WO2020116117A1 - Flavor-enhancing agent, method for enhancing flavor of oral product, and method for enhancing aroma of perfume - Google Patents

Abstract

The present invention addresses the problem of providing: a versatile flavor-enhancing agent that does not have a specific flavor; a method for enhancing flavor; and a method for enhancing the aroma of a perfume. The present invention uses a flavor-enhancing agent that comprises 7a-hydroxymintlactone to provide: an oral product that enhances sweetness, richness, and/or aroma; and a perfume that has an enhanced aroma. 7a-hydroxymintlactone is a component of mint essential oils but does not itself have a specific flavor and can enhance sweetness, richness, and/or aroma, i.e., is highly versatile.

Description

Flavor enhancer, method for enhancing flavor of oral product, and method for enhancing aroma of cosmetics

The present invention relates to a flavor enhancer for an oral product, a flavor enhancing method, and an aroma enhancing method for cosmetics.
Specifically, it is a flavor enhancer characterized by comprising 7a-hydroxymint lactone. The term "flavor enhancement" as used herein refers to one or more effects selected from a sweetness enhancing effect, a richness enhancing effect and an aroma enhancing effect. 7a-hydroxymint lactone is sweetness when applied to a product having sweetness. It functions as an enhancer, functions as a richness enhancer when applied to a product having a complex taste, and further functions as an aroma enhancer when applied to a product having an aroma characteristic.
Furthermore, in the case where the product has a rich taste other than sweetness, it can be used as a flavor enhancer having two or more enhancing effects such as sweetness, richness, and aroma.
Furthermore, the present invention relates to a method for enhancing one or more kinds selected from the sweetness enhancing effect, kokumi enhancing effect and aroma enhancing effect of an oral product by adding the flavor enhancing agent of the present invention.

There is a need in the food and beverage industry to reduce the sucrose content in foods and beverages, reflecting the diet-oriented tendency associated with the prevention of lifestyle-related diseases and the increased awareness of health promotion.
To solve this problem, artificial sweetness modifiers having a high degree of sweetness (so-called high-potency sweeteners), for example, aspartame, acesulfame potassium, sucralose, saccharin, etc. are used to partially or completely replace sucrose. That is generally done.

However, it is known that the above-mentioned sweetness modifier may impart undesired taste attributes other than sweetness, such as bitterness and astringent taste.
Therefore, an improved technique for enhancing sweetness without impairing the original flavor of sweeteners such as sucrose has been widely demanded.

In such an improved technique, as a sweetness enhancer and a sweetness enhancing method that have been reported so far, a sweetness enhancer containing a dry yeast powder as an active ingredient (Patent Document 1), a long-chain highly unsaturated fatty acid and/ Alternatively, a sweetness enhancer comprising an ester thereof (Patent Document 2), a sweetness enhancing method using adenosine and/or a physiologically acceptable salt and a monosaccharide or a disaccharide (Patent Document 3), and a food containing a natural sweetener. There is disclosed a method for enhancing sweetness (Patent Document 4) in which a licorice extract and a Hosen flower alcoholic extract are added.

However, the flavor of these sweetness enhancers themselves is by no means preferable. Therefore, it cannot be said to be versatile and applicable to various flavored oral products.
Therefore, there has been a demand for further development of various flavor products in terms of easily enhancing sweetness by an additional method without impairing the flavor.

In addition, along with prevention of lifestyle-related diseases or awareness of health promotion, reduction of salt and fat in foods and drinks is also required in the food industry.
In response to this problem, it has been pointed out that the reduction in the richness and volume of the food and drink due to the reduction of the salt content and the fat content of the food and drink. Various methods have been developed to enhance the richness, and natural extracts such as livestock meat extract, seafood extract, and vegetable extract are widely used as a richness enhancer. There are many. Therefore, at present, there are few that are versatile and applicable to various flavored oral products.

Specific taste-providing agents such as a specific Amadori compound (Patent Document 5) and pyroglutamyl dipeptide (Patent Document 6) have been proposed, but they cannot be said to have sufficient versatility.
With respect to foods and drinks having various flavors, it has been required to develop a further technique in that the rich flavor can be easily enhanced by an additional method without impairing the original flavor.

As a material having both sweetness and richness, application of a tetrahydrobenzofuranone derivative having a mild aroma and a sweet aroma has been proposed (Patent Document 7).
However, since each tetrahydrobenzofuranone derivative has a characteristic scent, it is difficult to use it in various foods and drinks in general, and further improvement techniques are required. Further, it has been pointed out that when the sucrose, salt content and fat content are reduced as described above, the aroma may be deteriorated.

The material for enhancing the flavor of a food or drink itself without affecting the taste or aroma of the food or drink, for example, a flavor enhancer for a food or drink characterized by comprising spilanthol or a plant extract containing spilanthol or a plant essential oil. Has been proposed (Patent Document 8).
Further, there has been proposed a method for enhancing flavor of food and drink (Patent Document 9), which comprises adding a lower fatty acid in a concentration of 0.01 to 0.5 times the threshold concentration.
However, each material has a unique flavor, and it may feel uncomfortable depending on the usage condition, and it is required to provide further improved technology.

Japanese Patent Laid-Open No. 2012-100562 JP, 2009-284859, A International Publication No. 2013/143822 Japanese Patent Laid-Open No. 10-248519 JP 2012-029615 A JP 2012-029616 A Japanese Patent Laid-Open No. 07-101952 JP, 2006-296356, A JP, 2008-263903, A

The problem to be solved by the present invention is a flavor enhancer that is in harmony with the original flavor of an oral product, specifically, a flavor enhancer effect is one selected from a sweetness enhancer effect, a body taste enhancer effect and an aroma enhancer effect, or It is to provide a flavor enhancer characterized by comprising two or more kinds. Furthermore, it is also to provide an aroma enhancer for enhancing the aroma of cosmetics.

In order to solve the above problems, the present inventors have searched for compounds having a flavor enhancing effect, and as a result, 7a-hydroxymint lactone, which is one of a very wide variety of components contained in mint essential oil, It was found that one or more effects selected from sweetness enhancing effect, kokumi enhancing effect and aroma enhancing effect are exhibited without showing a characteristic flavor.
Here, 7a-hydroxymint lactone is described in Patent Document 7 as 3-hydroxymint lactone. However, 3-hydroxy mint lactone is only used as a raw material for synthesizing 3-ethoxy mint lactone, and there is no description about the characteristics of 3-hydroxy mint lactone itself or the effect when added to food and drink. , There was nothing to suggest.

