Method for preparing flavoring compositions for food and beverages

Abstract

The present invention provides a method for preparing a flavoring composition for food and beverages, and a flavoring composition obtained by said preparation method. It also provides a method for producing citrus-flavored food and beverages using said flavoring composition, and a method for improving the aroma of citrus-flavored food and beverages. [Solution] A method for preparing a flavor composition for food and beverages comprising the following steps 1 to 3: (1) Step 1 involves extracting citrus fruit juice using an organic solvent 1 and recovering the organic solution phase fraction. (2) Step 2 involves drying the recovered organic solution phase fraction and dissolving the dried material in organic solvent 2 to prepare a solvent. (3) Step 3: The prepared solution is applied to an adsorbent, and the eluent is passed through the adsorbent to recover the eluate as the aroma fraction; Here, the organic solvent 1 is at least one organic solvent selected from the group consisting of non-polar solvents and aprotic polar solvents with a dielectric constant of 10 or less, and the organic solvent 2 is a non-polar solvent. The eluent is a mixture of a nonpolar solvent and a polar solvent with a dielectric constant of 10 or more.

Description

[Technical Field]

[0001] The present invention relates to a method for preparing a flavor composition for food and drink, and to a flavor composition for food and drink obtained by the preparation method. The present invention also relates to a method for producing a citrus food and drink using the flavor composition for food and drink, and to a method for improving the aroma properties of citrus food and drink. [Background Art]

[0002] Conventionally, juice-containing food and drink including fruit juice-containing beverages have been widely popular as palatable food and drink that can provide fruit juice flavor, and research and development for improving the juice-like flavor and aroma have been promoted.

[0003] For example, Patent Document 1 describes that blending a citrus flavor enhancer having rotundone as an active ingredient into a food or drink containing essential oil or fruit juice of citrus fruits enhances the fresh feeling and juiciness of citrus fruits. In addition, Patent Document 2 describes that blending a citrus flavor enhancer having (E)-6-nonenal as an active ingredient into a food or drink having citrus flavor can impart a flavor with a citrus-specific pericarp-like body feel. Furthermore, Patent Document 3 describes that blending a citrus flavor imparting or enhancing agent containing at least one selected from the group consisting of (E)-7-tridecenal, (Z)-7-tridecenal, (E)-8-tridecenal, (Z)-8-tridecenal, (E)-9-tridecenal, and (Z)-9-tridecenal as an active ingredient into a food or drink can impart or enhance a citrus-specific peel feel and wax-like flavor. [Prior Art Documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Unexamined Patent Application Publication No. 2016-198025 [Patent Document 2] Japanese Unexamined Patent Application Publication No. 2009-203438 [Patent Document 3] Japanese Unexamined Patent Application Publication No. 2018-007592 [Overview of the project] [Problems that the invention aims to solve]

[0005] The object of the present invention is to provide a method for preparing a flavoring composition for food and beverages, and a flavoring composition for food and beverages obtained by said preparation method. Another object of the present invention is to provide a method for producing citrus-flavored food and beverages to improve their citrus aroma, and a method for improving the aroma of citrus-flavored food and beverages. [Means for solving the problem]

[0006] The inventors of the present invention have been diligently studying to solve the aforementioned problems and have discovered that a fraction obtained by processing citrus juice or its concentrate (hereinafter referred to as "fruit juice") in a specific way has the effect of improving the aroma of citrus-based foods and beverages, particularly the fruity taste of citrus fruits. The present invention was completed by further research based on this finding and encompasses the following embodiments.

[0007] (I) Method for preparing a flavor composition for food and beverages (I-1) Method for preparing a fragrance composition comprising the following steps 1 to 3: (1) Step 1 involves extracting citrus fruit juice using an organic solvent 1 and recovering the organic solution phase fraction. (2) Step 2 involves drying the recovered organic solution phase fraction and dissolving the dried material in organic solvent 2 to prepare a solvent, and (3) Step 3: The prepared solution is applied to an adsorbent, and the eluent is passed through the adsorbent to recover the eluate as the aroma fraction; Here, the organic solvent 1 is at least one organic solvent selected from the group consisting of non-polar solvents and aprotic polar solvents with a dielectric constant of 10 or less. The organic solvent 2 is at least one organic solvent selected from the group consisting of nonpolar solvents. The eluent is a mixture of a nonpolar solvent and a polar solvent with a dielectric constant of 10 or more. The aforementioned fragrance composition is a fragrance composition for food and beverages used in food and beverages. (I-2) The nonpolar solvent is at least one selected from the group consisting of n-hexane, cyclohexane, toluene, diethyl ether, pentane, and heptane. The preparation method described in (I-1) wherein the aprotic polar solvent is at least one selected from the group consisting of dichloromethane, ethyl acetate, and tetrahydrofuran.

[0008] (II) Flavor composition for food and drink A flavoring composition for food and beverages obtained by the preparation method described in (II-1), (I-1), or (I-2).

[0009] (III) Citrus fruit-based food and beverages, and methods for producing the same. Citrus-flavored food or beverage to which the flavoring composition for food and beverages described in (III-1)(II-1) has been added. A method for producing citrus-flavored food and beverages, comprising the step of incorporating the food and beverage flavoring composition described in (III-2)(II-1).

