JP2022168377A - Warmth-feeling-imparting composition - Google Patents

Abstract

To provide a warmth-feeling-imparting composition including little stimulant and little flavor while having a warming effect.SOLUTION: A warmth-feeling-imparting composition includes 3-(4-alkoxyphenyl)prop-2-enal or 3-(4-alkenyloxyphenyl)prop-2-enal (where alkoxy group and alkenyloxy group is limited to that of C2 to C4) as active principles. In the-warmth-feeling-imparting composition, the composition is for a beverage/food product and is added with a compound concentration of 5-100 ppm based on the total mass of the beverage/food product. A method of fortifying a warmth feeling of the warmth-feeling-imparting composition includes a step of adding the warmth-feeling-imparting composition to other warmth-feeling-imparting compositions. A production method of a beverage/food product having a warming effect includes the step of adding the warmth-feeling-imparting composition to the beverage/food product with a compound concentration of 5-100 ppm based on the total mass of the beverage/food product.SELECTED DRAWING: None

Description

TECHNICAL FIELD The present invention relates to a warming sensation imparting composition that imparts a warming sensation to humans.

Conventionally, substances that give a warm feeling (hereinafter referred to as a warm feeling) to human skin, oral cavity, nose and/or throat, and compositions containing the same (hereinafter referred to as warm feeling imparting compositions) exist, Generally, it is widely known as a warm material. The warming sensation imparting composition is expected not only to give a warm sensation, but also to have effects such as warming the body, promoting blood flow, and activating the activity of the gastrointestinal tract. Therefore, in recent years, warming sensation imparting compositions are added to various articles (hereinafter sometimes referred to as consumer goods) such as food and drink, cosmetics, medicines, and health and hygiene products to obtain the effect of appealing to consumers. That's what happened.

As an example of a warming sensation imparting composition, Patent Document 1 describes ginger oleoresin. It is stated to contain shogaol. In addition, as other examples of the warming sensation imparting composition, Patent Document 2 discloses jambu oleoresin (active ingredient: spiranthol), Japanese pepper extract (active ingredient: sanshool (correctly sanshool), sanshoamide), Black pepper extract (active ingredients: moldicin, piperine) is described.

JP 2011-136953 A JP-A-2001-279227

However, the warming sensation imparting composition described in Patent Document 1 and Patent Document 2 has a strong stimulus and a unique aroma and flavor (hereinafter referred to as flavor), as the active ingredient is also known as a pungent component. )have. Therefore, there is a problem that the types and applications of target consumer goods to which the warming sensation imparting composition can be added are limited.

In view of the above, an object of the present invention is to provide a composition for imparting warmth that has a warming effect but is less irritating and less flavorful.

As a result of intensive studies aimed at solving the above problems, the present inventors have found a warming sensation-imparting composition that has a warming effect but is less irritating and less flavorful, and has completed the invention according to the present application. .

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

[1] 3-(4-alkoxyphenyl)prop-2-enal or 3-(4-alkenyloxyphenyl)prop-2-enal (wherein the alkoxy group and alkenyloxy group are each limited to those having 2 to 4 carbon atoms) ) as an active ingredient.
[2] In the warming sensation imparting composition according to [1], the warming sensation imparting composition is for food and drink, and the compound is added at a concentration of 5 to 100 ppm based on the total weight of the food and drink. A warming sensation imparting composition.
[3] A method for enhancing warmth sensation of a composition for imparting warmth, comprising the step of adding the composition for imparting warmth according to [1] to another composition for imparting warmth.
[4] It includes the step of adding the warming sensation imparting composition according to [1] to a food or drink, and has a warming effect in which the concentration of the compound is 5 to 100 ppm based on the total mass of the food or drink. Food and drink manufacturing method.

According to the present invention, it is possible to provide a warming sensation-imparting composition that has a warming effect and is less irritating and less flavorful.

