JP2016116476A - Method for inhibiting deterioration of fragrance and deterioration inhibitor for fragrance - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for inhibiting the generation of degradation odor for retaining the fragrance inherent to a citrus flavor.SOLUTION: The method for inhibiting the generation of degradation odor comprises adding, to a citrus flavor-containing product, a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to inhibit the generation of one kind or two or more kinds of compounds selected from the group consisting of p-cresol, p-cymene, p-methylacetophenone, α-terpineol and terpinolene.SELECTED DRAWING: None

Description

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

Conventionally, by adding citrus flavors to beverages, it has been widely used to add flavors peculiar to citrus fruits such as lemons to beverages. Further, by adding such a flavor unique to citrus fruits, it is possible to give a refreshing refreshment to those who drink.
Here, citral, limonene, etc. are mentioned as a typical aroma component of this citrus flavor.

  Here, it is known that the aroma component contained in such a citrus flavor is converted into another component by heating or storing for a long time. In addition, the following techniques are known as examples of measures against such knowledge.

  For example, Patent Document 1 discloses a solvent-extracted extract from karin, mango, mangosteen, myrobalan, pomegranate or cacao in order to suppress the production of p-methylacetophenone and the like that occur when citral is heated, A technique for adding epicatechin, epicatechin gallate, epigallocatechin gallate, enzyme-treated rutin, quercetin, ferulic acid, caffeic acid, rosmarinic acid, syringic acid or gallic acid is disclosed.

Patent Document 2 discloses a technique in which eriocitrin or an eriocitrin-containing material is used as a deterioration preventing agent for flavor components such as citral.
In addition, the use of solvent extracts such as Ashitaba, Avocado, Psyllium, etc. to suppress the generation of odors from citral and citral-containing products (see Patent Document 3), and the solvent extract from the pericarp of Vanilla genus plants to suppress fragrance degradation A technique used as an agent is known (see Patent Document 4).

JP 2002-180081 A JP 2001-61461 A JP 2004-18613 A JP 2004-292778 A

That is, as described in Patent Documents 1 to 4, research for maintaining the fragrance unique to citrus flavors is still actively conducted, and the development of technology for designing various products is desired. Yes.
In view of such circumstances, an object of the present invention is to provide a method for suppressing the generation of a deteriorated odor for maintaining a fragrance unique to citrus flavor.

According to the present invention, by adding a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a citrus flavor-containing product,
Deterioration odor production inhibiting method for inhibiting the production of one or more compounds selected from the group consisting of p-cresol, p-cymene, p-methylacetophenone, α-terpineol and terpinolene in the citrus flavor-containing product Is provided.

  Moreover, according to this invention, the dicarboxylic acid which has a conjugated double bond in a molecule | numerator, or its metal salt is added with respect to a citrus flavor containing product, The fragrance degradation suppression method characterized by the above-mentioned is provided.

  Moreover, according to this invention, the fragrance | flavor composition characterized by containing the citrus flavor and the dicarboxylic acid which has a conjugated double bond in a molecule | numerator, or its metal salt is provided.

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

  In the degradation odor production suppression method of the present invention, by adding a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a citrus flavor-containing product, a specific group of compounds that can cause a degradation odor. Generation can be suppressed.

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

(Deterioration odor generation suppression method, aroma deterioration suppression method)
First, the degradation odor production | generation suppression method and fragrance degradation suppression method concerning this embodiment are demonstrated.
The degradation odor production suppression method of the present embodiment adds p- in a beverage containing the citrus flavor by adding a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to the citrus flavor-containing product. It is a degradation odor production | generation suppression method which suppresses the production | generation of 1 type, or 2 or more types of compounds chosen from the group which consists of cresol, p-cymene, p-methylacetophenone, (alpha) -terpineol, and terpinolene.

Moreover, the fragrance degradation suppression method of this embodiment is as showing below.
A method for inhibiting fragrance degradation, comprising adding a dicarboxylic acid having a conjugated double bond in its molecule or a metal salt thereof to a citrus flavor-containing product.

