JP2023094865A - Milk feeling imparting composition - Google Patents

Abstract

To provide a novel milk feeling imparting composition, a method of imparting a milk feeling effect of a perfume imparting composition, and a milk feeling imparting method of food and drink.SOLUTION: A milk feeling imparting composition contains 2,6-dodecadienal as an active ingredient. The milky feeling imparting composition further exerts a taste-masking effect. A method for imparting a milk feeling effect to a flavor-imparting composition, comprises the step of adding the milk feeling imparting composition to the flavor-imparting composition. A method for imparting a milk feeling to food and drink comprises the step of adding the composition for imparting milk feeling to food and drink. A method of imparting a novel milk feeling imparting composition, and a milk feeling effect of the flavor imparting composition can be provided.SELECTED DRAWING: None

Description

TECHNICAL FIELD The present invention relates to a milky feeling-imparting composition for food and drink.

In recent years, consumer demand for various items such as food and drink (hereinafter sometimes referred to as "consumer goods") has extended to the aroma and/or flavor (hereinafter sometimes referred to as "flavor") of the consumer goods. I'm listening. In particular, milk, processed milk, dairy beverages, cheese and other dairy products (hereinafter referred to as "dairy products") have already permeated the Japanese diet as the diet has become westernized, and these flavors have been added. Processed foods with However, in order to impart the flavor of dairy products, high-quality butter and cheese cannot be added in large amounts due to the high cost burden, and even if they are added to processed foods, the flavor will decrease during the manufacturing process. Or, because of the loss, the actual situation is that there are surprisingly few opportunities for consumers to enjoy the mellow and rich flavor and richness inherent in dairy products.

So far, as an example of imparting or improving the flavor of dairy products, Patent Document 1 discloses that 12-methyltridecanal is added to dairy products such as butter, cheese, and milk at a concentration of 1 ppt to 100 ppm. It is described that the feeling, body feeling, richness, etc. can be enhanced. In Patent Document 2, by including (E)-6-nonenal at a concentration of 0.05 ppt to 2 ppb in milk, dairy products, foods and drinks containing milk or dairy products, or dairy product substitutes, It is described that it can impart or improve the rich richness and milky feeling of the milk.

JP 2010-158210 A JP 2017-18025 A

In order to sufficiently meet the demand for improving the flavor of food and drink, which is diversifying, the development of new flavor-imparting or improving agents is desired in addition to the conventionally proposed flavor-imparting or improving agents for dairy products. In this regard, the present inventors focused on the effect of imparting or improving milky feeling, and developed a new agent for imparting or improving flavor.

In view of the above, an object of the present invention is to provide a novel composition for imparting a milky sensation, a method for imparting a milky sensation effect to a flavor imparting composition, and a method for imparting a milky sensation to food and drink.

The inventors of the present invention have conducted intensive studies to solve the above problems, and as a result, found that a specific alkadienal has an excellent effect of imparting a milky feeling to food and drink. Arrived.

Thus, a brief outline of representative inventions among the inventions disclosed in the present application is as follows.

[1] A milk sensation imparting composition containing 2,6-dodecadienal as an active ingredient.
[2] The milky sensation-imparting composition according to [1], which further exhibits a taste-masking effect.
[3] A method for imparting a milk sensation effect to a flavor-imparting composition, comprising the step of adding the milk sensation-imparting composition according to [1] or [2] to a flavor-imparting composition.
[4] A method for imparting a milk sensation to a food or drink, comprising adding the composition for imparting a milk sensation according to [1] or [2] to the food or drink.

According to the present invention, it is possible to provide a novel composition for imparting a milky sensation, a method for imparting a milky sensation effect to a flavor imparting composition, and a method for imparting a milky sensation to food and drink.

An embodiment of the present invention will be described in detail below. In the present specification, "to" means a range including lower and upper limits, and "concentration (ppm, ppb, ppt)" and "%" are respectively "mass concentration" and "mass percent" unless otherwise specified. concentration”. Also, as used herein, the term "flavor" means one or more senses that can be changed by an odor (fragrance), typically including the sense of smell and/or the sense of taste. As used herein, the term “milk feeling” means a good flavor that evokes elements such as milk-derived aroma, milk fat feeling, thickness, richness, and taste in a well-balanced manner. In addition, the term "milk fat feeling" is different from the fat feeling (≒ oily feeling, fat-like, oil-like) derived from the smell of oil in cooking oil and frying oil (when it is strong, it is perceived as a deteriorated smell), it is unique to milk fat. Butter-like, coconut-like, or peach-like good fat feeling. As used herein, the term "giving a milky feeling (giving a milky feeling)" includes newly adding a milky feeling and/or enhancing the milky feeling, and as a result of giving or enhancing the milky feeling, It also contains those with improved flavor. Furthermore, the term "milk sensation impartation (providing milk sensation)" includes sensations other than olfactory and/or taste sensations as a result of imparting milk sensation, such as cold sensation, warm sensation, texture (going down the throat, hardness, It also includes those that enhance, suppress, or improve stimuli such as carbonic acid and hotness. Moreover, in this specification, the flavor of food and drink may be called flavor. In addition, as used herein, the term “addition” includes at least one of simply adding to a certain object by spraying, dropping, etc., and mixing with a certain object.

