JP2013021927A - Taste-improving agent for high-sweetness sweetener - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a taste-improving agent which effectively restrains an unpleasant taste; which is peculiar to a high-sweetness sweetener, and lingers on; such as bitterness, astringency and harsh taste, without adding a bad taste and a bad odor, and adds sharpness, a feeling of refreshment, and natural sweetness which is close to that of sugar.SOLUTION: The taste-improving agent for a high-sweetness sweetener is added to food and drink which contains a high-sweetness sweetener, the agent comprising 4,7-tridecadienal and/or 2,4,7-tridecatrienal.

Description

  The present invention relates to a taste improving agent for high-intensity sweeteners. More specifically, it suppresses the bitter taste, astringency, and savory taste that are characteristic of high-intensity sweeteners, adds a sharpness and clarity, and improves the natural sweetness close to sugar. A taste improver composition containing a taste improver, and a high sweetness sweetener containing the taste improver It is related with the taste improvement method of the high sweetness degree sweetener by adding the food / beverage products and the taste improving agent to the food / beverage products containing a high sweetness degree sweetener.

  Conventionally, sugars such as sugar (sucrose), glucose, and fructose have been widely used as sweeteners used in foods and drinks. Among them, in particular, sucrose has an extremely good sweetness, and also has a taste characteristic that it can impart a rich taste and body feeling to foods and drinks. Furthermore, it is excellent also in terms of physical properties such as moisture retention, imparting viscosity, and reducing water activity. However, sucrose has long been considered one of the causes of dental caries, and in recent years it can be a cause of lifestyle-related diseases due to overdose, so its use is refrained from recent health and low calorie orientation. Tend. In particular, the tendency is strong in luxury goods such as beverages and confectionery, and the trend toward low calories is progressing.

  In response to these consumer demand trends, so-called "high-intensity sweeteners" such as aspartame, sucralose, acesulfame K, saccharin, saccharin sodium, stevia, licorice and neotame are used as sweeteners instead of sucrose. It is. These high-intensity sweeteners have a feature as “low-calorie sweeteners” that have a much stronger sweetness than sucrose and can add sweetness to foods and drinks with a small amount of addition.

  However, many of the high-intensity sweeteners have a so-called “after-feel” in which the quality of the sweetness is insufficient in thickness and richness, and the aftertaste is a bitter taste or bitter taste. ing. For this reason, there has been a need for a method for improving the aftertaste disgust such as bitterness, astringency or savory taste.

  Various methods have been proposed for improving the taste of such high-intensity sweeteners. For example, a method for improving the aspartame sweetness by sorbitol, maltitol or other oligosaccharide alcohols (Patent Document 1), A method for improving the taste of high-intensity sweeteners by adding a malt extract to a high-intensity sweetener (Patent Document 2), and 0.002% of succinic acid and / or a salt thereof with respect to 1 part by mass of the high-intensity sweetener. A method for improving the taste of high-intensity sweeteners (Patent Document 3), spirantol, a plant extract containing spirantol, or an essential oil, characterized by adding ~ 5 parts by mass A sweetener taste improver (Patent Document 4), a sweet taste improver containing a yeast extract as an active ingredient (Patent Document 5), honey flavor or coconut flavor is added below the flavor threshold. High sweetness sweetener with improved sweetness (Patent Document 6), taste improving composition for sweetener (Patent Document 7), high-sweetness sweetener 1 containing sclareolide and 2-acetylpyrrole Beverages with improved taste of high-intensity sweeteners containing 0.1 parts by mass or more of liqueur flavor relative to parts by mass (Patent Document 8), 0.1 parts by mass with respect to 1 part by mass of high-intensity sweeteners. Beverage (Patent Document 9) containing 4-0001, 2 parts by mass of brandy absolute or wine lease oil with improved taste of high-intensity sweetener, 4- (2,2,3-trimethylcyclopenta-3 An off-note blocking method for artificial sweeteners using a compound such as -enyl) but-2-enoic acid has been proposed (Patent Document 10).

However, sweet ingredients such as Patent Document 1, plant extracts such as Patent Document 2, sour ingredients such as Cited Document 3, umami ingredients such as Cited Document 4 and the like increase their own taste. There is a drawback in that the original taste of foods and drinks to which high sweetness level sweeteners are added changes.
Moreover, the fragrance | flavor and other compounds currently used as a taste improving agent of a high sweetness degree sweetener in patent documents 4-10 are not enough in effect, and may change the original smell of food / beverage products. Therefore, without changing the original taste and odor of food and drink, it suppresses the bitterness, astringency, and savory taste that are characteristic of high-intensity sweeteners, and gives a sharp and clear feeling. It has been desired to develop a taste improving agent capable of improving the natural sweetness close to the above.