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)" and "%" are respectively "mass concentration" and "mass percent concentration" unless otherwise specified. shall represent 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 "flavor imparting (to impart flavor)" includes newly adding flavor and/or enhancing flavor. includes what is done. Furthermore, as a result of imparting flavor, sensations other than olfaction and / or taste, such as cold sensation, warm sensation, texture (such as throat, hardness, viscosity, etc., also referred to as texture), stimulating sensation such as carbonic acid and hotness, and the like may be enhanced, suppressed, or improved. Here, in the present specification, the term “food and drink to which a feeling of warmth is imparted” means that when a human ingests the food and drink, a feeling of warmth is imparted to the skin, oral cavity, nose and/or throat of the human. Means food and drink that can be given. Therefore, the “method for imparting warmth to food and drink” means making the food and drink into a food and drink to which a feeling of warmth is imparted. Moreover, in this specification, the flavor of food and drink may be called flavor. In addition, as used herein, "adding" includes at least one of simply adding to a certain object by spraying, dropping, etc., and mixing with a certain object. In addition, in the present specification, for example, the phrase "containing the subject compound or the subject warmth imparting composition" refers to the case where either the subject compound or the subject warmth imparting composition is contained, unless otherwise specified. In addition, the case of containing both the subject compound and the subject warmth imparting composition is also included.

(Composition for imparting warmth)
The warming sensation imparting composition according to one embodiment of the present invention (hereinafter sometimes referred to as the present warming sensation imparting composition) is 3-(4-alkoxyphenyl)prop-2-enal or 3-(4- alkenyloxyphenyl)prop-2-enal (wherein the alkoxy group and the alkenyloxy group are each limited to those having 2 to 4 carbon atoms; hereinafter sometimes collectively referred to as the present compound) is contained as an active ingredient.

The present warming sensation imparting composition can impart a warming effect to various articles by being added to the articles. An article to which the present warming composition is added can provide a warm sensation (warm sensation) to human skin, oral cavity, nose and/or throat. In particular, the present warming sensation imparting composition has the effect of being less irritating and less flavorful than conventional warming sensation imparting compositions, as shown in the examples below. As a result, the present warming sensation-imparting composition can be widely applied to various consumer goods without any particular limitation on the type or use of the substance to be added.

The composition for imparting warmth may be composed only of the present compound, or may contain other components such as a solvent as long as it contains a predetermined amount of the present compound.

Specific examples of the present compounds include 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-propoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal, 3-(4-(2-propenyloxy)phenyl)prop-2-enal, 3-(4-butoxyphenyl)prop-2-enal, 3-(4-isobutoxyphenyl)prop-2-enal, 3- (4-(sec-butoxy)phenyl)prop-2-enal, 3-(4-(tert-butoxy)phenyl)prop-2-enal, 3-(4-(3-butenyloxy)phenyl)prop-2- Enards may be mentioned. The cis-trans isomer of the present compound is not particularly limited, and a mixture of isomers may be used.

Although the present applicant has conducted a sufficient prior art search, there is no description of the present compound imparting a feeling of warmth.

The present compound can be obtained by any method that can be made by those skilled in the art. For example, among the present compounds, 3-(4-alkoxyphenyl)prop-2-enal can be prepared using the synthetic reactions described in . That is, 3-(4-alkoxyphenyl)prop-2-enal is obtained by reacting 4-alkoxybenzaldehyde dimethylacetal and methyl vinyl ether using a Lewis acid catalyst and hydrolyzing this compound.

The present compound obtained by the above synthesis method may be further purified using means such as column chromatography or vacuum distillation, if necessary.

The concentration of the present compound in the composition for imparting warmth can be arbitrarily determined according to the object of addition of the composition for imparting warmth. Examples of the concentration of the instant compound include a range of 1 ppm to 100%, preferably 100 ppm to 10%, based on the total mass of the warming composition. More specifically, the lower limit is 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. and any combination of these lower and upper limits, but are not limited thereto.