(Milk sensation imparting composition)
The milk feeling-imparting composition according to one embodiment of the present invention (hereinafter sometimes referred to as the present milk feeling-imparting composition) contains 2,6-dodecadienal (hereinafter sometimes referred to as the subject compound). ) is contained in a predetermined amount.

Since 2,6-dodecadienal has two double bonds in the molecule, the cis-trans isomers are (2E,6E)-2,6-dodecadienal, (2E,6Z)-2,6-dodecadienal, ( There are a total of four isomers of 2Z,6E)-2,6-dodecadienal and (2Z,6Z)-2,6-dodecadienal, and any of the isomers is included when referring to the present compound.

According to Japanese Patent Application Publication No. 2019-501121, it is described that (2E,6Z)-2,6-dodecadienal is used in a chicken-flavored preparation, but it is used in a milk-feeling composition. It was not known at all as a possible compound.

In this regard, the present inventors have conducted intensive research and found that the compound of the present invention is an active ingredient of a composition for imparting a milky feeling for food and drink. Then, it was found that the milky feeling-imparting composition containing a predetermined amount of the present compound can impart a milky feeling to various foods and drinks by adding it to various foods and drinks, as shown in the examples below. rice field. Furthermore, in certain foods and drinks such as low-fat milk and soy milk, by adding the present milk feeling-imparting composition, the green flavor and / or powderiness and wateriness derived from the food and drink can be improved. I found that masking is possible. Therefore, the present milk sensation-imparting composition can also be used as a taste-masking composition.

According to the studies of the inventors, dienal with a carbon number different from that of 2,6-dodecadienal and dodecadienal with a double bond position different from that of 2,6-dodecadienal not only do not exhibit the effect of imparting a milky sensation. , a different flavor (especially a green feeling) or a strong feeling of oils and fats that is completely different from the milky feeling, and it was found that it is not suitable as an active ingredient of a composition imparting a milky feeling.

The subject compounds may be derived from natural products or synthesized, and can be obtained by any method available to those skilled in the art. The obtained compound of the present invention may be further purified using means such as column chromatography or vacuum distillation, if necessary.

The present milk sensation-imparting composition may consist of the present compound only, or may contain other components such as a solvent as long as it contains the present compound in a predetermined amount. The concentration of the present compound in the present milk sensation-imparting composition can be arbitrarily determined according to the object to which the milk sensation-imparting composition is added. Examples of concentrations of the instant compounds include in the range of 100 ppb to 100%, preferably 1 ppm to 10%, more preferably 10 ppm to 1%, relative to the total weight of the milk sensitizing composition. More specifically, the lower limit is 100 ppb, 1 ppm, 10 ppm, 100 ppm, 0.1%, 1%, or 10%, and the upper limit is 100%, 10%, 1%, 0.1%, 100 ppm. , 10 ppm, 1 ppm, and any combination of these lower and upper limits, but are not limited thereto.

Flavor-imparting compositions (including flavoring compositions) or foods and drinks are examples of objects to which the present milk sensation-imparting composition is added. The details of each addition target will be described later.

The milk sensation-imparting composition itself may be added to food or drink, or may be added to one or more water-soluble/oil-soluble flavorings, emulsified flavoring compositions, arbitrary flavoring compounds, natural essential oils (e.g., Fragrance compounds described in the above-mentioned "Patent Office Gazette, Collection of Well-known and Commonly Used Techniques (Fragrance) Part II Food Flavors", "Survey on the Use of Food Flavoring Compounds in Japan", and "Synthetic Flavoring Chemistry and Product Knowledge") You may add to food-drinks in combination with 1 or more types selected from.

(Method for imparting milky effect to flavor-imparting composition)
A method for imparting a milk sensation effect to a flavor-imparting composition according to one embodiment of the present invention includes a step of adding the present milk sensation-imparting composition to a flavor-imparting composition. By adding an effective amount of the milk sensation imparting composition to the flavor imparting composition, the milk sensation effect can be imparted to the flavor imparting composition to which the composition is added. Here, the "milky feeling effect" means "the effect that the flavor-imparting composition to which the present milky feeling-imparting composition is added imparts a milky feeling to food or drink to which it is added".

In the method, the amount of the milk sensation-imparting composition to be added to the flavor-imparting composition to be added may be an effective amount in which the milk sensation effect is imparted by the present compound contained as an active ingredient. It can be arbitrarily set according to the type and form of the composition. Concrete examples of the concentration are as described above in the item "Composition for imparting milk feeling".

In the method, the method of adding the milk sensation-imparting composition to the flavor-imparting composition is not particularly limited. In addition, the time (timing) of adding the milky sensation-imparting composition to the flavor-imparting composition is not particularly limited.