  On the other hand, 2,4,7-tridecatrienal is found in the flavor of cooked chicken (Non-patent Document 1), and also a pyrolyzate of arachidonic acid (Non-patent Document 2) or a pyrolysate of phospholipid ( It is a naturally occurring volatile compound found in non-patent literature 3). As a fragrance use, a method for imparting a flavor reminiscent of chickens (Patent Document 11), a method of imparting a flavor reminiscent of chickens by using 4-cisdecenal and 2,4,7-tridecatrienal (patents) Document 12), a perfume application (Patent Document 13) as a fish-blossom flavor improving agent has been proposed.

  Moreover, 4,7-tridecadienal has been reported as a component of an exocrine product from the secretory line above the eyes of Olivia (Orebia auurebi) from natural products (Non-Patent Document 4). A method of imparting a flavor reminiscent of chicken (Patent Document 11), use as a cosmetic fragrance (Patent Document 14), and use of a fragrance as a fish-flavoring flavor improver (Patent Document 13) have been proposed. However, in Non-patent Documents 1 to 4 and Patent Documents 11 to 14, 2,4,7-tridecatrienal or 4,7-tridecadienal is used as a high-intensity sweetener or a high-intensity sweetener. There is no description or suggestion that the taste of high-intensity sweeteners can be improved by adding a trace amount to the food or drink contained.

JP 63-012263 A JP 2010-246474 A JP 2010-279350 A JP 2006-223104 A JP 2000-37170 A JP-A-4-222575 WO2003 / 007734 International Publication JP 2007-82491 A JP 2006-345810 A Special table 2010-522700 gazette Japanese Patent Publication No.41-7822 Japanese Patent Publication No.54-12550 Japanese Patent No. 4676572 JP-A 61-65814

Journal of American Oil Chemists' Society. 51 (8), 356-9 (1974) Frontiers of Flavor Science, [Proceedings of the Welman Flavor Research Symposium], 9th, Freising, Germany, June 22-25, 1999 (2000). Journal of Agricultural and Food Chemistry (2004), 52 (3), 581-586 Journal of Chemical Ecology (1995), 21 (8), 1191-1215

  The object of the present invention is a component that can be used in foods and drinks, and does not produce any off-flavors or off-flavors when added to foods or drinks. Another object of the present invention is to provide a taste improving agent that can suppress tastes such as astringency and savory taste, impart a sharp and clear feeling, and improve natural sweetness close to sugar.

［式中、・・・・は単結合または二重結合を示し、波線はシスまたはトランス配置の立体配置を示す］で表される不飽和アルデヒドからなる、高甘味度甘味料の呈味改善剤。
（ｂ）式（１）の不飽和アルデヒドが４，７−トリデカジエナールである（ａ）に記載の高甘味度甘味料の呈味改善剤。
（ｃ）式（１）の不飽和アルデヒドが２，４，７−トリデカトリエナールである（ａ）に記載の高甘味度甘味料の呈味改善剤。
（ｄ）（ａ）〜（ｃ）のいずれかに記載の高甘味度甘味料の呈味改善剤を０．０２ｐｐｂ〜１０ｐｐｍ含有することを特徴とする、高甘味度甘味料の呈味改善剤組成物。
（ｅ）（ａ）〜（ｃ）のいずれかに記載の高甘味度甘味料の呈味改善剤を、高甘味度甘味料を含有する飲食品に０．０２ｐｐｔ〜１０ｐｐｂ含有させることを特徴とする、高甘味度甘味料の呈味改善方法。
（ｆ）（ａ）〜（ｃ）のいずれかに記載の高甘味度甘味料の呈味改善剤を０．０２ｐｐｔ〜１０ｐｐｂ含有させたことを特徴とする、高甘味度甘味料の呈味が改善された飲食品。 As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that a very small amount of 2,4,7-tridecatrienal or 4,7-trideca is added to a food or drink containing a high-intensity sweetener. By adding dienal into foods and drinks, the unique bitterness, astringency, and savory taste of the tails of high-intensity sweeteners that do not add unnecessary flavor and flavor to these foods and drinks. The present inventors have found that it is possible to suppress unpleasant tastes such as crispness, give a sharp and refreshing feeling, and improve the natural sweetness close to that of sugar, thereby completing the present invention. Thus, the present invention provides the following.
(A)
Following formula (1)

[ Wherein , ... Represents a single bond or a double bond, and a wavy line represents a configuration of cis or trans configuration]. .
(B) The taste improving agent for high-intensity sweeteners according to (a), wherein the unsaturated aldehyde of formula (1) is 4,7-tridecadienal.
(C) The taste improving agent for high-intensity sweeteners according to (a), wherein the unsaturated aldehyde of formula (1) is 2,4,7-tridecatrienal.
(D) A taste improving agent for a high sweetness sweetener, comprising 0.02 ppb to 10 ppm of the taste improving agent for a high sweetness sweetener according to any one of (a) to (c). Composition.
(E) The taste improving agent for high-intensity sweeteners according to any one of (a) to (c) is characterized by containing 0.02 ppt to 10 ppb in a food or drink containing high-intensity sweeteners. A method for improving the taste of high-intensity sweeteners.
(F) The taste of a high sweetness sweetener characterized by containing 0.02 ppt to 10 ppb of the high sweetness taste improver according to any one of (a) to (c). Improved food and drink.