Examples of objects to which the present warming sensation imparting composition is added include other warming sensation imparting compositions, flavor imparting compositions, foods and beverages, cosmetics, pharmaceuticals, health and hygiene products, and various other articles. The details of each addition target will be described later.

The present warming sensation-imparting composition is preferably used by adding it to food and drink, in order to take advantage of the advantages of having less stimulus and less flavor than other warming sensation-imparting compositions. At this time, as shown in the examples below, it is preferable to add the present compound so that the concentration of the present compound is 5 to 100 ppm based on the total mass of the food and drink, and the concentration of the present compound is 5 to 40 ppm. It is more preferable to add

(Method for enhancing warming effect of warming sensation imparting composition)
A method for enhancing the warming effect of a warming sensation imparting composition according to an embodiment of the present invention (hereinafter sometimes referred to as the present warming effect enhancing method) is a method in which the present warming sensation imparting composition is mixed with another warming sensation imparting composition. including the step of adding to the product.

By adding an effective amount of the present warming sensation imparting composition to another warming sensation imparting composition, the warming effect of the warming sensation imparting composition to be added can be enhanced. More specifically, other warming compositions to which the present warming composition is added have enhanced warming effects on human skin, oral cavity, nose and/or throat. In particular, the present warming sensation-imparting composition has less stimulus and flavor than other warming sensation-imparting compositions. The effect can be enhanced.

Examples of compounds (spicy substances) contained in other warming sensation imparting compositions include capsaicin, dihydrocapsaicin, nordihydrocapsaicin, homocapsaicin, homodihydrocapsaicin, N-vanillyl-n-nonamide, piperine, shavicin, isopiperine, isoshavicine, piperrine, piperetine, piperanine, piperolein A, piperolein B, 6-shogaol, 8-shogaol, 10-shogaol, 6-gingerol, 8-gingerol, 10-gingerol, 6-paradol, 6-gingediol, 6-gingedione , propylthiosulfinate, allicin (diallyldithiosulfinate), allyl isothiocyanate, 4-methylthio-3-butenyl isothiocyanate, and the like.

In the present warming effect enhancing method, the amount of the present warming sensation imparting composition to be added to the warming sensation imparting composition to be added may be an effective amount that enhances the warming effect by the present compound contained as an active ingredient. It can be arbitrarily set according to the type and form of the warming sensation imparting composition to be added.

In the present warming effect enhancing method, the method of adding the present warming sensation imparting composition to another warming sensation imparting composition is not particularly limited. Also, the time (timing) of adding the present warming sensation imparting composition to another warming sensation imparting composition is not particularly limited.

(Flavor imparting composition)
The flavor imparting composition to which the present warming sensation imparting composition 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 consumer goods (food and drink, cosmetics, pharmaceuticals, hygiene products, etc.) can be exemplified. Examples of the flavor-imparting composition include perfume compositions, flavor-improving agents, flavor-modifying agents, taste-imparting agents, taste-improving agents, and taste-modifying agents.

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

In addition, the composition for imparting warmth can be used as a flavor imparting composition having a warming effect by forming the composition for imparting warmth with the compound of interest and a compound capable of imparting flavor (e.g., a flavoring compound). can also

Specific examples of the flavoring composition, which is one aspect of the flavoring composition, include flavoring compositions for food and drink (also referred to as flavor compositions) and flavoring compositions for cosmetics (also referred to as fragrance compositions). Examples of articles to which the additive is applied include consumer goods such as food and drink, cosmetics, pharmaceuticals, and hygiene products, as described above. 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.

The perfume composition 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 Perfume Manufacturers Association, March 2001), and "Synthetic Perfume Chemistry and Product Knowledge" (December 20, 2016, edited by the Synthetic Perfume Editorial Committee, published by 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 flavoring composition can be prepared by adding the flavoring composition to an appropriate solvent or dispersion medium by a known method.

The form of the flavoring composition is preferably a solution obtained by dissolving the flavor 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).

