Sweeteners and their uses

Abstract

To provide a novel sweetener and use thereof.SOLUTION: Provided is a sweetener that contains trans-2-hexenal as an active ingredient.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This invention relates to a sweetener containing trans-2-hexenal as an active ingredient and its use. [Background technology]

[0002] In order to reduce carbohydrate intake, various sweeteners that provide a sweet taste even in small amounts have been developed. High-intensity sweeteners have been developed that can provide the same sweetness as sucrose at 1 / 100 to 1 / 1000 the amount used, and aspartame, sucralose, stevia, etc. are known as representative sweeteners. Furthermore, sweeteners are broadly classified into chemically synthesized sweeteners and naturally derived sweeteners. Chemically synthesized sweeteners are said to have a negative image among consumers, and naturally derived sweeteners are increasingly preferred. Examples of naturally derived sweeteners include stevia and licorice.

[0003] On the other hand, trans-2-hexenal is a major component of the smell of grass and leaves, and is a known substance known as an aromatic component. For example, Patent Document 1 reports that by adding a leafy aroma component to a certain carbonated beverage, the bitter aftertaste caused by carbonation is suppressed, resulting in a carbonated beverage with a good aftertaste, and trans-2-hexenal is used as one of the aromatic components. Thus, although trans-2-hexenal has traditionally been used as a flavoring, its use as a sweetener has not been known. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 2019-170194 Summary of the Invention [Problem to be solved by the invention]

[0005] The present disclosure aims to provide new sweetening agents and uses thereof. [Means for solving the problem]

[0006] As a result of extensive research, the present inventors have found that trans-2-hexenal, a major component of the scent of grasses and leaves, has a sweetness intensity greater than that of sucrose and has a threshold value and sweetness quality that make it useful as a sweetener. The present invention was completed through further research based on this finding, and the present disclosure encompasses, for example, the following representative inventions. Item 1. A sweetener containing trans-2-hexenal as an active ingredient. Item 2. A method for using trans-2-hexenal as a sweetener in the production of an oral composition, comprising incorporating trans-2-hexenal to impart sweetness. Item 3. The method of use according to Item 2, wherein the oral composition is a food composition, a pharmaceutical composition, or an oral composition. [Effects of the Invention]

[0007] According to the present disclosure, it is possible to provide a new sweetener containing trans-2-hexenal as an active ingredient. [Brief explanation of the drawings]

[0008] [Figure 1] FIG. 1 is a graph showing the results of the sweetness evaluation test. [Figure 2] FIG. 2 is a graph showing the sweetness quality of trans-2-hexenal and the sweetness quality of sucrose. DETAILED DESCRIPTION OF THE INVENTION

[0009] Hereinafter, embodiments included in the present disclosure will be described in more detail. Note that in the present disclosure, "comprise" also means "consist essentially of" or "consist of."

[0010] The present disclosure encompasses sweeteners containing trans-2-hexenal as an active ingredient.

[0011] Trans-2-hexenal is known as a component of the smell of grass and leaves, and is a known component designated by CAS registration number 6728-26-3.

[0012] The sweetener of the present disclosure contains trans-2-hexenal as an active ingredient. The content of trans-2-hexenal in the sweetener is not limited to a range of more than 0% by mass to 100% by mass, and is preferably 0.005 to 99% by mass, more preferably 0.024 to 99% by mass, even more preferably 1 to 95% by mass, and particularly preferably 5 to 90% by mass, 10 to 80% by mass, or 30 to 70% by mass.

[0013] The form of the sweetener is not limited, and examples include liquid forms such as solutions, emulsions, and suspensions; powders, granules, fine granules, tablets, pills, capsules (including hard capsules, soft capsules, and microcapsules); chewable agents; gels, creams, pastes, sheets; semi-solid or solid forms such as dried liquid forms (freeze-dried products, spray-dried products, and the like); and sprays.

