JP2008194015A - Citrus-containing food and drink additive comprising kahweofuran or its related variety - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a citrus-containing food and drink additive with which food and drink having finely qualified aroma which just-squeezed citrus has. <P>SOLUTION: The citrus-containing food and drink additive is obtained by adding kahweofuran or its related variety to citrus-containing food and drink having 10<SP>-6</SP>-10<SP>-1</SP>ppb so as to increase natural sweetness and moderately acidic feeling without spoiling balance between the finely qualified profound aroma and taste inherent in just-squeezed citrus, to produce a citrus-containing food and drink having aroma with fruit juice feeling, and favorably qualified taste particular to respective citrus. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

The present invention relates to a citrus-containing food and drink additive, a flavor composition to which the citrus-containing food and drink additive is added, and a citrus-containing food and drink to which the citrus-containing food and drink additive or the flavor composition is added. .

At present, a wide variety of fragrances derived from citrus fruits have already been used. However, with the recent diversification of foods and cosmetics, discovery of materials having further characteristics is desired. For example, there is a demand for the development of a fragrance with enhanced natural sweetness and moderate sourness without breaking the balance of the high quality aroma and flavor of freshly squeezed citrus juice.

A method of using a flavor improver containing an epoxy alkanal to give a fresh fruit feeling inherent to fruits (see, for example, Patent Document 1), or a cis-4,5-epoxy-2E-decenal having a fresh fruit juice feeling It is known that the use of can enhance the feeling of fruit juice and give a natural feeling (see, for example, Patent Document 2).

JP 2004-115754 A Japanese Patent Laying-Open No. 2005-082771

However, these methods have not been able to impart a good flavor with enhanced natural sweetness and moderate sourness without losing the balance between the high-quality aroma and flavor of the squeezed citrus fruit juice.

The present invention relates to a citrus-containing food / beverage additive that has a natural sweetness and a moderate sour taste, and that imparts a fragrance that is inherently unique to citrus fruits and a high-quality flavor, and the citrus-containing food / beverage additive An object of the present invention is to provide a flavoring composition containing citrus and the citrus-containing food / beverage additive, or a citrus-containing food / beverage to which the flavoring composition is added.

In order to solve the above-mentioned problems, the present inventors have conducted intensive studies, and as a result, added café-off run or its analogs to citrus-containing foods and drinks, particularly beverages containing citrus juice or jelly containing citrus juice. It has been found that citrus-containing foods and drinks with natural sweetness and moderate sourness can be obtained without losing the balance of the high-quality aromas and flavors of freshly squeezed fruit juices, and each of them has a peculiar fruit juice feeling. The present invention has been completed. That is, this invention consists of the additive for citrus-containing food-drinks which consists of a cafe off run or its analog. Furthermore, the present invention comprises a flavoring composition characterized in that a concentration of 10 ⁻⁴ to 10 ppb of caffeine offran or an analog thereof is added. The present invention further comprises a citrus-containing food / beverage product characterized in that a concentration of 10 ⁻⁶ to 10 ⁻¹ ppb of caffeine offran or an analog thereof is added.

That is, the present invention is as follows:
Item 1. An additive for citrus-containing food and drink comprising a cafe-off run represented by the general formula (1) or an analogue thereof.

（式中、Ｒ^１およびＲ^２はそれぞれ同一または異なって水素原子または炭素数１乃至４の低級アルキル基を示す（但し、Ｒ^１およびＲ^２が同時に水素原子であるものは除く））
項２．一般式（１）で示されるカフェオフランまたはその類縁体を１０⁻⁴〜１０ｐｐｂの濃度添加したことを特徴とする柑橘類含有飲食品用香味料組成物。
項３．一般式（１）で示されるカフェオフランまたはその類縁体を１０⁻⁶〜１０⁻¹ｐｐｂの濃度添加したことを特徴とする柑橘類含有飲食品。
項４．柑橘類含有飲食品が柑橘果汁または果肉入り飲料である項３記載の柑橘類含有飲食品。

(In the formula, R ¹ and R ² are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms (except that R ¹ and R ² are hydrogen atoms at the same time)).
Item 2. A citrus-containing flavor composition for foods and drinks, wherein a concentration of 10 ⁻⁴ to 10 ppb of caffeine or its analog represented by the general formula (1) is added.
Item 3. A citrus-containing food or drink characterized by adding a concentration of 10 ⁻⁶ to 10 ⁻¹ ppb of caffeine offran represented by the general formula (1) or an analog thereof.
Item 4. Item 4. The citrus-containing food or drink according to Item 3, wherein the citrus-containing food or drink is a citrus juice or a beverage containing pulp.