(Flavor imparting composition)
The flavor imparting composition to which the milk sensation imparting composition of the present invention is added will be described below. The flavor-imparting composition exhibits an excellent flavor-imparting effect when added to various articles. The article to which the flavor imparting composition is added is not particularly limited, but other flavor imparting compositions or food and drink can be exemplified. Examples of the flavor-imparting composition include perfume compositions, flavor-improving agents, flavor-modifying agents, flavor-imparting agents, flavor-improving agents, flavor-modifying agents, taste-imparting agents, taste-improving agents, and taste-modifying agents.

The present milk sensation imparting composition can be added to a flavor imparting composition to impart a milk sensation effect. That is, the flavor imparting composition to which the present milk sensation imparting composition is added can be used as a flavor imparting composition having a milk sensation imparting effect.

In addition, the milk sensation-imparting composition can be used as a flavor-imparting composition having a milk sensation-imparting effect by forming the present milk sensation-imparting composition from the present compound and a flavor-imparting compound (for example, a flavoring compound). You can also

A specific example of the flavoring composition, which is one aspect of the flavoring composition, includes a flavoring composition for food and drink (also referred to as a flavor composition). Examples of articles to which the additive is applied include food and drink, as described above.

Flavoring compositions may contain the compounds or ingredients exemplified below. Examples thereof include various flavor compounds or flavor compositions, oil-soluble pigments, vitamins, functional substances, fish extracts, livestock meat extracts, plant extracts, yeast extracts, animal and plant proteins, and animal and plant protein decomposition products. , starch, dextrin, sugars, amino acids, nucleic acids, organic acids, solvents and the like. For example, "Patent Office Gazette, Collection of Well-known and Commonly Used Techniques (Fragrance) Part II Food Flavors, Issued on January 14, 2000", "Survey on the Usage of Food Flavoring Compounds in Japan" (2000 Welfare Science Research Report, Japan Perfumery Industry Association, published March 2001) and "Synthetic Perfume Chemistry and Product Knowledge" (published December 20, 2016, enlarged new edition, edited by the Synthetic Perfume Editorial Committee, The Chemical Daily) natural essential oils, natural fragrances, synthetic fragrances, and the like.

Specific examples of synthetic fragrance compounds include hydrocarbon compounds such as monoterpenes such as α-pinene, β-pinene, γ-terpinene, myrcene, camphene and limonene; sesquiterpenes such as valencene, cedrene, caryophyllene and longifolene; 3,5-undecatriene and the like.

Examples of alcohol compounds include saturated alcohols such as butanol, pentanol, 3-octanol, and hexanol, unsaturated alcohols such as (Z)-3-hexene-1-ol, prenol, and 2,6-nonadienol, linalool, geraniol, and citronellol. , tetrahydromyrcenol, farnesol, nerolidol, cedrol, α-terpineol, terpinen-4-ol and borneol; and aromatic alcohols such as benzyl alcohol, phenylethyl alcohol and cinnamyl alcohol.

Examples of aldehyde compounds include saturated aldehydes such as acetaldehyde, hexanal, octanal and decanal, unsaturated aldehydes such as (E)-2-hexenal and 2,4-octadienal, citronellal, hydroxycitronellal, citral, myrtenal and peryl. terpene aldehydes such as aldehydes; aromatic aldehydes such as benzaldehyde, cinnamylaldehyde, vanillin, ethyl vanillin, heliotropine, p-tolylaldehyde;

Ketone compounds include saturated and unsaturated ketones such as 2-heptanone, 2-undecanone, 1-octen-3-one, acetoin, 6-methyl-5-hepten-2-one (methylheptenone), diacetyl, 2,3 - diketones and hydroxyketones such as pentanedione, maltol, ethyl maltol, cyclotene, 2,5-dimethyl-4-hydroxy-3(2H)-furanone, terpene ketones such as carvone, menthone, nootkatone, α-ionone, β- Examples include ketones derived from terpene decomposition products such as ionone and β-damascenone, and aromatic ketones such as raspberry ketone.

Furan or ether compounds include furfuryl alcohol, furfural, rose oxide, linalool oxide, menthofuran, theaspirane, estragole, eugenol, 1,8-cineole, and the like.

Ester compounds include ethyl acetate, isoamyl acetate, octyl acetate, ethyl butyrate, ethyl isobutyrate, isoamyl butyrate, ethyl 2-methylbutyrate, ethyl isovalerate, 2-methylbutyl isobutyrate, ethyl hexanoate, allyl hexanoate, heptane Aliphatic esters such as ethyl acetate, ethyl octanoate, isoamyl isovalerate, ethyl nonanoate, terpene alcohol esters such as linalyl acetate, geranyl acetate, lavandulyl acetate, terpinyl acetate, neryl acetate, benzyl acetate, methyl salicylate, cinnamic acid aromatic esters such as methyl, cinnamyl propionate, ethyl benzoate, cinnamyl isovalerate, and ethyl 3-methyl-2-phenylglycidate;

The lactone compound includes saturated lactones such as γ-decenalactone, γ-dodecalactone, δ-decenalactone and δ-dodecalactone, and unsaturated lactones such as 7-decen-4-olide and 2-decen-5-olide. .

Acid compounds include saturated and unsaturated fatty acids such as acetic acid, butyric acid, isovaleric acid, hexanoic acid, octanoic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid.