The flavor improving agent of the present invention does not have a specific flavor as described above, and therefore, a sweetener, a food or drink containing the sweetener, or a savory product (vegetable-based, spice-based, nut-based, meat/seafood-based, By adding it to all oral products such as daily foods and beverages mainly having a salty taste), dairy products, and even oral care products, the sweetness-enhancing effect, body-enhancing effect and aroma can be achieved without impairing the flavor. One or more effects selected from the enhancing effects can be exhibited.
That is, the present invention provides one or more flavor enhancers selected from the following flavor enhancers, sweetness enhancers, kokumi enhancers and aroma enhancers, as well as sweetness enhancer, kokumi enhancer and aroma enhancer. The present invention relates to an oral product having an enhanced effect of one or more selected from
Furthermore, since it does not have a specific odor as described above, it is possible to exhibit the effect of enhancing the fragrance of cosmetics without modulating the fragrance.
Therefore, the present invention relates to the following fragrance enhancers and fragrance-enhanced cosmetics.

That is, the present invention is as follows.
[1] Flavor enhancer (1) A flavor enhancer comprising 7a-hydroxymint lactone.
(2) The flavor enhancer described above, wherein the flavor enhancer effect is one or more selected from a sweet taste enhancer effect, a rich flavor enhancer effect and an aroma enhancer effect.

[2] Sweetness enhancer A sweetness enhancer comprising 7a-hydroxymint lactone.
[3] Sweetener composition (1) A sweetener composition obtained by adding the above-mentioned sweetness enhancer to a sweetener, wherein the sweetener is sucrose, fructose, glucose, glucose-fructose syrup, or stevia extract. , Sweetener characterized in that it is one or more selected from the group consisting of, citrus extract, xylose, arabinose, rhamnose, erythritol, xylitol, mannitol, sorbitol, inositol, maltitol, isomaltulose and glycerin. Composition.
(2) The sweetener composition as described above, wherein the sweetener is sucrose, and 0.00625 to 12.5 mg of the sweetness enhancer is added to 100 g of sucrose.
(3) An oral product containing the above sweetener composition.

[4] Sweetness-enhancing flavor composition (1) A sweetness-enhancing flavor composition comprising the above-mentioned sweetness-enhancing agent added to the flavor.
(2) The sweetness enhancing flavor composition, wherein the amount of the sweetness enhancing agent added to the flavor is from 5 to 10,000 ppm.
(3) An oral product containing a sweetener with enhanced sweetness, characterized by comprising the above-mentioned sweetness enhancing flavor composition.
(4) An oral product containing a sweetener having an enhanced sweetness, characterized by comprising 0.01 to 1.0% by mass of the flavor-enhancing sweetening composition.

[5] Method for enhancing sweetness (1) A method for enhancing sweetness of a sweetener-containing oral product, which comprises adding the sweetness enhancer described above to an oral product containing a sweetener.
(2) Sweeteners include sucrose, fructose, glucose, high-fructose corn syrup, stevia extract, swingle extract, xylose, arabinose, rhamnose, erythritol, xylitol, mannitol, sorbitol, inositol, maltitol, isomaltulose and One or two or more selected from the group consisting of glycerin, wherein the sweetness enhancing method described above.
(3) The sweetness enhancing method as described above, wherein the amount of the sweetness enhancing agent added to the sweetener-containing oral product is in a concentration range of 0.005 to 10 ppm.
(4) A method for enhancing sweetness of an oral product containing a sweetener, which comprises adding 0.01 to 1.0% by mass of the above-mentioned sweetness enhancing flavor composition to an oral product containing the sweetener.

[6] Sweetness-enhancing oral product (1) In the step of producing an oral product containing a sweetener, 0.005 to 10 ppm of the sweetness-enhancing agent described above is added. Production method.
(2) In the step of producing an oral product containing a sweetener, 0.01 to 1.0% by mass of the above-mentioned sweetness enhancing flavor composition is added to the oral product having an enhanced sweetness. Production method.

[7] Rich taste enhancer (1) A rich taste enhancer comprising 7a-hydroxymint lactone.
(2) An oral product with enhanced kokumi, which is characterized in that the above kokumi enhancer is added (3) 0.005 to 10 ppm of the above kokumi enhancer is added An oral product with an enhanced rich taste.

[8] Fragrance composition for enhancing richness (1) A flavor composition for enhancing richness, characterized by comprising the flavor enhancing agent as described above.
(2) A flavor composition for enhancing body flavor, characterized in that the flavor enhancer is added to the flavor in an amount of 5 to 10,000 ppm.
(3) An oral product having an enhanced richness, which is obtained by adding the flavor composition for enhancing the richness.
(4) An oral product having an enhanced rich taste, which comprises 0.01 to 1.0% by mass of the flavor composition for enhancing the rich taste.

[9] Kokumi enhancement method (1) A kokumi enhancement method for an oral product, which comprises adding the above-mentioned kokumi enhancer to an oral product.
(2) A method for enhancing the full body taste of an oral product, which comprises adding 0.005 to 10 ppm of the above full body taste enhancer to the oral product.
(3) A method for enhancing the richness of an oral product, which comprises adding 0.01 to 1.0 mass% of the flavor composition for enhancing the richness to an oral product.

[10] Kokumi-enhanced oral product (1) In the step of producing an oral product, 0.005 to 10 ppm of the above-mentioned kokumi-enhancing agent is added, and a method for producing an oral product with enhanced kokumi ..
(2) A method for producing an oral product having an enhanced rich flavor, which comprises adding 0.01 to 1.0% by mass of the flavor composition for enhancing the rich flavor in the step of producing an oral product.

[11] Aroma enhancer (1) An aroma enhancer comprising 7a-hydroxymint lactone.
(2) A perfume-enhanced oral product or cosmetic product comprising the above-mentioned aroma enhancer.
(3) An oral product or cosmetic product having an enhanced aroma, which is characterized by comprising 0.005 to 500 ppm of the aroma enhancer described above.

