JP2013143930A - Bitter taste and astringent taste inhibitor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a bitter taste and/or astringent taste inhibitor capable of effectively inhibiting the bitter taste and/or astringent taste without imparting an off-taste and a nasty smell.SOLUTION: Provided is a bitter taste and/or astringent taste inhibitor consisting of 4,7-tridecadienal and/or 2,4,7-tridecatrienal, which is used by adding to food and drink having a bitter taste and/or an astringent taste.

Description

  The present invention relates to a bitterness / astringency inhibitor having an effect of suppressing the bitterness / astringency of food and drink, a bitterness / astringency inhibitor composition containing the same, a food / beverage product, and a method for suppressing bitterness / astringency. More specifically, bitterness / astringency inhibitors comprising unsaturated aldehydes composed of 4,7-tridecadienal and / or 2,4,7-tridecatrienal and bitterness / astringency containing the same The present invention relates to a method for suppressing bitterness / astringency by adding an inhibitor composition and food / beverage products, and the bitterness / astringency inhibitors to a food / beverage product having a bitterness / astringency.

  Bitter taste is one of the five basic tastes (acidity, sweetness, salty taste, bitter taste, umami), and is considered as a taste that functions as a signal of harmful substances that should be avoided by human beings from the beginning. As a result, humans are more sensitive to bitterness and feel less bitter than other tastes (threshold is low), but in fact, flavorful foods and drinks have some bitterness. In many cases, bitterness is considered to be an element of taste that must be intrigued. As a food and drink having a bitter taste, for example, a fruit such as grapefruit containing naringin, a bitter substance, a vegetable such as bittern, a roasted extract such as coffee, a tea beverage or beer, or a fragrance substance, Chemical substances such as peptides and protein hydrolysates are known to have a bitter taste.

On the other hand, astringency is also called astringent taste, and is often caused by catechins contained in tea beverages and red wines, chlorogenic acid contained in coffee, etc., and polyphenols such as tannins in strawberries, many of which are bitter. However, these polyphenols are attracting attention as health foods and drinks because of their antioxidant ability and active oxygen scavenging ability.

In addition, the taste that is considered to be a mixture of strong bitterness and astringency due to acupuncture contained in spinach, bamboo shoots, wild plants, etc. is an umami substance such as oxalic acid compounds and homogentisic acid contained in these foods It is said to be brought about by. When cooking foods containing a lot of ak, it is generally necessary to reduce these to the appropriate amount (without kneading), excluding these taste substances. Therefore, there is a need in the food field for a method that can easily remove the taste without losing the taste of the food.

  In this way, bitterness and astringency are useful elements for foods and drinks, but if the bitterness or astringency is too strong, an unpleasant taste remains, and it is avoided from the general public, especially infants, children, sick people, elderly people, etc. It tends to be. Therefore, it is expected to provide a bitter and / or astringent-containing food / beverage that is easy to eat and drink while suppressing such excessive bitterness / astringency, and to promote the widespread use of food / beverage that everyone likes. ing.

Examples of conventional techniques for alleviating the bitterness and astringency of food and drink include, for example, a bitterness inhibitor (Patent Document 1) containing one or more selected from poly-γ-glutamic acid, a decomposition product thereof, and salts thereof as an active ingredient, Bitterness and / or astringency characterized by consisting of a coffee bean hydrolyzate obtained by hydrolyzing coffee beans with an enzyme, removing insoluble matters, and then purifying the hydrolyzate by contacting with an adsorbent An inhibitor (Patent Document 2), a method of blending a sweet potato-derived extract with a food and drink having a bitter and astringent taste (Patent Document 3), a bitter and astringent inhibitor (Patent Document 4) containing cyclofructan as an active ingredient, cyclodextrin and A bitter and astringent taste inhibitor for polyphenol-containing objects, characterized in that it contains cyclofructan and the weight ratio of cyclofructan to cyclodextrin is 0.01 to 10 (patent document ), A bitterness inhibitor comprising the phosphatidic acid (PA) and phosphatidylinositol (PI), when the mass ratio in the bitterness inhibitor PA and PI was _{M PA} and _{M PI respectively, M} PA / (M Bitter taste inhibitor (Patent Document 6) in which _PA + M _PI ) is in the range of 0.55 to 0.82, bitter taste inhibitor (Patent Document 7) consisting of fruit juice of fruit fruits from which low molecular sugars have been removed, and average molecular weight Is a bitterness inhibitor (Patent Document 8), which contains a mammal-derived collagen peptide as an active ingredient, and contains a whey peptide having an average molecular weight of 550 to 5000 as an active ingredient. Patent Document 9), Bitter / Astringent Inhibitor (Patent Document 10) containing Grapefruit Cold Press Oil as an active ingredient, Bitter taste containing drink containing phthalides as an active ingredient Such goods bitter improving agent (Patent Document 11) have been proposed.

  However, when a polymer substance as described in Patent Document 1 is added to a food or drink, the viscosity of the food or drink increases, and there is a risk that the throat or texture of the food or drink will change. Ingredients used in the technology described in 9 increase the taste of the ingredients themselves, so that the original taste of foods and drinks to which the bitterness and / or astringency inhibitors comprising these ingredients are added may also change. There is sex. In addition, in the techniques described in Patent Documents 10 and 11, aroma substances used as bitter and / or astringent taste inhibitors may change the original odor of food and drink.

