannic acid and/' or at least one tannic acid derivative or a composition or extract containing tannic acid and/or at least one tannic acid derivative, wherein component d), based on the at least one tannin, in particular tannic acid and the at least one tannic acid derivative, is present in an amount in the range from 1 mg/l to 400 mg/l, preferably in the range from to mg/l to 300 mg/l and more preferably in the range from 25 to 250 mg/ l if the composition of said third embodiment is an aqueous com- position, in particular in the form of a beverage.

Alternatively or simultaneously, said third embodiment of a sweetening composition can be characterized in that, based on the total weight of component a), in particular acesulfarn, component b), in particular sucralose, component c), in particular neohesperidine, and component d), in particular tannic acid and/ or at least one tannic acid derivative, the com- ponent a) is present in an amount in the range from 10 to 50 wt-%,‘the component b) is pre- sent in an amount in the range from 15 to 65 wt—%, the component c) is present in an WO 2018/122383 PCT/EP2017/084826 amount in the range from 0,1 to 4 wt-%, and the component :1) is present in an amount in the range from 5 to 50 wt—%, wherein in each case the sum of components a, b), c) and cl) always adds up to 100 Wt—%.

According to a preferred embodiment the aforementioned alternate forms of the third em— bodiment of a sweetening composition, baserl on the total weight of component a), in par ticular acesnlfam, component b), in particular sucralose, component c), in particular nee» hesperidine, and component d), in particular tannic acid and/or at least one tannic acid derivative, the component at) is present in an amount in the range from 15 to 45 wt=%, in particular 20 to 40 wt-%,the component in) is present in an amount in the range from 20 to 55 wt~%, in particular 30 to 45 wt~%, the component C) is present in an amount in the range from 0,2 to 3 wt-%, in particular 0,5 to 2 wt—%, and the component d) is present in an amount in the range from 10 to 40 wt—%, in particular 15 to 35 wt—%, wherein in each case the sum of components a), b), c) and cl) always adds up to 100 Wt-%, Particularly preferable results as to an improved sweetening profile, i.e. a sweetening pro- file coming close to or being even essentially identical to that of natural sugar, that is a so- called natural sweetening profile, is obtained with the third embodiment of the sweetening composition of the present invention in which component b) comprises or consists of su- cralose, saecharin and cyclamate or, alternatively, in which component b) comprises or consists of at least one stevia compound, in particular selected from the group consisting of steviol glycosides, rebaudiosides and mixtures thereof, saccharin and cyclamate.

In the sweetening compositions of the third embodiment of the invention, in particular in the form of an aqueous composition, preferably in the form of a beverage, acesulfam and/ or aspartame is preferably present in an amount in the range from 25 to 250 mg/l, more pref- erably in the range from 50 to 200 mg/l and in particular in the range from 75 to 150 mg/l.

Alternatively or in addition? in said sweetening compositions of the third embodiment of the invention sucralose preferably is present in an amount in the range from 20 to 750 mg/l, more preferably in the range from 40 mg/1 to 550 mg/l and in particular in the range from no to 450 mg/’l. And, alternatively or in addition, in said sweetening compositions of the third embodiment of the invention, and also in the preferred embodiment of the first and second embodiment, neohesperidin preferably is present in an amount in the range from o.oi mg/l to 20 mg/l, more preferably in the range from 0,1 mg/l to 15 mg/l and in particular in the range from 1,0 to 10 mg/l. Alternatively or in acicijltion, in said sweetening compositions of the third embodiment of the invention saccharin preferably is present in an amount in the range from 10 mg/l to 750 mg/'1, more preferably in the range from 20 mg/l WO 2018/122383 PCT/EP2017/084826 to 50o mg/l and in particular in the range from 30 to 400 mg/l, And, alternatively or in addition, in said sweetening compositions of the third embodiment of the invention eyela- mate preferably is present in an amount in the range from 10 mg/l to 500 mg/1, more pref- erably in th.e range from 50 mg/1 to 300 mg/l and in particular in the range from 75 to 200 mg/l. And, alternatively or in addition, in said sweetening compositions ofthe third embod- iment of the invention, and also in the preferred embodiment of the first and second em- bodiment, thaumatine preferably is present in an amount in the range from 0.01 mg/l to 10 mg/l, more preferably in the range from 0,05 ‘mg/l to 5 mg/l and in particular in the range from o,1 to 2 mg/l. And, alternatively or in addition, in said sweetening compositions of the third embodiment of the invention rubusoside and/or at least one rubusoside derivative preferably is present in an amount in the range from 5 to 200 mg/1, more preferably in the range from 10 mg/1 to 150 mg/l and in particular in the range from 20 to 125 mg/l. And, alternatively or in addition, in said sweetening compositions of the third embodiment of the invention, and also in the preferred embodiment of the first and second embodiment, phloretin preferably is present in an amount in the range from 1 to 250 mg/l, more prefera- bly in the range from 5 mg/l to 20o mg/l and in particular in the range from 10 to 150 mg/l.