[12] Fragrance composition (1) A fragrance composition comprising the fragrance enhancer as described above.
(2) A fragrance composition comprising the fragrance as described above and 5 to 500000 ppm added to the fragrance.
(3) An oral product or a cosmetic product having an enhanced aroma, characterized by comprising the above-mentioned flavor composition.
(4) An oral product or a cosmetic product having an enhanced fragrance, which comprises the addition of 0.01 to 2.0% by mass of the fragrance composition.

[13] Aroma enhancing method (1) A method for enhancing an aroma of an oral product or a cosmetic, comprising adding the above-mentioned aroma enhancing agent to an oral product or a cosmetic.
(2) A method for enhancing aroma of oral products or cosmetics, which comprises adding 0.005 to 500 ppm of the aroma enhancer to oral products or cosmetics.
(3) A method for enhancing the fragrance of an oral product or a cosmetic product, which comprises adding 0.01 to 2.0% by mass of the above fragrance composition to an oral product.

[14] Aroma-enhancing oral product or cosmetic product.
(1) A method for producing an oral product or a cosmetic product with an enhanced aroma, which comprises adding 0.005 to 500 ppm of the aroma enhancer in the step of manufacturing an oral product or a cosmetic product.
(2) A method for producing an oral product or cosmetic product having an enhanced fragrance, which comprises adding 0.01 to 2.0% by mass of the above-mentioned fragrance composition in a step of producing an oral product or cosmetic product. ..

The flavor enhancer of the present invention has a flavor enhancing action in addition to a sweetness enhancing action and a rich flavor enhancing action, so that not only sweeteners such as sucrose contained in foods and drinks but also salt and fat can be reduced. It is excellent in that it can be achieved with one agent at the same time. That is, from the viewpoint of taste improvement, the types and amounts of components to be added to foods and drinks can be reduced, which is advantageous.
When the sweetness enhancer of the present invention is added to sweet foods and beverages, the content of sucrose can be reduced in the case of a sweetened product sweetened with sucrose, which contributes to a reduction in calories and a high content other than sucrose. In the case of a diet product sweetened with a high intensity sweetener, the content of the high intensity sweetener can be reduced, so that the undesired taste (bitterness, astringency, etc.) can be reduced.

When the richness enhancer of the present invention is added to foods and drinks containing fat and salt, the lack of taste such as light taste is eliminated by enhancing the richness even if the salt or fat content of foods and drinks is reduced. can do.
Further, while it has the effect of enhancing sweetness and richness, it does not have a unique flavor by itself, and thus it is excellent in versatility in that it can be widely used in various foods and drinks without impairing the flavor.

Furthermore, since it also has an aroma enhancing effect, it can give excellent palatability to foods and drinks with reduced sweeteners, salt content, fat and the like.

[1] Flavor enhancer 7a-Hydroxymintlactone (CAS No. 514-93-2) used in the present invention is known as 3,6-dimethyl-7a-hydroxy-5,6,7,7a. -Tetrahydro-2(4H)-benzofuranone, which has the structure of the following formula (1).

7a-Hydroxymint lactone is an aroma component contained in mint essential oil (Non-Patent Document 1). However, nothing has been known about the sweetness enhancing effect of the compound with respect to sweeteners, the richness enhancing effect of oral products, and the like.
7a-Hydroxy mint lactone can be separated from mint essential oil, or synthetically obtained.
In the present invention, the one synthesized according to the method described in Non-Patent Document 2 was used. That is, it is a method in which mentofuran is subjected to an oxidation treatment with chromium trioxide in a methanol solvent and then purified.

[2] Oral product The oral product in the present invention specifically refers to food and drink and oral care products (oral hygiene products for keeping teeth and mouth clean).
There are no particular restrictions on the form of food or drink that is the subject of the present invention.
For example, fruits or processed products thereof, vegetables or processed products thereof, seafood or processed products thereof, paste products, cooked foods, side dishes, snacks, delicacies, processed foods, nutritional foods, tea beverages and coffee beverages, etc. Favorite beverages, fruit juice beverages, carbonated beverages, soft drinks, functional beverages, alcoholic beverages, ice cream, frozen desserts such as sorbets, desserts such as jellies, puddings and sheep cans, cookies, cakes, chocolate, chewing gum, sweets such as buns. Examples thereof include breads such as breads, confectionery breads and loaves, jams, ramune confectionery, tablets, and tablet confectionery.
Preferred beverages such as tea beverages and coffee beverages, fruit juice beverages, carbonated beverages, soft drinks, functional beverages, beverages such as alcoholic beverages, and the like, particularly preferably fruit juice beverages, carbonated beverages, very useful in soft drinks is there.

The form of the oral care product to which the present invention is applied is not particularly limited.
Examples include dentifrices, tooth gels, mouthwashes, mouth sprays, oral mousses, denture care products, lozenges, chewable tablets, and oral compositions in the form of strips that are applied directly to the teeth.

[3] Cosmetics There is no particular limitation on the form of the cosmetics targeted by the present invention.
Examples thereof include soap, shampoo for washing hair or body shampoo, disinfectant and fragrance for toilet and room, deodorant and disinfectant for clothes/cloth products/space.

[4] Use as a sweetness enhancer In a mode of using 7a-hydroxymint lactone as a sweetness enhancer, the sweetness enhancer is mixed with a sweetener such as sucrose to prepare a sweetener composition. Can be applied to foods and drinks, and a sweetness enhancer can be applied to oral products already containing a sweetener.

(1) Sweetener composition The sweetness enhancer of the present invention can be made into a sweetener composition by combining it with a natural or synthetic sweetener, and further with other components such as an excipient.
Examples of the sweetener to which the sweetness enhancer of the present invention is added include, for example, sucrose, fructose, glucose, high-fructose corn syrup, stevia extract, swingle extract, xylose, arabinose, rhamnose, as well as sugar alcohols, for example, Examples include, but are not limited to, erythritol, xylitol, mannitol, sorbitol, inositol, isomaltulose, maltitol, glycerin and combinations thereof.

When the sweetness enhancer of the present invention is added to a sweetener, the amount added is not particularly limited. In order to enhance the sweetness while improving the flavor without impairing the flavor, when the sweetener is sucrose, 0.00625 to 12.5 mg, preferably 0.00625, of a sweetness enhancer is added per 100 g of sucrose. It is preferable to add ˜6.25 mg, particularly preferably 0.0625 to 1.25 mg to make a sweetener composition.
If the added concentration is less than the above concentration range, the sweetness enhancing effect may not be sufficiently exhibited, and if it exceeds the above concentration range, the flavor may be modulated.