  Therefore, a bitterness and / or astringency suppressing agent and a bitterness and / or astringency suppressing agent that suppress bitterness and astringency are added without changing the original taste, smell, throat texture and texture of the food and drink. Therefore, it has been desired to develop foods and drinks in which bitterness and / or astringency is suppressed.

  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 12), a method of imparting a flavor reminiscent of chickens by using 4-cisdecenal and 2,4,7-tridecatrienal (patent) Document 13), a perfume application (Patent Document 14) 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 for imparting a flavor reminiscent of chickens (Patent Document 12), use as a cosmetic fragrance (Patent Document 15), and use of a fragrance as a fish-flavoring flavor improver (Patent Document 14) have been proposed.

  However, in Non-Patent Documents 1 to 4 and Patent Documents 12 to 15, food and drink are obtained by adding a trace amount of 2,4,7-tridecatrienal or 4,7-tridecadienal to food and drink. There is no description or suggestion that the bitterness and / or astringency can be suppressed.

WO2000 / 21390 international pamphlet JP 2001-321116 A JP 2002-34471 A JP 2004-337132 A JP 2006-67895 A JP 2007-129936 A JP 2010-268707 A JP 2011-15632 A JP 2011-15633 A JP 2011-72242 A Japanese Patent No. 4562209 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 food and drink, and without adding any taste or odor to the food or drink, while maintaining the throat and texture of the food and drink, An object of the present invention is to provide a bitterness and / or astringency inhibitor capable of suppressing astringency.

As a result of intensive studies to solve the above problems, the present inventors have found that a very small amount of 2,4,7-tridecatrienal and / or 4,7- It has been found that by adding Tridecadienal, bitterness and astringency can be suppressed while maintaining the throat and texture of food and drink without adding unnecessary taste and flavor to these food and drink. The present invention has been completed. Thus, the present invention provides the following.
(A)
Following formula (1)
[In the formula, ... Indicates a single bond or a double bond, and a wavy line indicates a cis or trans configuration,] Bitterness and / or astringency suppression of a food or drink comprising the unsaturated aldehyde. Agent.
(B) The bitterness and / or astringency inhibitor according to (a), wherein the unsaturated aldehyde of the formula (1) is 4,7-tridecadienal.
(C) The bitterness and / or astringency inhibitor according to (a), wherein the unsaturated aldehyde of the formula (1) is 2,4,7-tridecatrienal.
(D) A bitterness and / or astringency inhibitor composition comprising 0.1 ppt to 10 ppm of the bitterness and / or astringency inhibitor according to any one of (a) to (c).
(E) The bitterness and / or astringency inhibitor according to any one of (a) to (c) is contained in a food or drink having a bitterness and / or astringency in a range of 0.0001 ppt to 10 ppb, A method for suppressing bitterness and / or astringency.
(F) Beverage and / or astringency-suppressing agent according to any one of (a) to (c), containing 0.0001 ppt to 10 ppb Goods.
(G) The following formula (1)
[In the formula, ... Represents a single bond or a double bond, and a wavy line represents a cis or trans configuration.] An unsaturated aldehyde represented by a bitterness and / or astringency The said food-drink characterized by containing 0.0001ppt-10ppb.
(H) The said food / beverage products which made the food / beverage products which have a bitter taste and / or astringency contain 0.0001ppt-10ppb of 4,7-tridecadienal.
(I) The said food / beverage product which made 0.004ppt-10ppb contain the 2,4,7- tridecatrienal in the food / beverage product which has a bitter taste and / or astringency.
(J) The food / beverage product having bitterness and / or astringency is at least one selected from tea products, coffee products, and flavor-containing food / beverage products imparting bitterness and / or astringency (g) ) -Food and beverage according to any one of (i). Here, the tea products include all kinds of beverages and foods produced using tea. The coffee products include all kinds of beverages and foods produced using coffee.

  Although 2,4,7-tridecatrienal and 4,7-tridecadienal used in the present invention have been found from natural products, and their use as chicken-like flavors has been proposed. It has not yet been reported to have a bitter and / or astringency-inhibiting action, and even more, by adding a trace amount to foods and drinks having a bitter and / or astringency, the bitterness and / or astringency is suppressed. The content has never been described or suggested in the literature.

  In the present invention, “bitter taste suppression” means that the bitter taste felt on the tongue is reduced (or the bitter taste is reduced) when eating a food or drink having a bitter taste. As described above, bitterness is one of the five basic tastes (acidity, sweetness, salty taste, bitterness, umami), and bitterness substances (for example, caffeine, naringin, quinine, momordesin) contained in food and drink. , Catechins, etc.) is a unique taste perceived by stimulating bitter taste receptors in the taste bud cells of the tongue.

  In the present invention, the presence or absence of bitterness suppression is evaluated by a sensory test in which an inspector (panelist) actually examines the taste when eating food and drink with the tongue, and the bitterness is digitized (numerized). It can also be evaluated by instrument analysis using a sensor or the like.

  Moreover, in this invention, astringency suppression means that the astringency which the food / beverage products which have astringency show (or the said astringency is reduced) reduces. In addition, astringency is considered to be a sensation obtained by binding a component such as tannin to a protein of the tongue or oral mucosa and denaturing it. In other words, astringent taste is considered to be a sensation close to the pain and tactile sensation caused by this protein denaturation rather than a kind of taste. However, there is a theory that astringency and bitterness cannot be distinguished physiologically, and there is a theory that they have the same sensation, and substances that actually have astringency (such as catechins, chlorogenic acids, and tannins) also have bitterness. Therefore, in the present invention, the bitterness and astringency are collectively represented by the expression bitterness and / or astringency.