The additive for citrus-containing food and drink according to the present invention is characterized by using café-off run or an analog thereof.

Here, caffeofran (compound name: 6-methyl-2,3-dihydrothieno [2,3-c] furan) is a characteristic aroma component substance present in coffee by M. Stoll et al. In 1963. Isolated compound (Helv. Chim. Acta, 50, 628, (1967)). The structure was determined by G. Buchi et al. And was found to have the structure shown in the following formula, and was named caffeine offrun (J. Org. Chem., 36,199, (1971))

カフェオフランの合成法は、G.Buchiらによる方法（J.Org.Chem., 36,199,(1971)）、E.Brennaらによる方法（J.Chem.Research(S),74,(1998)、J.Chem.Research(M),551,(1998)）などが知られている。本発明は、カフェオフランだけでなく、下式に示される構造をもつカフェオフランの類縁体を含むものである。カフェオフラン誘導体およびのその製法は、例えば特願２００６−０４５３９１を例示することができる。

The method of synthesizing caffeine off-run is the method by G. Buchi et al. (J. Org. Chem., 36,199, (1971)), the method by E. Brenna et al. (J. Chem. Research (S), 74, (1998), J. Chem. Research (M), 551, (1998)) is known. The present invention includes not only café-off run but also café-off run analogs having the structure shown in the following formula. Japanese Patent Application No. 2006-045391 can be cited as an example of the café-off-run derivative and its production method.

（式中、Ｒ^１およびＲ^２はそれぞれ同一または異なって水素原子または炭素数１乃至４の低級アルキル基を示す（Ｒ^１およびＲ^２が同時に水素原子であるものは除く））

(In the formula, R ¹ and R ² are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms (excluding those in which R ¹ and R ² are hydrogen atoms at the same time)).

Examples of the lower alkyl group having 1 to 4 carbon atoms of R ¹ and R ² include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert -A butyl group is mentioned, but a methyl group or an ethyl group is particularly preferred.

Preferred analogs of caffeofran include, for example, 6-ethyl-2,3-dihydrothieno [2,3-c] furan, 4,6-dimethyl-2,3-dihydrothieno [2,3-c] furan, 4 -Methyl-2,3-dihydrothieno [2,3-c] furan, 4-ethyl-2,3-dihydrothieno [2,3-c] furan, 4-methyl-6-ethyl-2,3-dihydrothieno [2 , 3-c] furan, 4-ethyl-6-methyl-2,3-dihydrothieno [2,3-c] furan, 4,6-diethyl-2,3-dihydrothieno [2,3-c] furan. be able to.

Caffe offrans (2,3-dihydrothieno [2,3c] furan compounds) have a unique aroma depending on the type of the compound. For example, caffeine offran is a 0.000005% by weight diluted aqueous solution. In some cases, it has a roasted nutty aroma, a vegetable-like green aroma, or a caramel-like sweet aroma.

Ethyl caffeofuran, in which R ¹ is hydrogen and R ² is an ethyl group, has a sweet and roasted scent when diluted to 0.000005% by mass, and both R ¹ and R ² are methyl groups. When a 0.000005 mass% diluted aqueous solution is used, the dimethyl caffeine offran exhibits a green bean-like scent with a green color, a green scent of vegetables, or a fresh scent.

When these cafe-off runs or their analogs are added to citrus juices and / or beverages containing pulp, natural sweetness and moderate sourness are enhanced without breaking the balance of the high-quality aromas and flavors of freshly squeezed juice It has not been known to impart a citrus-specific fruit juice feeling.