  2,4,7-tridecatrienal and 4,7-tridecadienal used in the present invention have been found to be found in natural products, and are used as chicken-like flavors, as a fish-flavoring agent. However, it has not yet been reported to have a taste-improving effect of high-intensity sweeteners, and by adding a trace amount to foods and drinks containing high-intensity sweeteners The content of the special sweeteners, such as the bitterness, astringency, and savory taste that can be tailed later, suppresses disgusting taste, gives a sharp and clear feeling, and improves the natural sweetness close to sugar. It has never been described or suggested.

In the present invention, the improvement in the taste of a high-intensity sweetener means that the high-intensity sweetener has a characteristic that suppresses disgusting tastes such as a bitter taste, astringency, and savory taste, and gives a sharp and clear feeling. And to improve the natural sweetness close to sugar.
In addition, high-intensity sweeteners have a very strong sweetness compared to sucrose, such as aspartame, sucralose, acesulfame potassium, saccharin, sodium saccharin, stevia, licorice, rahan fruit, neotame, thaumatin, mabinlin, brazein, and monelin. It means an artificial or natural sweetener capable of imparting sweetness to foods and drinks with a small amount of addition.
Sweetness is one of the five basic tastes (acidity, sweetness, salty taste, bitterness, umami), and is detected when sweet substances contained in food and drink stimulate the sweet taste receptors in the taste bud cells of the tongue. It has a distinctive taste. Therefore, when you feel sweetness, only the taste obtained through the taste bud cells of the tongue is related, and it can be felt that various factors such as hotness, astringency, richness, aroma, temperature, color, etc. influence each other. It is distinguished from sweetness as a “taste”.

  In the present invention, the presence or absence of improvement in taste of the high-intensity sweetener is evaluated by a sensory test in which the taste when the inspector (panelist) eats the food or drink is actually examined with the tongue. It can also be evaluated by instrumental analysis using a taste sensor or the like that digitizes (numerizes) the taste.

  According to the present invention, without adding unnecessary fragrance and flavor to foods and beverages containing high-intensity sweeteners, the unique high-intensity sweetener has a bitterness, astringency, and savory taste that has a tail. It can improve taste and natural sweetness close to sugar.

  As the 2,4,7-tridecatrienal which is one of the unsaturated aldehydes used in the present invention, four geometric isomers ((E, Z, Z) isomer, (E, E, Z) isomer) , (E, Z, E) isomer, (E, E, E) isomer), but in terms of the taste improving effect of high-intensity sweeteners, they are found in nature in Non-Patent Literatures 1 to 3 and the like. Particularly preferred is (E, Z, Z) -2,4,7-tridecatrienal.

  The 4,7-tridecadienal used in the present invention includes four types of geometric isomers ((Z, Z) isomer, (E, Z) isomer, (Z, E) isomer, (E, E) is present, but (Z, Z) -4,7-tridecadienal is particularly preferred in terms of the taste-improving effect of the high-intensity sweetener.

  (E, Z, Z) -2,4,7-tridecatrienal can be synthesized by a method described in known literatures, for example, after bromination using 2-octyn-1-ol as a starting material, ( E) Coupling using a Grignard derivative of 2-penten-4-in-1-ol and a copper catalyst, partially hydrogenating using a Lindlar catalyst, and then oxidizing and synthesizing with manganese dioxide. (J. Agric. Food Chem. 2001, 49, 2959-2965). For other geometric isomers of 2,4,7-tridecatrienal, the isomer mixture of 2,4,7-tridecatrienal can be separated using the difference in physical properties and chemical properties, It can be obtained by performing an isomerization treatment using a suitable catalyst, or can be synthesized by the method described in Japanese Patent Application No. 2011-042255 filed earlier by the present applicant.

  In addition, (Z, Z) -4,7-tridecadienal, which is one of the unsaturated aldehydes used in the present invention, can also be synthesized by a method according to known literature. It can be synthesized by the following method described. As an example, first, 2-octin-1-ol is partially hydrogenated with a Lindlar catalyst to be brominated to obtain Z-form 1-bromo-2-octene. On the other hand, 1-bromo-3-tetrahydropyranyloxypropane and sodium acetylenide are reacted in the presence of ammonia to obtain 5-tetrahydropyranyloxypropanyl-1-pentyne, and then converted into a Grignard derivative. The resulting 1-bromo-2-octene is coupled with copper chloride to give 1-tetrahydropyranyloxy-7-tridecene-1-in. Next, after partially hydrogenating with a Lindlar catalyst, the tetrahydropyranyl group which is a protecting group is eliminated, and the resulting hydroxyl group is oxidized to obtain (Z, Z) -4,7-tridecadienal. Can do. For other geometric isomers of 4,7-tridecadienal, the isomer mixture of 4,7-tridecadienal can be separated using the difference in physical properties and chemical properties, It can be obtained by performing an isomerization treatment using a catalyst, or can be synthesized by the method described in Japanese Patent Application No. 2011-042255 filed earlier by the present applicant.