And, alternatively or in addition, in said sweetening compositions of the third embodiment of the invention, and also in the preferred embodiment of the first and second embodiment, trilobatin preferably is present in an amount in the range from 0,1 to 250 mg/1, more pref- erably in the range from 1 mg/l to 1200 mg/l and in particular in the range from 5 to 150 mg/l. And, alternatively or in addition, in said sweetening compositions of the third embod- iment of the invention, and also in the preferred embodiment of the first and second em.- bodiment, rnonatin preferably is present in an amount in the range from 0.01 mg/l to 20 mg/l, more preferably in the range from 0,1 mg/l to 110 mg/l and in particular in the range from 0,05 to 5 mgfl. And, alternatively or in addition, in said sweetening compositions of the third embodiment of the invention hesperetin preferably is present in an amount in the range from 1 to 750 mg/l, more preferably in the range from 10 mg/l to 50o mg/l and in particular in the range from 25 to 250 mg/1.

In the sweetening compositions according to the first, second and third embodiment of the present invention the at least one stevia compound preferabiy is a mixture comprising, in particular consisting of, rebaudioside A, rebaudioside B and rebaudioside D wherein, based on the total weight of rebaudioside A, rebaudioside B and rebaudioside D, rebandioside A is present in an amount in the range from 80.0 to 99.0 wt—%, rebaudioside B is present in an amount in the range from 0.1 to 1.5 wt—%, and rebaudioside D is present in an amount in the range from 0.9 to 18.5 wt-%.

WO 2018/122383 PCT/EP2017/084826 Moreover, in the sweetening compositions according to the first, second and third embod- iment of the present invention the at least one stevia eomponncl preferably is a mixture comprising, in particular consisting of, rebeuclioside A, rehauclioside B and rehaudioside I) wherein, based on the totai weight of rebaudioside A, rebaudiosicle B and rebaudioside D, rebaudioside A is present in an amount in the range from 85.0 to 95.0 wt—%, rebaudioside B is present in an amount in the range from 0.2 to 1.2 wt~%, and rehaudioside D is present in an amount in the range from 4.8 to 13.8 wt-%.

Furthermore, in the sweetening compositions according to the first, seeoncl and third em- bodiment of the present invention rebaudioside A is present in an amount in the range from 86.0 to 94.3 wt-%, rebaudioside B is present in an amount in the range from 0.3 to 0.9 Wt»-%, and rehaudioside D is present in an amount in the range from 5.4 to 13.1 wt—%, in each case based on the total weight of rehaudioside A, rebaudioside B and rebaudioside D.

In a particular preferred version of the sweetening compositions according to the first, sec~ ond and third embodiment of the present invention rehauclioside A is present in an amount in the range from 90.5 to 94.0 wt-%, rehaudioside B is present in amount in the range from 0.2 to 1.0 wt—% and rebaudioside D is present in amount in the range from 5.8 to 8.5 wt-%, based on the total weight of rebaudiosicle A, rehaudioside B and rebaudioside D, or rehandioeide A is present in an amount in the range from 90.9 to 94.4 wt—%, rebeudioside B is present in amount in the range from 0.2 to 0.5 wt-% and rebaudioside D is present in amount in the range from 5.4 to 8.6 wt-%, in each case based on the total weight of rebau— clioside A, rebaucliosicle B and rebaudioside D.