The cafe-off run of the present invention or an analog thereof has the above-mentioned fragrance, but it is 10 ⁻⁶ to 10 ⁻¹ ppb, more preferably 10 ⁻⁵ to citrus-containing food and drink, particularly beverages containing citrus juice. Only when used in the range of 10 ⁻² ppb, more preferably 10 ⁻⁴ to 10 ⁻³ ppb, natural sweetness can be obtained without breaking the balance of the high quality aroma and flavor of the freshly squeezed fruit juice. A moderate increase in sourness and a fruit juice peculiar to each citrus fruit could be imparted. If the content is lower than 10 ^-6 ppb, it cannot give a natural sweetness and a moderately enhanced sour taste, and a fruity fragrance and a good quality flavor. If the content is higher than 10 ^-1 ppb, it is uncomfortable. The smell becomes strong and it is no longer suitable for citrus juice drinks.

Citrus-containing foods and beverages of the present invention are plants belonging to the citrus family, citrus subfamily, citrus, miscellaneous cans, oranges, grapefruits, perfumed citrus, buntans, tanzeros, tangoles, kumquats, karatachis ) Fruit itself, fruit juice, and foods and drinks to which these powders, extracts (extracts), etc. are added, for example, ice cream, frozen desserts such as sherbet, desserts such as jelly, pudding, jam, cookies, cakes, chocolate, Examples include confectionery such as chewing gum and candy, breads such as confectionery bread and bread, fillings such as flower paste, Japanese confectionery containing citrus fruits such as buns, sheep kan and iro, and confectionery, especially citrus juice and / or pulp Examples include beverages, soft drinks, carbonated drinks, and alcoholic drinks.

The additive for food and drink containing citrus fruits of the present invention only needs to contain café-off run or an analogue thereof, or only the cafe-off run or an analogue thereof is used, or a diluent, carrier or other component other than these ingredients. An additive may be contained.

The diluent or carrier is not particularly limited as long as it does not interfere with the effects of the present invention, and examples thereof include sugar, fructose, glucose, dextrin, starches, cyclodextrin, trehalose, lactose, maltose, starch syrup, and liquid sugar. Sugars; alcohols such as ethanol, propylene glycol, glycerin; sugar alcohols such as sorbitol, mannitol, xylitol, erythritol, maltitol; polysaccharides such as gum arabic, xanthan gum, carrageenan, guar gum, gellan gum; or water it can. Examples of the additive include antioxidants, auxiliaries such as chelating agents, fragrances, spice extracts, preservatives, and the like.

For convenience in use, etc., when preparing an additive for citrus-containing food or drink using these diluents, carriers or additives, the cafe-off run or its analog is 10 in the additive for citrus-containing food or drink. It is desirable to prepare such that it is contained at ^{−4 to} 10 ppb, preferably 10 ^{−3 to 1} ppb.

In addition, as an antioxidant used as an additive here, what is used as a food additive can be illustrated widely. For example, but not limited to, erythorbic acids such as erythorbic acid and its salts (for example, sodium erythorbate); sulfites such as sodium sulfite, sodium hyposulfite, sodium pyrosulfite or potassium pyrosulfite; α-tocopherol, mixed tocopherol, etc. Tocopherols; dibutylhydroxytoluene (BHT), butylhydroxyanisole (BHA), etc .; ethylenediaminetetraacetic acids such as disodium calcium ethylenediaminetetraacetate and disodium ethylenediaminetetraacetate; gallic acids such as gallic acid and propyl gallate; Extract, Aspergillus terreus extract, Licorice oily extract, Edible canna extract, Globe extract, Essential oil removal fennel extract, Horseradish extract, Sage extract, Seri Extract, tea extract, tempeh extract, dokudami extract, fresh coffee bean extract, sunflower seed extract, pimenta extract, grape seed extract, blueberry leaf extract, propolis extract, hego ginkgo biloba extract, Pepper extract, spinach extract, eucalyptus leaf extract, gentian root extract, rutin (extract) (red bean whole plant, enju, buckwheat whole plant extract), rosemary extract, clove extract, apple extract, etc. Extracts from various plants: Enzyme-treated rutin, quercetin, rutin enzyme-degraded product (isoquercitrin), enzyme-treated isoquercitrin, enzyme-decomposed apple extract, sesame oil extract, rapeseed oil extract, rice bran oil extract, A rice bran enzyme degradation product etc. can be mentioned. Preferably, plant extracts such as Enju extract, rutin (extract), green coffee bean extract, rosemary extract; enzyme-treated rutin, rutin enzyme degradation product (isoquercitrin), enzyme-treated isoquercitrin, etc. Can be mentioned.

