TW201628512A - Products containing citrus flavor, drink, fragrance composition, method for inhibiting generation of deterioration smell, and method for inhibiting deterioration of flavor - Google Patents

Abstract

A citrus flavor containing product according to the present invention is characterized by containing a citrus flavor and a dicarboxylic acid or a metal salt thereof that has an intramolecular conjugate double bond.

Description

Product containing citrus flavor, beverage, flavor composition, method for suppressing generation of deteriorated odor, and method for suppressing deterioration of aroma

The present invention relates to a citrus-flavored product, a beverage, a fragrance composition, a method for suppressing the generation of deterioration odor, and a method for suppressing aroma deterioration.

Previously, the practice of adding a lemon-like citrus-specific flavor to a beverage by adding a citrus flavor to the beverage has been widely practiced. Moreover, by adding the flavor unique to the citrus, the drinker can be given a refreshing pleasure.

Here, as a representative aroma component of the citrus flavor, citral or limonene can be mentioned.

Here, it is known that the aroma component contained in such a citrus flavor is converted into other components by heating or long-term storage. Further, as an example of countermeasures against such knowledge, the following techniques are known.

For example, Patent Document 1 discloses a technique for suppressing the formation of p-methylacetophenone or the like which is generated when citral is heated or the like, and adding papaya, mango, mangosteen, myrobalan, and pomegranate. Or cocoa solvent-extracted extract, or epicatechin, epicatechin gallate, epigallocatechin gallate, enzyme-modified rutin, quercetin, A Wei acid, caffeic acid, rosmarinic acid, syringic acid or gallic acid.

Further, Patent Document 2 discloses a technique in which a eriocitrin or a eriocitrin-containing substance is used as an anti-deterioration agent for a flavor component such as citral.

Further, a technique is known in which a solvent extract such as tomorrow leaves, avocado, and psyllium is used to suppress the formation of deterioration odor of citral or a citral-containing product (see Patent Document 3), or an anthraquinone plant. The solvent extract of the peel is used as a fragrance deterioration inhibitor (refer to Patent Document 4).

Prior technical literature

Patent literature

Patent Document 1: Japanese Patent Laid-Open Publication No. 2002-180081

Patent Document 2: Japanese Laid-Open Patent Publication No. 2001-61461

Patent Document 3: Japanese Patent Laid-Open Publication No. 2004-18613

Patent Document 4: Japanese Laid-Open Patent Publication No. 2004-292778

In other words, as described in the patent documents 1 to 4, research on the aroma of the citrus flavor is actively carried out, and development of various products is expected.

In view of such circumstances, the object of the present invention is to provide a "to maintain the citrus flavor There is a method of suppressing the formation of degraded odor.

Further, another object of the present invention is to provide a product or the like which stores an aroma inherent to citrus flavor.

According to the present invention, there is provided a citrus-containing product comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in a molecule or a metal salt thereof.

Further, according to the present invention, there is provided a beverage comprising a citrus flavor, a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof, and an alcohol. Further, the content of the dicarboxylic acid having a conjugated double bond or a metal salt thereof in the above molecule in the entire beverage is 0.5 ppm or more and 15,000 ppm or less.

Moreover, according to the present invention, there is provided a fragrance composition comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in a molecule or a metal salt thereof.

Moreover, according to the present invention, there is provided a method for suppressing generation of deterioration odor by adding a dicarboxylic acid having a conjugated double bond or a metal salt thereof to a product containing a citrus flavor, And one or more selected from the group consisting of p-cresol, p-isopropyltoluene, p-methylacetophenone, α-terpineol, and terpinolene in the citrus-containing product. The formation of a compound.

Moreover, according to the present invention, there is provided a method for suppressing deterioration of aroma, characterized in that a dicarboxylic acid having a conjugated double bond in a molecule or a metal salt thereof is added to a product containing a citrus flavor.

In the method for suppressing the generation of deteriorated odor of the present invention, by containing a citrus flavor The product is a dicarboxylic acid having a conjugated double bond or a metal salt thereof in the molecule, and it is possible to suppress the formation of a specific compound group which may cause deterioration of the odor.

Thereby, it is possible to provide a product or the like which retains the aroma inherent to the citrus flavor.

Hereinafter, the present invention will be described based on the embodiments.

(Method for suppressing generation of deterioration odor and method for suppressing deterioration of aroma)

First, the method for suppressing generation of deterioration odor and the method for suppressing deterioration of aroma in the present embodiment will be described.

The method for suppressing the generation of deterioration odor in the present embodiment is a method of suppressing the selection of the above-mentioned citrus-flavored product by adding a dicarboxylic acid having a conjugated double bond or a metal salt thereof to a citrus-containing product. The formation of one or two or more compounds of the group consisting of p-cresol, p-isopropyltoluene, p-methylacetophenone, α-terpineol, and terpinolene.