  That is, the deterioration odor production suppressing method and the fragrance deterioration suppressing method according to the present embodiment are those in which a dicarboxylic acid having a specific structure or a metal salt thereof is added to a citrus flavor-containing product, and thereby, a citrus flavor. The production | generation of the specific compound which arises when heating or long-term preservation | save with respect to can be suppressed, and deterioration of aroma can be suppressed as a result.

(Products containing citrus flavor)
The deterioration odor production suppressing method and the fragrance deterioration suppressing method according to the present embodiment can be applied to any product as long as it is a product conventionally used to include a citrus flavor.
Examples of such products include beverages, confectionery such as ice cream, strawberries, and gums, and foodstuffs such as seasonings such as dressings. Besides edible, it can also be applied to cosmetics such as perfumes, cosmetics, bathing agents, fragrances, detergents and mouthwashes.
Among these, the method of this embodiment is preferably used when the product is a beverage.

(Citrus flavor)
As the citrus flavor according to the method for suppressing the generation of a deteriorated odor of the present embodiment, a compound selected from the group consisting of the above-mentioned p-cresol, p-cymene, p-methylacetophenone, α-terpineol and terpinolene during heating and storage. From the group, it is selected from the flavors that contain components from which at least one compound can be produced.
Typical examples thereof include flavors containing citral that can be produced by p-cresol, p-cymene and p-methylacetophenone during heating and storage, and p-cresol, p-cymene, α- Examples include flavors containing limonene from which terpineol and terpinolene can be produced.

Here, in the case where the citrus flavor is heated or stored for a long time, various compounds other than the compounds shown as the above compound group are produced. It has been found that suppressing and managing the production of citrus is effective in securing the flavor and the like unique to citrus flavor.
That is, as the flavor according to the present embodiment, even a citrus flavor containing a fragrance component other than the citral and limonene described above can be applied as long as it can generate any one of the five components.

Further, in this embodiment, for example, when the citrus flavor contains citral, it is preferable to suppress the production of all the compounds that can be produced, such as p-cresol, p-cymene and p-methylacetophenone, and citrus flavor. In the case of containing limonene, it is preferable to suppress the production of all the compounds of p-cresol, p-cymene, α-terpineol and terpinolene that can be produced. Thereby, the fragrance peculiar to citrus flavor can be given enough as a product.
Specific methods for achieving this effect include, for example, adjusting the composition of the product and adjusting the amount of dicarboxylic acid having a conjugated double bond in its molecule or its metal salt. The effects as described above can be exhibited by appropriately screening.

In the present embodiment, the content of citrus flavor in the entire product can be appropriately set according to the product to be designed.
Among the components constituting this citrus flavor, the lower limit of the content of components that can be produced by a compound group selected from the group consisting of p-cresol, p-cymene, p-methylacetophenone, α-terpineol and terpinolene, For example, it is 1 ppm or more, preferably 3 ppm or more, more preferably 5 ppm or more.
Moreover, the upper limit of content in the whole product of the said component is 1000 ppm or less, for example, Preferably it is 500 ppm or less, More preferably, it is 300 ppm or less.
The content of the entire citrus flavor in the entire product can be appropriately set according to the product to be designed, but the lower limit is, for example, 5 ppm or more, preferably 20 ppm or more, more preferably 50 ppm. That's it.
Moreover, the upper limit of content of the whole citrus flavor in the whole product is 10,000 ppm or less, for example, Preferably it is 5000 ppm or less, More preferably, it is 3000 ppm or less.

(Dicarboxylic acid or metal salt thereof having a conjugated double bond in the molecule)
In the degradation odor production inhibiting method and the fragrance degradation inhibiting method of the present embodiment, in order to suppress the production of the above compound, a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is added to the product. It is characterized by doing.
Here, the “dicarboxylic acid having a conjugated double bond in its molecule or a metal salt thereof” satisfies the characteristics as a compound defined herein, and is appropriately selected from materials that can be added as a product. do it.
Here, it is considered that the conjugated double bond in the molecule brings about a reducing action on the citrus flavor contained in the product and can effectively suppress the generation of a deteriorated odor during heating and long-term storage. It is done.