  In the present invention, the presence or absence of astringency control is evaluated by a sensory test in which the taste when the inspector (panelist) eats food or drink is actually examined with the tongue, and the astringency is digitized (digitized). It can also be evaluated by instrument analysis using a taste sensor or the like.

  According to the bitterness and / or astringency suppressing agent of the present invention, and the inhibitor composition containing the inhibitor, without imparting unnecessary taste and aroma to the food or drink having bitterness and / or astringency. Bitterness and / or astringency can be reduced while retaining the throat and texture of food and drink. In addition, to food and drink having a bitter taste and / or astringency, not only food and drink having a bitter taste and / or astringency but also other components (bitter taste, astringency etc.) are added, Foods and drinks to which bitterness and / or astringency are imparted are also included.

  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 effect of suppressing bitterness and astringency, (E, Z, Z) -2,4,7-tridecatrienal, which is found from (1), is particularly preferred.

  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 effect of suppressing bitterness and astringency.

  (E, Z, Z) -2,4,7-tridecatrienal can be synthesized by a method according to known literature. For example, after bromination using 2-octyn-1-ol as a starting material, (E It can be synthesized by coupling with a Grignard derivative of 2-penten-4-in-1-ol and a copper catalyst, partially hydrogenating with a Lindlar catalyst, and then oxidizing 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, 2-octin-1-ol is first partially hydrogenated with a Lindlar catalyst and then 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 bitter and / or astringent taste inhibitor used in the present invention, that is, the unsaturated aldehyde represented by the formula (1) to the food or drink is generally that of the inhibitor contained in the food or drink. The amount is such that the concentration is 0.0001 ppt to 10 ppb. More specifically, the bitterness and / or astringency suppressant may vary depending on the type of geometric isomers of 2,4,7-tridecatrienal and 4,7-tridecadienal, or the type of food or drink. Is (E, Z, Z) -2,4,7-tridecatrienal and (Z, Z) -4,7-tridecadienal, for foods and drinks having a bitter and / or astringent taste The total amount thereof can be exemplified, for example, within the range of 0.0001 ppt to 10 ppb, preferably 0.001 ppt to 500 ppt, more preferably 0.01 ppt to 20 ppt, and still more preferably 0.1 ppt to 2 ppt.

  Further, the bitterness and / or astringency suppressing agent, that is, the unsaturated aldehyde represented by the formula (1) is converted into other geometric isomers, that is, (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 If so, the total amount of the food and drink having a bitter taste and / or astringency is, for example, 0.001 ppt to 10 ppb, preferably 0.01 ppt to 1 ppb, more preferably 0.1 ppt to 100 ppt, and even more preferably. Can be exemplified within the range of 1 ppt to 20 ppt. With the above blending ratio, the bitterness and / or astringency of the food / beverage product having a bitterness and / or astringency is alleviated and the bitterness / astringency is improved mildly.

  When the content of the unsaturated aldehyde represented by the above formula (1) exceeds 10 ppb, the odor of these aldehydes is imparted to the food or drink. Therefore, in the case of a food or drink that does not require these fragrances, it is preferable to suppress the addition amount to less than 10 ppb. 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.

  In addition, when the content of the bitterness and / or astringency suppressing agent of the present invention for food or drink, that is, the unsaturated aldehyde represented by the formula (1) is less than 0.0001 ppt, the bitterness and / or astringency suppressing effect is obtained. There is a risk that it will not be fully utilized. The bitterness and / or astringency suppressing agent of the present invention is any of (E, Z, Z) -2,4,7-tridecatrienal and (Z, Z) -4,7-tridecadienal. In the case where it is composed only of geometrical isomers not included, if the content of the bitterness and / or astringency suppressing agent of the present invention is less than 0.001 ppt, the bitterness and / or astringency suppressing effect may not be sufficiently exhibited. is there.

The unsaturated aldehyde which is the bitterness and / or astringency inhibitor of the present invention can be used as it is by adding it to foods and drinks, but these unsaturated aldehydes are oil-soluble, and as they are, they are dispersible in water. In addition, since it is difficult to add a trace amount to foods and drinks from the viewpoint of measurement and dilution, a very small amount of these unsaturated aldehydes is blended to obtain a bitterness and / or astringency inhibitor composition. A method of blending with food or 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 ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, propylene glycol and the like. 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.

  Moreover, 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 blending amount of the unsaturated aldehyde of the present invention in the above preparations is considered considering that these preparations are generally added to about 0.1% (about 0.01% to 1%) to food and drink. In the preparation, about 0.1 ppt to 10 ppm, that is, (E, Z, Z) -2,4,7-tridecatrienal and (Z, Z) -4,7-tridecadienal, bitterness In the astringency suppressing agent composition, for example, 0.1 ppt to 10 ppm, preferably 1 ppt to 500 ppb, more preferably 10 ppt to 20 ppb, and still more preferably 0.1 ppb to 2 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, 1 ppt to 10 ppm, preferably in the bitterness and / or astringency inhibitor composition Can be exemplified within the range of 10 ppt to 1 ppm, more preferably 0.1 ppb to 100 ppb, and still more preferably 1 ppb to 20 ppb.

