WO2016098515A1 - Citrus flavor containing product, beverage, perfume composition, method for suppressing generation of degradation odor, and method for suppressing aroma degradation - Google Patents

Citrus flavor containing product, beverage, perfume composition, method for suppressing generation of degradation odor, and method for suppressing aroma degradation Download PDF

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Publication number
WO2016098515A1
WO2016098515A1 PCT/JP2015/082358 JP2015082358W WO2016098515A1 WO 2016098515 A1 WO2016098515 A1 WO 2016098515A1 JP 2015082358 W JP2015082358 W JP 2015082358W WO 2016098515 A1 WO2016098515 A1 WO 2016098515A1
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Prior art keywords
citrus flavor
metal salt
double bond
molecule
dicarboxylic acid
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PCT/JP2015/082358
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French (fr)
Japanese (ja)
Inventor
たまみ 鈴木
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アサヒビール株式会社
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Publication of WO2016098515A1 publication Critical patent/WO2016098515A1/en

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/16—Inorganic salts, minerals or trace elements
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes

Definitions

  • the present invention relates to a citrus flavor-containing product, a beverage, a fragrance composition, a degradation odor production inhibiting method, and an aroma degradation inhibiting method.
  • the aroma component contained in such a citrus flavor is converted to other components by heating or storing for a long time.
  • the following techniques are known as examples of measures against such knowledge.
  • 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.
  • solvent extracts such as Ashitaba, Avocado, Psyllium, etc. to suppress the generation of odors from citral and citral-containing products (see Patent Document 3)
  • 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).
  • 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. At the same time, it is an object to provide a product or the like in which an aroma unique to citrus flavor is maintained.
  • 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.
  • a beverage in which the content of the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof in the whole beverage is 0.5 ppm or more and 15000 ppm or less.
  • a fragrance composition characterized by containing a citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof.
  • a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a product containing a citrus flavor
  • Deteriorated odor generation that suppresses the generation of one or more compounds selected from the group consisting of p-cresol, p-cymene, p-methylacetophenone, ⁇ -terpineol, and terpinolene in products containing the citrus flavor
  • a suppression method is provided.
  • a method for suppressing fragrance degradation characterized by adding a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a product containing a citrus flavor.
  • the degradation odor production suppressing method of the present embodiment adds a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a product containing a citrus flavor, thereby adding the citrus flavor to the product.
  • the production of a deteriorated odor is suppressed by suppressing the production of one or more compounds selected from the group consisting of p-cresol, p-cymene, p-methylacetophenone, ⁇ -terpineol and terpinolene.
  • 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 a molecule or a metal salt thereof to a product containing a citrus flavor.
  • 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.
  • save with respect to can be suppressed, and deterioration of aroma can be suppressed as a result.
  • 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.
  • it can also be applied to cosmetics such as perfumes, cosmetics, bathing agents, fragrances, detergents and mouthwashes.
  • the method of this embodiment is preferably used when the product is a beverage.
  • Typical examples include flavors containing citral, which can be produced by p-cresol, p-cymene and p-methylacetophenone during heating and storage, and p-cresol, p-cymene, ⁇ - Examples include flavors containing limonene from which terpineol and terpinolene can be produced.
  • the citrus flavor 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.
  • 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.
  • the content of citrus flavor in the entire product can be appropriately set according to the product to be designed.
  • 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, ⁇ -terpineol and terpinolene For example, it is 1 ppm or more, preferably 3 ppm or more, more preferably 5 ppm or more.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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
  • examples of such a dicarboxylic acid or a metal salt thereof include fumaric acid, itaconic acid, or a metal salt thereof.
  • fumaric acid is preferably used because of its high availability and high effect of suppressing the generation of deteriorated odor.
  • 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.
  • 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.
  • 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.
  • any of the techniques described in Patent Documents 1 to 4 described above suppresses 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.
  • dicarboxylic acids as described above are generally used to impart “sourness” to beverages and the like.
  • 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.
  • 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.
  • corresponding metal cations may be present.
  • examples of the metal cation include those of a monovalent cation and those of a divalent cation.
  • the monovalent cation sodium ion, potassium ion or the like can be adopted.
  • divalent cation calcium ion, magnesium ion or the like can be employed.
  • 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.
  • 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.
  • numerator, or its metal salt in a citrus flavor containing product it is 15000 ppm or less, for example.
  • 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. This makes it easier to suppress the formation of p-cresol and p-methylacetophenone. From the viewpoint of effectively suppressing not only p-cresol and p-methylacetophenone but also 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.