[0014] The sweetener of the present disclosure may contain any other ingredients, such as pharmaceutically acceptable ingredients, cosmetically acceptable ingredients, or edible ingredients, as needed, taking into consideration the above-mentioned form and the like, to the extent that the effects of the present disclosure are not impaired. Examples of such other components include water, lower alcohols (ethanol, 1-propanol, glycerin, etc., having from 1 to 5 carbon atoms, preferably from 1 to 3 carbon atoms), alcohols such as higher alcohols, oils such as animal and vegetable oils, excipients, disintegrants, diluents, lubricants, flavors, spices, colorants, flavorings, suspending agents, humectants, emulsifiers, solubilizers, dispersants, buffers, binders, stabilizers, bulking agents, preservatives, thickeners, gelling agents, pH adjusters, surfactants, coating agents, absorption promoters, adsorbents, fillers, antioxidants, refreshing agents, dietary fiber (such as indigestible dextrin), amino acids, vitamins, minerals, animal and plant extracts, enzymes, various functional components such as nutritional components, sweeteners other than trans-2-hexenal, etc. These may be used alone or in combination of two or more, and the amounts to be added may be determined appropriately.

[0015] While not limiting the present disclosure, examples of sweetening components other than trans-2-hexenal include, regardless of whether they are chemically synthesized or naturally derived, aspartame, saccharin, acesulfame K, sucralose, licorice, stevia, xylitol, sorbitol, reduced starch syrup, reduced palatinose, maltitol, mannitol, erythritol, sucrose, glucose, fructose, maltose, isomerized sugar, trehalose, palatinose, fructooligosaccharides, and galactooligosaccharides. These may be used alone or in combination of two or more. Thus, the sweetening agent of the present disclosure may or may not contain a sweetening component other than trans-2-hexenal.

[0016] Although not limiting the present disclosure, examples of the other ingredients include spices, such as wasabi, garlic, chili pepper, cinnamon, mint, etc. These may be used alone or in combination of two or more.

[0017] The sweetener of the present disclosure can be produced by mixing trans-2-hexenal and, if necessary, other ingredients according to a conventionally known procedure depending on the form, etc.

[0018] As shown in the examples below, the sweetness of trans-2-hexenal is 29.6 times that of sucrose, and even a smaller amount than sucrose can provide sufficient sweetness. Furthermore, the detection threshold of trans-2-hexenal is 0.0051% by mass, and the perception threshold is 0.0244% by mass, both of which are lower than those of sucrose. This also makes trans-2-hexenal useful as a sweetener. Furthermore, trans-2-hexenal has the same sweetness qualities as sucrose (sweetness mouthfeel, intensity, depth, crispness (refreshing feeling) of the aftertaste, breadth, and desirability). Thus, the sweetener of the present disclosure containing trans-2-hexenal as an active ingredient can be used as a substitute for conventional sweeteners such as sucrose, or together with conventional sweeteners.

[0019] For this reason, the sweetener of the present disclosure can be used in combination with a composition to be sweetened, either in place of or together with a known sweetener, for the purpose of imparting sweetness. Use in combination with a composition to be sweetened (hereinafter sometimes referred to as a raw material composition) typically involves mixing the sweetener of the present disclosure with the raw material composition. This allows for easy production of a composition to which sweetness is imparted by blending the sweetener of the present disclosure with the raw material composition. When the sweetener of the present disclosure is used in combination with a known sweetener, the sweetness imparted by blending the known sweetener may be enhanced by the combined use of the sweetener of the present disclosure. For this reason, the term "imparting sweetness" in the present disclosure refers not only to imparting sweetness to a non-sweetened composition, but also to imparting further sweetness to a sweetened composition (enhancing the sweetness).

[0020] The sweetened composition is not limited, but is typically an oral composition, such as a food composition (including beverages and supplements), a pharmaceutical composition, an oral composition, or a feed composition.

[0021] Examples of oral compositions include, but are not limited to, carbonated drinks, fruit drinks, tea drinks, sports drinks, soy milk drinks and other soft drinks, alcoholic drinks, milk drinks and other beverages, yogurt, cheese and other dairy products, candy, gummy candy, jelly, pudding, chewing gum, chocolate, cookies, biscuits, sponge cake, donuts, castella, hotcakes, pies, bread, sweets such as bean paste, rice crackers and other rice crackers, ice cream, sherbet and other frozen desserts, custard cream, butter cream, fruit jam, etc. Examples of food compositions include jams and pastes such as syrup, fruit preserves in syrup, flower paste, fruit paste, and peanut paste; oils such as edible oils such as margarine, shortening, vegetable oil, and animal oil; seasonings such as miso, soy sauce, sauces, ketchup, dressings, mayonnaise, grilled meat sauce, stew base, curry roux, and lightly pickled vegetables; pickles such as pickled radish; seafood products such as fish sausage, kamaboko, seasoned seaweed, and tsukudani; livestock products such as ham and sausage; and fried products such as fried tofu and instant ramen. Examples of oral compositions include pharmaceutical compositions such as various supplements, powders, granules, tablets, lozenges, and drinks; and oral compositions such as toothpaste, liquid toothpaste, and mouthwash. These also include compositions used as quasi-drugs. Examples of oral compositions include various pet foods and feed compositions such as feed for livestock such as poultry, cattle, and pigs. As will be shown in the Examples below, trans-2-hexenal can exhibit a desired sweetness even in an aqueous solution, and therefore the sweetener of the present disclosure can be used in a variety of compositions.