[0010] (IV) Methods for improving the aroma of citrus-based foods and beverages (IV-1) A method for improving the aroma of citrus-based food and beverages, characterized by incorporating the food and beverage flavoring composition described in (II-1) into the citrus-based food and beverage or its manufacturing process. (IV-2) The method for improving aroma as described in (IV-1), wherein the aroma is the juicy smell of citrus fruits. [Effects of the Invention]

[0011] According to the present invention, it is possible to prepare a fragrance composition that is suitably used to improve the aroma of citrus-flavored food and beverages, particularly the juicy taste of citrus fruits, and to provide such a fragrance composition. Furthermore, according to the manufacturing method of the present invention, it is possible to produce citrus-flavored food and beverages with improved citrus aroma, particularly the juicy taste of citrus fruits, and to provide such citrus-flavored food and beverages. Moreover, according to the method of the invention, it is possible to improve the citrus aroma, particularly the juicy taste of citrus fruits, of citrus-flavored food and beverages. [Brief explanation of the drawing]

[0012] [Figure 1] Shows the results of Test Example 1. In the figure, "T-1" means Test Sample 1-1, "T-2" means Test Sample 1-2, "T-3" means Test Sample 1-3, and "T-4" means Test Sample 1-4. [Figure 2] Shows the results of Test Example 2. In the figure, "T-1" means Test Sample 2-1, "T-2" means Test Sample 2-2, "T-3" means Test Sample 2-3, and "T-4" means Test Sample 2-4. [Figure 3] Shows the results of Test Example 3. In the figure, "T-1" means Test Sample 3-1, "T-2" means Test Sample 3-2, "T-3" means Test Sample 3-3, and "T-4" means Test Sample 3-4. MODE FOR CARRYING OUT THE INVENTION

[0013] The flavor composition for foods and drinks targeted by the present invention (hereinafter also referred to as "the present flavor composition") contains two or more types of aroma compounds derived from citrus fruits. In the present specification, an aggregate of two or more, preferably three or more aroma compounds is referred to as an "aroma component" for convenience. Although details of the types, the number, and the composition of the aroma compounds contained in the aroma component have not been specified yet, the aroma component can be recovered as an aroma fraction in step 3 of the preparation method of the present invention (hereinafter also referred to as "the present preparation method") described later. That is, according to the present preparation method, the aroma component which is the active ingredient of the present flavor composition can be prepared.

[0014] (I) Method for preparing this fragrance composition (this manufacturing method) The present preparation method comprises the following steps 1 to 3: (1) Step 1: extracting citrus fruit juice using a first organic solvent, and recovering an organic solution phase fraction, (2) Step 2: drying the recovered organic solution phase fraction, and dissolving the dried product in a second organic solvent to prepare a dissolving solution, and (3) Step 3: applying the prepared dissolving solution to an adsorbent, passing an eluent through the adsorbent, and recovering the eluate as an aroma fraction. These steps are described below.

[0015] (1) Process 1 (extraction process) The fruits from which the juice is derived in this manufacturing method are citrus fruits. Citrus fruits are the fruits of plants belonging to the genera Citrus, Fortunella, and Poncirus within the subfamily Rutaceae of the family Rutaceae. Preferably, they are some of the Citrus and Fortunella genera that are used for food. Fruits belonging to the genus Citrus include mandarins (Unshu mandarin, Ponkan (also known as mandarin orange), etc.), oranges (Navel orange, Valencia orange, bergamot, etc.), grapefruits (Ruby, Marshmallow, etc.), tangors (Iyokan, Kiyomi, Harumi, Setoka, Tankan, etc.), tanzeros (Seminole, Minneola), sour citrus fruits (Yuzu, Kabosu, Sudachi, Lemon, Shikuwasa, etc.), pomelos (Pomelo), and other citrus fruits (Natsumikan, Hassaku, Hyuganatsu, Dekopon (registered trademark), etc.). Furthermore, examples of fruits belonging to the genus Fortunella that are used for food include Ningbo kumquat, long kumquat, and round kumquat. Preferably, the fruits belong to the genus Citrus, and more preferably, mandarins, oranges, and grapefruits. While there are no particular limitations on the origin, ripeness, or size of the citrus fruits that can be used in this manufacturing method, ripeness is preferable, and it is preferable that the fruits be at their peak ripeness for eating.

[0016] Citrus juice refers to the liquid component (straight juice) obtained by squeezing citrus fruits whole, or by puncturing or crushing the fruit and then straining it. The juice may also include concentrated straight juice, or diluted or reconstituted straight juice or concentrated juice. Furthermore, it may contain pulp (fiber) in addition to the liquid component, or the pulp may have been removed by processing such as filtration or centrifugation. The juice may be clear, translucent, or opaque (cloudy).

[0017] The organic solvent 1 used in the extraction process is at least one organic solvent selected from the group consisting of non-polar solvents and aprotic polar solvents with a dielectric constant of 10 or less. A nonpolar solvent is a single compound that is liquid at room temperature and pressure with a dielectric constant less than 6. Specific examples of nonpolar solvents used in this invention include n-hexane, cyclohexane, toluene, diethyl ether, pentane, and heptane. Diethyl ether is preferred. Examples of aprotic polar solvents with a dielectric constant of 10 or less include dichloromethane, ethyl acetate, and tetrahydrofuran. Dichloromethane is preferred. These nonpolar and aprotic polar solvents may be used individually as organic solvent 1, or two or more may be used in any combination.

[0018] The amount of organic solvent 1 used in the extraction process is not limited, but from the viewpoint of extraction efficiency, the ratio of organic solvent 1 to 100 parts by mass of fruit juice can be adjusted to be in the range of 10 to 300 parts by mass. Preferably, it is in the range of 30 to 250 parts by mass, and more preferably in the range of 50 to 200 parts by mass.