When the sweetener is other than sucrose, it is preferable to determine the addition amount in consideration of the sweetness intensity of each sweetener, and as an index of the sweetness intensity, the ratio of the threshold value of sucrose to the threshold value of the sweetening substance is " It is appropriate to use "sweetness".
Generally, when sucrose is 1, fructose 1.73, glucose 0.74, stevia extract 100 to 150, swingle extract 300, xylose 0.67, erythritol 0.7 to 0.8, xylitol 1.08 , Mannitol 0.69, sorbitol 0.54, and maltitol 0.8 to 0.95.
Therefore, when the sweetness enhancer of the present invention is added to sweeteners other than sucrose, it is appropriate to divide the above-mentioned addition amount by the sweetness of other sweeteners to the sweetness of 1 of sucrose.

(2) Application to sweetness-containing oral product When the sweetness enhancer of the present invention is added to an oral product having sweetness, the addition amount thereof is not particularly limited. In order to improve the flavor and enhance the sweetness without impairing the flavor, 0.005 to 10 ppm is exemplified as an appropriate concentration, preferably 0.05 to 10 ppm, particularly preferably 0.1 to 5 ppm. ..
If the added concentration is less than the above concentration range, the sweetness enhancing effect may not be sufficiently exhibited, and if it exceeds the above concentration range, the flavor may be modulated.
The sweetness enhancer of the present invention can be appropriately added by an ordinary method in any manufacturing process of an oral product.

[5] Use as Kokumi enhancer The kokumi in the present invention is a taste that cannot be expressed by the five basic tastes (sweetness, saltiness, bitterness, sourness, and umami), and has a volume, unity, spread, thickness, and richness, It refers to the sensation of enhancing the five basic tastes and expressing the deliciousness of food and drink, which is expressed as persistence.

Here, the richness as a taste is explained as follows in pages 58 to 59, published by the Ministry of Agriculture, Forestry and Fisheries (March 2012), “Japanese-Traditional Japanese Food Culture” edited by Isao Kumakura. ..
"The word "Koku" is very often used in Japan. "Koku" is one of the most important keywords to understand Japanese food preferences. It is not a specific ingredient or substance but a complex taste. The adjectives of "rich", "rich", "rich", "rich", "rich", etc. are somewhat similar expressions. It is used in the image of a complex depth and a charm that is not shallow. "There is a richness" is a word that praises food. Although it is vague, people share a rough nuance. Generally, when there is richness, it often means that many ingredients are intricately entangled with each other to bring about a richness of taste.When the individual taste is strongly felt, it disappears instead of richness. It is said that the food is refreshed when added, but it can also be said that the richness disappears due to the sourness.There are many ingredients and dishes that are recognized as rich.Foagra, internal organs such as ginger liver, fresh cream, cheese, butter etc. Dairy products, raw sea urchin, fish eggs such as caviar and mustard, salmon roe etc. Miso, soy sauce, curry powder, mayonnaise and other seasonings, marbling beef, tuna toro and other animal fats, a complex of ramen popular in Japan There are innumerable types of soup stock and back fat.
The characteristic of Koku is the spread in time and space. Spatial spread can be explained by the taste of many parts of the mouth and neural pathways. When you eat food, the sweetness and saltiness immediately felt at the tip of the tongue is the taste mediated by the chorda tympani nerve, and the umami taste and taste of oils and fats felt on the back and both sides of the tongue are the tastes transmitted by the glossopharyngeal nerve. Is. Not only the tongue but also the gums are mobilized to the touch. It seems that it is important for me to fully mobilize the sense of taste and parts.
Spreading time is also important for the body. It starts with a scent that you can bring close to your mouth, and a sharp taste that instantly stands in the first half of the tongue, and a taste that you can feel behind your tongue after a breath. In addition, the taste that gradually reveals the face while it is held in the mouth. Comfortable taste with a lingering finish even after swallowing. When you fully convince the taste that you get over time, you feel strongly that it is rich. "

When the kokumi enhancer of the present invention is added to an oral product, the amount added is not particularly limited. 0.005 to 10 ppm is exemplified as an appropriate concentration in order to enhance the flavor while improving the flavor without impairing the flavor, preferably 0.05 to 10 ppm, particularly preferably 0.1 to 5 ppm. It
If the added concentration is less than the above concentration range, the full-bodied taste enhancing effect may not be sufficiently exhibited, and if it exceeds the above concentration range, the flavor may be modulated.
The kokumi enhancer of the present invention can be appropriately added by an ordinary method in any manufacturing process of an oral product.

[6] Use as an aroma enhancer The aroma enhancer in the present invention is an effect of increasing the odor intensity without changing the odor quality of the added fragrance. This is also called the booster effect. The fragrance enhancer of the present invention is an extremely useful material that increases only the intensity of fragrance without imparting a particular odor or offensive odor to the added fragrance.
When the aroma enhancer of the present invention is added to an oral product or a cosmetic product, the amount added is not particularly limited. In order to improve the fragrance and enhance the fragrance without impairing the fragrance, 0.005 to 500 ppm is exemplified as an appropriate concentration, preferably 0.05 to 500 ppm, particularly preferably 0.05 to 200 ppm. ..
If the added concentration is less than the above concentration range, the aroma enhancing effect may not be sufficiently exerted, and if it exceeds the above concentration range, aroma may be modulated.

Oral products or cosmetics in which the aroma enhancer of the present invention is used are not particularly limited.
For example, fruits or processed products thereof, vegetables or processed products thereof, seafood or processed products thereof, paste products, cooked foods, side dishes, snacks, delicacies, processed foods, nutritional foods, tea beverages and coffee beverages, etc. Favorite beverages, fruit juice beverages, carbonated beverages, soft drinks, functional beverages, alcoholic beverages, ice cream, frozen desserts such as sorbets, desserts such as jellies, puddings and sheep cans, cookies, cakes, chocolate, chewing gum, sweets such as buns. Breads such as sweets, sweet bread, loaf bread, jams, ramune sweets, tablets, confectionery, toothpaste, tooth gel, mouthwash, mouth spray, oral mousse, denture care products, lozenges, Oral products such as chewable tablets and strips directly attached to teeth, soaps, shampoos for hair washing or body shampoos, sanitizers and fragrances for toilets and rooms, deodorants and sanitizers for clothes, cloth products and spaces. Agents and the like.
Among them, preferred beverages such as tea beverages and coffee beverages, fruit juice beverages, carbonated beverages, soft drinks, functional beverages, beverages such as alcoholic beverages, and the like, particularly preferably fruit juice beverages, carbonated beverages, very soft drinks It is useful.