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 flavor imparting composition can be emulsified with a water-soluble solvent and an emulsifier. The method for emulsifying the flavor-imparting composition is not particularly limited, and emulsifiers conventionally used in foods and beverages, such as fatty acid monoglycerides, fatty acid diglycerides, fatty acid triglycerides, propylene glycol fatty acid esters, and sucrose. 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 sodium caseinate An emulsifying liquid having excellent stability can be obtained by emulsifying using an emulsifier such as 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 be varied over a wide range depending on the type of emulsifier used. 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 obtained in this way 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 perfume composition may, if necessary, contain components commonly used in perfume compositions. 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, hakoline, medium chain fatty acid triglyceride, medium chain fatty acid diglyceride, etc. agent.

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

By adding an effective amount of the present warming sensation imparting composition to a food or drink, a warming effect can be imparted to the food or drink to which the composition is added. In particular, the present warming sensation imparting composition has less stimulation and flavor than other warming sensation imparting compositions, so it imparts a warming effect without affecting the flavor of the food or drink to which it is added. can do.

In particular, in the present food and beverage manufacturing method, the amount of the present warming sensation imparting composition added to the food and drink to which it is added is, as shown in the examples below, based on the total mass of the food and drink to which the compound is added. Add so that the concentration is 5 to 100 ppm. As a result, the warming effect can be sufficiently imparted without substantially affecting the flavor of the food or drink to which it is added. Further, more preferably, in the present method for producing a food or drink, the amount of the present warming sensation imparting composition added to the food or drink to be added is based on the total mass of the food or drink to be added, as shown in the examples below. , so that the concentration of the present compound is 5 to 40 ppm. As a result, the warming effect can be sufficiently imparted without affecting the flavor of the food or drink to which it is added.

In the method for producing food and drink, the method of adding the composition for imparting warmth to food and drink is not particularly limited. In addition, the time (timing) of adding the present warming sensation imparting composition to the food or drink is not particularly limited.

(consumer goods)
The consumer goods to which the composition for imparting warmth is added will be described below. Consumer goods are various items such as food and drink, cosmetics, medicines, or hygiene products.

In the subject consumer goods, the amount of the subject warming sensation imparting composition added to the subject matter can be arbitrarily determined according to the flavor of the subject matter and the degree of desired effect of the subject compound contained as an active ingredient.

As an example of the concentration, if it is a food or drink, the concentration of the present compound is 5 ppm to 0.1%, preferably 5 ppm to 100 ppm, more preferably 5 ppm to 40 ppm with respect to the total weight of the food or drink. be done. Within such a range, a warming effect can be imparted without affecting the flavor of the food or drink to which it is added. In particular, as shown in the examples below, by adding the present compound at a concentration in the range of 5 ppm to 100 ppm with respect to the total mass of the food and drink, the flavor of the food and drink to which it is added is hardly affected. A warming effect can be imparted. Furthermore, as shown in the examples below, by adding the present compound at a concentration in the range of 5 ppm to 40 ppm with respect to the total weight of the food and drink, the flavor of the food and drink to which it is added is completely affected. A warm feeling effect can be imparted.

In addition, if the concentration of the present compound in food and drink is 5 ppm or more, the warming effect can be reliably exhibited. may be added. In addition, although it depends on the type and flavor of the food or drink, if the concentration of the subject compound in the food or drink is 0.1% or less, the flavor of the subject compound itself will have an unfavorable effect on the flavor of the food or drink to which it is added. However, depending on the flavor of the food or drink, the present compound may be added at a concentration exceeding 0.1%.

As an example of the concentration, in the case of cosmetics, the concentration of the present compound is in the range of 5 ppm to 1% with respect to the total weight of the cosmetics.

If the concentration of the present compound in the cosmetic product is 5 ppm or more, the warming effect can be reliably exhibited. may be added. In addition, although it depends on the type and fragrance of the cosmetic product, if the concentration of the present compound in the cosmetic product is 1% or less, the fragrance of the compound itself will not have an unfavorable effect on the fragrance of the cosmetic product to which it is added. However, depending on the fragrance of the cosmetic product, the present compound may be added at a concentration exceeding 1%.