Note that the conjugated double bond may have a plurality of double bonds at a site isolated from the carboxyl group in the molecule, and these may be in a conjugated relationship. An embodiment conjugated to a heavy bond is preferred.
The double bond contributing 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. Moreover, you may comprise the ring through the double bond like an aromatic compound, for example.
Here, as the number of atoms contributing to conjugation increases, the effect of suppressing the generation of deteriorated odor becomes more prominent. More specifically, conjugation occurs due to the double bond provided in the molecule of the two carboxylic acids in the molecule. It is preferable to have a relationship of

Here, examples of such a dicarboxylic acid or a metal salt thereof include fumaric acid, itaconic acid, or a metal salt thereof. In particular, fumaric acid is preferably used because of its high availability and high effect of suppressing the generation of deteriorated odor.
In addition, dicarboxylic acid having a conjugated double bond in the molecule such as fumaric acid is generally used as an additive in food applications, and thereby attempts have been made to develop an antioxidant effect. However, as a conventional technique, no knowledge has been found that an addition to a citrus flavor-containing product is suppressed to suppress the generation of a compound that causes the above-mentioned deterioration odor.
On the other hand, as a result of diligent studies, the present inventor added dicarboxylic acid or the like having this specific structure to a product containing a citrus flavor, thereby suppressing the generation of a deteriorated odor and suppressing aroma deterioration. I found out that I can do it.

Here, all of the techniques described in Patent Documents 1 to 4 described above suppress the deterioration of the citrus flavor by adding a third component other than the aroma component such as citral. Therefore, for example, when producing a beverage containing citrus flavor, there is room for improvement in that the flavor of the beverage is affected by adding this third component.
On the other hand, dicarboxylic acids as described above are generally used to impart “sourness” to beverages and the like. On the other hand, since the citrus flavor to be applied usually has an effect of imparting a refreshing fragrance like lemon, the purpose of adding these is not contradictory.
Therefore, even if it is applied to beverages, for example, it can be said that the generation of a deteriorated odor can be suppressed without impairing the aroma and flavor unique to citrus flavor. In addition, from such a viewpoint, the range of development of products containing not only beverages but also citrus flavors can be dramatically expanded.

Here, the metal salt according to the present embodiment may be one in which a corresponding metal cation exists for the anion with respect to one of the two carboxyl groups provided in the dicarboxylic acid, or provided in the dicarboxylic acid. For the anions for both carboxyl groups, corresponding metal cations may be present.
Here, examples of the metal cation include those of a monovalent cation and those of a divalent cation. As the monovalent cation, sodium ion, potassium ion or the like can be adopted. As the divalent cation, calcium ion, magnesium ion or the like can be employed.

In the present embodiment, whether to add the dicarboxylic acid to the product or to add the metal salt of the dicarboxylic acid to the product may be appropriately selected according to the product to be designed.
For example, when applied to beverages, when dicarboxylic acid is added as it is, the flavor derived from this dicarboxylic acid tends to disappear quickly when drunk, and the whole tends to have a crisp flavor. When salt is added, this flavor tends to remain until later.

The addition amount of the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof according to the degradation odor production inhibiting method and the fragrance degradation inhibiting method of the present embodiment can be appropriately adjusted according to the purpose. .
For example, in the citrus flavor-containing product, the lower limit of the amount of dicarboxylic acid having a conjugated double bond in its molecule or its metal salt is preferably 0.5 ppm or more, more preferably 10 ppm or more. More preferably, it is 100 ppm or more, and particularly preferably 250 ppm or more.
Moreover, as an upper limit of the addition amount of the dicarboxylic acid which has a conjugated double bond in a molecule | numerator, or its metal salt in a citrus flavor containing product, it is 15000 ppm or less, for example.

More specifically, when a citral-containing flavor is used as the citrus flavor, the amount of dicarboxylic acid having a conjugated double bond in the molecule or the metal salt thereof is preferably 0.5 ppm or more relative to the entire product. By doing in this way, it becomes easy to suppress the production | generation of p-cresol and p-methylacetophenone.
In addition, from the viewpoint of effectively suppressing not only p-cresol and p-methylacetophenone but also generation of p-cymene, the amount of dicarboxylic acid having a conjugated double bond in the molecule or the metal salt thereof is added to the entire product. More preferably, it is 10 ppm or more.
In addition, when using a flavor containing citral as the citrus flavor as described above, the upper limit of the amount of dicarboxylic acid having a conjugated double bond or a metal salt thereof in the molecule that can be contained in the product is particularly limited. However, it is 15000 ppm or less, for example.