Nitrogen-containing compounds include indole, skatole, pyridine, alkyl-substituted pyrazine, methyl anthranilate, trimethylpyrazine, and the like.

Sulfur-containing compounds include methanethiol, dimethylsulfide, dimethyldisulfide, allyl isothiocyanate, 3-methyl-2-butene-1-thiol, 3-methyl-2-butanethiol, 3-methyl-1-butanethiol, 2 -methyl-1-butanethiol, 3-mercaptohexanol, 4-mercapto-4-methyl-2-pentanone, 3-mercaptohexyl acetate, p-mentha-8-thiol-3-one and furfuryl mercaptan. .

Natural essential oils include sweet orange, bitter orange, petitgrain, lemon, bergamot, mandarin, neroli, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, hyacinth, lilac, geranium, jasmine, ylang ylang. , anise, clove, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, labdanum.

Various animal and plant extracts include herb or spice extracts, coffee, green tea, black tea, or oolong tea extracts, milk or processed milk products, and various enzymatic decomposition products thereof such as lipase or protease.

The form of the perfume composition is not particularly limited, and examples thereof include a water-soluble perfume composition, an oil-soluble perfume composition, an emulsified perfume composition, and a powdered perfume composition. Preferred examples of the form of the fragrance composition include a solution obtained by dissolving the milk sensation-imparting composition or other components in a water-soluble or oil-soluble solvent, an emulsified formulation, a powder formulation, or other solid formulations (such as solid fats). It is mentioned as.

Examples of water-soluble solvents include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, propylene glycol and dipropylene glycol. Among these, ethanol or glycerin is particularly preferable from the viewpoint of use in foods and drinks. Oil-soluble solvents include vegetable oils, animal oils, refined oils and fats (for example, processed oils and fats such as medium-chain fatty acid triglycerides, and short-chain fatty acid triglycerides such as triacetin and tripropionin), various essential oils, and triethylcitrate. A rate etc. can be illustrated.

Moreover, in order to prepare an emulsified preparation, the present flavor imparting composition can be emulsified with a water-soluble solvent and an emulsifier. The method for emulsifying the present flavor-imparting composition is not particularly limited, and various types of emulsifiers conventionally used in foods and beverages, such as fatty acid monoglycerides, fatty acid diglycerides, fatty acid triglycerides, propylene glycol fatty acid esters, Sugar fatty acid ester, polyglycerin fatty acid ester, lecithin, modified starch, sorbitan fatty acid ester, quillaya extract, gum arabic, tragacanth gum, guar gum, karaya gum, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, casein quillayasaponin, or casein A highly stable emulsified liquid can be obtained by using an emulsifier such as sodium and performing emulsification using a homomixer, a colloid mill, a rotating disc type homogenizer, a high pressure homogenizer, or the like. The amount of these emulsifiers to be used is not strictly limited, and can vary over a wide range depending on the type of emulsifier used. Parts by weight, preferably in the range of about 0.1 to about 50 parts by weight are suitable. In order to stabilize the emulsified state, the emulsified liquid contains, in addition to water, polyhydric alcohols such as glycerin, propylene glycol, sorbitol, maltitol, sucrose, glucose, trehalose, sugar solution, and reduced starch syrup. One type or a mixture of two or more types can be added.

Moreover, the emulsion thus obtained can be made into a powder formulation by drying if desired. At the time of powderization, if necessary, sugars such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, and reduced starch syrup can be added as appropriate. The amount of these agents to be used can be appropriately selected according to the desired properties of the powder formulation.

In addition to the above, the present perfume composition may contain components commonly used in perfume compositions, if necessary. For example, solvents such as water and ethanol, and perfume retention such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, hacoline, medium chain fatty acid triglyceride, medium chain fatty acid diglyceride, etc. agent.

(Method for imparting milkiness to food and drink)
A method for imparting a milk sensation to a food or drink according to an embodiment of the present invention (hereinafter referred to as the "method for imparting a milk sensation") includes a step of adding the present composition for imparting a milk sensation to a food or drink.

By adding an effective amount of the milky feeling-imparting composition to a food or drink, a milky feeling can be imparted to the food or drink to which the composition is added.

In the method, the amount of the milky feeling-imparting composition to be added to the food and drink to be added may be an effective amount that gives the milky feeling by the present compound contained as an active ingredient, and the type of food and drink to be added, It can be arbitrarily set according to the form.

As a preferable concentration of the present compound, when the object to be added is a beverage, based on the total mass of the beverage, at least 1 to 500 ppb can impart a milky feeling, and 3 to 150 ppb. can be given well. More specifically, the lower limit is 1 ppb, 3 ppb, 5 ppb, 10 ppb, 50 ppb, 100 ppb, 150 ppb, 200 ppb, or 300 ppb, and the upper limit is 500 ppb, 300 ppb, 200 ppb, 150 ppb, 100 ppb, 50 ppb, 10 ppb, 5 ppb. , Any combination of these lower and upper limits, such as, but not limited to, 3 ppb.

In addition, when the object of addition is food (excluding beverages), the preferred concentration of the compound of the present invention is within the range of 10 to 500 ppb based on the total mass of the food. Not limited.