The amount of the taste improver used in the present invention added to the food or drink is generally such an amount that the concentration of the taste improver contained in the food or drink is 0.02 ppt to 10 ppb. More specifically, although depending on the type of geometric isomers of 2,4,7-tridecatrienal and 4,7-tridecadienal, or the type of food or drink, the taste improver is ( E, Z, Z) -2,4,7-tridecatrienal and (Z, Z) -4,7-tridecadienal, for foods and beverages containing high-intensity sweeteners, Can be exemplified, for example, in the range of 0.02 ppt to 10 ppb, preferably 0.1 ppt to 500 ppt, more preferably 0.5 ppt to 20 ppt.
In addition, the taste improver may contain other geometric isomers, that is, (E, E, Z)-, (E, Z, E)-and (E, E, E) -2,4,7-tridecatrie. Nar, and (E, Z)-, (Z, E)-and (E, E) -4,7-tridecadienal, for foods and beverages containing high intensity sweeteners, The total amount of them can be exemplified, for example, in the range of 0.2 ppt to 10 ppb, preferably 1 ppt to 1 ppb, more preferably 5 ppt to 100 ppt.
Due to the above blending ratio, foods and drinks containing high-intensity sweeteners have the unique bitterness, astringent taste, and savory taste that are characteristic of high-intensity sweeteners, and are crisp and clear. To improve the natural sweetness close to that of sugar.

If these additions to foods and drinks exceed 10 ppb, the foods and drinks may be given the odor of these aldehydes. Therefore, in the case of foods and drinks that do not require these fragrances, the additions are kept below 10 ppb. It is preferable. In addition, even if these aldehydes are imparted with a fragrance, there is no problem, or for foods and beverages that are favorably influenced by the fragrance of these aldehydes, it may be added in excess of 10 ppb. Absent.
Moreover, when content of the taste improving agent of this invention with respect to food-drinks is less than 0.02ppt, there exists a possibility that the taste improvement effect of a high sweetness degree sweetener may not fully be exhibited. The taste improving agent of the present invention contains geometric isomerism that does not include any of (E, Z, Z) -2,4,7-tridecatrienal and (Z, Z) -4,7-tridecadienal. When comprised only with a body, when the content of the taste improving agent of the present invention is less than 0.2 ppt, the taste improving effect of the high-intensity sweetener may not be sufficiently exhibited.

  The unsaturated aldehyde, which is a taste improving agent for high-intensity sweeteners according to the present invention, can be used as it is by adding it to foods and drinks, but these unsaturated aldehydes are oil-soluble, Dispersibility is poor, and adding a trace amount to foods and drinks is difficult from the viewpoint of weighing and dilution. The method of obtaining and blending it into food and drink can be employed.

Examples of such a composition include a solution obtained by dissolving the unsaturated aldehyde of the present invention in a water-miscible organic solvent, an emulsion preparation, and a powder preparation.
Examples of the water-miscible organic solvent for dissolving the unsaturated aldehyde of the present invention include, for example, ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-methyl ethyl ketone, 2-propanol, methyl ethyl ketone, glycerin, propylene glycol and the like. Can do. Among these, ethanol or glycerin is particularly preferable from the viewpoint of use in foods and drinks.

  Moreover, in order to set it as an emulsion formulation, it can obtain by emulsifying the unsaturated aldehyde of this invention with an emulsifier. The method for emulsifying the unsaturated aldehyde of the present invention is not particularly limited, and various emulsifiers conventionally used in foods and drinks, such as fatty acid monoglyceride, fatty acid diglyceride, fatty acid triglyceride, propylene glycol fatty acid ester, Using sugar fatty acid ester, polyglycerin fatty acid ester, lecithin, modified starch, sorbitan fatty acid ester, quilaya extract, gum arabic, tragacanth gum, guar gum, caraya gum, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, casein, etc. An emulsified liquid having excellent stability can be obtained by emulsifying using a homomixer, a colloid mill, a rotating disk type homogenizer, a high-pressure homogenizer, or the like. The amount of these emulsifiers to be used is not strictly limited, and can be varied over a wide range depending on the type of emulsifier to be used. Usually, about 0. A suitable range is 01 to about 100 parts by weight, preferably about 0.1 to about 50 parts by weight. In order to stabilize the emulsification, the water-soluble solution is one of polyhydric alcohols such as glycerin, propylene glycol, sorbitol, maltitol, sucrose, glucose, trehalose, sugar solution, and reduced starch syrup, in addition to water. A seed or a mixture of two or more can be blended.