Moreover, the method of suppressing the deterioration of the aroma in the present embodiment is as follows.

A method for suppressing deterioration of aroma, characterized in that a dicarboxylic acid having a conjugated double bond in a molecule or a metal salt thereof is added to a product containing a citrus flavor.

In other words, the method for suppressing the generation of the deterioration odor and the method for suppressing the deterioration of the aroma of the present embodiment are to add a dicarboxylic acid having a specific structure or a metal salt thereof to a product containing a citrus flavor, thereby suppressing heating of the citrus flavor or Specific compounds produced during long-term storage The result is that the deterioration of the aroma can be suppressed.

(products containing citrus flavor)

The method for suppressing generation of deterioration odor and the method for suppressing deterioration of aroma according to the present embodiment can be applied to any product as long as it is conventionally obtained from a citrus-containing flavor.

As such a product, a beverage is representative, and examples thereof include ice cream, candy, sweets such as chewing gum, and seasonings such as sauces. In addition to consumption, it can also be applied to perfumes or cosmetics, body washes, or fragrances, detergents, mouthwashes and the like.

Among them, the method of the present embodiment can be preferably used in the case where the product is a beverage.

(citrus flavor)

The citrus flavor which is a method for suppressing the generation of deterioration odor according to the present embodiment is selected from the group consisting of a flavor selected from the above-mentioned p-cresol, p-isopropyltoluene, p-methylbenzene during heating or storage. A component of at least one compound of the group of compounds in the group consisting of ethyl ketone, α-terpineol, and terpinolene.

As a typical example, the flavor of citral which can generate p-cresol, p-isopropyltoluene and p-methylacetophenone during heating or storage can be mentioned, or can be contained during heating or storage. The flavor of p-cresol, p-isopropyltoluene, α-terpineol and terpinolene is produced.

Here, when the citrus flavor is heated or stored for a long period of time, in addition to the compound represented by the above-mentioned compound group, a compound having a large amount of a compound is formed, and the present inventors have found that the above five compounds are produced when a beverage or the like is produced. It is effective in suppressing and managing it in order to ensure the flavor inherent in citrus flavor.

In other words, as the flavor of the present embodiment, even if it is a citrus flavor containing an aroma component other than the above citral or limonene, it is possible to produce a flavor of any of the above five components. It can be applied.

Further, in the present embodiment, for example, when the citrus flavor contains citral, it is preferred that the formation of all the compounds of p-cresol, p-isopropyltoluene and p-methylacetophenone which can be formed is suppressed. Further, in the case where the citrus flavor contains limonene, it is preferred that the formation of all compounds of p-cresol, p-isopropyltoluene, α-terpineol, and terpinolene which can be produced is suppressed. Thereby, as a product, the scent of the citrus flavor can be sufficiently maintained.

Specific examples of the method for achieving the effect include adjusting the composition of the product, or adjusting the amount of the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof, and the like, and performing the appropriate screening. The effect as described above.

In the present embodiment, the content of the citrus flavor in the entire product can be appropriately set according to the designed product.

Among the components constituting the citrus flavor, "the ability to form a compound selected from the group consisting of p-cresol, p-isopropyltoluene, p-methylacetophenone, α-terpineol, and terpinolene The lower limit of the content of the component is, for example, 1 ppm or more, preferably 3 ppm or more, and more preferably 5 ppm or more.

Further, the upper limit of the content of the component in the entire product is, for example, 1000 ppm or less, preferably 500 ppm or less, more preferably 300 ppm or less.

In addition, the content of the whole citrus flavor in the whole product can be appropriately set according to the designed product, and the lower limit thereof is, for example, 5 ppm or more, preferably 20 ppm or more, and more preferably 50 ppm or more.

Further, the upper limit of the content of the entire citrus flavor in the entire product is, for example, 10,000 ppm or less, preferably 5,000 ppm or less, more preferably 3,000 ppm or less.

(dicarboxylic acid having a conjugated double bond in its molecule or a metal salt thereof)

In the method for suppressing generation of deterioration odor and the method for suppressing deterioration of aroma according to the present embodiment, a dicarboxylic acid having a conjugated double bond in a molecule or a metal salt thereof is added to the product in order to suppress the formation of the above compound.

Here, the "dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof" may be appropriately selected from "a material which can be added as a product" to satisfy the characteristics of the compound specified herein.

Here, it is considered that the conjugated double bond in the molecule has a reducing action on the citrus flavor contained in the product, and the generation of the deterioration odor at the time of heating or long-term storage can be effectively suppressed.