Steviolglycosides such as rebauciioside A, reband.iosicle B, rebaudioeide D, rehaudioside C, rebauclioside E, rehaudioside F, stevioside, dnleosicle, ruhusoside and steviolhioside can be detected and determined according to HPLC~UV as specified in J ECFA (2010) Steviol Gly- eosides, FAD J ECFA Monograph 10, FAQ, Rome.

The problem underlying the present invention has also been solved by a sweetening compo» sition, also referred to as fourth embodiment of a sweetening composition of the present invention, comprising a) 0,1 to 50 g/l of a natural sweet-tasting carbohydrate, in particular selected from the group consisting of natural sweet—tasting monosaccharirles, h) 40 to 120 g/l of a natural sweebtasting carbohydrate different from as), in particular selected from the group consisting of natural sweebtasting disaecharides, and c) 30 to 300 mg/l rubusoeide and/or at least one ruhueoside derivative and/or 0.01 mg/l to 20 mg/l, preferably in the WO 2018/122383 PCT/EP2017/084826 range from 0,1 mg/i to 15 mg/l and more preferably in the range from 1,0 to 10 mg/l, neo- hesperidin, or (1.01 mg/l to 10 mg/l, preferably in the range from 0,05 mg/l to 5 mg/l and more preferably in the range from 0,1 to 2 mg/l, thaumatine or 1 to 250 mg/l, preferably in the range from 5 mg/l to 200 mg/l and more preferably in the range from 10 to 150 mg/l, phloretin or 0,1 to 250 mg/1, preferably in the range from 1 mg/l to 20o mg/l and more preferably in the range from 5 to 150 mg/l, trilobatin or 0,01 mg/l to 20 mg/1, preferably in the range from 0,1 mg/1 to 10 mg/l and more preferably in the range from o,o5 to 5 mg/l, monatin or 1 to 750 mg/1, preferably in the range from 111 mg/l to 500 mg/l and more pref- erably in the range from 25 to 250 mg/l, hesperetin or at least one enzyn1e~treated steviol glyeosirle or any mixture thereof, in particular rubusosicle and/or at least one rubusoside derivative am:l/ or neohesperidin and/or at least one enzymotreated steviol glyeoside.

Among the compounds of component C) of the fourth embodiment of the sweetening com- position of the present invention rubusoside and/or at least one rubusoside derivative are preferred, rubusoside being particularly preferred.

Said versions of the fourth embodiment of the present. invention are particularly preferred which comprise a) o,5 to 30 g/l. of a natural sweet—tasting carbohydrate selected from the group consisting of natural sweet-tasting rnonosaceharides, b) 70 to 110 g/l of a natural sweet~tasting carbohydrate selected from the group consisting of natural sweet-tasting di- saccharides, and e) 40 to 220 mg/l rubusosicile and/or at least one rubusoside derivative or 0,1 mg/l to 15 mg/l and ‘preferably 1,0 to 10 mg/l neohesperidin, or o,o5 mg/l to 5 mg/l and preferably 0,1 to 2 mg/l thaumatine or 5 mg/l to 20o mg/l and preferably 1o to 150 mg/l phloretin or 1 mg/l to 200 mg/l and preferably 5 to 150 mg/l trilobatin or 1),: mg/l to 10 mg/l and preferably o,o5 to 5 mg/l monatin or 10 mg/l to 500 mg/l and preferably 25 to 250 mg/l hesperetin, In the sweetening compositions of the first to fourth embodiment of the present invention the at least one natural sweet—tasting carbohydrate preferably is selected from the group consisting of a natural sweet-tasting monosaccharide, a natural sweet—tasting disaceharide, a sweet-tasting sugar alcohol and a mixture thereof. While said the sweet—tasting natural monosaccharide preferably is selected from the group Consisting of fructose, glucose, man- nose, rhamnose, xylose, tagatose, galactose, and mixtures thereof, said sweet-tasting natu- ral disaeeharide is preferably selected from the group consisting of sucrose, lactose, maltose and mixtures thereof. Moreover, said sweet-«tasting sugar alcohol preferably is selected from the group consisting of erythritol, glycerol, lactltol, maltitol, mannitol, sorbitol, xylitol, galaetitol and mixtures thereof, WO 2018/122383 PCT/EP2017/084826 With the sweetening compositions of the first to fourth embodiment of the present inven- tion it is particularly preferred to make use of sucrose as the sweet—tasting natural disaccha- ride.