  Further, the emulsion thus obtained can be made into a powder formulation by drying if desired. In pulverization, saccharides such as trehalose, dextrin, sugar, lactose, glucose, starch syrup, and reduced starch syrup can be appropriately blended as necessary. The amount of these used can be appropriately selected according to the properties desired for the powder preparation.

  The amount of the unsaturated aldehyde of the present invention in the above preparation is generally about 0.1% (about 0.01% to 1%) of these preparations added to food and drink, About 0.02 ppb to 10 ppm in the preparation, specifically (E, Z, Z) -2,4,7-tridecatrienal and (Z, Z) -4,7-tridecadienal In the preparation, for example, 0.02 ppb to 10 ppm, preferably 0.1 ppb to 500 ppb, more preferably 0.5 ppb to 20 ppb can be exemplified. Other geometric isomers, namely (E, E, Z)-, (E, Z, E)-and (E, E, E) 2,4,7-tridecatrienal, and (E, Z )-, (Z, E)-and (E, E) -4,7-tridecadienal, for example, 0.2 ppb to 10 ppm, preferably 1 ppb to 1 ppm, more preferably 5 ppb in the formulation. A range of ˜100 ppb can be exemplified.

  Although the addition amount to the food / beverage products of the taste improving agent composition of the high sweetness degree sweetener of this invention changes also with kinds of food / beverage products, it is 0.01% with respect to the food / beverage products containing a high sweetness degree sweetener. About 1% can be exemplified. However, the addition amount of the composition is adjusted according to the blending amount of the unsaturated aldehyde of the present invention in the composition so that the unsaturated aldehyde of the present invention in the food and drink is the aforementioned blending amount. It is preferable to adjust.

  The food / beverage product in which the taste improver of the high-intensity sweetener of the present invention or the taste improver composition of the high-intensity sweetener is blended is not particularly limited, and includes, for example, fruit juice and fruit granules Fruit juices, fruit beverages, fruit juice beverages, fruit juice beverages, fruit juices or vegetable juice drinks such as vegetable juices, vegetable juices, fruit vegetable mixed juices; carbonated beverages such as cola, ginger ale, cider; sports drinks, near water, etc. Soft drinks; Tea-based or taste drinks such as coffee, cocoa, tea, matcha, green tea, oolong tea; milk drinks, coffee with milk ingredients, cafe au lait, milk tea, matcha milk, fruit milk drinks, drink yogurt, lactic acid bacteria drinks, etc. Beverages such as beverages containing dairy milk ingredients in general; yogurt, jelly, drink jelly, pudding, bavaroa, bra Desserts such as Nge and mousse (sweetened foods that are eaten after a meal); Ice creams such as ice cream, ice milk, and lacto ice (added sweeteners and other ingredients to dairy products and frozen with stirring Frozen confectionery such as confectionery foods, ice confectionery such as sherbet and cracked ice (food that is frozen by stirring by adding various other ingredients to sugar solution); baked confectionery including Western confectionery such as cakes, crackers, biscuits and buns Confectionery such as steamed confectionery; rice confectionery, snacks; sugar confectionery such as chewing gum, hard candy, nougat candy and jelly in general; sauces including fruit flavor sauce and chocolate sauce; creams such as butter cream, flower paste and whipped cream ; Jam such as strawberry jam and marmalade; Bread including sweet bread; Seasonings such as sauce, tomato ketchup, sauce, noodle soup used for grilled meat, yakitori, salmon roasts etc. A wide range of agricultural, livestock and fishery products including foods can be exemplified. Among these, preferred foods include beverages, desserts, and frozen desserts. Particularly preferred is a beverage. In particular, according to the method of the present invention, a beverage containing a high-intensity sweetener has an unpleasant taste such as a bitterness, astringency, a savory taste, and a aftertaste such as a bitterness caused by the high-intensity sweetener Can be significantly suppressed and the taste of the beverage can be improved satisfactorily.

  Hereinafter, the present invention will be described more specifically with reference to examples. In addition, this invention is not limited to these.

(Example 1) Sweetness improvement of stevia-containing beverage by (Z, Z) -4,7-tridecadienal 0.15 g of citric acid, 0.02 g of trisodium citrate, stevia sweetener (α-glucosyl rebaudio After mixing 0.04 g of side A (containing 85%) and 0.1 g of lemon flavor (manufactured by Hasegawa Fragrance Co., Ltd.), water was added to make the total volume 100 mL. A stevia sweetener-containing beverage to which (Z, Z) -4,7-tridecadienal was added at a concentration shown in Table 1 as a taste improver (sweetness improver) of the present invention was obtained.
Sensory evaluation is performed by 10 panelists, and is attached to each beverage. A: Sweetness is unnatural and feels unpleasant in the aftertaste (no difference from no addition) B: Sweetness is somewhat unnatural and the taste is somewhat unpleasant ( C: Slightly unnatural sweetness, aftertaste (slightly improved compared to no addition), N: Natural sweetness, good aftertaste, and off-flavor No (feels sweet like sugar), X: The sweetness is natural, but the odor like an aldehyde-like keen is a concern. The aroma such as aldehyde-like keen is a peculiar odor common to all aldehydes, and means an irritating off-flavor such as an image of deteriorated oils, soaps, metals, and dokudami. In addition, in the flavor determination, the effect was compared between the concentrations of the taste improver of the high-intensity sweetener, and one point with the best sweetness quality was selected. The results are shown in Table 1.