[0019] The extraction process can be carried out under conditions of room temperature (25±5℃) or below using a standard method (liquid-liquid partition extraction method), such as immersion extraction, stirring extraction, shaking extraction, and ultrasonic extraction. Stirring extraction is preferred. Standard methods can also be used for the extraction conditions, such as room temperature extraction or pressurized extraction. The extraction time is not particularly limited, but is preferably 5 minutes to 24 hours. pH adjustment may be performed during extraction, but is not particularly necessary. The above extraction operation may be performed once, or the aqueous phase fraction obtained after the extraction operation may be extracted again with organic solvent 1 and this process may be repeated multiple times. Furthermore, solid-liquid separation treatments such as filtration, as described later, may be performed before or after the extraction process, if necessary.

[0020] By allowing the extract obtained above to stand, the liquid phase can be separated into an aqueous phase fraction and an organic solution phase fraction. If necessary, the extract can also be separated into an aqueous phase fraction and an organic solution phase fraction by centrifugation. By removing the aqueous phase fraction through this process, the organic solution phase fraction can be recovered. For example, if an organic solvent with a higher density than water, such as dichloromethane, is used as organic solvent 1, the upper layer will be the aqueous phase fraction, and by removing this, the organic solution phase fraction (e.g., the dichloromethane phase fraction) can be recovered. On the other hand, if an organic solvent with a lower density than water, such as diethyl ether, is used as organic solvent 1, the upper layer will be the organic solution phase fraction (e.g., the diethyl ether phase fraction), and this can be recovered.

[0021] (2) Process 2 (solution preparation process) Step 2 is a pretreatment step for the organic solution phase fraction recovered in Step 1, which is then subjected to the adsorption and desorption treatment in Step 3, described later. In this pretreatment step, a dissolving solution to be used in the adsorption and desorption treatment is prepared.

[0022] Specifically, in step 2, the organic solution phase fraction recovered in step 1 is first dried. The drying process can be carried out according to standard methods, except that it is performed under temperature conditions of room temperature (25±5℃) or lower. Since the recovered organic solution phase fraction contains water derived from fruit juice, it is possible to first absorb water using an absorbent such as anhydrous sodium sulfate. After that, it is preferable to perform concentration and drying. Although not limited, the concentration and drying process is preferably carried out under reduced pressure to increase efficiency. Also, although not limited, when air-drying, it is preferable to air-dry using nitrogen gas to prevent oxidation. The dried product thus prepared may contain a small amount of water, as long as it does not hinder dissolution by the organic solvent 2, and the drying process does not require complete dehydration.

[0023] The dried product thus prepared can be dissolved in organic solvent 2 to prepare a solvent for the adsorption and desorption treatment in step 3. The organic solvent 2 used in the dissolution process is a non-polar solvent. As mentioned above, a nonpolar solvent is an elemental compound that is liquid at room temperature and pressure and has a dielectric constant less than 6. Specific examples of nonpolar solvents used in the present invention include n-hexane, cyclohexane, toluene, diethyl ether, pentane, and heptane. Preferably, n-hexane and cyclohexane are used.

[0024] The solubility concentration of the dried product in organic solvent 2 (concentration of the solvent) is not limited, but can be prepared in the range of 0.1 to 50% by mass. Preferably, it is 0.1 to 20% by mass, and more preferably 0.1 to 10% by mass.

[0025] (3) Step 3 (Adsorption and Desorption Process) Step 3 is a step in which the solution prepared in Step 2 is subjected to adsorption and desorption treatment using an adsorbent to recover the aroma fraction containing the aroma components.

[0026] The adsorbent used here can be any material that can adsorb and desorb (separate) the components of the liquid in stages by utilizing the difference in polarity of the substances. Examples include porous adsorbents such as silica gel, alumina, and zeolite. Preferably, it is highly polar silica gel. In this case, highly polar substances are easily adsorbed and desorbed (leached out) slowly because they have a strong interaction with silica gel. On the other hand, less polar substances are quickly desorbed and leached out because they have a weak interaction with silica gel. Adsorption and desorption treatment using adsorbents can be carried out using column chromatography.

[0027] After the dissolving solution is applied to the adsorbent, the eluent passed through the adsorbent can be a mixture of a nonpolar solvent and a polar solvent with a dielectric constant of 10 or more. Examples of nonpolar solvents include those mentioned above. Preferably, n-hexane and cyclohexane, and more preferably n-hexane. Examples of polar solvents with a dielectric constant of 10 or more include aprotic polar solvents such as acetone, acetonitrile, and dimethyl sulfoxide; and protic polar solvents such as isopropanol, ethanol, methanol, and water. Preferably, ethanol, isopropanol, and water, and more preferably ethanol and isopropanol. These nonpolar and polar solvents are used in any combination of one or more types. Preferably, the combination is a nonpolar solvent and a protic polar solvent, and more preferably, the nonpolar solvent is n-hexane or cyclohexane and the protic polar solvent is ethanol, isopropanol, or water. Particularly preferred are the combination of n-hexane and ethanol, and the combination of cyclohexane and isopropanol.

[0028] The mixing ratio of nonpolar solvent to polar solvent is not limited, but a volume ratio of 100 parts nonpolar solvent to 1 to 500 parts polar solvent can be given. Preferably, the ratio is 10 to 200 parts nonpolar solvent to 100 parts polar solvent, more preferably 10 to 100 parts, even more preferably 10 to 50 parts, and particularly preferably 10 to 30 parts.