Particularly preferred antioxidants in the present invention include flavonols. Examples of the flavonols include flavonols and flavonol glycosides having flavonols in the aglycon part. For example, what can be obtained by extracting from plants such as Enju, Tartary buckwheat, and Dokudami, and purified products obtained by purifying them, and those subjected to various treatments such as enzyme treatment or hydrolysis can be mentioned. Specifically, rutin, isoquercitrin, and the like, and glycosylrutin obtained by processing by a known method using a glycosyltransferase in the presence of rutin, isoquercitrin and starch are exemplified. Can do. These flavonols may be used alone or in any combination of two or more.

Moreover, it can replace with flavonol itself and can also use the plant extract containing various flavonols hung up above as it is. Examples of such are an enju extract, a tartary buckwheat extract and a dokudami extract. In addition, such a plant extract can be obtained by extracting a corresponding part of a plant containing a relatively large amount of flavonols with water, alcohol or other organic solvent. It can also be used after enzymatic treatment. In addition, even if these plant extracts are used individually by 1 type, 2 or more types can also be used in arbitrary combinations.

In addition, since some of the flavonols mentioned above are poorly water-soluble and difficult to handle, flavonols may be dissolved in a lower alcohol such as ethanol or a polyhydric alcohol such as glycerin or propylene glycol as necessary. .

When using an antioxidant, the proportion of the antioxidant blended in 100% by mass of the citrus-containing food and drink additive is not limited. For example, when using enzyme-treated isoquercitrin, 0.0001 to 20 mass%, Preferably 0.001-10 mass% can be mentioned. Other antioxidants can be used in accordance with this.

The form of the citrus-containing food / beverage food additive of the present invention is not particularly limited, and for example, a solid form such as a powder, granule, or tablet; a solution such as a liquid or emulsion; or a half such as a paste It can be prepared in any form, such as a solid.

The citrus fruit-containing food / beverage additive of the present invention may be added in advance to the flavor composition. Examples thereof include citrus flavor components such as the above-mentioned citrus fruit juice, pulp and essential oil, and natural materials and synthetic materials. A fragrance composition obtained by blending the above. Citrus, citronellal, octanal, nonanal, decanal, perilaldehyde, α-sinensal, β-sinensal, citronellol, geraniol, linalool, nerol, octanol, α-terpineol , Thymol, citronellyl acetate, geranyl acetate, linalyl acetate, neryl acetate, nootkatone, carvone, 1,8-cineole, 1-p-menthen-8-thiol, etc. Can be used.

By adding the citrus-containing food / beverage additive of the present invention to the food / beverage product, natural sweetness and moderate sourness are enhanced without destroying the balance of the high-quality aroma and flavor inherent in the squeezed citrus fruit juice. And citrus-containing foods and drinks having a flavor that has a fruit juice peculiar to each citrus fruit.

EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated, this invention is not limited to these Examples. Unless otherwise specified, “%” means “% by mass” and “parts” means “parts by mass”.

Example 1 Beverage with orange juice First, 100 parts of a flavoring composition for orange beverages in Table 1 was mixed with 6-ethyl-2,3-dihydrothieno [2,3-c] furan from among caffeo-offlan or its analogs. 1 part each of 1-ppb ethanol solution of 4-methyl-2,3-dihydrothieno [2,3-c] furan, and three kinds of flavoring compositions of the present invention containing 0.01 ppb of caffeofuran or its analog Obtained. This was added from 0.000001 to 10,000 parts to 100 parts of water, respectively, and the addition effect range was determined. Similarly, 5 parts of each were added to obtain 3 types of the flavoring composition of the present invention containing 0.05 ppb of caffeine orchid or 2 analogs thereof. One part of each of these was added to 100 parts of the beverage containing orange juice shown in Table 2 to prepare 3 kinds of beverages containing orange juice containing 0.0005 ppb of two types of caffeine offrun or its analogs.