In the method, the method of adding the milk sensation-imparting composition to the food or drink is not particularly limited. In addition, the time (timing) of adding the milky sensation-imparting composition to the food or drink is not particularly limited.

(Method for masking taste of food and drink)
A method for masking the taste of a food or drink according to an embodiment of the present invention (hereinafter referred to as "the present taste masking method") comprises a step of adding the present milk sensation imparting composition as a taste masking composition to a food or drink. include.

By adding an effective amount of the present milk feeling-imparting composition to specific food and drink such as low-fat milk and soy milk, the green flavor and / or powderiness and wateriness derived from the food and drink to which it is added (hereinafter referred to as (referred to as “taste”) can be masked.

In the method, the amount of the milk sensation-imparting composition to be added to the food or drink to be added may be an effective amount that masks the taste derived from the food or drink to be added by the present compound contained as an active ingredient. It can be arbitrarily set according to the type and form of the target food and drink.

When the subject compound is added to a beverage (low-fat milk or soy milk), the preferable concentration of the present compound is at least 5 to 150 ppb based on the total mass of the beverage, and the concentration is 50 to 100 ppb. Can better mask lower body within range. More specifically, the lower limit is any one of 5 ppb, 10 ppb, 50 ppb, and 100 ppb, and the upper limit is any one of 150 ppb, 100 ppb, 50 ppb, and 10 ppb, and any combination of these lower and upper limits can be, but are not limited to.

In the method, the method of adding the milk sensation-imparting composition to the food or drink is not particularly limited. In addition, the time (timing) of adding the milky sensation-imparting composition to the food or drink is not particularly limited.

(food and drink)
The foods and drinks to which the present composition for imparting milk sensation is added will be described below.

Examples of food and drink include various citrus flavors such as lemon, orange, grapefruit, lime, mandarin, mandarin orange, kabosu, sudachi, hassaku, iyokan, yuzu, shikuwasa, and kumquat; strawberry, blueberry, raspberry, apple, cherry, plum, and apricot. , peach, pineapple, banana, melon, mango, papaya, kiwi, pear, grape, muscat grape, kyoho grape; milky flavor such as milk, yogurt, butter; vanilla flavor; green tea, black tea, oolong tea, herbal tea, etc. various tea flavors; coffee flavor; cola flavor; cacao flavor; cocoa flavor; various mint flavors such as spearmint and peppermint; Various spices or herbal flavors such as star anise, thyme, capsicum, nutmeg, basil, marjoram, rosemary, laurel, garlic, wasabi; various nut flavors such as almonds, cashews, walnuts; wine, brandy, whiskey, rum, gin, Liqueur, sake, shochu, beer, and other alcoholic beverage flavors; onion, celery, carrot, tomato, cucumber, and other vegetable flavors; chicken, duck, pork, beef, mutton, and horse meat flavors; red meat fish, such as tuna , mackerel, sea bream, salmon, horse mackerel, freshwater fish such as ayu, trout, carp, shellfish such as turban shells, clams, short-necked clams, and freshwater clams, various crustaceans such as shrimp and crabs, and various seaweeds such as wakame and kelp. , various seafood and seaweed flavors; various grain flavors such as barley such as rice, barley, wheat and malt; Foods and beverages having one or more flavors are included. That is, it may be a food or drink that makes you feel only one of the above flavors, or it may be a food or drink that makes you feel two or more flavors, and the plurality of flavors may be the same or different. Examples of fruit flavors include those that make you feel multiple fruit flavors such as banana, peach and apple flavors (so-called mixed fruit flavors), and examples of the latter include those that make you feel citrus flavors such as lemon and milk flavors (citrus Flavored lactic acid bacteria drink, etc.), and those with mint flavor, citrus flavor, and cola flavor (mint or lemon flavored cola drink, etc.).