Further, the conjugated double bond has a plurality of double bonds at a position away from the carboxyl group in the molecule, and the conjugated double bond may be in a conjugated relationship, but is preferably conjugated to a C=O double bond having a carboxyl group in the molecule. Aspect.

Further, the double bond which contributes to the conjugated double bond is not limited to the carbon-carbon double bond, and may be a double bond of a carbon atom and a hetero atom. Further, for example, a ring may be formed via a double bond as in the case of an aromatic compound.

Here, by increasing the number of atoms contributing to the conjugate, the effect of suppressing the generation of deterioration odor is more remarkable, and more specifically, it is preferable that the two carboxylic acids possessed by the molecule are intramolecularly It has a double bond and is in a conjugate relationship.

Here, examples of such a dicarboxylic acid or a metal salt thereof include fumaric acid or itaconic acid or a metal salt thereof. In particular, fumaric acid can be preferably used because of the high ease of obtaining or the effect of suppressing the generation of deteriorated odor.

Further, a dicarboxylic acid having a conjugated double bond in the molecule like fumaric acid is generally used as an additive in food applications, whereby an attempt is made to exhibit an antioxidant action. However, prior art did not The following knowledge was found to be known: the addition of a citrus-flavored product was carried out to suppress the formation of a compound which causes the above-mentioned deteriorated odor.

On the other hand, the inventors of the present invention conducted intensive studies and found that by adding a dicarboxylic acid or the like having the specific structure to a product containing a citrus flavor, generation of deterioration odor can be suppressed, and deterioration of aroma can be suppressed.

Here, as described in the above-described Patent Documents 1 to 4, the third component other than the aroma component such as citral is added to suppress deterioration of the citrus flavor. Therefore, for example, when a beverage containing a citrus flavor is produced, there is room for improvement in the aspect in which the flavor of the beverage is affected by the addition of the third component.

On the other hand, the dicarboxylic acid as described above is generally used to impart "sour taste" to a beverage or the like. On the other hand, the applied citrus flavor usually also gives the effect of giving a lemon-like aroma, so the purpose of adding these does not conflict.

Therefore, for example, even if it is applied to a beverage, it is possible to suppress the generation of deterioration odor without impairing the aroma and flavor inherent to the citrus flavor. Moreover, from this point of view, it is possible to dramatically expand the range of development of not only beverages but also products containing citrus flavors.

Here, the metal salt of the present embodiment may be a metal cation corresponding to an anion of one of the two carboxyl groups of the dicarboxylic acid, or may be present with two carboxyl groups of the dicarboxylic acid. The anion corresponding to the metal cation.

Here, examples of the metal cation include a monovalent cation and a divalent cation, and as the monovalent cation, a sodium ion or a potassium ion can be used. Further, as the divalent cation, calcium ion, magnesium ion or the like can be used.

In the present embodiment, the above dicarboxylic acid is added to the product, or the dicarboxylic acid is added. The metal salt is added to the product as long as it is appropriately selected according to the designed product.

For example, when a dicarboxylic acid is directly added to a beverage, the flavor derived from the dicarboxylic acid rapidly disappears when drinking, and the whole has a tendency to have a refreshing flavor, and further, a metal salt of a dicarboxylic acid is added. In the case of this, there is a tendency that the flavor remains.

In the method for suppressing the generation of the deterioration odor and the method for suppressing the deterioration of the aroma of the present embodiment, the amount of the dicarboxylic acid having a conjugated double bond or a metal salt thereof in the molecule can be appropriately adjusted depending on the purpose.

For example, the lower limit of the amount of addition of the "dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof" in the citrus-containing product is preferably 0.5 ppm or more, more preferably 10 ppm or more. Further, it is preferably 100 ppm or more, and particularly preferably 250 ppm or more.

In addition, the upper limit of the amount of addition of the "dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof" in the citrus-flavored product is, for example, 15,000 ppm or less.

More specifically, when the flavor containing citral is used as the citrus flavor, it is preferred that the amount of the dicarboxylic acid or the metal salt having a conjugated double bond in the molecule is 0.5 with respect to the entire product. In the above manner, it is easy to suppress the formation of p-cresol and p-methylacetophenone.

Further, it is not only effective for suppressing p-cresol and p-methylacetophenone but also effective for suppressing the formation of isopropyltoluene, and more preferably having two conjugated double bonds in the molecule. The amount of the carboxylic acid or its metal salt added is 10 ppm or more based on the entire product.

Further, when the citral-containing flavor is used as the citrus flavor as described above, the upper limit of the amount of the dicarboxylic acid having a conjugated double bond or a metal salt thereof contained in the molecule in the product is not It is particularly limited and can be appropriately selected depending on the design of the product, and is, for example, 15,000 ppm or less.