The sweetening compositions of the first to fourth embodiment of the present invention can further comprise at least one flavoring ingredient selected from the group consisting of ga- langal, cocoa, cinnamon, lemon, lemon juice concentrate, coca leaf, orange, orange oil, corn mint, pine, cardamom, mace, clove, lime, lime oil, nutmeg, nutmeg oil, mustard seeds, mustard seed oil, caramel, rosemary, pepper, honey, ginger, vanilla, licorice; licorice ex- tract, cola nut and cola nut extract or mixtures thereof.

In a particularly preferred embodiment the sweetening compositions of the first to fourth embodiment of the present invention further comprise taurine and/ or caffeine. According- ly, the sweetening compositions of the first to fourth embodiment of the present invention can be used for sweetening beverages, in particular soft drinks or energy drinks.

Interestingly, the sweetening compositions of the present invention are also suited to pre- pare precursor compositions in the form of a syrup which can be easily stored and trans- ported and can be used on demand for the preparation of in particular carbonated beverag- The problem underlying the present invention has also been solved by a beverage compris- ing; a sweetening composition according to any of the first to fourth embodiment of the pre- sent invention. Here, the sweetening composition according to any of the first to fourth embodiments of the present invention can already as such represent an aqueous composi- tion, in particular a beverage. Aiternatively, said sweetening composition according to any of the first to fourth embodiments of the present invention, without added water present, can also represent a dry mixture, in particular in powder and/or particulate form. However, even if the sweetening composition according to any of the first to fourth embodiments of the present invention represent aqueous compositions still further ingredients such as fla- vors or thickening agents may be added to form, for example, a commercial beverage.

Suitable beverages according to preferred embodiments are characterized in that rebaudi— oside A, B and D in combination are present in the beverage in a concentration in the range from 0.01 to 1.0 g/l, preferably from (32.05 to (3.75 g/l and more preferably from 0.1 to 0.6 g/l (determin.e~d at ambient temperature and 1 bar).

WO 2018/122383 PCT/EP2017/084826 Also those beverages according to the present invention are preferred in which the sweet- tasting natural carbohydrates and the sweet-tasting sugar alcohols are present in combinae tion in the beverage in a concentration not above 40 g/l, preferably in the range from 5 g/l to 35 g/i and more preferably in the range from 10 g/l to 25 g/l (determined at ambient temperature and 1 bar). Ambient temperature in the meaning of the present invention shall mean room temperature, is a temperature in the range from 20°C to 25°C.

The beverages of the present invention comprise, in particular carbonated, soft drinks and energy drinks. Suitable soft drinks also include cola—flavored soft drinks, wherein cola- fiavorecl soft drinks also encompass cola-flavored-type soft drinks. Also these beverages, when being sweetened with the sweetening composition in accordance with the present irrvention, do not or do essentially not exhibit a slow onset of the sensation of sweetness but provide a rather harmonic sweetening profile and do not or do essentially not have a bitter or licorice-like aftertaste.

It is another benefit of sweetening compositions of the first to fourth embodiment of the present invention that beverages can be obtained which, if at ail, contain natural sugars such as sweetwtasthig carbohydrates andfor sweet—tasting sugar alcohois in a very reduced amount.