More specific examples of food and drink include senbei, arare rice crackers, rice cakes, rice cakes, steamed buns, uiro, red bean paste, yokan, mizu yokan, kingyoku, jelly, castella, hard candy, biscuits, crackers, potato chips, cookies, Confectionery such as pie, pudding, butter cream, custard cream, cream puff, waffle, sponge cake, donut, chocolate, chewing gum, caramel, candy, peanut paste or other pastes; bread, udon, ramen, Chinese noodles, sushi , gomoku rice, fried rice, pilaf, gyoza skin, shumai skin, okonomiyaki, takoyaki, and other breads, noodles, rice, and other grains; Pickles such as pickles and their bases for pickles; Fish such as mackerel, sardines, saury, salmon, tuna, bonito, whales, flatfish, sand eels, and sweetfish, squid such as flying squid, spear squid, crested squid, and firefly squid octopus such as common octopus and octopus, prawns such as tiger prawns, botan prawns, spiny lobsters and black tigers, crabs such as red king crabs, snow crabs, blue crabs and horse crabs, clams, clams, scallops, oysters, mussels and other shellfish, etc. seafood; canned, boiled fish, tsukudani, surimi, fish paste products (chikuwa, kamaboko, fried kamaboko, crab leg kamaboko, etc.), fried foods, tempura, and other processed seafood foods; chicken, pork, beef, mutton , Livestock meat such as horse meat; curry, stew, beef stew, hayashi rice sauce, meat sauce, mapo tofu, hamburger steak, gyoza, boiled rice, soups (corn soup, tomato soup, consommé soup, etc.), meatballs, boiled cubes, Processed foods and drinks using livestock meat such as canned meat; table salt, seasoning salt, soy sauce, powdered soy sauce, miso, powdered miso, unrefined sake, hishio, furikake, ochazuke mix, margarine, mayonnaise, dressing, vinegar, sanbaizu, Powdered sushi vinegar, Chinese noodles, tempura sauce, mentsuyu (kelp or bonito broth, etc.), sauces (chuno sauce, tomato sauce, etc.), ketchup, grilled meat sauce, curry roux, stew ingredients, soup ingredients, dashi ingredients ( kombu dashi or bonito dashi), compound seasonings, seasonings such as new mirin, mixed powders such as fried chicken powder and takoyaki powder, animal or plant-based dashi-flavored foods and beverages to which these seasonings are added Dairy products such as cheese, yogurt, and butter; Various yeasts such as brewer's yeast and baker's yeast; various microbial fermentation products such as lactic acid bacteria; fruit juices and soft drinks containing fruit such as apples, grapes, citrus fruits (grapefruit, orange, lemon, etc.), fruit juices containing fruit pulp and fruit juices; tomatoes, green peppers, celery, gourds, bitter melons, carrots, potatoes , asparagus, bracken, fern and other vegetables, vegetable drinks containing these vegetables, vegetable-containing food and drink such as vegetable soup; coffee, cocoa, green tea, black tea, oolong tea, soft drinks, cola drinks, carbonated drinks (citrus Cider with various flavors such as flavor), luxury beverages such as lactic acid beverages; beverages containing herbal medicines and herbs; cola beverages, fruit juice beverages, milk beverages, non-alcoholic beer Functional drinks such as beer-taste drinks, sports drinks, honey drinks, vitamin supplement drinks, mineral supplement drinks, nutritional drinks, nutrition drinks, lactic acid drinks; various alcoholic beverages (beer, plum wine, chuhai, etc.) flavor Non-alcoholic beverages such as alcoholic beverages; wine, shochu, awamori, refined sake, beer, chuhai, cocktail drinks, low-malt beer, fruit wine, condiments, other brewed liquor (sparkling) or liqueur (sparkling), etc. or alcoholic beverages containing these;

As described above, the food and drink to which the milk sensation-imparting composition is added is not particularly limited, but milk and alternative milk, and various beverages and Food (synonymous with dairy or dairy substitute), specifically milk, low-fat milk, soy milk, coffee with milk, tea with milk, matcha with milk, coffee with soy milk, black tea with soy milk, with soy milk Matcha, drinking yogurt, yogurt, ice cream, cream sauce, cheese, butter, cheese sauce and the like are preferred.

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to Examples. In addition, this invention is not limited to these. In the following examples, (2E,6Z)-2,6-dodecadienal will be described as an example. It was confirmed that both 6E)-2,6-dodecadienal and (2Z,6Z)-2,6-dodecadienal had similar effects at the same concentration.

[Example 1] Effect of addition to food and drink (milk) Commercially available milk (milk fat content 3.5%, non-fat milk solid content 8.3%) was prepared, and the ratio of milk: water = 40: 60 diluted. In this diluted milk, a commercially available product of (2E,6Z)-2,6-dodecadienal (hereinafter simply referred to as "2,6-dodecadienal") is diluted with ethanol as necessary, and the milk sensation imparting composition is added. As a product, 2,6-dodecadienal was added to the diluted milk so that the concentration shown in Table 1 was obtained, and milk beverages of products 1-1 to 1-13 of the present invention were prepared.

On the other hand, as a comparison target for 2,6-dodecadienal, 2,4-decadienal or a commercially available product of 2,4-dodecadienal diluted with ethanol was added to the diluted milk as necessary. The concentration of 2,4-decadienal or 2,4-dodecadienal in the mixture was added to the concentration shown in Table 1 to prepare milk drinks of comparative products 1-1 to 1-9. Then, the obtained milk beverages of the products 1-1 to 1-13 of the present invention and the comparative products 1-1 to 1-9 were sensory evaluated by 15 well-trained panelists (10 years or more of experience). rice field. In the sensory evaluation, the above diluted milk to which 2,6-dodecadienal was not added was used as control product 1, and products 1-1 to 1-13 of the present invention and comparative products 1-1 to 1-9 were used as control product 1. The panelists were asked to comment on the difference in flavor when compared, and the milkiness was evaluated by averaging the scores given by the panelists according to the following criteria.