  As shown in Table 1, a stevia-containing beverage without (Z, Z) -4,7-tridecadienal has a unique and unnatural sweetness and feels unpleasant in the aftertaste, but (Z, Z) Stevia-containing beverages to which 0.04ppt to 10ppb of -4,7-tridecadienal are added have an effect of improving sweetness, and the odor peculiar to (Z, Z) -4,7-tridecadienal is not so much I couldn't feel it strongly. The range in which the sweetness was improved relatively well and the odor peculiar to (Z, Z) -4,7-tridecadienal was hardly felt was 0.1 ppt to 500 ppt. Furthermore, within the range of 0.5ppt to 20ppt, no odor peculiar to (Z, Z) -4,7-tridecadienal is felt, and most panelists feel a natural sugary sweetness. evaluated.

(Example 2) Sweetness improvement of stevia-containing beverage by (E, Z, Z) -2,4,7-tridecatrienal (Z, Z) -4,7-tridecadienal in Example 1 (E , Z, Z) Beverage preparation and sensory evaluation were carried out in the same manner as in Example 1, except that it was replaced with 2,4,7-tridecatrienal. The results are shown in Table 2.

  As shown in Table 2, stevia-containing beverages without (E, Z, Z) -2,4,7-tridecatrienal have a unique and unnatural sweetness, but they have an unpleasant aftertaste. , Z, Z) -2,4,7-tridecatrienal containing 0.02 ppt to 10 ppb of stevia-containing beverage has an effect of improving sweetness, and (E, Z, Z) -4,7-tride The odor peculiar to Catrienal was not so strong. The range in which the sweetness was improved relatively well and the odor peculiar to (E, Z, Z) -2,4,7-tridecatrienal was hardly felt was 0.1 ppt to 500 ppt. Furthermore, within the range of 0.5 ppt to 20 ppt, the odor peculiar to (E, Z, Z) -2,4,7-tridecatrienal is not felt at all, and most panelists have a natural sugar-like sweetness. I felt that I felt.

(Example 3) Sweetness improvement of stevia-containing beverage by (E, Z) -4,7-tridecadienal (Z, Z) -4,7-tridecadienal in (E, Z) in Example 1 Beverage preparation and sensory evaluation were performed in the same manner as in Example 1 except that it was replaced with -4,7-tridecadienal. The results are shown in Table 3.

  As shown in Table 3, a stevia-containing beverage without (E, Z) -4,7-tridecadienal has a unique and unnatural sweetness and feels unpleasant in the aftertaste, but (E, Z) Stevia-containing beverages to which -4,7-tridecadienal is added at 0.2 ppt to 10 ppb have an effect of improving sweetness, and the odor peculiar to (E, Z) -4,7-tridecadienal is not so much. I couldn't feel it strongly. Further, the range in which the sweetness was improved relatively well and the odor peculiar to (E, Z) -4,7-tridecadienal was hardly felt was 1 ppt to 1 ppb. Furthermore, within the range of 5ppt to 100ppt, no odor peculiar to (E, Z) -4,7-tridecadienal was felt, and most panelists rated it as having a natural sugary sweetness. .

(Example 4) Sweetness improvement of stevia-containing beverage by (Z, E) -4,7-tridecadienal (Z, Z) -4,7-tridecadienal in (Z, E) Beverage preparation and sensory evaluation were performed in the same manner as in Example 1 except that it was replaced with -4,7-tridecadienal. The results are shown in Table 4.

  As shown in Table 4, the stevia-containing beverage without (Z, E) -4,7-tridecadienal has a unique unnatural sweetness and feels unpleasant in the aftertaste, but (Z, E) Stevia-containing beverages to which 0.2ppt to 10ppb of -4,7-tridecadienal are added have an effect of improving sweetness, and the odor peculiar to (Z, E) -4,7-tridecadienal is not so much I couldn't feel it strongly. Further, the range in which the sweetness was improved relatively well and the odor peculiar to (Z, E) -4,7-tridecadienal was hardly felt was 1ppt to 1ppb. Furthermore, within the range of 5ppt to 100ppt, no (Z, E) -4,7-tridecadienal-specific odor was felt at all, and most panelists rated it as having a sugar-like natural sweetness. .

(Example 5) Sweetness improvement of stevia-containing beverage by (E, E) -4,7-tridecadienal (Z, Z) -4,7-tridecadienal in (E, E) Beverage preparation and sensory evaluation were performed in the same manner as in Example 1 except that it was replaced with -4,7-tridecadienal. The results are shown in Table 5.