[0022] Although not limiting the present disclosure, preferred examples of oral compositions include soft drinks, alcoholic drinks, and the like.

[0023] Without being limiting of the present disclosure, the sweeteners of the present disclosure may generally be mixed with the raw material compositions during the preparation of the oral compositions according to conventional procedures.

[0024] The content of the sweetener of the present disclosure in the sweetened composition is not limited, and may be appropriately determined depending on the type of composition, the desired sweetness, the presence or absence, type, and content of a sweetener used in combination, as well as the sweetness level, etc. Although not limited thereto, for example, the content of the sweetener of the present invention in an oral composition is, for example, about 0.005 to 0.1% by mass, and preferably about 0.024 to 0.06% by mass, in terms of trans-2-hexenal.

[0025] According to the present disclosure, in order to provide sweetness, some or all of known sweetening components can be replaced with trans-2-hexenal. Furthermore, sweetening components are broadly divided into two types: carbohydrate-based sweeteners and non-carbohydrate-based sweeteners. Trans-2-hexenal is a non-carbohydrate substance, and sucrose, for example, is a type of carbohydrate-based sweetener. For this reason, the sweetener of the present disclosure can be preferably used, for example, when the goal is to reduce carbohydrate intake.

[0026] Therefore, the present disclosure can also be said to provide a method for using trans-2-hexenal as a sweetener, which comprises incorporating trans-2-hexenal in the preparation of an oral composition to impart sweetness. In this method, trans-2-hexenal, the oral composition, the incorporation of trans-2-hexenal, etc. are all described in the same manner as above.

[0027] Furthermore, vanilla has traditionally been known as a flavoring agent with a sweet scent, and its main component is known to be vanillin. However, as will be shown in the Examples below, vanillin does not substantially produce a sweet taste. Thus, just because an aroma component has a sweet scent does not mean that the aroma component is useful as a sweetener. It is surprising that trans-2-hexenal, which is a major component of the scent of grass and leaves and has a green leafy scent, is useful as a sweetener. [Example]

[0028] Hereinafter, the embodiments of the present disclosure will be described more specifically with reference to examples, but the embodiments of the present disclosure are not limited to the following examples.

[0029] Test Example 1: Sweetness 1-1) Sample preparation Trans-2-hexenal was mixed with water and stirred until homogeneous, and five different concentrations of trans-2-hexenal aqueous solutions (0.0663 to 0.0083 mass%, 0.0145 mass% intervals, i.e., 0.0663, 0.0518, 0.0373, 0.0228, 0.0083 mass%) were prepared. Sucrose was also mixed with water and stirred until homogeneous, and a sucrose aqueous solution (concentration: 1.48 mass%) was prepared. The trans-2-hexenal, sucrose, and water used in this test example are as follows. Trans-2-hexenal: Trade name: trans-2-hexenal (manufactured by Inoue Fragrance Manufacturing Co., Ltd.) Sucrose: Granulated sugar (manufactured by Mitsui Sugar Co., Ltd.) Water: Baby no Jikan Baby's Pure Water (manufactured by Asahi Group Foods Co., Ltd.)

[0030] 1-2) Sweetness evaluation A modified version of the Pauli full series test was performed using the method of Watanabe et al. (Watanabe Takeo, Bulletin of the Starch Sugar Technology Research Association, 14, 44-50, (1956)). Specifically, after rinsing their mouths with water to ensure there was no residual taste, participants were fitted with nose plugs. With the nose plugs in place, they drank 5 mL of the sucrose solution prepared as described above, checked the sweetness, and then spat out the solution. The nose plugs were removed, their mouths were rinsed with water, and the nose plugs were reinserted. With the nose plugs still in place, participants drank 5 mL of trans-2-hexenal solution, checked the sweetness, and then spat out the solution. The sweetness of the trans-2-hexenal solution was compared to that of the sucrose solution and rated as "great," "equal," or "less sweet" using a three-point scale. After drank the trans-2-hexenal solution, participants gargled and waited 3 minutes. This was performed for each concentration of trans-2-hexenal solution. The presentation order of the trans-2-hexenal solutions was randomized using a Latin square design. After discriminating between all five concentrations of trans-2-hexenal solutions, the order of presentation of the trans-2-hexenal solutions was reversed and the results were compared with those of sucrose solutions in the same manner.