[0029] The ratio of nonpolar solvent to polar solvent can be gradually changed in the eluent used for passing the adsorbent through. For example, after applying the dissolution to the adsorbent, a nonpolar solvent or an eluent mainly composed of a nonpolar solvent (for example, an eluent with a ratio of less than 1 part polar solvent to 100 parts nonpolar solvent (volume ratio)) can be used for the first pass, and then the eluent can be sequentially eluted using an eluent with an increasing proportion of polar solvent. In this case, the eluent obtained when passing an eluent containing the nonpolar solvent and polar solvent in the aforementioned ratio (ratio of polar solvent to 100 parts nonpolar solvent: 1 to 500 parts, preferably 10 to 300 parts, more preferably 20 to 200 parts (volume ratio)) is used is recovered as the aroma fraction.

[0030] The aroma fraction prepared in step 3 above may remain in its liquid form, but can be subsequently subjected to concentration and drying processes to be prepared into a solid form. Furthermore, if necessary, it can be prepared into a powder or granular form by grinding or granulation processes. The concentration and drying processes are preferably carried out under temperature conditions below room temperature (25±5℃), similar to the processes used in step 2. Preferably, the concentration process is carried out under reduced pressure conditions, and more preferably, it is air drying using nitrogen gas, vacuum drying, or freeze-drying.

[0031] (II) Fragrance composition The fragrance composition of the present invention (this fragrance composition) is characterized by containing a fragrance fraction prepared by the method described above. The proportion of the fragrance fraction in this fragrance composition is not particularly limited, but is greater than 0 and 100% by mass or less. Preferably it is 0.001 to 50% by mass, more preferably 0.001 to 20% by mass. Other components constituting this fragrance composition are those that do not interfere with the effects of the fragrance fraction, and examples include carriers such as excipients and fillers, and additives such as antioxidants.

[0032] This fragrance composition can be used as an ingredient in the preparation of citrus-flavored foods and beverages to enhance their aroma. Here, aroma refers to the juicy sensation of citrus fruits that can be perceived as an odor in the nasal cavity. The juicy sensation of citrus fruits refers to the complex flavor characteristics inherent in the citrus fruit itself. Specifically, it is the overall sensation of the aroma derived from the citrus peel (peel sensation), the deep aroma of the citrus fruit (richness sensation), and the expansive sweet aroma.

[0033] Food and beverages are a general term for "drinks" and "food" that humans ingest. It refers to all foods consumed to satisfy appetite, replenish nutrients, and sustain life, and includes prepared foods such as staple foods and side dishes (including ready-made meals), as well as confectionery, desserts, beverages, and frozen desserts. In particular, the citrus-based food and beverages targeted by this invention are food and beverages containing citrus fruit juice. Examples include soft drinks such as fruit juice beverages, fruit juice drinks, vegetable drinks, sports drinks, vitamin supplements, mineral supplements, nutritional drinks, lactic acid bacteria drinks, milk drinks, and carbonated drinks; beverages such as herbal tea and black tea; alcoholic beverages such as chuhai, cocktail drinks, sparkling wine, fruit wine, and herbal drinks; dairy products such as yogurt, bavarian cream, and pudding; desserts such as ice cream, lacto ice cream, ice milk, frozen desserts, and jelly, and mixes for making them; confectionery such as candy, caramel, tablets, chocolate, snacks, and biscuits; and bread, soup, and various other food and beverages.

[0034] (III) Citrus fruit-based food and beverages, and methods for producing the same. The citrus-flavored food and beverage of the present invention (this citrus-flavored food and beverage) is characterized by having the aforementioned flavoring composition added to it. This citrus-flavored food and beverage can be manufactured by the usual method for manufacturing citrus-flavored food and beverages, except for the step of blending the flavoring composition. This citrus-flavored food and beverage is characterized by having an improved aroma compared to citrus-flavored food and beverage that does not contain this flavoring composition. Here, aroma refers to the juicy taste of citrus fruits as described above. The sensory evaluation test method will be explained in the Examples section.

[0035] The proportion of this flavoring composition in this citrus-flavored food and beverage is not particularly limited, as long as the addition of this flavoring composition improves the aroma compared to this citrus-flavored food and beverage without it, as described above. For example, it can be appropriately set in the range of more than 0% by mass and up to 10% by mass per 100% by mass of this citrus-flavored food and beverage. Preferably, it is in the range of 0.0001 to 5% by mass, more preferably 0.001 to 1% by mass, and even more preferably 0.01 to 0.5% by mass.

[0036] Furthermore, if this fragrance composition contains furaneol, the amount of furaneol added per 100% by mass of this citrus food and beverage is equivalent to 1.0 × 10⁻⁶ furaneol. ―7 ~1.0×10 ―5 The amount can be appropriately set within a range that is equal to mass%. Similarly, if this flavoring composition contains phenylacetaldehyde, the amount of phenylacetaldehyde added per 100% by mass of this citrus food and beverage is 1.0 × 10 -8 ~1.0×10 -6 It can be appropriately set within a range that results in mass%. Also, if this flavor composition contains vanillin, the amount of vanillin added per 100% by mass of this citrus food and beverage is 1.0 × 10 -7 ~1.0×10 -5 It can be set appropriately within a range that results in a mass percentage.