The present warming composition may itself be added to consumer goods, or may be added to one or more water-soluble fragrances, emulsified fragrance compositions, arbitrary fragrance compounds, natural essential oils (for example, the above " Patent Office Gazette, Collection of Well-known and Commonly Used Techniques (Fragrance) Part II Food Flavor”, “Survey on the Actual Use of Food Flavoring Compounds in Japan”, and “Synthetic Flavoring Chemistry and Product Knowledge”), selected from may be added to consumer goods in conjunction with one or more of the

The food and drink to which the present warming composition can be added are not particularly limited, but examples include various citrus fruits such as lemon, orange, grapefruit, lime, mandarin, mandarin orange, kabosu, sudachi, hassaku, iyokan, yuzu, shikuwasa, and kumquat. Flavor: Various fruit flavors such as strawberry, blueberry, raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, papaya, kiwi, pear, grape, muscat, and Kyoho; milk, yogurt, butter, etc. Milk flavor; Vanilla flavor; Various tea flavors such as green tea, black tea, oolong tea, and herbal tea; Coffee flavor; Cola flavor; Cacao flavor; Cocoa flavor; Various spices or herbal flavors such as cumin, cloves, pepper, coriander, Japanese pepper, perilla, ginger, star anise, thyme, capsicum, nutmeg, basil, marjoram, rosemary, laurel, garlic, wasabi; almonds, cashews, walnuts, etc. various nut flavors; alcoholic beverage flavors such as wine, brandy, whiskey, rum, gin, liqueur, sake, shochu, and beer; vegetable flavors such as onions, celery, carrots, tomatoes, and cucumbers; chicken, duck, pork, and beef , various livestock meat flavors such as mutton and horse meat; red fish such as tuna; white fish such as mackerel, sea bream, salmon and horse mackerel; freshwater fish such as sweetfish, trout and carp; Various seafood and seaweed flavors such as various crustaceans such as crabs, various seaweeds such as wakame and kelp; various grain flavors such as rice, barley, wheat and malt; livestock meat such as beef tallow, chicken oil and lard and various oil and fat flavors such as oil and various fish oils; 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 rice crackers, 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 beer yeast and baker's yeast; Seed microbial fermented products; Boiled vegetables, Chikuzen simmered dishes, oden, hot pot dishes, etc.; Ingredients for take-out lunches and side dishes; Fruit juice drinks and fruit juice-containing beverages of apples, grapes, citrus fruits (grapefruit, orange, lemon, etc.) Soft drinks, fruit pulp drinks and fruit drinks containing fruit; vegetables such as tomatoes, green peppers, celery, gourds, bitter melons, carrots, potatoes, asparagus, bracken, and fern, vegetable drinks containing these vegetables, vegetable soups Vegetable-containing beverages such as; coffee, cocoa, green tea, black tea, oolong tea, soft drinks, cola beverages, carbonated drinks (such as cider with various flavors such as citrus), lactic acid beverages, and other beverages; beverages containing herbal medicines and herbs ；Cola drinks, fruit juice drinks, dairy drinks, non-alcoholic beer, beer-taste drinks including so-called "third beer", sports drinks, honey drinks, vitamin supplement drinks, mineral supplement drinks, nutrition drinks, nutrition drinks, lactic acid beverages Functional beverages such as; Non-alcoholic beverages such as alcohol-taste beverages with various alcoholic beverages (beer flavor, plum wine flavor, Chuhai flavor, etc.); wine, shochu, awamori, sake, beer, chuhai, cocktail drinks, sparkling wine, fruit liquor, spice liquor, other brewed liquor (sparkling), liqueur (sparkling), etc., or alcoholic beverages containing these;