<Evaluation criteria for milk feeling>
Significantly increased compared to Control 1: Greatly increased compared to 5-point Control 1: Slightly increased compared to 4-point Control 1: Slightly increased compared to 3-point Control 1: 2-point Control Equal to product 1 or decreased compared to control product 1: 1 point

The results of the sensory evaluation of the products 1-1 to 1-13 of the present invention and the comparative products 1-1 to 1-9 performed based on the above are compared with the following criteria, and the judgment of ◎, 〇, △, and × is made for each. ⊙ and ∘ are examples that can be suitably used as a composition imparting milk sensation, Δ are examples that can be used as a composition imparting milk sensation, and × are examples that are unsuitable as a composition imparting milk sensation.

<Judgment criteria for milk feeling>
Those with an average score of less than 2 points or with a strong flavor of the compound: ×
The average score is 2 or more and less than 3 or the flavor of the compound is slightly felt: △
Average score of 3 or more and less than 4: 〇 Average score of 4 or more: ◎

Table 1 shows the results of the sensory evaluation of the products 1-1 to 1-13 of the present invention and the comparative products 1-1 to 1-9 with respect to milk beverages.

As shown in Table 1, it was confirmed that milk beverages to which 2,6-dodecadienal was added particularly enhanced the feeling of milk fat, as well as the flavor, thickness, and richness of milk, and as a result, the feeling of milk was enhanced. .

On the other hand, as shown in Table 1, it was confirmed that 2,4-decadienal and 2,4-dodecadienal, which are compounds having different carbon numbers or positions of double bonds from 2,6-dodecadienal, do not enhance milkiness. did it. The above results demonstrate the usefulness of the milk sensation-imparting composition containing 2,6-dodecadienal as an active ingredient.

[Example 2] Effect of addition to food and drink (low-fat milk) was diluted with ethanol as necessary to obtain the milk sensation-imparting composition, and the concentration of 2,6-dodecadienal in the low-fat milk was added to the concentration shown in Table 2. -1 to 2-4 milk drinks were prepared. Then, sensory evaluation was performed by 15 well-trained panelists (with experience of 10 years or more) on the obtained milk beverages of products 2-1 to 2-4 of the present invention. In the sensory evaluation, the above commercially available low-fat milk to which 2,6-dodecadienal was not added was used as control product 2, and the products 2-1 to 2-4 of the present invention were compared with control product 2. Panellists were asked about the difference in flavor. In addition to commenting on the feeling of milk, the scores given by the panelists according to the following criteria were averaged.

<Evaluation criteria for milk feeling>
Significantly increased compared to control product 2: Greatly increased compared to 5-point control product 2: Somewhat increased compared to 4-point control product 2: Slightly increased compared to 3-point control product 2: 2-point control Equal to product 2 or decreased compared to control product 2: 1 point

The results of the sensory evaluation of the products 2-1 to 2-4 of the present invention performed based on the above are compared with the following criteria, and each of them is evaluated as ◎, ◯, △, ×, and ◎ and ◯ are the milk feeling imparting composition. An example that can be suitably used as a product, an example that can be used as a milk sensation-imparting composition with Δ, and an unsuitable example as a composition that imparts milk sensation with ×.

<Judgment criteria for milk feeling>
Those with an average score of less than 2 points or with a strong flavor of the compound: ×
The average score is 2 or more and less than 3 or the flavor of the compound is slightly felt: △
Average score of 3 or more and less than 4: 〇 Average score of 4 or more: ◎

Table 2 shows the results of sensory evaluation of products 2-1 to 2-4 of the present invention for milk beverages.

As shown in Table 2, it was confirmed that the 2,6-dodecadienal-added milk beverage has an especially enhanced feeling of milk fat, and as a result, an enhanced feeling of milk. In addition, as shown in Table 2, the milk beverages to which 2,6-dodecadienal was added were suppressed in the green flavor and wateriness derived from low-fat milk, and the taste-masking effect of 2,6-dodecadienal. was also confirmed. From the above, it can be said that 2,6-dodecadienal is excellent in improving the flavor of low-fat milk.

[Example 3] Effect of addition to food and drink (soymilk) Commercially available unadjusted soymilk (soybean solid content 8%) was diluted with ethanol if necessary, and 2,6-dodecadienal was diluted with ethanol. As the imparting composition, 2,6-dodecadienal was added to the unadjusted soymilk so that the concentrations shown in Table 3 were obtained, and soymilk beverages 3-1 to 3-8 of the present invention were prepared. Then, sensory evaluation was performed by 15 well-trained panelists (with experience of 10 years or more) on the obtained soymilk beverages of Products 3-1 to 3-8 of the present invention. In the sensory evaluation, the above commercially available unadjusted soymilk to which 2,6-dodecadienal was not added was used as the control product 3, and the products 3-1 to 3-8 of the present invention were compared with the control product 3. Panellists were asked about the difference in flavor. In addition to commenting on the feeling of milk, the scores given by the panelists according to the following criteria were averaged.

<Evaluation criteria for milk feeling>
Significantly increased compared to control product 3: Greatly increased compared to 5-point control product 3: Somewhat increased compared to 4-point control product 3: Slightly increased compared to 3-point control product 3: 2-point control Equal to product 3 or decreased compared to control product 3: 1 point

The results of the sensory evaluation of the products 3-1 to 3-8 of the present invention performed based on the above are compared with the following criteria, and each of them is evaluated as ◎, ◯, △, ×, and ◎ and ◯ are the milk feeling imparting composition. An example that can be suitably used as a product, an example that can be used as a milk sensation-imparting composition with Δ, and an unsuitable example as a composition that imparts milk sensation with ×.