[0037] In this specification, the terms “contains” and “include” include the meanings of “consisting of” and “substantially consisting of.” [Examples]

[0038] The present invention will be described below using experimental examples to aid in understanding its structure and effects. However, the present invention is not limited in any way by these experimental examples. Unless otherwise specified, the following experiments were conducted at room temperature (25±5℃) and under atmospheric pressure conditions. Unless otherwise specified, "%" below means "mass percent" and "parts" means "parts by mass".

[0039] Manufacturing example: Method for preparing aroma fractions Production Example 1: Preparation of Aroma Fractions 1-1 to 1-3 (derived from orange juice) Orange juice is used as the citrus juice. Specifically, 200g of Valencia Orange 5x Concentrated Cloudy Juice (manufactured by Kako Co., Ltd.) is diluted with 800g of ion-exchanged water to make orange juice. Valencia Orange 5x Concentrated Cloudy Juice is generally prepared by using the whole Valencia orange fruit (including the peel and pulp), obtaining a cloudy juice containing pulp by inline juicing (making holes in the fruit and applying pressure from above), then concentrating it 5 times by vacuum concentration while removing some insoluble components by coarse filtration (the same applies to production examples 2-3 below).

[0040] To this, 1 L of dichloromethane is added, and the mixture is stirred and extracted for 1 hour at a rotation speed of 100-300 rpm using a stirring device (Super Stirrer MS-2: manufactured by Ishii Rika Co., Ltd.). After extraction, it is allowed to stand for 30 minutes, and then decanted to separate the aqueous phase (upper layer) and the dichloromethane phase (lower layer), and the dichloromethane phase fraction is recovered (Step 1).

[0041] Next, the recovered dichloromethane phase (approximately 1 L) is dried using anhydrous sodium sulfate, concentrated under reduced pressure until it reaches a volume of 1 mL, and then air-dried using nitrogen. This is then dissolved in 1 mL of hexane to prepare the solution (step 2).

[0042] A column (20 mm × 140 mm) packed with approximately 30 g (dry state) of silica gel (Wako Gel R C-200: manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (fully porous, crushed silica gel with a pore size of approximately 70 Å) is set upright, and 1 mL of the dissolution prepared in step 2 is charged into it. Next, 40 mL of hexane (eluent 1), 40 mL of a mixed solvent of hexane and ethanol in a volume ratio of 5:1 (eluent 2), and 40 mL of ethanol (eluent 3) are passed through the column in sequence, and 40 mL of the fraction is recovered at each eluent eluent eluent step (recovery of fractions 1-1, 1-2, and 1-3 for each eluent 1, 2, and 3) (step 3).

[0043] Each of the resulting fractions is concentrated under reduced pressure, air-dried under nitrogen, and then dissolved in 5 mL of ethanol. These three fractions are designated as aroma fractions 1-1, 1-2, and 1-3. In the test examples 1-5 described later, aroma fractions 1-2 were used. Aroma fractions 1-2 contain phenylacetaldehyde, vanillin, and furaneol (test example 7).

[0044] Manufacturing Example 2: Preparation of Aroma Fractions 2-1 to 2-3 (derived from orange juice) As the citrus juice, 200g of orange juice prepared by diluting Valencia orange 5x concentrated cloudy juice with deionized water five times is used.

[0045] Steps 1 to 3 were carried out in the same manner as in Production Example 1, except that diethyl ether (200 mL) was used instead of dichloromethane (1 L) as the organic solvent for extraction in Step 1 of Production Example 1.

[0046] Each fraction obtained in step 3 (fractions 2-1, 2-2, and 2-3 were collected for each eluent 1, 2, and 3) was concentrated under reduced pressure, air-dried under nitrogen, and then dissolved in 1 mL of ethanol to obtain aroma fractions 2-1, 2-2, and 2-3.

[0047] In Test Example 6, described later, aroma fraction 2-2 was used. Aroma fraction 2-2 contains phenylacetaldehyde, vanillin, and furaneol.

[0048] Manufacturing Example 3: Preparation of Aroma Fractions 3-1 to 3-3 (derived from orange juice) As the citrus juice, 200g of orange juice prepared by diluting Valencia orange 5x concentrated cloudy juice with deionized water five times is used.

[0049] Steps 1 to 3 were carried out in the same manner as in Production Example 1, except that in step 3 of Production Example 1, cyclohexane was used instead of hexane used as eluent 1, a mixed solvent of cyclohexane and isopropanol (volume ratio 1:2) was used instead of a mixed solvent of hexane and ethanol (volume ratio 5:1) used as eluent 2, and isopropanol was used instead of ethanol used as eluent 3.

[0050] Each fraction obtained in step 3 (fractions 3-1, 3-2, and 3-3 were collected for each eluent 1, 2, and 3) was concentrated under reduced pressure, air-dried under nitrogen, and then dissolved in 1 mL of ethanol to obtain aroma fractions 3-1, 3-2, and 3-3.

[0051] In Test Example 6, described later, aroma fraction 3-2 was used. Aroma fraction 3-2 contains phenylacetaldehyde, vanillin, and furaneol.

[0052] Manufacturing Example 4: Preparation of Aroma Fractions 4-1 to 4-3 (derived from mandarin orange juice) Mandarin orange juice is used as the citrus fruit juice. Specifically, 33.3g of 6x concentrated clear juice of Satsuma mandarin oranges (manufactured by Kako Co., Ltd.) is diluted with 166.7g of ion-exchanged water to make 200g of mandarin orange juice. 6x concentrated clear juice of Satsuma mandarin oranges is generally prepared by using whole Satsuma mandarin oranges, obtaining a cloudy juice containing pulp by inline juicing, then coarse filtration, followed by ultrafiltration to remove suspended components and make it clear, and finally concentrating it 6 times by vacuum concentration.