  As shown in Table 5, stevia-containing beverages without (E, E) -4,7-tridecadienal have a unique and unnatural sweetness and feel unpleasant in the aftertaste, but (E, E) Stevia-containing beverages to which -4,7-tridecadienal is added at 0.2 ppt to 10 ppb have an effect of improving sweetness, and the odor peculiar to (E, E) -4,7-tridecadienal is not so much I couldn't feel it strongly. Further, the range in which the sweetness was improved relatively well and the odor peculiar to (E, E) -4,7-tridecadienal was hardly felt was 1ppt to 1ppb. Furthermore, within the range of 5ppt to 100ppt, no (E, E) -4,7-tridecadienal-specific odor was felt at all, and most panelists rated it as having a sugar-like natural sweetness. .

(Example 6) Sweetness improvement of stevia-containing beverage by (E, E, Z) -2,4,7-tridecatrienal (Z, Z) -4,7-tridecadienal in Example 1 (E , E, Z) Beverage preparation and sensory evaluation were performed in exactly the same manner as in Example 1, except that it was replaced with -2,4,7-tridecatrienal. The results are shown in Table 6.

  As shown in Table 6, stevia-containing beverages without (E, E, Z) -2,4,7, -tridecatrienal have a unique and unnatural sweetness, and the taste after taste is unpleasant ( E, E, Z) -2,4,7,-Stevia-containing beverage added with 0.2 ppt to 10 ppb of tridecatrienal has an effect of improving sweetness, and (E, E, Z) -2, 4 , 7, -The odor peculiar to Tridecatrienal was not so strong. In addition, the range in which the sweetness was improved relatively well and the odor peculiar to (E, E, Z) -2,4,7, -tridecatrienal was hardly felt was 1ppt to 1ppb. Furthermore, within the range of 5 ppt to 100 ppt, the odor peculiar to (E, E, Z) -2,4,7, -tridecatrienal is not felt at all, and most panelists have a natural sugar-like sweetness. Evaluated to feel.

(Example 7) Sweetness improvement of stevia-containing beverage by (E, Z, E) -2,4,7-tridecatrienal (Z, Z) -4,7-tridecadienal in Example 1 (E , Z, E) Beverage preparation and sensory evaluation were carried out in the same manner as in Example 1 except that it was replaced with -2,4,7-tridecatrienal. The results are shown in Table 7.

  As shown in Table 7, stevia-containing beverages without (E, Z, E) -2,4,7, -tridecatrienal have a unique and unnatural sweetness, but they have an unpleasant aftertaste. Stevia-containing beverages added with 0.2 ppt to 10 ppb of E, Z, E) -2,4,7, -tridecatrienal have an effect of improving sweetness, and (E, Z, E) -2,4 , 7, -The odor peculiar to Tridecatrienal was not so strong. In addition, the range in which sweetness was improved relatively well and the odor peculiar to (E, Z, E) -2,4,7, -tridecatrienal was hardly felt was 1ppt to 1ppb. Furthermore, within the range of 5ppt to 100ppt, no (E, Z, E) -2,4,7, -tridecatrienal odor is felt at all, and most panelists have a natural sugary sweetness. Evaluated to feel.

(Example 8) Sweetness improvement of stevia-containing beverage by (E, E, E) -2,4,7-tridecatrienal (Z, Z) -4,7-tridecadienal in Example 1 (E , E, E) Beverage preparation and sensory evaluation were carried out in the same manner as in Example 1, except that it was replaced with 2,4,7-tridecatrienal. The results are shown in Table 8.

  As shown in Table 8, stevia-containing beverages without (E, E, E) -2,4,7, -tridecatrienal have a unique and unnatural sweetness, and the taste after taste is unpleasant ( Stevia-containing beverages to which 0.2 ppt to 10 ppb of E, E, E) -2,4,7, -tridecatrienal are added have an effect of improving sweetness, and (E, E, E) -2,4 , 7, -The odor peculiar to Tridecatrienal was not so strong. Further, the range in which sweetness was improved relatively well and the odor peculiar to (E, E, E) -2,4,7, -tridecatrienal was hardly felt was 1ppt to 1ppb. Furthermore, within the range of 5 ppt to 100 ppt, the odor peculiar to (E, E, E) -2,4,7, -tridecatrienal is not felt at all, and most panelists have a sugar-like natural sweetness. Evaluated to feel.

(Example 9) Sweetness improvement of beverage containing aspartame by (Z, Z) -4,7-tridecadienal 0.15 g of citric acid, 0.02 g of trisodium citrate, 0.025 g of aspartame, lemon flavor (Hasegawa fragrance) After mixing 0.1 g), water was added to make a total volume of 100 mL. An aspartame-containing beverage to which (Z, Z) -4,7-tridecadienal was added at a concentration shown in Table 9 below as a taste improving agent (sweetness improving agent) of the present invention was obtained.
Flavor Comparison Table 9 below shows the flavor comparison evaluation of the aspartame-containing beverage with and without the addition of the product of the present invention by 10 panelists.