The sweetening compositions of the first to fourth embodiment of present invention can also comprise, for example when usedwith energy drinks, further ingredients such as sodi- um citrate, glncoronolactone, inositol, at least one vitamin, e.g. niacin, pantothenic acid, vitamin B6, vitamin B12, riboflavin, caustic caramel, caustic sulfite caramel, ammonia car- amel, sulfite ammonia caramel or ascorbic acid or mixtures thereof.

The sweetening composition of the present invention can be used for sweetening beverages, in particular soft drinks or energy drinks. The beneficial effects coming along with the use of the sweetening composition of the present invention can in particular also be accom- plished with carbonated beverages.

The problem of the present invention has also been solved by a method comprising the steps of a) providing a sweetening composition according to the first to fourth embodiment of the present invention, b) providing water and c) mixing components provided under a) and la). The process of the present invention particularly further comprises the step (step d}) of carbonating the beverage.

WO 2018/122383 PCT/EP2017/084826 According to another embodiment, the process of the present invention can further com- prise the step of adding at least one thickening agent, at least one sweet—tasting natural car- bohydrate, at least one sweetntasting sugar alcohol, at least one organic acid and/ or at least one flavoring ingredient to the sweetening composition according to the first to fourth em~ bodiment of the present invention or to a mixture comprising water and one of said sweet» ening compositions of the present invention. The aforementioned components may also be added to water prior to mixing with any of said sweetening compositions of the present invention. Here, the definitions provided above for thickening agent, sweet—tasting natural carbohydrate, sweet—tasting sugar alcohol, organic acid and flavoring ingredient are appli- cable as well both in terms of general information and preferred embodiments.

Furthermore, it is also possible that the sweet—tasting natural carbohydrates and/or at least one sweet-tasting sugar alcohol are added to the mixture comprising water and one of the first to fourth embodiment of the sweetening compositions of thevpresent invention prior to and / or after the carbonating step, preferably prior to the carbonating step.

The first to fourth embodiments of the sweetening compositions of the present invention as well as the beverages of the present invention, e. g. soft drinlrs or energy drinks, in one em- bodiment can also comprise common additives such as amino acids, coloring agents, bulk- ing agents, modified starches, texturizers, preservatives, antioxidants, emulsifiers, stabi- iizers, gelling agents or arbitrary mixtures thereof.

With the present invention it hasvbeen surprisingly found that sweetening compositions are accessible which do not exhibit a slow onset in the sweetening sensation. As an additionai effect it is also possible to arrive at such sweetening compositions which do not have a bit- ter aftertaste and/or which also do not have a metailic aftertaste. Moreover, it has surpris- ingiy been found that with the sweetening cornpositions of the present invention an aroma or sweetening profile can be accomplished which resembles that of beverages having been sweetened with natural sugars, even with carbonated beverages. Furthermore, it has sur- prisingly been found that with at least one tannin, in particular tannic acid and/ or tannic acid derivatives, being present in the compositions of the present invention the long-lasting sweetening sensations of artificial sweeteners as, for example, stevia compounds can be shortened furnishing a natural or an essential natural sweetening sensation, that is a sweet- ening profiie regularly caused by known high caloric sugars.

It is, thus, possible with the sweetening composition of the present invention to prepare beverages, in particuiar carbonated beverages, such as soft drinks and energy drinks which WO 2018/122383 PCT/EP2017/084826 though having a significantly reduced caloric content exhibit an improved sweetness and aroma profile and which in a preferred embodiment also do not differ significantly in their taste from conventional beverages having been sweetened with natural sugars and] or artifi- cial sweeteners. This also includes that a sweetened sensation is perceived by the consumer already at the very beginning. In addition, with the sweetening composition of the present invention beverages can be obtained which do not have an insipid or blunt taste or mouth- feel.

In the meaning of the present invention artificial sweeteners shall comprise all sweeteners different from natural sweeteners such as natural rnonosaecharide and disaecharide sweet- eners, e.g. glucose and sucrose.