[0053] Steps 1 to 3 were carried out in the same manner as in Production Example 1, except that the volume of dichloromethane used as the organic solvent for extraction in step 1 of Production Example 1 was reduced from 1 L to 200 mL.

[0054] Each fraction obtained in step 3 (fractions 4-1, 4-2, and 4-3 were collected for each eluent 1, 2, and 3) was concentrated under reduced pressure, air-dried under nitrogen, and then dissolved in 1 mL of ethanol to obtain aroma fractions 4-1, 4-2, and 4-3.

[0055] In Test Example 6, described later, aroma fraction 4-2 was used. Aroma fraction 4-2 contains phenylacetaldehyde, vanillin, and furaneol.

[0056] Manufacturing Example 5: Preparation of Aroma Fractions 4-1 to 4-3 (derived from grapefruit juice) Grapefruit juice is used as the citrus juice. Specifically, 40g of 5x concentrated clear grapefruit juice (manufactured by Kako Co., Ltd.) is diluted with 160g of deionized water to make 200g of grapefruit juice. 5x concentrated clear grapefruit juice is generally prepared by using whole grapefruits, obtaining a cloudy juice containing pulp by inline juicing, then coarse filtration, followed by ultrafiltration to remove suspended components and make it clear, and finally concentrating it 5 times by vacuum concentration.

[0057] Steps 1 to 3 were carried out in the same manner as in Production Example 1, except that the volume of dichloromethane used as the organic solvent for extraction in Step 1 of Production Example 1 was changed from 1 L to 200 mL.

[0058] Each fraction obtained in step 3 (fractions 5-1, 5-2, and 5-3 were collected for each eluent 1, 2, and 3) was concentrated under reduced pressure, air-dried under nitrogen, and then dissolved in 1 mL of ethanol to obtain aroma fractions 5-1, 5-2, and 5-3.

[0059] In Test Example 6, described later, aroma fraction 5-2 was used. Aroma fraction 5-2 contains phenylacetaldehyde, vanillin, and furaneol.

[0060] Test method: Sensory evaluation test method In the test examples 1 to 6 described later, the sensory evaluation tests were conducted according to the following method.

[0061] [panel] The applicant's employee panel consists of 5-8 specialists in analytical sensory evaluation who are engaged in fragrance development (average years of experience in fragrance development: 9.6 years).

[0062] [How to present the sample on the panel] After adjusting the samples to room temperature (25±5℃), approximately 10 mL of each sample is poured into plastic cups (cup diameter 4.5 cm) and presented to each panel. At this time, the panel is not informed of the presence or proportion of fractions added to each sample, and samples are presented randomly to each test group.

[0063] [Evaluation Item] The "fruit juice feeling" is evaluated based on the aroma that rises to the mouth (nose area) when the opening of the cup containing the sample is brought to the mouth (nose area) (top note aroma), and the aroma contained in the mouth when the sample is taken into the mouth (both aromas perceived in the nasal cavity). Here, "fruit juice feeling" is defined as the complex flavor characteristics inherent to the fruit of each citrus type perceived as an olfactory sensation in the nasal cavity. Specifically, it is defined as the comprehensive sensation of the aroma derived from citrus peel (peel note), the deep aroma of citrus fruit flavor (richness note), and the expansive sweet aroma.

[0064] [Evaluation Criteria and Evaluation Method Using the Same] As samples for evaluation criteria, three types of samples (reference samples 1 to 3) with different citrus juice concentrations (A < B < C) are prepared. For each reference sample, the "fruit juice feeling" is scored according to the juice concentration as described below, and this is used as an evaluation index. Note that when concentrated citrus juice is used as the citrus juice, each reference sample is prepared by diluting the concentrated juice with ion-exchanged water according to its concentration degree to adjust to the original concentration of citrus juice.

[0065] Score to be used as evaluation criterion 1 point: Fruit juice feeling of citrus juice with concentration A (reference sample 1) 2 points: Fruit juice feeling between reference sample 1 and reference sample 2 3 points: Fruit juice feeling of citrus juice with concentration B (reference sample 2) 4 points: Fruit juice feeling between reference sample 2 and reference sample 3 5 points: Fruit juice feeling of citrus juice with concentration C (reference sample 3)

[0066] [Panel Pre-training and Evaluation Method] For each test, each panelist evaluated the "fruit juice feeling" of three samples (reference samples 1 to 3) with different juice concentrations (A < B < C) for the target citrus fruit in advance according to the above method. This evaluation is repeatedly carried out, and by coordinating the evaluation results among panelists, the internal criteria of each panelist are organized, and adjustments are made so that no differences occur among panelists.

[0067] [Panel-based evaluation method] For each test sample to which the aroma fraction was added, its fruit juice quality was compared and evaluated against the fruit juice quality of reference samples 1-3 using a "one-to-one comparison method," and the fruit juice quality of each test sample was scored using the method described above.

[0068] Test Example 1 (1) Preparation of test samples All of the components listed in Table 1 were mixed together to prepare test samples 1-1 to 1-4 (samples containing the equivalent of 1% orange juice).