[0031] The number of subjects in this test example was six, and as mentioned above, each aqueous solution was placed in the mouth twice, so the discrimination number n for each aqueous solution was set to 12. The room temperature was 20°C, and each aqueous solution was left to stand at room temperature for one hour before the start of the test.

[0032] The responses of the subjects were compiled, and the sweetness level was calculated according to the following formula. The compiled results are shown in Table 1 and Figure 1. Figure 1 is a graph of the results in Table 1.

[0033] [Table 1]

[0034] Eo=(Do+i / 2)-Σgr×i / n=0.0409 Eu=(Du-i / 2)+Σkl×i / n=0.0276 Em=(Eo+Eu) / 2=0.0342 S = (N + 100) / Em = 2.96 × 10 3

[0035] In the formula, the symbols have the following meanings: ·Concentration interval i=0.0145 Number of discriminations n=12 "Large" discrimination threshold Eo "Equal" threshold Em "Small" discrimination threshold Eu The concentration of the sample solution that all subjects answered as "larger" than the sucrose solution, Do = 0.0663 The concentration of the sample solution that all subjects answered as "smaller" than the sucrose solution, Du=0.0083 · Sum of discriminations for "large" Σgr=27 · Sum of discriminations for "small" Σkl=22 · Sweetness intensity S of trans-2-hexenal solution when 1.48 mass% sucrose solution is set as 100 Sucrose aqueous solution concentration N=1.48

[0036] 1-3) Results When calculated according to the formula above, the sweetness (sweetness intensity S) was 2.96 x 10 3 In other words, the sweetness of trans-2-hexenal was 29.6 times that of sucrose. This indicates that trans-2-hexenal can provide sufficient sweetness even in smaller amounts than sucrose.

[0037] Test Example 2: Threshold 2-1) Sample preparation Trans-2-hexenal and water were mixed in the same manner as in Test Example 1, and eight concentrations of trans-2-hexenal aqueous solutions (0.0663 to 0.0005 mass%, a dilution series of folds, i.e., 0.0663, 0.0331, 0.0166, 0.0083, 0.0041, 0.0021, 0.0010, 0.0005 mass%) were prepared. The same trans-2-hexenal and water as those in Test Example 1 were used.

[0038] 2-2) Threshold evaluation A whole-mouth method was performed using a modified version of the methods used by Owada et al. (Owada Kunio et al., Japanese Journal of Hygiene, 27, 2, 243-247, (1972)) and Somekawa et al. (Somekawa Masataka et al., Meikai University Journal of Dentistry, 48, 2, 27-34, (2019)). Ten subjects were tested, the room temperature was 20°C, and each aqueous solution was left to stand at room temperature for one hour before the start of the test.

[0039] Specifically, participants rinsed their mouths with water to ensure there was no residual taste, then inserted nasal plugs. With the nasal plugs in place, they drank water and recorded the sensation as "tasteless." After spitting out the water, they held 10 mL of trans-2-hexenal solution in their mouths for 2 seconds and then spat it out. They were asked to indicate whether or not they felt a difference in taste compared to water, rating it "yes" if they felt it was different, or "no" if they felt it wasn't. If they selected "yes," they were then asked to describe the perceived taste as "sweet," "sour," "bitter," "salty," "umami," or "other." Multiple choices were permitted. After sipping the trans-2-hexenal solution, participants gargled and waited a minute. The trans-2-hexenal solutions were presented in ascending order of concentration. The average of the concentrations when participants selected "yes" for the difference in taste two or more consecutive times was used as the detection threshold. The average of the lowest concentrations when participants selected "sweet" for the taste two or more consecutive times was used as the sweetness perception threshold.

[0040] 2-3) Results According to the above-mentioned procedure, the detection threshold of trans-2-hexenal was calculated to be 0.0051% by mass, and the perception threshold was 0.0244% by mass. These thresholds were higher than those of, for example, aspartame, a conventionally known sweetener, but lower than those of sucrose. This also demonstrated that trans-2-hexenal is useful as a sweetener.