Further, when a limonene-containing flavor is used as the citrus flavor, the addition amount of the dicarboxylic acid having a conjugated double bond in the molecule or the metal salt thereof is preferably 0.5 ppm or more, as described above. By doing, it becomes easy to suppress the production | generation of p-cresol.
In addition, from the viewpoint of effectively suppressing not only p-cresol but also the production of p-cymene, α-terpineol and terpinolene, the amount of dicarboxylic acid having a conjugated double bond in the molecule or the metal salt thereof with respect to the entire product Is more preferably 10 ppm or more, further preferably 100 ppm or more, and particularly preferably 250 ppm or more.
In addition, when using a flavor containing limonene as a citrus flavor, the upper limit value of the amount of dicarboxylic acid having a conjugated double bond or a metal salt thereof in the molecule that can be included in the product is not particularly limited, Although it can select suitably according to the design of a product, it is 15000 ppm or less, for example.

In this embodiment, by appropriately setting the type and amount of dicarboxylic acid having a conjugated double bond in its molecule or its metal salt, the deterioration of citrus flavor can be effectively suppressed, and dicarboxylic acid or its metal can be effectively suppressed. Compared with the case where no salt is added, the amount (remaining amount) of the aroma component in the citrus flavor in the product can be increased.
As the kind of dicarboxylic acid or its metal salt, fumaric acid or its metal salt exhibits this effect remarkably, and when this fumaric acid is added, the addition amount of fumaric acid or its metal to the whole product By setting the addition amount of the salt to 0.5 ppm or more, such an effect is easily exhibited.
From such an effect, even if the product containing the citrus flavor is heated or stored for a long period of time, the aroma can be sufficiently retained.

(Beverage)
The deteriorated odor production suppressing method and the aroma deterioration suppressing method of the present embodiment can be preferably applied to beverages. Such a beverage contains the above-mentioned citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof, and other compositions can be appropriately set.
The beverage may be an alcoholic beverage or a non-alcoholic beverage. In addition, the lower limit of the alcohol concentration as an alcoholic beverage is 1% or more, for example, Preferably it is 2% or more, More preferably, it is 3% or more.
Moreover, the upper limit of the alcohol concentration as an alcoholic beverage is 15% or less, for example, Preferably it is 12% or less, More preferably, it is 10% or less.
In this embodiment, by adding the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to the beverage as described above, generation of a deteriorated odor is suppressed even during heating and long-term storage, and as a result It is possible to provide a beverage in which deterioration of aroma is suppressed.

Regarding the pH of the beverage according to this embodiment, the citrus flavor tends to be denatured as the pH of the beverage is lowered, and as a result, it tends to easily generate a compound that causes a deteriorated odor.
From this, in the degradation odor production | generation suppression method and fragrance degradation suppression method which concern on this embodiment, when a drink is acidic, ie, the pH of a drink is less than 7, the effect becomes remarkable. From the same viewpoint, the pH of the beverage can be less than 6, or the pH can be less than 5.
In addition, pH of a drink can be measured in accordance with a well-known method, for example, can be measured using pH meter HM-30R by Toa DKK Corporation.

Moreover, in order to adjust to pH as mentioned above, a pH adjuster can also be suitably added with respect to a drink. The pH adjuster may be appropriately selected according to the product to be designed, and examples thereof include carboxylic acids such as citric acid and carboxylates such as sodium citrate.
Moreover, what is necessary is just to adjust the addition amount of this pH adjuster, monitoring the pH of a drink sequentially.

(Fragrance composition)
In the above-described degradation odor production suppression method and the like, an embodiment in which a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is added to a citrus flavor-containing product has been described. A fragrance composition containing a citrus flavor and a dicarboxylic acid or a metal salt thereof having a conjugated double bond in the molecule is prepared, and the desired effect is exhibited by adding the fragrance composition to the product. be able to.