In the case where the flavor containing limonene is used as the citrus flavor, it is preferred that the amount of the dicarboxylic acid or the metal salt having a conjugated double bond in the molecule is 0.5 ppm or more with respect to the entire product. In this way, it becomes easy to suppress the formation of p-cresol.

Further, it is effective not only to suppress p-cresol but also to effectively inhibit the formation of isopropyl toluene, α-terpineol and terpinolene, and more preferably to have a conjugate in the molecule. The amount of the dicarboxylic acid or a metal salt added thereto is 10 ppm or more, more preferably 100 ppm or more, and particularly preferably 250 ppm or more.

In addition, when the flavor containing limonene is used as the citrus flavor, the upper limit of the amount of the dicarboxylic acid or the metal salt having a conjugated double bond in the molecule which is included in the product is not particularly limited. It can be appropriately selected according to the design of the product, for example, 15000 ppm or less.

Further, in the present embodiment, by appropriately setting the type and amount of the dicarboxylic acid having a conjugated double bond in the molecule or the amount thereof, it is possible to effectively suppress the deterioration of the citrus flavor without adding the dicarboxylic acid. In comparison with the case of the metal salt thereof, the amount (residual amount) of the aroma component of the citrus flavor in the product can be increased.

That is, the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof in the present embodiment can be used as an aroma deterioration inhibitor for a citrus-containing product.

As the kind of the dicarboxylic acid or the metal salt thereof, fumaric acid or a metal salt thereof remarkably exhibits the effect, and as the addition amount in the case of adding the fumaric acid, the antibutene The addition amount of the acid or the metal salt thereof to the entire product is set to 0.5 ppm or more, whereby the effect is more easily exhibited.

Based on such an effect, even when the citrus-flavored product is heated or stored for a long period of time, the aroma can be sufficiently maintained.

(Drink)

The method for suppressing generation of deteriorated odor and the method for suppressing deterioration of aroma in the present embodiment can be preferably applied to a beverage. The beverage contains the above-described citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof, and other compositions and the like can be appropriately set.

Further, the beverage may be an alcoholic beverage or a non-alcoholic beverage. Further, the lower limit of the alcohol concentration as the alcoholic beverage is, for example, 1% or more, preferably 2% or more, and more preferably 3% or more.

Further, the upper limit of the alcohol concentration as the alcoholic beverage is, for example, 15% or less, preferably 12% or less, more preferably 10% or less.

In the present embodiment, by adding the dicarboxylic acid having a conjugated double bond or a metal salt thereof to the beverage, the generation of deterioration odor is suppressed even during heating or long-term storage, and as a result, deterioration of aroma can be provided. A suppressed drink.

Regarding the pH of the beverage of the present embodiment, the lower the pH of the citrus-flavored beverage, the more likely it is to be deteriorated, and as a result, the compound which causes deterioration of the odor tends to be formed.

In this case, in the method for suppressing the generation of deterioration odor and the method for suppressing the deterioration of aroma in the present embodiment, the effect is remarkable when the beverage is acidic, that is, when the pH of the beverage is less than 7. From the same point of view, the pH of the beverage can be set to less than 6, and the pH can be set to less than 5.

Further, the pH of the beverage can be measured by a known method, and can be measured, for example, by using a pH meter HM-30R manufactured by Toago Corporation of East Asia.

Further, in order to adjust the pH as described above, a pH adjuster may be appropriately added to the beverage. The pH adjuster may be appropriately selected depending on the designed product, and examples thereof include a carboxylic acid such as citric acid or a carboxylate such as sodium citrate.

Further, the pH adjuster may be adjusted by adjusting the pH of the beverage one by one.

(fragrance composition)

In the method for suppressing the generation of the deterioration odor, etc., it has been disclosed that a dicarboxylic acid having a conjugated double bond or a metal salt thereof is added to a product containing a citrus flavor, and as another embodiment, a citrus flavor is prepared in advance. And a perfume composition having a dicarboxylic acid or a metal salt thereof having a conjugated double bond in the molecule, and adding the perfume composition to the product, whereby the desired effect can be exhibited.

Such a flavoring composition is, for example, 0.01 parts by mass or more of a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof, more preferably 0.1 part by mass or more, more preferably 100 parts by mass of the citrus flavor. In the case of containing 1 part by mass or more, it is particularly preferably 5 parts by mass or more.

Further, the fragrance composition of the present embodiment does not need to be uniform as a whole, and the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof may be mixed in a solid form.

In addition, the upper limit of the dicarboxylic acid having a conjugated double bond in the molecule contained in the fragrance composition of the present embodiment or a metal salt thereof is, for example, 50 parts by mass or less based on 100 parts by mass of the citrus flavor.