The beverages of the present invention comprise, in particular carbonated, soft drinks and energy drinks. Suitable soft drinks also include cola-flavored soft drinks, wherein cola- ilavored soft drinks also encompass cola—ilaVored—type soft drinks. Also these beverages, when being sweetened with the sweetening composition in accordance with the present invention, do not or do essentially not exhibit a slow onset of the sensation of sweetness but provide 3 rather harmonic sweetening profile and do not or do essentially not have a bitter or licorice—1ike aftertaste.

That is, with the present invention, in particular with the combined use of rubusoside and/ or at least one rubusoside derivative and/ or neohesperidin and/ or thegurnatine and/’ or phloretin and/’ or trilobatin and/or rnonatin and/or hesperetin and/or at least one enzyme- treated steviol glyc-oside, inparticnlar rubusoside and / or at least one rubusoside derivative, and at least one tannin, in particular tannic acid and/or a tannic acid derivative, beverages are accessible which though having been sweetened or eo—sweetened with artificial sweet- eners such as stevia compounds exhibit a temporal sweetness profile as to onset time, dura- tion, i.e. linger, and, if need be, intensity of sweetness being rather similar to that of su— crose. Accordingly, the present invention not only allows shifting the slow onset of, for ex- ample, stevia compounds towards that of sucrose, i.e. thereby exhibiting a more rapid on~ set, but also aids in significantly reducing the lingering effect.

Although modifications and changes maybe suggested by those skilled in the art, it is the intention of the applicant to embody within the patent warranted hereon all changes and modifications as reasonably and probably come within the scope of this contribution to the art. The features of the present invention which are believed to be novel are set forth in de- tail in the appended claims. The features disclosed in the description and in the claims WO 2018/122383 PCT/EP2017/084826 could be essential alone 01‘ in every cornbinatian far the realization of the ixwention in its different embodiments.

Claims (1)

1. ClaimsA sweetening composition comprisingat least one natural sweet-tasting carbohydrate, in particular sucrose,at least one Stevie compound, in particular selected from the group consist-ing of steviol glycosicles, rebaudiosides and mixtures thereof,rnhusoside and/or at least one rubusoside derivative and/or neohesperidinand/ or thaumatine and/or phloretin and/ or trilobatin and/ or rnonatinand/or hesperetin and/or at least one enzyrne~treated steviol glycoside, inparticuiar rubusoside or at least one rubnsoside derivative or neohesperidinor at least one enzymewtreated steviol glycoside or any combination thereof,at least one tannin, in particular tannic acid anéf or at least one tannic acidderivative or a composition or extract containingtannic acid and/ or at leastone tannic acid derivative,wherein component (1), in particular tannic acid and/ or at least one tannicacid derivative, is present in an amount, based on the at least one tannin, inparticular tannic acid and the at least one tannic acid derivative, in the rangefrom 1 _mg/l to .400 mg/l, preferably in the range from 10 mg/1 to 300 mg/land more preferably in the range from 25 to 250 mg/1,and/ orwherein based on the total weight of component lo), component c), in par-ticular rubusoside and/ or at least one rubusoside derivative, and componentcl), in particular tannic acid and/ or at least one tannin acici derivative, thecomponent b) is present in an amount in the range from 45 to 75 wt-%, thecomponent (3), in particular the rubusosicle and/ or at least one rubusosidederivative, is present in an amount in the range from 2 to ago wt—%, and thecomponent d), in particular tannic acid and/’ or at least one tannic acid deriwative, is present in an amount in the range from 2 to 40 wt——%, wherein ineach case the sum of components b), c) and ti) aiwaye adds up to 100 wt~%.The sweetening composition according to claim 1, whereinthe at least one natural sweet—tasting, carbohydrate, in particular sucrose, is presentin an amount in the range from 5 to 80 g/l, preferably in the range from 15 g/1 to 70g/l and more preferably in the range from 25 to 55 g/1, and/or whereinWO