Comparative Example 1
To 100 parts of the flavor composition for orange beverages in Table 1, 6-ethyl-2,3-dihydrothieno [2,3-c] furan, 4-methyl-2,3-dihydrothieno out of caffeoflane or its analogs. One part each of a 1 ppb ethanol solution of [2,3-c] furan was added to obtain three flavoring compositions of the present invention containing 0.01 ppb of two types of caffeofuran or its analogs. 0.001 part of this is added to 100 parts of beverage containing orange juice in Table 2, each containing 0.0000001 ppb of an excessive amount of caffeine or its analog, and a total of 3 drinks of beverages containing orange juice Was prepared. In addition, 2 parts of each 100 ppm ethanol solution was added to obtain 3 kinds of flavoring compositions containing 2 ppm of caffeofloran or 2 kinds thereof. One part of each of these was added to 100 parts of the orange juice-containing beverage in Table 2, 20 ppb of an excessive amount of caffeine or two analogs thereof was prepared, and three kinds of orange juice-containing beverages were prepared.

攪拌→静置→油層分液（一昼夜冷却−10℃〜−20℃）→油層部分除去→水層部分濾過 これにより得られた溶液を香味料組成物とした。

Stirring → Standing → Separation of oil layer (cooled overnight −10 ° C. to −20 ° C.) → Partial removal of oil layer → Partial filtration of water layer The solution thus obtained was used as a flavoring composition.

Test example 1
The orange fruit juice-containing beverages of Example 1 and Comparative Example 1 were evaluated in four stages by a panel of 8 people, and the results of appropriate amount concentration, fragrance tone and the like are shown in Table 3.

◎：本来、搾り立てのオレンジが持つ良質な香気・香味のバランスを崩すことなく、自然な甘味と程よい酸味感が得られるオレンジ果汁入り飲料
○：やや物足りないが、搾り立てのオレンジ果汁の香味のバランスを保ち、自然な甘味と程よい酸味感が得られるオレンジ果汁入り飲料
△：通常見受けられるオレンジ果汁入り飲料
×：本来持つ、オレンジのイメージが損なわれたオレンジ果汁入り飲料

◎: Orange juice drink with natural sweetness and moderate sourness without breaking the balance of high quality aroma and flavor of freshly squeezed orange ○: Slightly unsatisfactory, but the flavor of squeezed orange juice Beverage drink with orange juice that keeps balance, natural sweetness and moderate acidity △: Beverage drink with orange juice that can be seen normally ×: Beverage drink with orange juice that has the original image of orange

As described above, cafeofflan, 6-ethyl-2,3-dihydrothieno [2,3-c] furan and 4-methyl-2,3-dihydrothieno [2,3-c] furan 0.000001 to 0.1 ppb By using each of these in an orange juice-containing beverage, an orange juice-containing beverage with natural sweetness and moderate sourness can be obtained without destroying the balance of the high-quality aroma and flavor inherent in the squeezed orange.

Example 2 Lemon juice-containing beverage First, 100 parts of a flavoring composition for lemon beverage shown in Table 4 was added to 6-ethyl-2,3-dihydrothieno [2,3-c] furan from among caffeo-offlan or its analogs. 1 part each of 1-ppb ethanol solution of 4-methyl-2,3-dihydrothieno [2,3-c] furan, and three kinds of flavoring compositions of the present invention containing 0.01 ppb of caffeofuran or its analog Obtained. This was added from 0.000001 to 10,000 parts to 100 parts of water, respectively, and the addition effect range was determined. Similarly, 5 parts of each were added to obtain 3 types of the flavoring composition of the present invention containing 0.05 ppb of caffeine orchid or 2 analogs thereof. One part of this was added to 100 parts of the beverage containing lemon juice shown in Table 5 to prepare 3 types of beverages containing lemon juice containing 0.0005 ppb of two types of cafe-off run or its analogs.