Such a fragrance composition contains, for example, 0.01 parts by mass or more of a dicarboxylic acid or a metal salt thereof having a conjugated double bond in the molecule with respect to 100 parts by mass of citrus flavor, and more preferably 0. .1 part by mass or more, more preferably 1 part by mass or more, and particularly preferably 5 parts by mass or more.
In addition, the fragrance | flavor composition which concerns on this embodiment does not necessarily need to be uniform as a whole, The dicarboxylic acid which has a conjugated double bond in a molecule | numerator, or its metal salt may be mixed with solid form.
Moreover, the upper limit of the dicarboxylic acid which has a conjugated double bond in the molecule | numerator contained in the fragrance | flavor composition which concerns on this embodiment, or its metal salt is 50 mass parts or less with respect to 100 mass parts of citrus flavors, for example. .

Here, as described above, the citrus flavor is likely to be denatured when heated, stored for a long time, or placed in an environment having a low pH. On the other hand, in the fragrance composition of the present embodiment, the fragrance unique to the citrus flavor can be sufficiently maintained even if the addition amount is as described above by appropriately managing the storage environment.
More specifically, it is a preferable embodiment from the viewpoint of keeping the fragrance unique to the citrus flavor by sealing the fragrance composition together with an inert gas in a container and then storing the fragrance composition in a cool and dark place.

  The fragrance composition according to the present embodiment can be added to foods such as ice cream, candy, confectionery such as gum, seasonings such as dressing, as well as addition to beverages. . Moreover, even if it is other than foodstuffs, it can be added also to cosmetics, such as a perfume, cosmetics, a bath agent, a fragrance | flavor, a detergent, and a mouthwash.

  As mentioned above, although embodiment of this invention was described, these are illustrations of this invention and various structures other than the above are also employable.

  EXAMPLES Hereinafter, although this invention is demonstrated in detail using an Example, this invention is not limited to description of these Examples at all.

First, in this Example section, the amount of each component contained in the beverage is quantified using gas chromatography (GC) analysis. The procedure for this analysis is as follows.
(Sample preparation method)
Weigh 50.0 g of the sample, add 100 μL of 2-octanol as an internal standard, and dilute with 50 mL of water. Separately, a solid phase (Oasis HLB 200 mg / 6 cc manufactured by Waters) that was sequentially conditioned with dichloromethane (5 mL), ethanol (5 mL), and water (20 mL) was prepared and included in the diluted sample obtained above. Adsorb all organic components. Thereafter, elution is performed with 5 mL of dichloromethane, and the eluate is dehydrated with anhydrous sodium sulfate. The supernatant is transferred to a Spitz tube and concentrated to 200 μL with a nitrogen purge to prepare a sample for analysis.
(Quantitative method)
This analysis sample is subjected to gas chromatography (GC) analysis under the following conditions. The amount of the component in the sample is calculated from the area ratio with the 2-octanol peak used as the internal standard. Further, the GC analysis is performed twice for the same sample, and the average value is quantified as the amount of the component in the sample.
(GC condition)
Device name: 5973inert Mass Selective Detector manufactured by Agilent Technologies
Column: DB-WAX (60 m × 0.25 mm × 0.25 μm)
Oven temperature: 40 ° C. (1 min) − (3 ° C./min)−210° C. (3 min)
Flow rate: 1 ml / min
Injection temperature: 250 ° C
Injection volume: 1 μL
Split ratio: 10: 1

Example 1
As a model liquid A, a beverage containing an alcohol concentration of 5% and citral of 10 ppm was prepared, and the pH of this beverage was adjusted to 3.1 using trisodium citrate as a pH adjuster. Here, the pH was measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
To this beverage, monosodium fumarate was added so as to be 250 ppm of the entire beverage, sealed, and allowed to stand at a temperature of 37 ° C. for 7 days. After standing, the amount of citral contained in the beverage, the amount of p-cresol, the amount of p-cymene, and the amount of p-methylacetophenone were quantified.
About this content, it showed in Table 1 as ratio with content of each component in the comparative example 1 mentioned later.