Here, as described above, the citrus flavor is liable to cause deterioration due to heating or long-term storage, or in an environment of low pH. On the other hand, in the fragrance composition of the present embodiment, by appropriately managing the environment for storage, the fragrance inherent to the citrus flavor can be sufficiently maintained even in the above-described addition amount.

More specifically, from the viewpoint of maintaining the aroma inherent to the citrus flavor, it is preferred that the flavor composition is contained in a container together with an inert gas, sealed, and stored in a cool dark place.

The flavor composition of the present embodiment can of course be added to a beverage, and can be added to foods such as ice cream, candy desserts such as candy, chewing gum, and seasonings such as sauces. also, In addition to food, it can also be added to perfumes such as perfumes or cosmetics, body washes, fragrances, detergents, mouthwashes, and the like.

Although the embodiments of the present invention have been described above, these are examples of the present invention, and various configurations other than the above may be employed.

The present invention includes the following.

(A1) A citrus-flavored product comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in a molecule or a metal salt thereof.

(A2) A citrus-flavored product as described in (A1), which is an alcoholic beverage.

(A3) The citrus-flavored product according to (A1) or (A2), wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid or itaconic acid or Metal salt.

(A4) The citrus-flavored product according to any one of (A1) to (A3), wherein the citrus flavor comprises citral.

(A5) The citrus-flavored product according to any one of (A1) to (A3), wherein the citrus flavor comprises limonene.

(A6) The citrus-flavored product according to any one of (A1) to (A5), wherein the citrus-flavored product has a dicarboxylic acid having a conjugated double bond or a metal salt thereof in the above molecule. The content is 0.5 ppm or more and 15,000 ppm or less.

(A7) a beverage comprising a citrus flavor, a dicarboxylic acid having a conjugated double bond in a molecule or a metal salt thereof, and an alcohol, and the whole of the beverage has a dicarboxylic acid having a conjugated double bond or The content of the metal salt is 0.5 ppm or more and 15,000 ppm or less.

(A8) The beverage according to (A7), wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid or itaconic acid or a metal salt thereof.

(A9) The beverage according to (A7) or (A8), wherein the citrus flavor comprises citral.

(A10) The beverage according to (A7) or (A8), wherein the citrus flavor comprises limonene.

(A11) A fragrance composition comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in a molecule or a metal salt thereof.

(A12) A method for suppressing generation of deteriorated odor by inhibiting a dicarboxylic acid having a conjugated double bond in a molecule or a metal salt thereof in a citrus-containing product, thereby suppressing selection of the citrus-flavored product The formation of one or more compounds of the group consisting of p-cresol, p-isopropyltoluene, p-methylacetophenone, α-terpineol, and terpinolene.

(A13) The method for suppressing generation of deterioration odor according to (A12), wherein the citrus-flavored product is an alcoholic beverage.

(A14) The method for suppressing generation of deterioration odor according to (A13), wherein the pH of the alcoholic beverage is less than 7.

(A15) The method for suppressing generation of deterioration odor according to any one of (A12) to (A14), wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is a transbutene Acid or itaconic acid or a metal salt thereof.

(A16) The method for suppressing generation of deterioration odor according to any one of (A12) to (A15), wherein the citrus-flavored product has a conjugated double bond in the molecule The amount of the carboxylic acid or its metal salt added is 0.5 ppm or more and 15,000 ppm or less.

(A) The method for suppressing the generation of deterioration odor according to any one of (A12) to (A16), wherein the citrus flavor comprises citral.

(A18) The method for suppressing generation of deterioration odor according to (A17), which suppresses generation of a compound of p-cresol, p-isopropyltoluene and p-methylacetophenone.

(A19) The method for suppressing generation of deterioration odor according to any one of (A12) to (A16), wherein the citrus flavor comprises limonene.

(A20) The method for suppressing generation of deterioration odor according to (A19), wherein the production of a compound of p-cresol, p-isopropyltoluene, α-terpineol, and terpinolene is affected inhibition.

(A21) A method for suppressing deterioration of aroma, characterized in that a dicarboxylic acid having a conjugated double bond in a molecule or a metal salt thereof is added to a product containing a citrus flavor.

(A22) The method for suppressing deterioration of aroma according to (A21), wherein the citrus-flavored product is an alcoholic beverage.

(A23) The method for suppressing deterioration of aroma according to (A21) or (A22), wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid or itaconic acid Or such metal salts.

(B1) A method for suppressing deterioration of aroma, characterized in that fumaric acid or a metal salt thereof is added to a beverage or food containing citral, and 0.5 ppm or more of the above-mentioned beverage containing citral or the whole food is added And 15,000 ppm or less of the above fumaric acid or a metal salt thereof.

(B2) The method for suppressing deterioration of aroma as described in (B1), which comprises citral The above beverage or the above food contains a citral beverage.