Comparative Example 2
To 100 parts of the flavoring composition for lemon beverages in Table 4, 6-ethyl-2,3-dihydrothieno [2,3-c] furan, 4-methyl-2,3-dihydrothieno out of caffeo-offlan or its analogs. One part each of a 1 ppb ethanol solution of [2,3-c] furan was added to obtain three flavoring compositions of the present invention containing 0.01 ppb of two types of caffeofuran or its analogs. 0.001 part each of this with respect to 100 parts of beverage containing lemon juice in Table 2, containing 0.0000001 ppb of a too small amount of caffeine or its analog, and a total of 3 kinds of beverages containing lemon juice Was prepared. In addition, 2 parts of each 100 ppm ethanol solution was added to obtain 3 kinds of flavoring compositions containing 2 ppm of caffeofloran or 2 kinds thereof. One part of each of these was added to 100 parts of the beverage containing lemon juice in Table 5, 20 ppb of an excessive amount of caffeine or two analogs thereof, and 3 kinds of beverages containing lemon juice were prepared.

攪拌→静置→油層分液（一昼夜冷却−10℃〜−20℃）→油層部分除去→水層部分濾過 これにより得られた溶液を香味料組成物とした。

Stirring → Standing → Separation of oil layer (cooled overnight −10 ° C. to −20 ° C.) → Partial removal of oil layer → Partial filtration of water layer The solution thus obtained was used as a flavoring composition.

Test example 2
The beverages containing lemon juice of Example 2 and Comparative Example 2 were evaluated in four stages by a panel of 8 persons, and the results of appropriate amount concentration, fragrance tone and the like are shown in Table 3.

◎：本来、搾り立てのレモンが持つ良質な香気・香味のバランスを崩すことなく、自然な甘味と程よい酸味感が得られるレモン果汁入り飲料
○：やや物足りないが、搾り立てのレモン果汁の香味のバランスを保ち、自然な甘味と程よい酸味感が得られるレモン果汁入り飲料
△：通常見受けられるレモン果汁入り飲料
×：本来持つ、レモンのイメージが損なわれたレモン果汁入り飲料

◎: Naturally sweet and moderately soured lemon juice drink that does not break the balance of the high-quality aroma and flavor of freshly squeezed lemon ○: Slightly unsatisfactory, but the flavor of freshly squeezed lemon juice Lemon juice-containing beverage that maintains balance, natural sweetness and moderate acidity △: Lemon juice-containing beverage usually found ×: Lemon juice-containing beverage in which the original lemon image is impaired

As described above, cafeofflan, 6-ethyl-2,3-dihydrothieno [2,3-c] furan and 4-methyl-2,3-dihydrothieno [2,3-c] furan 0.000001 to 0.1 ppb By using each of these in a lemon juice-containing beverage, a lemon juice-containing beverage was obtained in which natural sweetness and moderate acidity were obtained without losing the balance of the high-quality aroma and flavor inherent in the freshly squeezed lemon.

Example 3 Grapefruit juice-containing beverage First, 100 parts of a flavoring composition for grapefruit beverages shown in Table 7 was added to 6-ethyl-2,3-dihydrothieno [2,3-c] furan from among cafe coffran or its analogs. 1 part each of 1-ppb ethanol solution of 4-methyl-2,3-dihydrothieno [2,3-c] furan, and three kinds of flavoring compositions of the present invention containing 0.01 ppb of caffeofuran or its analog Obtained. This was added from 0.000001 to 10,000 parts to 100 parts of water, respectively, and the addition effect range was determined. Similarly, 5 parts of each were added to obtain 3 types of the flavoring composition of the present invention containing 0.05 ppb of caffeine orchid or 2 analogs thereof. One part of each of these was added to 100 parts of the grapefruit juice-containing beverage shown in Table 8 to prepare a total of three beverages containing grapefruit juice containing 0.0005 ppb of two types of cafe-off run or its analogs.