  Although the addition amount to the food / beverage products of the bitterness and / or astringency inhibitor composition of this invention changes also with kinds of food / beverage products, it is 0.01% -1 with respect to the food / beverage products which have a bitter taste and / or astringency. % 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 to.

  The bitterness and / or astringency suppressing agent of the present invention, or the bitterness and / or astringency suppressing food / beverage product containing the bitterness and / or astringency suppressing composition is not particularly limited. Citrus fruit juice (fruit juice, grapefruit, orange, lemon, etc.), juice drinks, soft drinks with fruit juice, citrus fruit drinks, fruit drinks with fruits, tomatoes, peppers, celery, cucumbers, cucumbers, carrots, potatoes, alparagus, bracken, Vegetables such as springs, vegetable-based beverages and vegetable soups containing these vegetables; coffee, cocoa, green tea, tea, oolong tea, soft drinks, wine, beer and other beverages; beverages containing herbal medicines and herbs; powdered beverages, concentrated beverages , Sports drinks, nutrition drinks, alcoholic drinks, etc .; bread, macaroni, spaghetti, noodles, cake mix Flour products such as fried rice flour, bread crumbs, gyoza skin; seasonings such as sauces, soy sauce, miso, tomato processed seasonings, mirin, vinegar, chili, curry powder, spice mix, umami seasoning; tofu, soy milk Soy foods such as creams, dressings, mayonnaise, margarine and other emulsified foods; processed meat products such as meat or processed foods, canned meat paste, ham, chicken nuggets, and meat sausages; fish meat, surimi, fish eggs, canned fish , Fish ham, fish sausage, marine products, marine delicacies, marine dried foods, seafood processed foods such as Tsukudani; nuts such as peanuts, cashew nuts, pecan nuts, macadamia nuts, walnuts; fermented foods such as natto; pickles; Dairy products such as cheese, milk, processed milk, skim milk powder, milk drinks, yogurt; caramel, candy Chewing gum, chocolate, confectionery of cookies, biscuits, cakes, pies, snacks, crackers, Japanese sweets, rice crackers, beans confectionery, and desserts confectionery; baby food, sprinkled, mention may be made of a commercially available foods such as Green Tea over Rice glue. Of these, so-called tea products such as tea extracts and tea beverages such as green tea, black tea, and oolong tea, and so-called coffee products such as coffee extract and coffee beverages are particularly preferable.

  A food or drink containing bitterness and / or astringency is given a bitterness and / or astringency by addition of a bitterness and / or astringency having a bitter taste in addition to a food or drink having a bitter taste and / or astringency. It may be a food or drink.

  Examples of flavors (bitterings and / or astringents) used for foods and beverages having bitterness and / or astringency that impart bitterness and / or astringency to foods and beverages include, for example, catechins (epicatechin (EC)) , Epicatechin gallate (ECg), epigallocatechin (EGC), epigallocatechin gallate (EGCg, etc.), caffeine, gallic acid, tyrosol, amino acids (arginine, leucine, isoleucine, tyrosine, prolyl leucine, phenylalanine, etc. ), Anthocyanidin, quercetin, saponin, α-G rutin, naringin, limonin, α-G hesperidin, chlorogenic acid, magnesium chloride, calcium chloride, magnesium sulfate, various basic drugs (aloenin, alkaloids, promethazine, propranolol, berberyl , Chlorpromazine, chlorpheniramine, papaverine, thiamine, quinine, etc.) and inorganic acid salts (hydrochloride, nitrate, sulfate, etc.) and organic acid salts (acetate, citrate, carbonate, maleate, etc.) Used as a bitter and astringent ingredient, surfactant, etc. derived from Auren, assembly, Keihi, Kujin, yellowfin, Kouka, Daio, Ogon, Oobak, Gymnema, Logai, Ginkgo, Chlorella, Natsume etc. Menthol, linalool, phenylethyl alcohol, ethyl propionate, geraniol, linalyl acetate, benzyl acetate, etc. used as a perfume, such as sodium alkyl sulfate and sodium monoalkyl phosphate, methyl paraben, propyl paraben used as a bactericidal agent, etc. Chiruparaben like, such as lactic acid and sodium lactate used as such a humectant, such as 8-acetylated sucrose and Purushin used as such as alcohol-modified agents and aluminum lactate used as such astringents.

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

(Example 1) Bitterness suppression of green tea beverage (strongly bitter type) by (Z, Z) -4,7-tridecadienal Chinese steamed green tea (No. 2 tea) 120 g to 70 ° C. hot water 5000 g (ascorbic acid) The mixture was extracted for 5 minutes with occasional stirring, and solid-liquid separation was performed with a flannel filter cloth to obtain 4500 g (Bx 0.7 °) of the extract. To this extract, 0.04 g of tannase (manufactured by Kikkoman; 5000 u / g) was added and left at 40 ° C. for 1 hour to decompose gallate catechin into non-gallate catechin (gallate catechin has strong astringency After non-gallate catechins have a strong bitter taste, the enzyme is inactivated by heating at 90 ° C. for 1 minute, cooled to 20 ° C., and Bx 0.6 ° with ion-exchanged water (about 2 times the normal drinking concentration). To obtain a green tea extract of strong bitterness type. A green tea beverage was obtained by adding (Z, Z) -4,7-tridecadienal to the concentration shown in Table 1 below as a bitterness inhibitor of the present invention.
Sensory evaluation is performed by 10 panelists, and is attached to each beverage. A: Strong bitterness, hard to drink (no difference from no addition), B: Slightly strong bitterness, slightly hard to drink (slightly improved compared to no addition) C: bitterness is slightly worrisome (it is considerably improved compared to no addition), N: bitterness is relaxed and mild bitterness, X: bitterness is relaxed, aldehyde It was chosen whether it falls under the odor that makes me feel like a keen. The aldehyde-like odor is a peculiar odor common to aldehydes in general, and means an irritating odor that makes an image of deteriorated oils, soaps, metals, dokudami, and the like. In addition, for the flavor determination, the effect was compared between the concentrations of the bitterness inhibitor, and one point having the best bitterness quality was selected. The results are shown in Table 1.