<Judgment criteria for milk feeling>
Those with an average score of less than 2 points or with a strong flavor of the compound: ×
The average score is 2 or more and less than 3 or the flavor of the compound is slightly felt: △
Average score of 3 or more and less than 4: 〇 Average score of 4 or more: ◎

Table 3 shows the results of sensory evaluation of products 3-1 to 3-8 of the present invention for soymilk beverages.

As shown in Table 3, it was confirmed that soymilk beverages to which 2,6-dodecadienal was added imparted or enhanced a feeling of milk fat, thickness, and aroma of milk, and as a result, a feeling of milk was imparted or enhanced. did it. In addition, as shown in Table 3, the soymilk beverages to which 2,6-dodecadienal was added suppressed the chalkiness and green flavor derived from soymilk, and the taste-masking effect of 2,6-dodecadienal was also confirmed. did it. From the above, it can be said that 2,6-dodecadienal is excellent in improving the flavor of soymilk.

[Example 4] Effect of addition to food and drink (coffee with milk) Commercially available milk-containing coffee (caffe latte), diluted with ethanol as necessary, 2,6-dodecadienal commercially available product of this milk feeling imparting composition 2,6-dodecadienal was added to the milk-containing coffee so that the concentrations shown in Table 4 were obtained, and milk-containing coffee beverages 4-1 to 4-4 of the present invention were prepared. The milk-containing coffee beverages of Products 4-1 to 4-4 of the present invention thus obtained were sensory evaluated by 15 well-trained panelists (with experience of 10 years or more). Sensory evaluation was conducted by comparing the commercially available milk-containing coffee to which 2,6-dodecadienal was not added as control product 4, and comparing products 4-1 to 4-4 of the present invention with control product 4. Panellists were asked about the difference in flavor. In addition to commenting on the feeling of milk, the scores given by the panelists according to the following criteria were averaged.

<Evaluation criteria for milk feeling>
Significant increase compared to control 4: Great increase compared to 5-point control 4: Some increase compared to 4-point control 4: Slight increase compared to 3-point control 4: 2-point control Equal to product 4 or decreased compared to control product 4: 1 point

The results of the sensory evaluation of the products 4-1 to 4-4 of the present invention performed based on the above are compared with the following criteria, and each of them is evaluated as ◎, ◯, △, ×, and ◎ and ◯ are the milky feeling imparting composition. An example that can be suitably used as a product, an example that can be used as a milk sensation-imparting composition with Δ, and an unsuitable example as a composition that imparts milk sensation with ×.

<Judgment criteria for milk feeling>
Those with an average score of less than 2 points or with a strong flavor of the compound: ×
The average score is 2 or more and less than 3 or the flavor of the compound is slightly felt: △
Average score of 3 or more and less than 4: 〇 Average score of 4 or more: ◎

Table 4 shows the sensory evaluation results for the milk-containing coffee beverages of Products 4-1 to 4-4 of the present invention.

As shown in Table 4, it was confirmed that milk-containing coffee beverages to which 2,6-dodecadienal was added had a particularly enhanced feeling of milk fat, resulting in an enhanced feeling of milk. In addition, as shown in Table 4, the milk-containing coffee beverage to which 2,6-dodecadienal is added has not only a milky feeling, but also has enhanced elements suitable for milk-containing coffee beverages, such as coffee-like bitterness and richness. I was able to confirm that.

[Example 5] Effect of addition to food and drink (cheese sauce) A commercial product of 2,6-dodecadienal diluted with ethanol as necessary in a commercially available cheese sauce was used as the milk sensation-imparting composition, and the cheese The concentrations of 2,6-dodecadienal in the sauces were added to the concentrations shown in Table 5 to prepare cheese sauces 5-1 to 5-3 of the present invention.

Then, the obtained cheese sauces of products 5-1 to 5-3 of the present invention were subjected to sensory evaluation by five well-trained panelists (10 years or more of experience). In the sensory evaluation, the cheese sauce to which 2,6-dodecadienal was not added was used as control product 5, and the panelists commented on the difference in flavor when products 5-1 to 5-3 of the present invention were compared with control product 5. I went by.

Table 5 shows the results of sensory evaluation.

As shown in Table 5, it was confirmed that the cheese sauce to which 2,6-dodecadienal was added was particularly enhanced in the feeling of milk fat, thickness and richness, and as a result the feeling of milk was enhanced.

Claims (4)

A milk feeling imparting composition containing 2,6-dodecadienal as an active ingredient. 2. The milky sensation-imparting composition according to claim 1, further exhibiting a taste-masking effect. A method for imparting a milk sensation effect to a flavor-imparting composition, comprising the step of adding the milk sensation-imparting composition according to claim 1 or 2 to a flavor-imparting composition. A method for imparting a milky sensation to a food or drink, comprising adding the composition for imparting a milky sensation according to claim 1 or 2 to the food or drink.