(Examples 2 and 3)
In the method of Example 1, except that the addition amount of monosodium fumarate is adjusted as described in Table 1, it is allowed to stand in the same manner as in Example 1, and the amount of each component contained in the beverage is determined. Quantified. The results are shown in Table 1.

Example 4
In the method of Example 1, in place of monosodium fumarate, fumaric acid was added so as to be 210 ppm, and the mixture was allowed to stand in the same manner as in Example 1, and the amount of each component contained in the beverage Was quantified. The results are shown in Table 1.

(Comparative Example 1)
In the method of Example 1, it left still by the method similar to Example 1 except not adding monosodium fumarate, and the quantity of each component contained in a drink was quantified. The results of Comparative Example 1 are shown in Table 1 as a control (100.0%).

Here, in Examples 1-4, sensory evaluation was performed on the items of “citrus feeling”, “deteriorated scent”, and “taste”.
The sensory evaluation is performed by three panelists. The panelists are +1 for those with a good impression compared to Comparative Example 1, -1 for those with a bad impression, and 0 for those that do not change the impression. The average score was shown in Table 1 as a score.
Note that “degraded incense” is evaluated as a good case where a citral deteriorated aroma is not felt.

(Example 5)
As a model liquid A, a beverage containing an alcohol concentration of 5% and citral 10 ppm was prepared, and the pH of this beverage was adjusted to 3.3 using trisodium citrate as a pH adjuster. Here, the pH was measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
To this beverage, monosodium fumarate was added so as to be 250 ppm of the entire beverage, sealed, and allowed to stand at a temperature of 37 ° C. for 7 days. After standing, the amount of citral contained in the beverage, the amount of p-cresol, the amount of p-cymene, and the amount of p-methylacetophenone were quantified.
About this content, it showed in Table 2 as ratio with content of each component in the comparative example 2 mentioned later.

(Examples 6 and 7)
In the method of Example 5, except that the addition amount of monosodium fumarate is adjusted as described in Table 2, it is allowed to stand in the same manner as in Example 5, and the amount of each component contained in the beverage is determined. Quantified. The results are shown in Table 2.

(Comparative Example 2)
In the method of Example 5, it left still by the method similar to Example 5 except not having added monosodium fumarate, and quantified the quantity of each component contained in a drink. The results of Comparative Example 2 are shown in Table 2 as a control (100.0%).

(Example 8)
As a model liquid A, a beverage containing an alcohol concentration of 5% and citral 10 ppm was prepared, and the pH of the beverage was adjusted to 3.5 using trisodium citrate, which is a pH adjusting agent. Here, the pH was measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
To this beverage, monosodium fumarate was added so as to be 250 ppm of the entire beverage, sealed, and allowed to stand at a temperature of 37 ° C. for 7 days. After standing, the amount of citral contained in the beverage, the amount of p-cresol, the amount of p-cymene, and the amount of p-methylacetophenone were quantified.
About this content, it showed in Table 2 as ratio with content of each component in the comparative example 3 mentioned later.

Example 9
In the method of Example 8, except that the addition amount of monosodium fumarate is adjusted as described in Table 2, it is allowed to stand in the same manner as in Example 8, and the amount of each component contained in the beverage is determined. Quantified. The results are shown in Table 2.

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

Here, in Examples 5-9, sensory evaluation was performed according to the items of “citrus feeling”, “deteriorated scent”, and “taste”.
The specific method is the same as that performed in Example 1-4. Examples 5-7 are for Comparative Example 2 and Examples 8 and 9 are for Comparative Example 3. Stats. The results are as shown in Table 2.

(Example 10)
As model liquid B, a beverage containing no alcohol and containing 10 ppm of citral was prepared, and the pH of this beverage was adjusted using trisodium citrate, which is a pH adjusting agent, to a pH of 3.0. Here, the pH was measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
To this beverage, monosodium fumarate was added so as to be 250 ppm of the entire beverage, sealed, and allowed to stand at a temperature of 37 ° C. for 7 days. After standing, the amount of citral contained in the beverage, the amount of p-cresol, the amount of p-cymene, and the amount of p-methylacetophenone were quantified.
About this content, it showed in Table 3 as ratio with content of each component in the comparative example 4 mentioned later.