Cosmetics to which the present warming composition can be added are not particularly limited, but examples include perfumes such as eau de cologne, eau de toilette, eau de parfum, and parfum; hair care products such as shampoos, rinses, and hair styling products (hair cream, pomade, etc.). ;Cosmetics such as foundation, lipstick, lip balm, lip gloss, lotion, cosmetic milky lotion, cosmetic cream, cosmetic gel, serum, and pack; Antiperspirant spray, deodorant sheet, deodorant cream, deodorant stick, etc. Deodorant products; inorganic salt-based, refreshing, carbon dioxide-based, skin-care, enzyme-based, and crude drug-based bath agents; suntan products, sunscreen products, and other suntanning cosmetics; Health and hygiene detergents such as body soap, body soap, laundry soap, laundry detergent, disinfectant detergent, deodorant detergent, softener, kitchen detergent, cleaning detergent; toothpaste, tissue paper, toilet paper, etc. health and sanitary materials; aromatic deodorants for rooms and cars, aromatic products such as room fragrances; and the like.

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

[Example 1] Evaluation of the warming effect of the present compound Hereinafter, the warming effect of consumer goods to which the present warming sensation imparting composition was added was evaluated according to the following procedure.

First, 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal and 3-(4-butoxyphenyl)prop-2-enal were diluted with ethanol. , and 10% ethanol solutions were prepared respectively (both correspond to the present warming sensation imparting composition).

Also, an aqueous solution containing 7% granulated sugar and 0.12% citric acid (hereinafter sometimes referred to as sugar acid solution) was prepared. Then, 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal and 3-(4-butoxyphenyl)prop-2-enal are added to this sugar acid solution. Each 10% ethanol solution was used as a warming sensation imparting composition and added so that the concentration of the present compound in the sugar acid solution was as shown in Table 1 to prepare beverages of present invention products 1-1 to 1-23. .

On the other hand, 6-shogaol was diluted with ethanol to prepare a 10% ethanol solution. This was added to the sugar-acid solution so that the concentration of 6-shogaol in the sugar-acid solution became the concentration shown in Table 1 to prepare beverages of comparative products 1-1 to 1-6.

Then, sensory evaluation and skin temperature by 5 well-trained panelists (with experience of 10 years or more) for the obtained drinks of the present invention products 1-1 to 1-23 and comparative products 1-1 to 1-6 I made a measurement.

Sensory evaluation was performed on 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal, 3-(4-butoxyphenyl)prop-2-enal and 6-ginger Using a sugar acid solution to which no all was added as a control product, the panelists drank 70 mL each of the products 1-1 to 1-23 of the present invention, the comparative products 1-1 to 1-6, and the control product, and as a result, In addition to commenting on the aroma when comparing the products 1-1 to 1-23 of the present invention and the comparative products 1-1 to 1-6 with the control product, the following evaluation criteria were used for the aroma, pungency and warmth compared to the control product. This was done by averaging the scores given by the panelists accordingly. The term “feeling of warmth” as used herein refers to a subjective evaluation by a panelist of the sensible temperature based on the following evaluation criteria.

The skin temperature was measured after the panelists rested for 5 minutes before drinking and drank 70 mL of each of the products 1-1 to 1-23 of the present invention, the comparative products 1-1 to 1-6, and the control product at room temperature (24 ° C.). After 20 minutes had passed, the temperature of the surface of the back of the hand of the panelist was measured with a thermograph, and the points scored according to the following evaluation criteria were averaged.

<Evaluation criteria for aroma, spiciness, and warmth>
Significantly increased compared to the control product: Slightly increased compared to the 3-point control product: Slightly increased compared to the 2-point control product: Equivalent to the 1-point control product: 0 points

<Evaluation criteria for skin temperature rise>
Increased by 1.0°C or more compared to the control product: Increased by 0.5°C or more and less than 1.0°C compared to the 3-point control product: Increased by 0.1°C or more and less than 0.5°C compared to the 2-point control product Increased: 1 point Increased less than 0.1 ° C compared to the control product (including cases where it did not increase): 0 points

The results of sensory evaluation and skin temperature measurement of products 1-1 to 1-23 of the present invention and comparative products 1-1 to 1-6 based on the above were compared with the following criteria, and each was evaluated as ○, △, or ×. made a judgment.