[0041] Test Example 3: Sweetness quality 3-1) Sample preparation An aqueous solution of trans-2-hexenal (0.0373% by mass) and an aqueous solution of sucrose (1.48% by mass) were prepared in the same manner as in Test Example 1. The same trans-2-hexenal, sucrose, and water as in Test Example 1 were used.

[0042] 3-2) Evaluation of sweetness quality Ten subjects were tested at a room temperature of 20°C. Each aqueous solution was left at room temperature for one hour before the start of the test. After rinsing their mouths with water to ensure there was no lingering taste, they put on nose plugs. With the nose plugs still in place, they took 5 mL of a 1.48% by mass sucrose solution into their mouths, checked the quality of the sweetness, and then spat it out. After removing the nose plugs and rinsing their mouths with water, they put the nose plugs back in. With the nose plugs still in place, they took 5 mL of a trans-2-hexenal solution into their mouths, checked the quality of the sweetness, and then spat it out.

[0043] The quality of sweetness was evaluated according to the evaluation criteria described below. Specifically, the taste quality of the trans-2-hexenal aqueous solution was evaluated on a 7-point scale in comparison with the 1.48% by mass sucrose aqueous solution in terms of sweetness "mouthfeel," "strength," "depth," "clean aftertaste (refreshing feeling)," "broadness," and "likability." In this case, the trans-2-hexenal aqueous solution was ranked as follows: slightly better: +1 point, fairly good: +2 points, very good: +3 points, slightly inferior: -1 point, quite inferior: -2 points, very inferior: -3 points, and neither: 0 point. In this evaluation, the subjects were compared in advance to standardize the standards for mouthfeel, strength, depth, clean aftertaste (refreshing feeling), breadth, and likability.

[0044] [Evaluation criteria] Mouthfeel: Sweetness immediately felt in the mouth Taste: If you feel the sweetness increase quickly after putting it in your mouth, it is considered to be good taste. Depth: A deep, rich sweetness Sharp aftertaste (refreshing): A drink is considered to have a sharp aftertaste if it disappears without lingering and the sweetness does not linger in the mouth. Spread: After sensing the sweetness, the sensation of the sweetness spreading throughout the mouth was considered to be spread. Liking: Overall preference for sweetness

[0045] 3-3.Results The results are shown in Figure 2. As shown in Figure 2, trans-2-hexenal received slightly lower scores than sucrose in terms of sweetness preference, mouthfeel, and depth, but it had the same sharpness as sucrose and received higher scores than sucrose in terms of sweetness intensity and spread. Although some differences were observed compared to sucrose, as can be seen from the graph in Figure 2, the evaluation results obtained when trans-2-hexenal was used (hexagonal) and the evaluation results obtained when sucrose was used (hexagonal) were generally the same shape. This demonstrates that trans-2-hexenal can be used as a sweetener with sweetness qualities similar to those of sucrose, which has traditionally been used as a sweetener.

[0046] Trans-2-hexenal is a non-carbohydrate substance. Sweeteners are broadly divided into two types: carbohydrate-based sweeteners and non-carbohydrate-based sweeteners, and sucrose is a type of carbohydrate-based sweetener. The results of the above test showed that trans-2-hexenal has a sweetness quality similar to that of sucrose. This indicates that trans-2-hexenal can be used in place of sucrose, for example, when aiming to reduce carbohydrate intake. Furthermore, as described above, trans-2-hexenal has a higher sweetness intensity than sucrose and is useful as a sweetener in terms of threshold value. Therefore, it can be used in various compositions to impart sweetness, either in place of or together with various conventionally known sweeteners, including sucrose.

[0047] Vanilla has traditionally been known as a flavoring agent with a sweet scent, and its main component is known to be vanillin. The inventors of the present invention investigated the sweetness of vanillin and found that vanillin had virtually no sweetness. This finding suggests that just because a flavor component has a sweet scent, it is not necessarily useful as a sweetener. Furthermore, it was a surprising result that trans-2-hexenal, a major component of the scent of grass and leaves and possessing the scent of green leaves, is useful as a sweetener.

Claims

1. A sweetener containing trans-2-hexenal as an active ingredient.

2. A method for using trans-2-hexenal as a sweetener in the production of an oral composition, the method comprising incorporating trans-2-hexenal to impart sweetness.

3. The method of claim 2, wherein the oral composition is a food composition, a pharmaceutical composition, or an oral composition.

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