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

(Example 11)
As a model liquid C, a beverage containing an alcohol concentration of 5% and limonene of 10 ppm was prepared, and the pH of this beverage was adjusted to 3.3 using trisodium citrate, which is a pH adjusting agent. Here, the pH was measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
To this beverage, monosodium fumarate was added so as to be 250 ppm of the entire beverage, sealed, and allowed to stand at a temperature of 37 ° C. for 7 days. After standing, the amounts of limonene, p-cresol, p-cymene, α-terpineol and terpinolene contained in the beverage were quantified.
About this content, it showed in Table 4 as ratio with content of each component in the comparative example 5 mentioned later.

(Comparative Example 5)
In the method of Example 11, it left still by the method similar to Example 11 except not adding monosodium fumarate, and the quantity of each component contained in a drink was quantified. The results of Comparative Example 5 are shown in Table 4 as a control (100.0%).

(Example 12)
As a model liquid A, a beverage containing an alcohol concentration of 5% and citral 10 ppm was prepared, and the pH of this beverage was adjusted to 3.0 with trisodium citrate, which is a pH adjuster. Here, the pH was measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
To this beverage, monosodium fumarate was added so as to be 10 ppm of the whole beverage, and after sealing, the mixture was allowed to stand at a temperature of 37 ° C. for 7 days. After standing, the amount of citral contained in the beverage, the amount of p-cresol, the amount of p-cymene, and the amount of p-methylacetophenone were quantified.
About this content, it showed in Table 5 as ratio with content of each component in the comparative example 6 mentioned later.

(Example 13)
In the method of Example 12, except that the addition amount of monosodium fumarate is adjusted as described in Table 5, it is allowed to stand in the same manner as in Example 12, and the amount of each component contained in the beverage is determined. Quantified. The results are shown in Table 5.

(Example 14)
In the method of Example 12, except that itaconic acid was used in place of monosodium fumarate and the content was set to 250 ppm, the mixture was allowed to stand in the same manner as in Example 12, and each component contained in the beverage was The amount was quantified. The results are shown in Table 5.

(Comparative Example 6)
In the method of Example 12, it left still by the method similar to Example 12 except not adding monosodium fumarate, and the quantity of each component contained in a drink was quantified. The results of Comparative Example 6 are shown in Table 5 as a control (100.0%).

As shown in each example, the addition of a specific dicarboxylic acid or a metal salt thereof to a beverage having a citrus flavor suppressed generation of a component that causes a deteriorated odor.
Moreover, by suppressing the production | generation of the component which brings about a deterioration odor in this way, the citrus feeling and deliciousness which were comfortable to the drinker were able to be brought about.

  The degradation odor production | generation suppression method of this invention can maintain the fragrance intrinsic | native to a citrus flavor effectively. From this, it is possible to dramatically expand the range of development of products having citrus flavors.

The present invention relates to incense care degradation control how you and fragrance deterioration inhibitor.

Relative beverage or foodstuffs containing citral According to the present invention, is characterized by the addition of fumaric acid or a metal salt thereof, a flavor deterioration inhibiting method, the entire beverage or the food products containing citral On the other hand, there is provided a method for suppressing fragrance degradation, characterized by adding 0.5 to 15000 ppm of fumaric acid or a metal salt thereof .
In addition, according to the present invention, it is an aroma deterioration inhibitor composed of fumaric acid or a metal salt thereof, and is characterized by being added in an amount of 0.5 ppm or more and 15000 ppm or less with respect to the entire beverage or food product containing citral. A fragrance degradation inhibitor is provided.