[7] Use as a flavor composition In the case of adding a flavor enhancer showing one or more effects selected from the sweetness enhancing effect, kokumi enhancing effect and aroma enhancing effect of the present invention to oral products or cosmetics It is also effective to use as a perfume composition added to the perfume.
The fragrance used in that case is not particularly limited, and various conventionally used fragrances can be used according to the use and purpose.

For example, "Public Office Official Gazette Well-known Conventional Techniques Collection (Fragrance) Part II Food Flavors" (published on January 14, 2000, Japan Patent Office) and "JPO Official Gazette Well-known Conventional Technique Collection (fragrances)" ) Part III Fragrances for cosmetics" (published June 15, 2001, Japan Patent Office), etc. (essential oil, essence, concrete, absolute, extract, oleoresin, resinoid, Recovery flavor, carbon dioxide-extracted essential oil, isolated flavor, synthetic flavor, etc.).

When the fragrance enhancer of the present invention is added to a fragrance to form a fragrance composition, the addition amount is not particularly limited, but usually 5 to 500000 ppm is shown as an appropriate concentration in the fragrance composition, It is preferably 50 to 100,000 ppm, particularly preferably 50 to 10,000 ppm.
If the added concentration is less than the above concentration range, the aroma enhancing effect may not be sufficiently exhibited, and if it exceeds the above concentration range, the flavor may be modulated.

The above-mentioned fragrance composition is preferably used as a liquid fragrance containing a solvent, if necessary, for oral products, cosmetics and the like.
Here, as the solvent, esters such as diethyl phthalate and triethyl citrate; triacetin, medium chain fatty acid triglycerides, triglycerides such as animal and vegetable oils and fats; propylene glycol, dipropylene glycol, hexylene glycol, butyl diglycol, 1,3 -Glycols such as butylene glycol; alcohol ethers such as propylene glycol monomethyl ether, diethylene glycol monoethyl ether, 3-methyl-3-methoxybutanol; alcohols such as ethanol.
In addition, a mode of using the perfume composition as an emulsified perfume emulsified with a surfactant, and further by mixing with an excipient (modified starch, cyclodextone, etc.) and then drying (spray drying, freeze drying, etc.) The aspect used as a powdered flavor is also suitable.

Also. When the above fragrance composition is added to an oral product or a cosmetic product, the amount of addition is not particularly limited.
In order to enhance the aroma while improving the aroma without spoiling the peculiar aroma of the oral product or the cosmetic, 0.01 to 2.0 mass% in the oral product or the cosmetic is exemplified as an appropriate concentration, It is preferably 0.01 to 1.0% by mass, and particularly preferably 0.1 to 1.0% by mass.
If the added concentration is less than the above concentration range, the effect of improving and enhancing aroma may not be sufficiently exerted, and if it exceeds the above concentration range, the aroma of oral products or cosmetics may be modulated. is there.

When the flavor enhancer (sweetness and richness) of the present invention is added to the flavor composition, the addition amount thereof is not particularly limited.
In order to exert the sweetness enhancing effect and/or the richness enhancing effect while improving the flavor without impairing the flavor peculiar to the oral product, 5 to 10000 ppm in the flavor composition is exemplified as an appropriate concentration, and preferably 5 to 5000 ppm, particularly preferably 10 to 5000 ppm is exemplified.
If the added concentration is less than the above concentration range, the flavor improving effect may not be sufficiently exhibited, and if it exceeds the above concentration range, the flavor of the oral product may be modulated.

Also. When the flavor composition is added to an oral product, the amount added is not particularly limited.
In order to exert the sweetness enhancing effect and/or the rich body enhancing effect while improving the flavor without deteriorating the peculiar flavor of the oral product, 0.01 to 1.0% by mass in the oral product is a proper concentration. It is exemplified, preferably 0.01 to 0.5% by mass, particularly preferably 0.1 to 0.5% by mass.
If the added concentration is less than the above concentration range, the flavor improving effect may not be sufficiently exhibited, and if it exceeds the above concentration range, the flavor of the oral product may be modulated.

The flavor enhancer (sweetness enhancer, kokumi enhancer, aroma enhancer) of the present invention may optionally contain other components in addition to the above-mentioned flavors.
Components that can be optionally added include various acidulants, various emulsifiers, various solvents that can be used in food and drink, various excipients, various sweeteners, various colorants, and the like.
The flavor improving agent of the present invention can be appropriately added at any stage of processing oral products and cosmetics.

The present invention will be specifically described below with reference to examples, but the present invention is not limited to the description of the examples.

[raw materials]
7a-hydroxymint lactone, which is a flavor enhancer (sweetness enhancer, kokumi enhancer, aroma enhancer), was produced according to the method described in Non-Patent Document 2. That is, a commercially available mentfuran was produced by subjecting it to oxidation treatment with chromium trioxide in a methanol solvent and then performing a refining operation.
In addition, commercial products were used for the granulated sugar (sucrose), milk, etc. used for sample preparation, and our products were used for various flavors such as lemon flavors.

[Examples 1 to 3]
Using the sweetness improver of the present invention, granulated sugar, and water, the granulated sugar solutions of Examples 1 to 3 were prepared according to the formulations shown in Table 1.
As a control, a granulated sugar solution was prepared in which only ethanol was added instead of the sweetness enhancer.

[Test Example 1]
A sensory evaluation was conducted on the granulated sugar solutions of Examples 1 to 3 and the control product.
The evaluation items were sweetness and presence/absence of off-flavours, and were evaluated by a panel of 10 trained persons. The sweetness evaluation standard was a 7-point relative evaluation in which the evaluation value of the control product was 4, the feeling was 7 when it was very strongly felt, and 1 was when it was felt very weakly.
The results are shown in Table 2.

From the results shown in Table 2, it was found that the addition of the appropriate amount of the sweetness enhancer of the present invention has the effect of enhancing the sweetness of the granulated sugar without causing a strange off-flavor.