  As shown in Table 1, green tea beverages without (Z, Z) -4,7-tridecadienal have a strong bitter taste and are difficult to drink, but (Z, Z) -4,7-tridecadienal. In the green tea beverage added with 0.0001ppt to 10ppb, the bitterness-inhibiting effect was recognized, and the odor peculiar to (Z, Z) -4,7-tridecadienal was not felt so strong. Moreover, the range which bitterness was suppressed comparatively favorable and the odor peculiar to (Z, Z) -4,7-tridecadienal was hardly felt was 0.001ppt-500ppt. Furthermore, within the range of 0.01 ppt to 20 ppt, the odor peculiar to (Z, Z) -4,7-tridecadienal is not felt at all, and most of the panelists have mild bitterness with alleviated bitterness. Rated it.

(Example 2) (E, Z, Z) -2,4,7-Tridecatrienal bitterness suppression of green tea beverage (bitter taste type) (Z, Z) -4,7-Trideca in Example 1 Beverage preparation and sensory evaluation were carried out in exactly the same manner as in Example 1, except that dienal was replaced with (E, Z, Z) -2,4,7-tridecatrienal. The results are shown in Table 2.

  As shown in Table 2, green tea beverages without (E, Z, Z) -2,4,7-tridecatrienal have a strong bitter taste and are difficult to drink, but (E, Z, Z) -2,4 , 7-tridecatrienal added with 0.0001ppt to 10ppb green tea beverage has a bitter-inhibiting effect, and the odor peculiar to (E, Z, Z) -4,7-tridecatrienal feels so strong I couldn't. Moreover, the range in which bitterness was suppressed comparatively well and the odor peculiar to (E, Z, Z) -2,4,7-tridecatrienal was hardly felt was 0.001 to 500 ppt. Furthermore, within the range of 0.01 ppt to 20 ppt, the odor peculiar to (E, Z, Z) -2,4,7-tridecatrienal is not felt at all, and most panelists have mild taste and mildness. It was evaluated that it had a bitter taste.

(Example 3) Bitterness suppression of green tea beverage (strong bitter type) by (E, Z) -4,7-tridecadienal (Z, Z) -4,7-tridecadienal in Example 1 Beverage preparation and sensory evaluation were performed in exactly the same manner as in Example 1 except that (E, Z) -4,7-tridecadinal was used. The results are shown in Table 3.

  As shown in Table 3, green tea beverages without (E, Z) -4,7-tridecadienal have a strong bitter taste and are difficult to drink, but (E, Z) -4,7-tridecadienal In the green tea beverage added with 0.001ppt to 10ppb, an effect of suppressing bitterness was recognized, and the odor peculiar to (E, Z) -4,7-tridecadienal was not felt so strong. Further, the range in which the bitterness was suppressed relatively well and the odor peculiar to (E, Z) -4,7-tridecadienal was hardly felt was 0.01 ppt to 1 ppb. Furthermore, within the range of 0.1 ppt to 100 ppt, the odor peculiar to (E, Z) -4,7-tridecadienal is not felt at all, and most of the panelists have mild bitterness with alleviated bitterness. Rated it.

(Example 4) (Z, E) -4,7-tridecadienal bitterness suppression of green tea beverage (bitter taste type) (Z, Z) -4,7-tridecadienal in Example 1 Beverage preparation and sensory evaluation were performed in the same manner as in Example 1 except that (Z, E) -4,7-tridecadienal was used. The results are shown in Table 4.

  As shown in Table 4, green tea beverages without (Z, E) -4,7-tridecadienal have a strong bitter taste and are difficult to drink, but (Z, E) -4,7-tridecadienal In the green tea beverage added with 0.001ppt to 10ppb, an effect of suppressing bitterness was recognized, and the odor peculiar to (Z, E) -4,7-tridecadienal was not felt so strong. Further, the range in which the bitterness was suppressed relatively well and the odor peculiar to (Z, E) -4,7-tridecadienal was hardly felt was 0.01 ppt to 10 ppb. Furthermore, within the range of 0.1 ppt to 100 ppt, the odor peculiar to (Z, E) -4,7-tridecadienal is not felt at all, and most panelists have a mild bitterness with a reduced bitterness. Rated it.

(Example 5) (E, E) -4,7-Tridecadienal Bitterness control of green tea beverage (type with strong bitterness) (Z, Z) -4,7-Tridecadienal in Example 1 Beverage preparation and sensory evaluation were performed in the same manner as in Example 1 except that (E, E) -4,7-tridecadienal was used. The results are shown in Table 5.