<Judgment Criteria>
Average score of 5 panelists is less than 1 point: ×
The average score of 5 panelists is 1 or more and less than 2: △
The average score of 5 panelists is 2 points or more: ○

Table 1 shows the results of sensory evaluation and skin temperature measurement for products 1-1 to 1-23 of the present invention and comparative products 1-1 to 1-6.

As shown in Table 1, 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal and 3-(4-butoxyphenyl)prop-2-enal are , the effect of raising skin temperature was observed at concentrations of 5 ppm or more. On the other hand, as shown in Table 1, 6-shogaol slightly raised the skin temperature at concentrations of 10 ppm or more, and sufficiently at concentrations of 40 ppm or more.

Also, as shown in Table 1, 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal and 3-(4-butoxyphenyl)prop-2-enal In the sensory evaluation, the aroma and pungent taste of Enal were hardly perceived at concentrations of 100 ppm or less, and were not perceived at all at concentrations of 40 ppm or less. On the other hand, as shown in Table 1, sensory evaluation showed that 6-shogaol had almost no odor and pungent taste at concentrations of 5 ppm or less, and was not felt at all at concentrations of 1 ppm or less.

In summary, 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal and 3-(4-butoxyphenyl)prop-2-enal are It was also found that, compared to 6-shogaol, a sufficient warming effect can be obtained at a concentration that does not give a pungent taste.

Notably, 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal and 3-(4-butoxyphenyl)prop-2-enal are At concentrations of 5 ppm or more and 100 ppm or less, almost no (i.e., subjective) warmth is felt as a sensory evaluation, and at concentrations of 5 ppm or more and 40 ppm or less, no (i.e., subjective) warmth is felt as a sensory evaluation. It turns out not. As shown in Table 1, a sensory evaluation (i.e., subjective) warmth is judged by whether or not a person feels a pungent taste, and conventional compositions for giving warmth have appealed from this point of view. However, whether or not an essential warming effect can be obtained should be judged based on objective information such as an increase in skin temperature. It can be said that the present invention provides a novel warm sensation material different from the sensation-imparting composition.

From the sensory evaluation results in Table 1, 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal and 3-(4-butoxyphenyl)prop- An attempt was made to calculate the pungency threshold of 2-enal. According to the method described in Japanese Patent Application Laid-Open No. 2010-68749, when a pungent substance whose pungent threshold is not clear is included, the pungent threshold can be calculated from the result of the sensory evaluation. As shown in Table 1, 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal and 3-(4-butoxyphenyl)prop-2-enal The pungent threshold is estimated to be about 100 ppm.

Similarly, from the results of the sensory evaluation in Table 1, the pungent threshold of 6-shogaol can be estimated to be about 5 to 10 ppm. , and the results are considered valid.

From the above, it was shown that the present warming sensation imparting composition has less stimulus and less flavor than conventional warming sensation imparting compositions while having a warming effect.

Claims (4)

3-(4-alkoxyphenyl)prop-2-enal or 3-(4-alkenyloxyphenyl)prop-2-enal (however, the alkoxy group and alkenyloxy group are each limited to those having 2 to 4 carbon atoms); A warming sensation imparting composition containing as an active ingredient. In the composition for imparting warmth according to claim 1,
The composition for imparting warmth is for food and drink, and the composition for imparting warmth is added at a concentration of 5 to 100 ppm based on the total weight of the food and drink. A method for enhancing the warming sensation of a warming sensation imparting composition, comprising the step of adding the warming sensation imparting composition according to claim 1 to another warming sensation imparting composition. A step of adding the warming sensation imparting composition according to claim 1 to a food or drink,
A method for producing food and drink having a warming effect, wherein the concentration of the compound is 5 to 100 ppm based on the total weight of the food and drink.