(B3) The method for suppressing deterioration of aroma as described in (B2), characterized in that the pH of the beverage containing citral is less than 7.

(B4) An aroma deterioration inhibitor which is composed of fumaric acid or a metal salt thereof, which is characterized in that 0.5% or more and 15,000 ppm or less of the above-mentioned aroma deterioration inhibitor is added to a whole beverage or food containing citral .

Example

Hereinafter, the present invention will be described in detail using the examples, but the present invention is not limited by the description of the examples.

First, in the present embodiment, the amount of each component contained in the beverage was quantified by gas chromatography (GC) analysis. The order of this analysis is as follows.

(sample preparation method)

A sample of 50.0 g was weighed, and 100 μL of 2-octanol as an internal standard was added, followed by dilution with 50 mL of water. In addition, a solid phase (Oasis HLB 200 mg/6 cc manufactured by Waters Co., Ltd.) adjusted in dichloromethane (5 mL), ethanol (5 mL), and water (20 mL) was used to prepare the diluted sample obtained above. The total amount of organic components is adsorbed. Thereafter, the mixture was eluted with 5 mL of dichloromethane, and the eluate was dehydrated with anhydrous sodium sulfate, and the supernatant was transferred to a Spitz tube and concentrated to 200 μL with nitrogen to prepare a sample for analysis.

(quantitative method)

The sample for analysis was subjected to gas chromatography (GC) analysis under the conditions shown below. The amount of the components in the sample was calculated based on the area ratio of the peak of 2-octanol used as an internal standard. In addition, two GC analyses were performed on the same sample, and the average value was used as the component amount in the sample. The method is quantified.

(GC condition)

Machine Name: 5973inert Mass Selective Detector manufactured by Agilent Technologies

Column: DB-WAX (60m × 0.25mm × 0.25μm)

Oven temperature: 40 ° C (1 min) - (3 ° C / min) - 210 ° C (3 min)

Flow rate: 1ml/min

Injection temperature: 250 ° C

Injection volume: 1μL

Split ratio: 10:1

(Example 1)

As the sample liquid A, a beverage containing 5% alcohol concentration and 10 ppm citral was prepared, and the pH of the beverage was adjusted so that the pH was 3.1 using trisodium citrate as a pH adjuster. Here, the pH was measured using a pH meter HM-30R manufactured by Toagos Corporation of East Asia.

To the beverage, monosodium fumarate was added so as to be 250 ppm as a whole of the beverage, and after the plug, it was allowed to stand at 37 ° C for 7 days. After standing, the amount of citral, the amount of p-cresol, the amount of p-isopropyltoluene, and the amount of p-methylacetophenone contained in the beverage were quantified.

The content is shown in Table 1 in the form of a ratio to the content of each component in Comparative Example 1 below.

(Examples 2 and 3)

In the method of Example 1, the addition amount of monosodium fumarate was adjusted as described in Table 1, and the sample was allowed to stand still in the same manner as in Example 1, and was contained in the beverage. The amount of each component is quantified. The results are shown in Table 1.

(Example 4)

In the method of Example 1, except that fumaric acid was added in place of monosodium fumarate so as to be 210 ppm, it was left to stand still in the same manner as in Example 1, and was contained in the beverage. The amount of each component is quantified. The results are shown in Table 1.

(Comparative Example 1)

In the method of Example 1, except that monosodium fumarate was not added, the amount of each component contained in the beverage was quantified by the same method as in Example 1. The results of Comparative Example 1 are shown in Table 1 as a control (100.0%).

Here, in the above Examples 1-4, the "citrus taste", "deteriorated" and "taste" items were evaluated for the sensory function.

The functional evaluation was performed by three professional inspectors, and those who had a good impression compared with Comparative Example 1 were recorded as +1, those who had a bad impression were recorded as -1, those who had a bad impression were recorded as 0, and 3 were changed. The average score of the functional inspectors is shown in Table 1 as a score.

In addition, as for the "deteriorated scent", the odor of the deterioration of citral is not perceived as a preferable case.

(Example 5)

As the sample liquid A, a beverage containing 5% alcohol concentration and 10 ppm citral was prepared, and the pH of the beverage was adjusted so that the pH was 3.3 using trisodium citrate as a pH adjuster. Here, the pH was measured using a pH meter HM-30R manufactured by Toagos Corporation of East Asia.

To the beverage, monosodium fumarate was added so as to be 250 ppm as a whole of the beverage, and after the plug, it was allowed to stand at 37 ° C for 7 days. After standing, the amount of citral, the amount of p-cresol, the amount of p-isopropyltoluene, and the amount of p-methylacetophenone contained in the beverage were quantified.

The content is shown in Table 2 in terms of the ratio of the contents of the respective components in Comparative Example 2 described below.