  As shown in Table 5, green tea beverages without (E, E) -4,7-tridecadienal have a strong bitter taste and are difficult to drink, but (E, E) -4,7-tridecadienal In the green tea beverage added with 0.001ppt to 10ppb, the bitterness-inhibiting effect was recognized, and the odor peculiar to (E, E) -4,7-tridecadienal was not felt so strong. Moreover, the range in which bitterness was suppressed comparatively well and the odor peculiar to (E, E) -4,7-tridecadienal was hardly felt was 0.01 ppt to 1 ppb. Furthermore, within the range of 0.1 ppt to 100 ppt, the odor peculiar to (E, E) -4,7-tridecadienal is not felt at all, and most of the panelists have mild bitterness with alleviated bitterness. Rated it.

(Example 6) (E, E, Z) -2,4,7-Tridecatrienal suppresses bitterness of green tea beverage (bitter taste type) (Z, Z) -4,7-Trideca in Example 1 Beverage preparation and sensory evaluation were carried out in exactly the same manner as in Example 1, except that dienal was replaced with (E, E, Z) -2,4,7-tridecatrienal. The results are shown in Table 6.

  As shown in Table 6, green tea beverages without (E, E, Z) -2,4,7-tridecatrienal have a strong bitter taste and are difficult to drink, but (E, E, Z) -2,4 , 7-tridecatrienal added with 0.001ppt to 10ppb has a bitter taste suppressing effect, and (E, E, Z) -2,4,7-tridecatrienal has a particular odor I couldn't feel it strongly. Further, the range in which the bitterness was suppressed relatively well and the odor peculiar to (E, E, Z) -2,4,7-tridecatrienal was hardly felt was 0.01 ppt to 1 ppb. Furthermore, within the range of 0.1 ppt to 100 ppt, the odor peculiar to (E, E, Z) -2,4,7-tridecatrienal is not felt at all, and most panelists have mild taste and mildness. It was evaluated that it had a bitter taste.

Example 7 (Z, Z) -4,7-Trideca in Example 1 (Z, Z) -4,7-Trideca (E, Z, E) -2,4,7-Tridecatrienal Beverage preparation and sensory evaluation were performed in exactly the same manner as in Example 1, except that dienal was replaced with (E, Z, E) -2,4,7-tridecatrienal. The results are shown in Table 7.

  As shown in Table 7, green tea beverages without (E, Z, E) -2,4,7-tridecatrienal have strong bitterness and are difficult to drink, but (E, Z, E) -2,4 , 7-tridecatrienal added with 0.001ppt to 10ppb has a bitter taste-inhibiting effect, and (E, Z, E) -2,4,7-tridecatrienal has a particular odor I couldn't feel it strongly. Moreover, the range in which bitterness was suppressed comparatively well and the odor peculiar to (E, Z, E) -2,4,7-tridecatrienal was hardly felt was 0.01 ppt to 1 ppb. Furthermore, within the range of 0.1 ppt to 100 ppt, the odor peculiar to (E, Z, E) -2,4,7-tridecatrienal is not felt at all, and most panelists have mild taste and mildness. It was evaluated that it had a bitter taste.

(Example 8) (Z, Z) -4,7-Trideca in Example 1 of bitterness suppression of green tea beverage (bitter taste type) by (E, E, E) -2,4,7-Tridecatrienal Beverage preparation and sensory evaluation were carried out in exactly the same manner as in Example 1, except that dienal was replaced with (E, E, E) -2,4,7-tridecatrienal. The results are shown in Table 8.

  As shown in Table 8, green tea beverages without (E, E, E) -2,4,7-tridecatrienal have a strong bitter taste and are difficult to drink, but (E, E, E) -2,4 , 7-tridecatrienal added with 0.001ppt to 10ppb has a bitter taste-inhibiting effect, and (E, E, E) -2,4,7-tridecatrienal has a particular odor I couldn't feel it strongly. The range in which the bitterness was suppressed relatively well and the odor peculiar to (E, E, E) -2,4,7-tridecatrienal was hardly felt was 0.01 ppt to 1 ppb. Furthermore, within the range of 0.1 ppt to 100 ppt, the odor peculiar to (E, E, E) -2,4,7-tridecatrienal is not felt at all, and most panelists have mild taste and mildness. It was evaluated that it had a bitter taste.

(Example 9) Astringency control of green tea beverage (strong astringency type) by (Z, Z) -4,7-tridecadienal To 95 g (100% by high temperature extraction) of 100 g of domestic green tea (No. 2 tea) Of hot epigallocatechin gallate is extracted). Add warm water 5000g (containing 0.03% sodium ascorbate), extract for 5 minutes with occasional stirring, solid-liquid separate with Nell filter cloth, extract 4500g (Bx 0.7 °) was obtained. This was adjusted to Bx 0.6 ° (about twice the normal drinking concentration) with ion-exchanged water to obtain a green tea extract with a strong astringency. A green tea beverage was obtained by adding (Z, Z) -4,7-tridecadienal at a concentration shown in Table 9 below as an astringency inhibitor of the present invention.
Sensory evaluation is performed by 10 panelists, and each drink is attached to each beverage. A: Strong astringency and difficult to drink (no difference from additive-free) B: Slightly strong astringency and slightly difficult to drink (slightly compared to additive-free) C: Astringency is slightly worrisome (much improved compared to the additive-free), N: Astringency is relaxed and mild astringency, X: Astringency is relaxed However, it was selected whether the odor like an aldehyde-like keen was concerned. The aldehyde-like odor is a peculiar odor common to aldehydes in general, and means an irritating odor that makes an image of deteriorated oils, soaps, metals, dokudami, and the like. In addition, in the flavor determination, the effect was compared between the concentrations of the astringency suppressing agent, and one concentration having the best astringency was selected. The results are shown in Table 9.