  As shown in Table 9, the (Z, Z) -4,7-tridecadienal-free aspartame-containing beverage has a unique and unnatural sweetness and is unpleasant in the aftertaste, but (Z, Z) Aspartame-containing beverages to which 0.02ppt to 10ppb of -4,7-tridecadienal are added have an effect of improving sweetness, and the odor peculiar to (Z, Z) -4,7-tridecadienal is not so much I couldn't feel it strongly. The range in which the sweetness was improved relatively well and the odor peculiar to (Z, Z) -4,7-tridecadienal was hardly felt was 0.1 ppt to 500 ppt. Furthermore, within the range of 0.5ppt to 20ppt, no odor peculiar to (Z, Z) -4,7-tridecadienal is felt, and most panelists feel a natural sugary sweetness. evaluated.

(Example 10) Sweetness improvement of sucralose-containing beverage by (Z, Z) -4,7-tridecadienal 0.15 g of citric acid, 0.02 g of trisodium citrate, 0.008 g of sucralose, lemon flavor (Hasegawa fragrance) After mixing 0.1 g), water was added to make a total volume of 100 mL. A sucralose-containing beverage to which (Z, Z) -4,7-tridecadienal was added at a concentration shown in Table 10 below as a taste improving agent (sweetness improving agent) of the present invention was obtained.
Flavor Comparison Table 10 below shows the flavor comparison evaluation of the sucralose-containing beverage with and without the addition of the product of the present invention by 10 panelists.

  As shown in Table 10, the sucralose-containing beverage without (Z, Z) -4,7-tridecadienal has a unique and unnatural sweetness, and the taste after taste is unfavorable, but (Z, Z) Sucralose-containing beverages to which -4,7-tridecadienal is added in an amount of 0.02 ppt to 10 ppb have an effect of improving sweetness, and the odor peculiar to (Z, Z) -4,7-tridecadienal is not so much I couldn't feel it strongly. The range in which the sweetness was improved relatively well and the odor peculiar to (Z, Z) -4,7-tridecadienal was hardly felt was 0.1 ppt to 500 ppt. Furthermore, within the range of 0.5ppt to 20ppt, no odor peculiar to (Z, Z) -4,7-tridecadienal is felt, and most panelists feel a natural sugary sweetness. evaluated.

(Example 11) Sweetness improvement of acesulfame K-containing beverage by (Z, Z) -4,7-tridecadienal 0.15 g of citric acid, 0.02 g of trisodium citrate, 0.026 g of acesulfame K, lemon flavor (Hasegawa Fragrance Co., Ltd.) After mixing 0.1 g, water was added to make the total volume 100 mL. An acesulfame K-containing beverage to which (Z, Z) -4,7-tridecadienal was added at a concentration shown in Table 10 below as a taste improving agent (sweetness improving agent) of the present invention was obtained.
Flavor comparison Table 11 below shows the flavor comparison evaluation of the acesulfame K-containing beverage with and without the addition of the product of the present invention by 10 panelists.

  As shown in Table 11, the beverage containing acesulfame K without addition of (Z, Z) -4,7-tridecadienal has a unique and unnatural sweetness and feels unpleasant aftertaste. ) Acesulfame K-containing beverage added with 0.02ppt to 10ppb of -4,7-tridecadienal has an effect of improving sweetness and has an odor peculiar to (Z, Z) -4,7-tridecadienal Did not feel so strong. The range in which the sweetness was improved relatively well and the odor peculiar to (Z, Z) -4,7-tridecadienal was hardly felt was 0.1 ppt to 500 ppt. Furthermore, within the range of 0.5ppt to 20ppt, no odor peculiar to (Z, Z) -4,7-tridecadienal is felt, and most panelists feel a natural sugary sweetness. evaluated.

Claims (6)

Following formula (1)

[ Wherein , ... Represents a single bond or a double bond, and a wavy line represents a configuration of cis or trans configuration]. . The taste improving agent for high-intensity sweeteners according to claim 1, wherein the unsaturated aldehyde of the formula (1) is 4,7-tridecadienal. The taste improving agent for high-intensity sweeteners according to claim 1, wherein the unsaturated aldehyde of the formula (1) is 2,4,7-tridecatrienal. A taste improver composition for high-intensity sweeteners, comprising 0.02 ppb to 10 ppm of the taste improver for high-intensity sweeteners according to any one of claims 1 to 3. A high taste sweetener taste improver according to any one of claims 1 to 3 is contained in a food or drink containing a high sweetness sweetener in an amount of 0.02 ppt to 10 ppb. A method for improving the taste of sweeteners. The taste improver of high sweetness sweetener characterized by containing 0.02 ppt to 10 ppb of the taste improving agent for high sweetness sweetener according to any one of claims 1 to 3. Food and drink.