[0069] [Table 1]

[0070] [Table 2]

[0071] (2) Sensory evaluation test Eight panelists evaluated the fruit juice content of the test samples 1-1 to 1-4 prepared as described above, according to the sensory evaluation test method described previously. For the sensory evaluation test, the following three reference samples (1-3) were established. Reference sample 1: A sample containing orange juice at a concentration of 1% (concentration A). Reference sample 2: A sample containing orange juice at a concentration of 5% (concentration B). Reference sample 3: A sample containing orange juice at a concentration of 10% (concentration C). The average of the evaluation results from the eight panel members is shown in Table 3 and Figure 1.

[0072] [Table 3]

[0073] As shown in Table 3 and Figure 1, it was confirmed that adding aroma fractions 1-2 to a citrus beverage (orange juice concentration 1%) at a concentration of 0.05% or more, preferably 0.1% or more, and more preferably 0.2-0.4%, improved the fruitiness of the citrus beverage in a concentration-dependent manner.

[0074] Test Example 2 (1) Preparation of test samples All of the components listed in Table 4 were mixed together to prepare test samples 2-1 to 2-4 (samples containing the equivalent of 10% orange juice) (Table 5).

[0075] [Table 4]

[0076] [Table 5]

[0077] (2) Sensory evaluation test Eight panelists evaluated the fruit juice content of the test samples 2-1 to 2-4 prepared as described above, according to the sensory evaluation test method described previously. For the sensory evaluation test, the following three reference samples (1-3) were established. Reference sample 1: A sample containing orange juice at a concentration of 10% (concentration A). Reference sample 2: A sample containing orange juice at a concentration of 15% (concentration B). Reference sample 3: A sample containing orange juice at a concentration of 20% (concentration C). The average of the evaluation results from the eight panel members is shown in Table 6 and Figure 2.

[0078] [Table 6]

[0079] As shown in Table 6, adding aroma fractions 1-2 to a citrus beverage (orange juice concentration 10%) at a concentration of 0.05% or more, preferably 0.05-0.4%, improved the fruitiness of the citrus beverage.

[0080] Test Example 3 (1) Preparation of test samples All of the components listed in Table 7 were mixed together to prepare test samples 3-1 to 3-4 (samples containing an equivalent amount of orange juice from 20% to 70%) (Table 8).

[0081] [Table 7]

[0082] [Table 8]

[0083] (2) Sensory evaluation test The seven panelists evaluated the fruit juice content of the test samples 3-1 to 3-4 prepared as described above, according to the sensory evaluation test method described previously.

[0084] For the sensory evaluation test, reference samples 1 to 3, as described below, were established for each test sample from 3-1 to 3-4, and comparisons were made with these reference samples. [Test subject sample 3-1] Reference sample 1: A sample containing orange juice at a concentration of 20% (concentration A). Reference sample 2: A sample containing orange juice at a concentration of 25% (concentration B). Reference sample 3: A sample containing orange juice at a concentration of 30% (concentration C). [Test Sample 3-2] Reference sample 1: A sample containing orange juice at a concentration of 30% (concentration A). Reference sample 2: A sample containing orange juice at a concentration of 35% (concentration B). Reference sample 3: A sample containing orange juice at a concentration of 40% (concentration C). [Test Sample 3-3] Reference sample 1: A sample containing orange juice at a concentration of 50% (concentration A). Reference sample 2: A sample containing orange juice at a concentration of 55% (concentration B). Reference sample 3: A sample containing orange juice at a concentration of 60% (concentration C). [Test Samples 3-4] Reference sample 1: A sample containing orange juice at a concentration of 70% (concentration A). Reference sample 2: A sample containing orange juice at a concentration of 75% (concentration B). Reference sample 3: A sample containing orange juice at an 80% concentration (concentration C). The average of the evaluation results from the seven panel members is shown in Table 9 and Figure 3.

[0085] [Table 9]

[0086] As shown in Table 9 and Figure 3, it was confirmed that the effect of adding aroma fractions 1-2 at a rate of 0.2% decreases as the juice concentration of citrus beverages (orange juice 20% to 70%) increases.

[0087] Test Example 4 (1) Preparation of test samples Test sample 4 (a sample containing 10% mandarin orange juice) was prepared by mixing all the ingredients listed in Table 10. The straight mandarin orange juice used was "Mandarin Orange Juice (Straight)" (manufactured by Nippon Dairy Cooperative Co., Ltd.).

[0088] [Table 10]

[0089] (2) Sensory evaluation test The juiciness of the test sample 4 prepared as described above was evaluated by eight panelists according to the sensory evaluation test method described above. For the sensory evaluation test, the following three reference samples (1-3) were established. Reference sample 1: A sample containing 10% straight mandarin orange juice (concentration A). Reference sample 2: A sample containing 15% straight mandarin orange juice (concentration B). Reference sample 3: A sample containing 20% ​​straight mandarin orange juice (concentration C). Table 11 shows the average of the evaluation results from the eight panel members.

[0090] [Table 11]

[0091] As shown in Table 11, adding aroma fractions 1-2 to a citrus beverage (10% mandarin orange juice concentration) at a concentration of 0.2% improved the fruitiness of the citrus beverage.

[0092] Test Example 5 (1) Preparation of test samples Test sample 5 (sample containing 10% grapefruit juice) was prepared by mixing all the components listed in Table 12. The grapefruit juice used was "Tropicana 100% Grapefruit" (concentrated and reconstituted, manufactured by Kirin Beverage Co., Ltd.).