  As shown in Table 9, green tea beverages without (Z, Z) -4,7-tridecadienal have strong astringency and are difficult to drink, but (Z, Z) -4,7-tridecazier. The green tea beverage added with 0.001 ppt to 10 ppb of Naral showed an astringent taste suppressing effect, and the odor peculiar to (Z, Z) -4,7-tridecadienal was not felt so strong. Moreover, the range in which astringency is suppressed comparatively well and the odor peculiar to (Z, Z) -4,7-tridecadienal is hardly felt was 0.001 to 500 ppt. Furthermore, within the range of 0.01 ppt to 20 ppt, the odor peculiar to (Z, Z) -4,7-tridecadienal is not felt at all, and most panelists have mild astringency with moderate astringency. Evaluated to be taste.

(Example 10) (Z, Z) -4,7-Tridecadienal inhibits bitterness of containerized coffee beverages Roasted coffee beans (Arabica seeds) (L value 24) are pulverized by Nippon Granulator Co., Ltd. ) (Degree of pulverization: medium fine grinding) and drip extraction with hot water at 94 ° C. to obtain a Brix 3.8 ° coffee extract (an extract of roasted coffee beans). The coffee extract was adjusted to 1.34% by weight based on the total weight of the beverage with ion-exchanged water, and (Z, Z) -4 was used as a bitterness and astringency inhibitor of the present invention. , 7-tridecadienal was added at the concentrations shown in Table 10 below. Each of these coffee beverages was filled in 190 g cans and sterilized by retort (121 ° C., 20 minutes) to obtain a sterilized container-packed coffee beverage. Next, these beverages were refrigerated at 5 ° C. for 2 weeks, and then sensory evaluation was performed.
The sensory evaluation was performed by 10 panelists, attached to each drink, A: strong bitter and astringent taste, hard to drink (no difference from no addition), B: slightly bitter taste, slightly hard to drink (slightly compared to no addition) C: bitter astringency is slightly worrisome (much improved compared to no addition), N: bitter astringency is relaxed and mild bitter astringency, X: bitter astringency is relaxed However, it was selected whether the odor like an aldehyde-like keen was concerned. The aldehyde-like odor is a peculiar odor common to aldehydes in general, and means an irritating odor that makes an image of deteriorated oils, soaps, metals, dokudami, and the like. In addition, in the flavor determination, the effect was compared between the concentrations of the bitter and astringent inhibitors, and one point having the best bitter and astringent taste quality was selected. The results are shown in Table 10.

  As shown in Table 10, the container-packed coffee beverage without (Z, Z) -4,7-tridecadienal has a strong bitter taste and is difficult to drink, but (Z, Z) -4,7-tri Container-packed coffee beverages with decadienal added at 0.0001ppt to 10ppb have a bitter and astringent taste-inhibiting effect, and the odor peculiar to (Z, Z) -4,7-tridecadienal is felt so strongly. There wasn't. Moreover, the range in which bitter astringency was suppressed comparatively well and the odor peculiar to (Z, Z) -4,7-tridecadienal was hardly felt was 0.001 ppt to 500 ppt. Furthermore, within the range of 0.01 ppt to 20 ppt, the odor peculiar to (Z, Z) -4,7-tridecadienal is not felt at all, and most of the panelists have mild bitterness with moderate bitterness. Evaluated to be taste.

Example 11 Suppression of Grapefruit Juice by (Z, Z) -4,7-Tridecadienal (Z, Z) -4,7-Trideca as a bitterness inhibitor of the present invention in commercially available grapefruit juice Grapefruit juice to which dienal was added at the concentrations shown in Table 11 below was obtained.
Sensory evaluation is performed by 10 panelists, and is attached to each beverage. A: Strong bitterness, hard to drink (no difference from no addition), B: Slightly strong bitterness, slightly hard to drink (slightly improved compared to no addition) C) bitterness is a little worrisome (it is considerably improved compared to no addition), N: bitterness is relaxed and mild bitterness, X: bitterness is relaxed, It was selected whether the odor like an aldehyde-like keen was concerned. The aldehyde-like odor is a peculiar odor common to aldehydes in general, and means an irritating odor that makes an image of deteriorated oils, soaps, metals, dokudami, and the like. In addition, for the flavor determination, the effect was compared between the concentrations of the bitterness inhibitor, and one point having the best bitterness quality was selected. The results are shown in Table 11.

  As shown in Table 11, grapefruit juice without (Z, Z) -4,7-tridecadienal has a strong bitter taste and is difficult to drink, but (Z, Z) -4,7-tridecadienal. Grapefruit juice to which was added 0.0001ppt to 10ppb was found to have an effect of suppressing bitterness, and the odor peculiar to (Z, Z) -4,7-tridecadienal was not felt so strong. Moreover, the range which bitterness was suppressed comparatively favorable and the odor peculiar to (Z, Z) -4,7-tridecadienal was hardly felt was 0.001ppt-500ppt. Furthermore, within the range of 0.01 ppt to 20 ppt, the odor peculiar to (Z, Z) -4,7-tridecadienal is not felt at all, and most of the panelists have mild bitterness with alleviated bitterness. Rated it.