[Examples 4 to 6]
Using the flavor enhancers (sweetness enhancer and kokumi enhancer) of the present invention, granulated sugar, water and milk, the milk beverages of Examples 4 to 6 were prepared according to the formulations shown in Table 3.
As a control, a milk drink was prepared in which only ethanol was added instead of the flavor enhancer.

[Test Example 2]
A sensory evaluation was performed on the milk drinks of Examples 4 to 6 and the control product.
As the evaluation items, a richness (spreading, thickness, persistence) was added in addition to the sweetness, the evaluation criteria were the same as in Test Example 1, and the results are shown in Table 4.

From the results of Table 4, by adding an appropriate amount of the flavor enhancer (sweetness enhancer, kokumi enhancer) of the present invention, the effect of enhancing the sweetness and kokumi of a milk drink without impairing the flavor of milk. Was seen.

[Examples 7 to 11]
Using the flavor enhancer of the present invention, water, and orange flavor, the orange beverages (flavored water) of Examples 7 to 11 were prepared according to the formulations in Table 5. As a control, an orange drink was prepared in which only ethanol was added instead of the aroma enhancer.

[Test Example 3]
A sensory evaluation was conducted on the orange beverages of Examples 7 to 11 and the control product.
The evaluation items were the strength of the scent and the presence/absence of off-flavor and off-flavor. The evaluation standard of the scent intensity was a 7-point relative evaluation in which the evaluation value of the control product was 4, 7 was a strong feeling, and 1 was a very weak feeling. The results are shown in Table 6.

From the results shown in Table 6, the effect of enhancing the flavor of the orange beverage was observed by adding an appropriate amount of the flavor enhancer of the present invention without imparting a strange off-flavor to the orange flavor.

[Examples 12 to 16]
Using the flavor enhancer of the present invention, water, plain yogurt, fructose-glucose liquid sugar, and yogurt flavor, the yogurt beverages of Examples 12 to 16 were prepared according to the formulations in Table 7. As a control, a yogurt drink was prepared in which only ethanol was added instead of the aroma enhancer.

[Test Example 4]
Sensory evaluation was performed on the yogurt beverages of Examples 12 to 16 and the control product.
The evaluation items were the strength of the scent and the presence/absence of off-flavor and off-flavor.
The evaluation standard of the scent intensity was a 7-point relative evaluation in which the evaluation value of the control product was 4, 7 was a strong feeling, and 1 was a very weak feeling. The results are shown in Table 8.

From the results in Table 8, it was found that the addition of the appropriate amount of the flavor enhancer of the present invention has the effect of enhancing the flavor without imparting an off-flavor to the yogurt flavor.

[Examples 17 to 20]
The lemon beverages of Examples 17 to 20 were prepared according to the formulation of Table 9 using the flavor enhancer (sweetness, richness, aroma) of the present invention, granulated sugar, water, citric acid and lemon flavor.
As a control, a lemon drink to which only ethanol was added instead of the flavor enhancer was prepared.

[Comparative Examples 1 to 3]
In Comparative Examples 1 to 3, instead of the flavor enhancer of the present invention according to the formulation of Table 10, 7a-ethoxymint lactone (an analogue of 7a-hydroxymint lactone described as 3-ethoxymint lactone in Patent Document 7) was used. A lemon drink was prepared by adding a compound (synthesized according to the patent document).
Moreover, the lemon drink which added ethanol was prepared as a control.

[Test Example 5]
Sensory evaluation was performed on the lemon beverages obtained in Examples 17 to 20 and Comparative Examples 1 to 3.
The evaluation items were sweetness, richness, presence/absence of aroma enhancing effect, and presence/absence of off-taste and off-odor, and evaluated by a panel of 10 trained persons. For the evaluation of sweetness, richness (spreading, thickness, persistence) and aroma enhancing effect, the presence or absence was evaluated based on the evaluation value of each item of the control product. The results are shown in Table 11.

From the results in Table 11, it was found that the addition of the flavor enhancer of the present invention in an appropriate amount has the effect of enhancing the sweetness, richness and aroma of the lemon beverage without impairing the flavor of the lemon. In addition, 7a-ethoxy mint lactone has a strong scent of itself, and even if added at 0.1 ppm, it has an offensive odor, and it is difficult to enhance the sweetness, richness and aroma without impairing the flavor of the lemon beverage. there were.

[Example 21]
Fragrance composition 1 was prepared by adding 0.5% by mass of 7a-hydroxymint lactone to vanilla flavor (Ogawa Fragrance Co., Ltd.).
This vanilla flavored ice cream of the present invention containing 5 ppm of 7a-hydroxymint lactone (0.1 ml by weight of the flavor composition 1) (this ice cream contains sucrose as a sweetener) is 7a-hydroxymint. Compared to the vanilla flavored ice cream prepared using a vanilla flavor without addition of lactone, the sweetness, richness and aroma were enhanced without impairing the flavor.

[Example 22]
Fragrance composition 2 was prepared by adding 1.0% by mass of 7a-hydroxymint lactone to chocolate flavor (Ogawa Fragrance Co., Ltd.).
The chocolate-flavored soft candy of the present invention containing 10 ppm of 7a-hydroxy mint lactone (this soft candy contains sucrose as a sweetener) containing 0.1 ppm by mass of the flavor composition 2 is 7a-hydroxy mint. Compared to the soft candy produced by using the chocolate flavor without addition of lactone, the sweetness, richness and aroma were enhanced without impairing the flavor.

[Example 23]
A flavor composition 3 was prepared by adding 1.0% by mass of 7a-hydroxymint lactone to butter flavor (Ogawa Fragrance Co., Ltd.).
The butter flavored cookie of the present invention containing 200 ppm of 7a-hydroxymint lactone, to which 2.0% by mass of the flavor composition 3 was added, was compared with a cookie prepared using a butter flavor without addition of 7a-hydroxymint lactone. The aroma was enhanced without impairing the flavor.

[Example 24]
Fragrance composition 4 was prepared by adding 1.0% by mass of 7a-hydroxymint lactone to grapefruit flavor (Ogawa Fragrance Co., Ltd.).
The grapefruit-flavored tablet candy of the present invention containing 10 ppm of 7a-hydroxy mint lactone (0.1 tablet) containing 0.1% by mass of the flavor composition 4 is 7a-hydroxy mint. Compared with the tablet candy produced using the grapefruit flavor without addition of lactone, the sweetness and richness and the aroma were enhanced without impairing the flavor.