(Examples 6, 7)

In the method of Example 5, the addition amount of monosodium fumarate was adjusted as described in Table 2, and the rest was carried out in the same manner as in Example 5, and it was contained in the beverage. The amount of each component is quantified. The results are shown in Table 2.

(Comparative Example 2)

In the method of Example 5, the amount of each component contained in the beverage was quantified by the same method as in Example 5 except that monosodium fumarate was not added. The results of Comparative Example 2 are shown in Table 2 as a control (100.0%).

(Example 8)

As the sample liquid A, a beverage containing 5% alcohol concentration and 10 ppm citral was prepared, and the pH of the beverage was adjusted so that the pH was 3.5 using trisodium citrate as a pH adjuster. Here, the pH was measured using a pH meter HM-30R manufactured by Toagos Corporation of East Asia.

To the beverage, monosodium fumarate was added so as to be 250 ppm as a whole of the beverage, and after the plug, it was allowed to stand at 37 ° C for 7 days. After standing, the amount of citral contained in the beverage, p-cresol The amount, the amount of isopropyl toluene, and the amount of p-methylacetophenone were quantified.

The content is shown in Table 2 in the form of a ratio to the content of each component in Comparative Example 3 below.

(Example 9)

In the method of Example 8, the addition amount of monosodium fumarate was adjusted as described in Table 2, and the rest was carried out in the same manner as in Example 8, and it was contained in the beverage. The amount of each component is quantified. The results are shown in Table 2.

(Comparative Example 3)

In the method of Example 8, the amount of each component contained in the beverage was quantified by the same method as in Example 8 except that monosodium fumarate was not added. The results of Comparative Example 3 are shown in Table 2 as a control (100.0%).

Here, in the examples 5-9, the sensory evaluation was performed according to the items of "citrus taste", "deterioration", and "taste".

The specific method was carried out according to the examples 1-4, the examples 5-7 were compared with the comparative example 2, and the examples 8 and 9 were compared with the comparative example 3, and the impression of each item was counted. The results are shown in Table 2.

(Embodiment 10)

As the sample liquid B, a beverage containing no alcohol and containing 10 ppm of citral was prepared, and the pH of the beverage was adjusted so that the pH was 3.0 using trisodium citrate as a pH adjuster. Here, the pH was measured using a pH meter HM-30R manufactured by Toagos Corporation of East Asia.

To the beverage, monosodium fumarate was added so as to be 250 ppm as a whole of the beverage, and after the plug, it was allowed to stand at 37 ° C for 7 days. After standing, the amount of citral, the amount of p-cresol, the amount of p-isopropyltoluene, and the amount of p-methylacetophenone contained in the beverage were quantified.

The content is shown in Table 3 in the form of a ratio to the content of each component in Comparative Example 4 below.

(Comparative Example 4)

In the method of Example 10, the amount of each component contained in the beverage was quantified by the same method as in Example 10 except that monosodium fumarate was not added. The results of Comparative Example 4 are shown in Table 3 as a control (100.0%).

(Example 11)

As the sample liquid C, a beverage containing 5% alcohol concentration and 10 ppm limonene was prepared, and the pH of the beverage was adjusted so that the pH was 3.3 using trisodium citrate as a pH adjuster. Here, the pH was measured using a pH meter HM-30R manufactured by Toagos Corporation of East Asia.

To the beverage, monosodium fumarate was added so as to be 250 ppm as a whole of the beverage, and after the plug, it was allowed to stand at 37 ° C for 7 days. After standing, the amount of limonene contained in the beverage, the amount of p-cresol, the amount of isopropyl toluene, the amount of α-terpineol, and terpinolene were quantified.

The content is shown in Table 4 in terms of the ratio of the contents of the respective components in Comparative Example 5 described below.

(Comparative Example 5)

In the method of Example 11, except that monosodium fumarate was not added, the amount of each component contained in the beverage was quantified by the same method as in Example 11. The results of Comparative Example 5 are shown in Table 4 as a control (100.0%).

(Embodiment 12)

As the sample liquid A, a beverage containing 5% alcohol concentration and 10 ppm citral was prepared, and the pH of the beverage was adjusted so that the pH was 3.0 using trisodium citrate as a pH adjuster. Here, the pH was measured using a pH meter HM-30R manufactured by Toagos Corporation of East Asia.

To the beverage, monosodium fumarate was added so as to be 10 ppm of the whole beverage, and after being tied, it was allowed to stand at 37 ° C for 7 days. After standing, the amount of citral, the amount of p-cresol, the amount of p-isopropyltoluene, and the amount of p-methylacetophenone contained in the beverage were quantified.

The content is shown in Table 5 in the form of a ratio to the content of each component in Comparative Example 6 below.