(Example 12) Astringency control of red wine by (E, Z, Z) -2,4,7-tridecatrienal To commercially available red wine (Chile full-body type), as a bitterness inhibitor of the present invention (E, Z, Z) -2,4,7-tridecatrienal was added at a concentration shown in Table 12 below to obtain red wine.
Sensory evaluation is performed by 10 panelists, and each drink is attached to each beverage. A: Strong astringency and difficult to drink (no difference from additive-free) B: Slightly strong astringency and slightly difficult to drink (slightly compared to additive-free) C: Astringency is slightly worrisome (much improved compared to the additive-free), N: Astringency is relaxed and mild astringency, X: Astringency is relaxed However, it was selected whether the odor like an aldehyde-like keen was concerned. The aldehyde-like odor is a peculiar odor common to aldehydes in general, and means an irritating odor that makes an image of deteriorated oils, soaps, metals, dokudami, and the like. In addition, in the flavor determination, the effect was compared between the concentrations of the astringency suppressing agent, and one concentration having the best astringency was selected. The results are shown in Table 12.

  As shown in Table 12, red wine without (E, Z, Z) -2,4,7-tridecatrienal has a strong astringency and is difficult to drink, but (E, Z, Z) -2,4 Red wine added with 0.0001ppt to 10ppb of, 7-tridecatrienal has an astringent inhibitory effect, and the odor peculiar to (E, Z, Z) -4,7-tridecatrienal feels so strong I couldn't. Moreover, the range in which astringency was suppressed comparatively well and the odor peculiar to (E, Z, Z) -2,4,7-tridecatrienal was hardly felt was 0.001 ppt to 500 ppt. Furthermore, within the range of 0.01 ppt to 20 ppt, the odor peculiar to (E, Z, Z) -2,4,7-tridecatrienal is not felt at all, and most panelists relax the astringency, Evaluated that it had a mild astringency.

(Example 13) Bitter taste suppression of carbonated water by (Z, Z) -4,7-tridecadienal Carbonate gas was enclosed in drinking water to adjust carbonated water (gas pressure 3.0 Kg / cm ² ), Carbonated water was obtained in which (Z, Z) -4,7-tridecadienal was added at a concentration shown in Table 13 below as a bitterness inhibitor of the present invention.
The sensory evaluation was performed by 10 panelists, and attached to each carbonated water. A: Strong bitterness, difficult to drink (no difference from additive-free), B: Slightly strong bitterness, slightly difficult to drink (slightly improved compared to additive-free) C: bitterness is a little worrisome (it is considerably improved compared to no addition), N: bitterness is relaxed and mild bitterness, X: bitterness is moderated The odor of aldehyde-like keen is a concern. The aldehyde-like odor is a peculiar odor common to aldehydes in general, and means an irritating odor that makes an image of deteriorated oils, soaps, metals, dokudami, and the like. In addition, for the flavor determination, the effect was compared between the concentrations of the bitterness inhibitor, and one point having the best bitterness quality was selected. The results are shown in Table 13.

As shown in Table 13, carbonated water without additive (Z, Z) -4,7-tridecadienal has a strong bitter taste and is difficult to drink, but (Z, Z) -4,7-tridecadienal. In the carbonated water added with 0.0001 ppt to 10 ppb, the effect of suppressing bitterness was recognized, and the odor peculiar to (Z, Z) -4,7-tridecadienal was not felt so strong. Moreover, the range which bitterness was suppressed comparatively favorable and the odor peculiar to (Z, Z) -4,7-tridecadienal was hardly felt was 0.001ppt-500ppt. Furthermore, within the range of 0.01 ppt to 20 ppt, the odor peculiar to (Z, Z) -4,7-tridecadienal is not felt at all, and most of the panelists have mild bitterness with alleviated bitterness. Rated it.

Claims (10)

Following formula (1)
[In the formula, ... Indicates a single bond or a double bond, and a wavy line indicates a cis or trans configuration,] Bitterness and / or astringency suppression of a food or drink comprising the unsaturated aldehyde. Agent. The bitterness and / or astringency inhibitor according to claim 1, wherein the unsaturated aldehyde of the formula (1) is 4,7-tridecadienal. The bitterness and / or astringency inhibitor according to claim 1, wherein the unsaturated aldehyde of the formula (1) is 2,4,7-tridecatrienal. A bitterness and / or astringency inhibitor composition comprising 0.1 ppt to 10 ppm of the bitterness and / or astringency inhibitor according to any one of claims 1 to 3. The bitterness and / or astringency inhibitor according to any one of claims 1 to 3 is contained in 0.0001 ppt to 10 ppb in a food or drink having a bitterness and / or astringency. Or astringency control method. The food-drinks by which the bitterness and / or astringency were suppressed characterized by including 0.0001ppt-10ppb of the bitterness and / or astringency suppressing agent of any one of Claims 1-3. Following formula (1)
[In the formula, ... Represents a single bond or a double bond, and a wavy line represents a cis or trans configuration.] An unsaturated aldehyde represented by a bitterness and / or astringency The said food-drink characterized by containing 0.0001ppt-10ppb. The said food-drinks which made 0.007ppt-10ppb contain the foodstuffs which have a bitter taste and / or astringency for 4,7- tridecadienal. The said food / beverage products which made the food / beverage products which have a bitter taste and / or astringency taste 0.0001ppt-10ppb for 2,4,7- tridecatrienal. The food / beverage product having a bitter and / or astringent taste is at least one selected from tea products, coffee products, and flavor-containing food / beverage products that impart a bitter and / or astringent taste. Food / beverage products as described in any one of.