[0093] [Table 12]

[0094] (2) Sensory evaluation test The juiciness of the test sample 5 prepared as described above was evaluated by eight panelists according to the sensory evaluation test method described above. For the sensory evaluation test, the following three reference samples (1-3) were established. Reference sample 1: A sample containing grapefruit juice at a concentration of 10% (concentration A). Reference sample 2: A sample containing grapefruit juice at a concentration of 15% (concentration B). Reference sample 3: A sample containing grapefruit juice at a concentration of 20% (concentration C). Table 13 shows the average of the evaluation results from the eight panel members.

[0095] [Table 13]

[0096] As shown in Table 13, adding aroma fractions 1-2 to a citrus beverage (10% grapefruit juice concentration) at a concentration of 0.2% improved the fruitiness of the citrus beverage.

[0097] Test Example 6 (1) Preparation of test samples All of the components listed in Table 14 were mixed together to prepare test samples 6-9 (samples containing 10% orange juice). Valencia orange 5x concentrated cloudy juice (manufactured by Kako Co., Ltd.) was used to prepare the orange juice.

[0098] [Table 14]

[0099] (2) Sensory evaluation test The juice content of the test samples 6-9 prepared as described above was evaluated by five panelists according to the sensory evaluation test method described above. For the sensory evaluation test, the following three reference samples (1-3) were established. Reference sample 1: A sample containing orange juice at a concentration of 10% (concentration A). Reference sample 2: A sample containing orange juice at a concentration of 15% (concentration B). Reference sample 3: A sample containing orange juice at a concentration of 20% (concentration C). The panel of five members evaluated the product, with four giving a rating of 3 and one giving a rating of 4. The mean and standard deviation are shown in Table 15.

[0100] [Table 15]

[0101] As shown in Table 15, adding aroma fractions 2-2, 3-2, 4-2, and 5-2 to a citrus beverage (10% orange juice concentration) at a concentration of 0.2% each improved the fruitiness of the citrus beverage.

[0102] Test Example 7: Calculation of the content of components in citrus fruit juice The content (μg / g) of furaneol, phenylacetaldehyde, and vanillin in the citrus juices (orange juice, mandarin orange juice, grapefruit juice) used to prepare the aroma fractions in Production Examples 1-5 was calculated using the following method. Commercially available reagents were used as standards for the substances to be measured: furaneol, phenylacetaldehyde, and vanillin (furaneol: Xiamen Bestally Biotechnology Co., Ltd., phenylacetaldehyde: Toyotama Fragrance Co., Ltd., vanillin: JIAXING ZHONGHUA CHEMICAL CO.,LTD.).

[0103] Each citrus fruit juice was diluted with deionized water to produce 200g of straight juice. 50 μg of 3-heptanol (used as an internal standard) and 200 mL of dichloromethane were added to this mixture, and the mixture was stirred and extracted for 1 hour at a rotation speed of 100-300 rpm using a stirrer (Super Stirrer MS-2: manufactured by Ishii Rika Co., Ltd.). After extraction, the mixture was allowed to stand for 30 minutes, and then decanted to separate the aqueous phase (upper layer) and the dichloromethane phase (lower layer), and the dichloromethane phase was recovered.

[0104] Next, the recovered dichloromethane phase (approximately 200 mL) was dried using anhydrous sodium sulfate and concentrated under reduced pressure until it reached a volume of 1 mL. It was then subjected to gas chromatography-mass spectrometry (GC / MS analysis), and the approximate content of each component was determined by the ratio of the peak areas of each component to that of the internal standard.

[0105] The approximate content is calculated using the following formula; [(Peak area of ​​each component) / (Peak area of ​​3-heptanol)] × 50 / 200.

[0106] <GC / MS measurement conditions> ·GC / MS instrument: Agilent 5977B GC / MSD (manufactured by Agilent Technologies) ·Column: DB-WAX UI / length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm (manufactured by Agilent Technologies) ·Column temperature conditions: 50°C (held for 2 minutes) to 220°C, temperature increase at 3°C / minute (held for 75 minutes) ·Carrier gas: Helium.

[0107] The quantification results are shown in Table 16. Table 16 also shows the ratios (parts by mass) of phenylacetaldehyde and vanillin relative to 1 part by mass of furaneol contained in citrus fruit juice.

[0108]

Table 16

Claims

1. A method for preparing a fragrance composition comprising the following steps 1 to 3: (1) Step 1 involves extracting citrus fruit juice using an organic solvent 1 and recovering the organic solution phase fraction. (2) Step 2, in which the recovered organic solution phase fraction is dried and the dried material is dissolved in organic solvent 2 to prepare a solvent, (3) Step 3: The prepared solution is applied to an adsorbent, and the eluent is passed through the adsorbent to recover the eluate as the aroma fraction; Here, the organic solvent 1 is at least one organic solvent selected from the group consisting of non-polar solvents and aprotic polar solvents with a dielectric constant of 10 or less. The aforementioned organic solvent 2 is a nonpolar solvent. The eluent is a mixture of a nonpolar solvent and a polar solvent with a dielectric constant of 10 or more. The aforementioned fragrance composition is a fragrance composition for food and beverages.

2. A fragrance composition obtained by the preparation method described in claim 1.

3. A citrus-flavored food or beverage to which the fragrance composition described in claim 2 has been added.

4. A method for producing citrus-flavored food or beverages, comprising the step of incorporating the fragrance composition described in claim 2.

5. A method for improving the aroma of citrus-flavored food or beverage, characterized by incorporating the fragrance composition described in claim 2 into the manufacturing process of the same.

6. The method for improving aroma according to claim 5, wherein the aforementioned aroma is the juice-like quality of citrus fruits.

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