As mentioned above, although embodiment of this invention was described, these are illustrations of this invention and various structures other than the above are also employable.
Hereinafter, examples of the reference form will be added.
<1>
By adding a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a product containing citrus flavor,
Deterioration odor production inhibiting method for inhibiting the production of one or more compounds selected from the group consisting of p-cresol, p-cymene, p-methylacetophenone, α-terpineol and terpinolene in the citrus flavor-containing product .
<2>
<1> The method for suppressing the generation of a deteriorated odor according to <1>, wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid, itaconic acid or a metal salt thereof.
<3>
In the citrus flavor-containing product, the addition amount of the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is 0.5 ppm or more and 15000 ppm or less, <1> or <2> Deterioration odor production suppression method as described in 2.
<4>
The deterioration odor production suppressing method according to any one of <1> to <3>, wherein the citrus flavor includes citral.
<5>
The production method of a deteriorated odor according to <4>, wherein production of all compounds of p-cresol, p-cymene and p-methylacetophenone is inhibited.
<6>
The deterioration odor production suppressing method according to any one of <1> to <3>, wherein the citrus flavor includes limonene.
<7>
<6> The method for inhibiting degradation odor production according to <6>, wherein production of all compounds of p-cresol, p-cymene, α-terpineol and terpinolene is inhibited.
<8>
The deterioration odor production suppressing method according to any one of <1> to <7>, wherein the citrus flavor-containing product is a beverage including a citrus flavor.
<9>
<6> The method for suppressing deterioration odor production according to <8>, wherein the beverage containing the citrus flavor has a pH of less than 7.
<10>
A method for inhibiting fragrance degradation, comprising adding a dicarboxylic acid having a conjugated double bond in its molecule or a metal salt thereof to a citrus flavor-containing product.
<11>
The method for inhibiting fragrance degradation according to <10>, wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid, itaconic acid or a metal salt thereof.
<12>
The citrus flavor-containing product is a fragrance deterioration suppressing method according to <10> or <11>, which is a beverage containing a citrus flavor.
<13>
A fragrance composition comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof.
<14>
The fragrance composition according to <13>, wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid, itaconic acid or a metal salt thereof.
<15>
A citrus flavor-containing product comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof.
<16>
The citrus flavor-containing product according to <15>, wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid, itaconic acid, or a metal salt thereof.
<17>
The citrus flavor-containing product according to <15> or <16>, wherein the citrus flavor-containing product is a beverage containing a citrus flavor.

Claims (17)

By adding a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a product containing citrus flavor,
Deterioration odor production inhibiting method for inhibiting the production of one or more compounds selected from the group consisting of p-cresol, p-cymene, p-methylacetophenone, α-terpineol and terpinolene in the citrus flavor-containing product .   2. The method for inhibiting the generation of a deteriorated odor according to claim 1, wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid, itaconic acid, or a metal salt thereof.   The addition amount of the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof in the citrus flavor-containing product is 0.5 ppm to 15000 ppm. Of suppressing deterioration odor production.   The method of suppressing deterioration odor generation according to any one of claims 1 to 3, wherein the citrus flavor includes citral.   The method for inhibiting the generation of a deteriorated odor according to claim 4, wherein the production of all compounds of p-cresol, p-cymene and p-methylacetophenone is inhibited.   The method of suppressing deterioration odor generation according to any one of claims 1 to 3, wherein the citrus flavor includes limonene.   The method for inhibiting the production of a deteriorated odor according to claim 6, wherein the production of all compounds of p-cresol, p-cymene, α-terpineol and terpinolene is inhibited.   The degradation odor production | generation suppression method of any one of Claims 1 thru | or 7 with which the said citrus flavor containing product is a drink containing a citrus flavor.   The method for inhibiting the generation of a deteriorated odor according to claim 8, wherein the beverage containing the citrus flavor has a pH of less than 7.   A method for inhibiting fragrance degradation, comprising adding a dicarboxylic acid having a conjugated double bond in its molecule or a metal salt thereof to a citrus flavor-containing product.   The fragrance deterioration suppressing method according to claim 10, wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid, itaconic acid or a metal salt thereof.   The citrus flavor-containing product according to claim 10 or 11, wherein the citrus flavor-containing product is a beverage containing a citrus flavor.   A fragrance composition comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof.   The perfume composition according to claim 13, wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid, itaconic acid or a metal salt thereof.   A citrus flavor-containing product comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof.   The citrus flavor-containing product according to claim 15, wherein the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof is fumaric acid, itaconic acid or a metal salt thereof.   The citrus flavor-containing product according to claim 15 or 16, wherein the citrus flavor-containing product is a beverage containing a citrus flavor.