(Example 13)

In the method of Example 12, the addition amount of monosodium fumarate was adjusted as described in Table 5, and the mixture was allowed to stand still in the same manner as in Example 12, and was contained in the beverage. The amount of each component is quantified. The results are shown in Table 5.

(Example 14)

In the method of Example 12, the reaction was carried out in the same manner as in Example 12 except that ikonic acid was used instead of monosodium fumarate and the content was changed to 250 ppm. The amount of each component is quantified. The results are shown in Table 5.

(Comparative Example 6)

In the same manner as in Example 12, the amount of each component contained in the beverage was quantified in the same manner as in Example 12 except that the monosodium fumarate was not added. The results of Comparative Example 6 are shown in Table 5 as a control (100.0%).

As shown in the respective examples, by adding a specific dicarboxylic acid or a metal salt thereof to a beverage having a citrus flavor, generation of a component which causes deterioration of odor is suppressed.

Further, by suppressing the generation of the component which causes deterioration of the odor, it is possible to impart a pleasant citrus taste and taste to the drinker.

[Industrial availability]

The method for suppressing the generation of deteriorated odor of the present invention can effectively maintain the aroma inherent to the citrus flavor. In this case, the scope of development of products with citrus flavors can be dramatically expanded.

Further, by this, it is possible to provide a product or the like which retains the aroma inherent to the citrus flavor.

The application is based on the priority of Japanese Patent Application No. 2014-258052, filed on Dec.

Claims (23)

A citrus-flavored product comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof. For example, the citrus-flavored product of claim 1 is an alcoholic beverage. The citrus-flavored product according to claim 1 or 2, wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid or itaconic acid or a metal salt thereof . A citrus-flavored product according to claim 1 or 2, wherein the citrus flavor comprises citral. A citrus-flavored product according to claim 1 or 2, wherein the citrus flavor comprises limonene. The citrus-flavored product according to claim 1 or 2, wherein the citrus-flavored product has a content of a dicarboxylic acid having a conjugated double bond or a metal salt thereof in the above molecule of 0.5 ppm or more and 15000 ppm. the following. A beverage comprising a citrus flavor, a dicarboxylic acid having a conjugated double bond in a molecule or a metal salt thereof, and an alcohol, and the dicarboxylic acid having a conjugated double bond or a metal thereof in the above-mentioned whole of the beverage The content of the salt is 0.5 ppm or more and 15,000 ppm or less. The beverage according to claim 7, wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid or itaconic acid or a metal salt thereof. A beverage according to claim 7 or 8, wherein the citrus flavor comprises citral. A beverage according to claim 7 or 8, wherein the citrus flavor comprises limonene. A fragrance composition comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof. A method for suppressing the generation of degraded odor by inhibiting a dicarboxylic acid having a conjugated double bond or a metal salt thereof in a citrus-containing product, and suppressing the citrus-like product selected from the group consisting of p-cresol And the formation of one or more compounds of the group consisting of isopropyl toluene, p-methylacetophenone, α-terpineol, and terpinolene. The method for suppressing generation of deteriorated odor according to claim 12, wherein the citrus-flavored product is an alcoholic beverage. The method for suppressing generation of deteriorated odor according to claim 13 of the invention, wherein the pH of the alcoholic beverage is less than 7. The method for inhibiting the generation of deterioration odor according to any one of the items 12 to 14, wherein the dicarboxylic acid having a conjugated double bond or a metal salt thereof is fumaric acid or itaconic acid or These metal salts. The method for suppressing the generation of deterioration odor according to any one of the items 12 to 14, wherein the citrus-flavored product is added to a dicarboxylic acid having a conjugated double bond or a metal salt thereof in the molecule. The amount is 0.5 ppm or more and 15,000 ppm or less. The method for suppressing the generation of deterioration odor according to any one of claims 12 to 14, wherein the citrus flavor comprises citral. For example, the method for suppressing the generation of degraded odor generated in claim 17 of the patent application, which makes p-cresol, the opposite The formation of all compounds of propyl toluene and p-methylacetophenone is inhibited. The method for suppressing generation of deterioration odor according to any one of claims 12 to 14, wherein the citrus flavor comprises limonene. The method for suppressing the generation of deterioration odor according to claim 19 of the patent application, wherein the formation of a compound of p-cresol, p-isopropyltoluene, α-terpineol, and terpinolene is suppressed. A method for suppressing deterioration of aroma is to add a dicarboxylic acid having a conjugated double bond or a metal salt thereof to a product containing a citrus flavor. The method for suppressing aroma deterioration according to claim 21, wherein the citrus-flavored product is an alcoholic beverage. The method for inhibiting aroma deterioration according to claim 21 or 22, wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid or itaconic acid or a metal salt thereof .