[Example 25]
Perfume composition 5 was prepared by adding 0.5% by mass of 7a-hydroxymint lactone to Peach fragrance (manufactured by Ogawa Fragrance Co., Ltd.).
The peach flavored soft drink of the present invention containing 5 ppm of 7a-hydroxy mint lactone (this soft drink contains fructose and glucose as sweeteners) containing 7 ppm of 7a-hydroxy mint lactone containing 0.1% by mass of the flavor composition 5 is 7a-hydroxy. Compared to the soft drink prepared from peach flavor without mint lactone, sweetness, richness and aroma were enhanced without impairing the flavor.

[Example 26]
The peach-flavored soft drink of the present invention containing 5 ppm of 7a-hydroxy mint lactone, to which 0.5% by mass of the flavor composition 5 was added (the soft drink contains stevia extract as a sweetener) is 7a-hydroxy mint. Compared with the soft drink produced using the peach flavor without addition of lactone, sweetness and richness and aroma were enhanced without impairing the flavor.

[Example 27]
Fragrance composition 6 was prepared by adding 1.0% by mass of 7a-hydroxymint lactone to grape flavor (Ogawa Fragrance Co., Ltd.).
Grape-flavored yogurt of the present invention containing 10 ppm of 7a-hydroxymint lactone containing 0.1% by mass of the flavor composition 6 (the yogurt contains sucrose as a sweetener) does not contain 7a-hydroxymint lactone. Compared with the yogurt prepared using the added grape flavor, the sweetness and richness and the aroma were enhanced without impairing the flavor.

[Example 28]
Fragrance composition 7 was prepared by adding 0.5% by mass of 7a-hydroxymint lactone to Apple flavor (Ogawa Fragrance Co., Ltd.).
The apple flavored jelly of the present invention containing 5 ppm of 7a-hydroxymint lactone (this jelly contains Stevia extract as a sweetener) containing 0.1% by mass of the flavor composition 7 is 7a-hydroxymint lactone. Compared with the jelly produced using the additive-free apple flavor, the sweetness, richness, and aroma were enhanced without impairing the flavor.

Example 29
A flavor composition 8 was prepared by adding 0.1% by mass of 7a-hydroxymint lactone to Matcha flavor (manufactured by Ogawa Fragrance Co., Ltd.).
The matcha-flavored chocolate of the present invention containing 1 ppm of 7a-hydroxymint lactone (this chocolate contains sucrose as a sweetener) containing 0.1% by mass of the flavor composition 8 does not contain 7a-hydroxymint lactone. The sweetness, richness and aroma were enhanced without impairing the flavor, as compared with the chocolate produced using the added matcha flavor.

[Example 30]
Perfume composition 9 was prepared by adding 5.0% by mass of 7a-hydroxymint lactone to peppermint flavor (Ogawa Fragrance Co., Ltd.).
The mint flavored gum of the present invention containing 500 ppm of 7a-hydroxy mint lactone containing 1.0% by mass of the flavor composition 9 is a mint flavored gum prepared using a peppermint flavor without addition of 7a-hydroxy mint lactone. In comparison, the aroma was enhanced without impairing the flavor.

[Example 31]
The mint flavored toothpaste of the present invention containing 0.1 ppm by mass of the fragrance composition 9 and containing 50 ppm of 7a-hydroxymint lactone is compared with the toothpaste prepared by using the peppermint flavor without addition of 7a-hydroxymint lactone. The aroma was enhanced without impairing the flavor.

[Example 32]
1.0% by mass of 7a-hydroxymint lactone was added to coffee flavor (manufactured by Ogawa Fragrance Co., Ltd.) to prepare flavor composition 10.
The coffee beverage of the present invention containing 10 ppm of 7a-hydroxymint lactone containing 0.1% by mass of the flavor composition 10 (the coffee beverage contains sugar and milk) contains 7a-hydroxymint lactone. Compared to the coffee drink produced using a flavor, the sweetness and richness and the aroma were enhanced without impairing the flavor.

[Example 33]
The sugar-free black coffee of the present invention containing 10 ppm of 7a-hydroxymint lactone, to which 0.1% by mass of the flavor composition 10 is added, is a sugar-free black coffee produced using a flavor without addition of 7a-hydroxymint lactone. In comparison, the rich taste and the aroma were enhanced without impairing the flavor.

Example 34
A flavoring composition 11 was prepared by adding 0.1% by mass of 7a-hydroxymint lactone to black tea flavoring (Ogawa Fragrance Co., Ltd.).
The black tea beverage of the present invention containing 0.1% by mass of the flavor composition 11 (the black tea beverage contains a saccharide) is compared with a black tea beverage prepared using a flavor without addition of 7a-hydroxymintlactone. The sweetness, richness and aroma were enhanced without impairing the flavor.

Example 35
5.0% by mass of 7a-hydroxymint lactone was added to a spice flavor (Ogawa Fragrance Co., Ltd.) to prepare a flavor composition 12.
The meat sauce of the present invention containing 100 ppm of 7a-hydroxy mint lactone, to which 0.2% by mass of the fragrance composition 12 is added, has a flavor that is higher than that of the meat sauce prepared using the fragrance without 7a-hydroxy mint lactone. The fragrance was enhanced without damaging.

Example 36
Fragrance composition 13 was prepared by adding 0.5% by mass of 7a-hydroxymint lactone to a fragrance fragrance manufactured by Ogawa Fragrance Co., Ltd.
A suitable amount of this fragrance composition 13 added to ethanol in an amount of 1% by mass was dropped on a test paper, and the fragrance intensity was confirmed several minutes later. As a result, it was compared with a fragrance fragrance containing no 7a-hydroxymint lactone. The fragrance was enhanced.

By adding the flavor enhancer of the present invention, there is an effect of simply enhancing the sweetness of the sweetener without impairing the flavor of the oral product containing the sweetener, and also enhancing the richness of the oral product. In addition, the fragrance can be enhanced, and it can be widely used including cosmetics.