Comparative Example 3
To 100 parts of the flavoring composition for grapefruit beverages in Table 7, 6-ethyl-2,3-dihydrothieno [2,3-c] furan, 4-methyl-2,3-dihydrothieno is selected from caffeofranc or its analogs. One part each of a 1 ppb ethanol solution of [2,3-c] furan was added to obtain three flavoring compositions of the present invention containing 0.01 ppb of two types of caffeofuran or its analogs. Add 0.001 part of each of these to 100 parts of grapefruit juice beverages in Table 8, contain 0.0000001 ppb of an excessively small amount of café-off run or its analog, and a total of 3 beverages containing grapefruit juice beverages Was prepared. In addition, 2 parts of each 100 ppm ethanol solution was added to obtain 3 kinds of flavoring compositions containing 2 ppm of caffeofloran or 2 kinds thereof. One part of each of these was added to 100 parts of the grapefruit juice-containing beverage in Table 5, 20 ppb of an excessive amount of caffeofloran or two analogs thereof was prepared, and three kinds of beverages containing grapefruit juice were prepared.

攪拌→静置→油層分液（一昼夜冷却−10℃〜−20℃）→油層部分除去→水層部分濾過 これにより得られた溶液を香味料組成物とした。

Stirring → Standing → Separation of oil layer (cooled overnight −10 ° C. to −20 ° C.) → Partial removal of oil layer → Partial filtration of water layer The solution thus obtained was used as a flavoring composition.

Test example 3
The grapefruit juice-containing beverages of Example 3 and Comparative Example 3 were evaluated on a 4-stage scale using a panel of 8 people, and the results of appropriate amount concentration, fragrance tone and the like are shown in Table 3.

◎：本来、搾り立てのグレープフルーツが持つ良質な香気・香味のバランスを崩すことなく、自然な甘味と程よい酸味感が得られるグレープフルーツ果汁入り飲料
○：やや物足りないが、搾り立てのグレープフルーツ果汁の香味のバランスを保ち、自然な甘味と程よい酸味感が得られるグレープフルーツ果汁入り飲料
△：通常見受けられるグレープフルーツ果汁入り飲料
×：本来持つ、グレープフルーツのイメージが損なわれたグレープフルーツ果汁入り飲料

◎: Grapefruit juice-containing beverage with natural sweetness and moderate sourness without breaking the balance of the high-quality aroma and flavor of freshly squeezed grapefruit Grapefruit juice-containing beverages that maintain balance, natural sweetness, and moderate acidity △: Grapefruit juice-containing beverages that are usually found ×: Grapefruit juice-containing beverages that have inherently impaired the image of grapefruit

As described above, cafeofflan, 6-ethyl-2,3-dihydrothieno [2,3-c] furan and 4-methyl-2,3-dihydrothieno [2,3-c] furan 0.000001 to 0.1 ppb By using each of these in a beverage containing grapefruit juice, a beverage containing grapefruit juice was obtained that naturally provided a natural sweetness and moderate sourness without losing the balance of the high-quality aroma and flavor of freshly squeezed grapefruit.

By adding the citrus-containing food / beverage additive of the present invention to the citrus-containing food / beverage product, natural sweetness and moderate sourness can be achieved without breaking the balance of the high quality aroma and flavor of the squeezed citrus juice. The citrus-containing food / beverage products which have the flavor which has an increase | augmentation and each fruit juice peculiar to citrus can be provided.

Claims (4)

An additive for citrus-containing food and drink comprising a cafe-off run represented by the general formula (1) or an analogue thereof.

(In the formula, R ¹ and R ² are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms (except that R ¹ and R ² are hydrogen atoms at the same time)). A citrus-containing flavor composition for foods and drinks, wherein a concentration of 10 ⁻⁴ to 10 ppb of caffeine or its analog represented by the general formula (1) is added. A citrus fruit-containing food or drink comprising ^10-6 to 10 ^-1 ppb concentration of caffeine offran represented by the general formula (1) or an analog thereof. 4. The citrus-containing food or drink according to claim 3, wherein the citrus-containing food or drink is a citrus juice or a beverage containing pulp.