Claims (40)

1. A flavor enhancer characterized by comprising 7a-hydroxymint lactone.
2. The flavor enhancer according to claim 1, wherein the flavor enhancing effect is one or more selected from a sweetness enhancing effect, a rich flavor enhancing effect and an aroma enhancing effect.
3. A sweetness enhancer characterized by comprising 7a-hydroxymint lactone.
4. A sweetener composition comprising a sweetener and 7a-hydroxymint lactone as a sweetness enhancer added, wherein the sweetener is sucrose, fructose, glucose, glucose-fructose syrup, stevia extract, lakhanga extract, A sweetener composition comprising one or more selected from the group consisting of xylose, arabinose, rhamnose, erythritol, xylitol, mannitol, sorbitol, inositol, maltitol, isomaltulose and glycerin.
5. 5. The sweetener composition according to claim 4, wherein the sweetener is sucrose, and 0.00625 to 12.5 mg of 7a-hydroxymint lactone as a sweetness enhancer is added per 100 g of sucrose.
6. An oral product comprising the sweetener composition according to claim 4 or 5 added thereto.
7. A sweetness-enhancing fragrance composition, wherein 7a-hydroxymint lactone as a sweetness-enhancing agent is added to the fragrance.
8. The sweetness enhancing flavor composition according to claim 7, wherein the amount of the sweetness enhancing agent added to the flavor is 5 to 10,000 ppm.
9. An oral product containing a sweetener with enhanced sweetness, comprising the flavor composition for sweetness enhancement according to claim 7 or 8.
10. An oral product containing a sweetener, wherein the sweetness enhancing flavor composition according to claim 7 or 8 is added in an amount of 0.01 to 1.0% by mass.
11. A method for enhancing sweetness of a sweetener-containing oral product, which comprises adding 7a-hydroxymint lactone as a sweetness enhancer to an oral product containing a sweetener.
12. The sweetener consists of sucrose, fructose, glucose, fructose corn syrup, stevia extract, swingle extract, xylose, arabinose, rhamnose, erythritol, xylitol, mannitol, sorbitol, inositol, maltitol, isomaltulose and glycerin. The method for enhancing sweetness according to claim 11, wherein the method is one or more selected from the group.
13. 13. The sweetness enhancing method according to claim 11 or 12, wherein the amount of 7a-hydroxymint lactone added as a sweetness enhancing agent to the sweetener-containing oral product is in the concentration range of 0.005 to 10 ppm.
14. 9. A sweetness enhancer for an oral product containing a sweetener, comprising adding 0.01 to 1.0% by mass of the flavor enhancer composition for sweetening according to claim 7 or 8 to an oral product containing the sweetener. Method.
15. A method for producing an oral product with enhanced sweetness, which comprises adding 0.005 to 10 ppm of 7a-hydroxymint lactone as a sweetness enhancer in the step of producing an oral product containing a sweetener.
16. In the process of producing an oral product containing a sweetener, 0.01 to 1.0% by mass of the sweetness enhancing flavor composition according to claim 7 or 8 is added, and the oral sweetness is enhanced. Product manufacturing method.
17. A rich flavor enhancer characterized by comprising 7a-hydroxymint lactone.
18. An oral product with enhanced richness, which is characterized in that 7a-hydroxymint lactone is added as a richness enhancer.
19. An oral product with an enhanced aroma, which is characterized by adding 0.005 to 10 ppm of 7a-hydroxymint lactone as an aroma enhancer.
20. A flavor composition for enhancing aroma, characterized in that 7a-hydroxymint lactone as a flavor enhancer is added to the flavor.
21. A flavor composition for enhancing aroma, characterized in that 5 to 10000 ppm of 7a-hydroxymint lactone as a flavor enhancer is added to the flavor.
22. An oral product with an enhanced richness, characterized by comprising the flavor composition for enhancing the richness according to claim 20 or 21.
23. An oral product with an enhanced richness, characterized by comprising 0.01 to 1.0% by mass of the flavor-enhancing flavoring composition according to claim 20 or 21.
24. A method for enhancing the richness of an oral product, which comprises adding 7a-hydroxymint lactone as a richness enhancer to the oral product.
25. A method for enhancing the full-bodied taste of an oral product, which comprises adding 0.005 to 10 ppm of 7a-hydroxymint lactone as a full-bodied taste enhancer to the oral product.
26. A method for enhancing the richness of an oral product, which comprises adding 0.01 to 1.0 mass% of the flavor composition for enhancing the richness according to claim 20 or 21 to the oral product.
27. A method for producing an oral product having an enhanced body taste, which comprises adding 0.005 to 10 ppm of 7a-hydroxymint lactone as a body taste enhancer in the step of producing the oral product.
28. In the step of producing an oral product, 0.01 to 1.0% by mass of the flavor-enhancing flavoring composition according to claim 20 or 21 is added to produce an oral product with enhanced aroma. Method.
29. An aroma enhancer characterized by comprising 7a-hydroxymint lactone.
30. An aroma-enhanced oral product or cosmetic product, which is characterized by comprising 7a-hydroxymint lactone as an aroma enhancer.
31. An aroma-enhanced oral product or cosmetic product comprising 0.005 to 500 ppm of 7a-hydroxymint lactone as an aroma enhancer.
32. A fragrance composition characterized in that 7a-hydroxymint lactone as a fragrance enhancer is added to the fragrance.
33. A fragrance composition characterized in that 5 to 500000 ppm of 7a-hydroxymint lactone as a fragrance enhancer is added to the fragrance.
34. An oral product or a cosmetic product having an enhanced fragrance, which is obtained by adding the fragrance composition according to claim 32 or 33.
35. An aroma-enhanced oral product or cosmetic product, comprising 0.01 to 2.0% by mass of the fragrance composition according to claim 32 or 33.
36. A method for enhancing aroma of oral products or cosmetics, which comprises adding 7a-hydroxymint lactone as an aroma enhancer to oral products or cosmetics.
37. A method for enhancing aroma of oral products or cosmetics, which comprises adding 0.005 to 500 ppm of 7a-hydroxymint lactone as an aroma enhancer to oral products or cosmetics.
38. A method for enhancing aroma of an oral product or cosmetic, comprising adding 0.01 to 2.0 mass% of the perfume composition according to claim 32 or 33 to the oral product or cosmetic.
39. A method for producing an oral product or cosmetic product having an enhanced aroma, which comprises adding 0.005 to 500 ppm of 7a-hydroxymint lactone as an aroma enhancer in the process of manufacturing an oral product or a cosmetic product.
40. An oral product or cosmetic product having an enhanced fragrance, which comprises adding 0.01 to 2.0% by mass of the fragrance composition according to claim 32 or 33 in the step of producing an oral product or cosmetic product. Production method.