  • 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.
  • 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 so, it becomes easy to suppress the formation of p-cresol. From the viewpoint of effectively suppressing not only p-cresol but also p-cymene, ⁇ -terpineol and terpinolene, the amount of dicarboxylic acid having a conjugated double bond in the molecule or the metal salt thereof in the whole product Is more preferably 10 ppm or more, further preferably 100 ppm or more, and particularly preferably 250 ppm or more.
  • 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.
  • the deterioration of citrus flavor can be effectively suppressed, and dicarboxylic acid or its metal can be effectively suppressed.
  • the amount (remaining amount) of the aroma component in the citrus flavor in the product can be increased. That is, the dicarboxylic acid or a metal salt thereof having a conjugated double bond in the molecule according to the present embodiment can be used as an aroma deterioration inhibitor for products containing citrus flavor.
  • 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.
  • the deteriorated odor production suppressing method and the aroma deterioration suppressing method of the present embodiment can be preferably applied to beverages.
  • 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.
  • 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.
  • 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.
  • 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
  • the pH of the beverage can be measured according to a known method. For example, it can be measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
  • 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.
  • 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.
  • flavor composition which concerns on this embodiment does not necessarily need to be uniform as a whole
  • numerator, or its metal salt may be mixed with solid form.
  • 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.
  • the citrus flavor is likely to be denatured when heated, stored for a long time, or placed in an environment having a low pH.
  • 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, an aromatic agent, a detergent, and a mouthwash.
  • cosmetics such as a perfume, cosmetics, a bath agent, an aromatic agent, a detergent, and a mouthwash.
  • 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.
  • A2) The citrus flavor-containing product according to (A1), which is an alcoholic beverage.
  • A3) The citrus flavor-containing 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, itaconic acid, or a metal salt thereof.
  • (A7) In a beverage containing citrus flavor, dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof, and alcohol, Content of the dicarboxylic acid which has a conjugated double bond in the said molecule
  • (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, itaconic acid or a metal salt thereof.
  • 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 fragrance composition comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof.
  • A12 By adding a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a product containing a citrus flavor, Deteriorated odor generation that suppresses the generation of one or more compounds selected from the group consisting of p-cresol, p-cymene, p-methylacetophenone, ⁇ -terpineol, and terpinolene in products containing the citrus flavor Suppression method.
  • (A13) The degradation odor production
  • (A14) The degradation odor production
  • (A15) Any one of (A12) to (A14), 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. Deterioration odor production suppression method as described in one.
  • 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
  • A19 The degradation odor production
  • A20 The method for inhibiting degradation odor production according to (A19), wherein the production of all compounds of p-cresol, p-cymene, ⁇ -terpineol and terpinolene is inhibited.
  • A21 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 product containing a citrus flavor.
  • A22 The fragrance deterioration suppressing method according to (A21), wherein the product containing the citrus flavor is an alcoholic beverage.
  • (A23) The fragrance 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, itaconic acid or a metal salt thereof.
  • Deterioration suppression method To a beverage or food containing citral, fumaric acid or a metal salt thereof is added. A method for suppressing aroma degradation, comprising adding 0.5 ppm or more and 15000 ppm or less of the fumaric acid or a metal salt thereof to the beverage or the entire food containing citral.
  • B2 The fragrance deterioration suppression method according to (B1), wherein the beverage or food product containing citral is a beverage containing citral.
  • (B3) The method of inhibiting fragrance deterioration according to (B2), wherein the beverage containing citral has a pH of less than 7.
  • a fragrance degradation inhibitor comprising fumaric acid or a metal salt thereof, A fragrance degradation inhibitor 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.
  • Example preparation method Weigh 50.0 g of the sample, add 100 ⁇ L 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.
  • GC gas chromatography
  • 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.
  • Example 2 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%).
  • 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.
  • Example 6 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.
  • the pH was measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
  • 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%).
  • 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.
  • the pH was measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
  • 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.
  • the pH was measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
  • 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, ⁇ -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.
  • the pH was measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
  • 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%).
  • generation suppression method of this invention can maintain the fragrance intrinsic

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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

シトラスフレーバー含有製品、飲料、香料組成物、劣化臭生成抑制方法および香気劣化抑制方法Citrus flavor-containing product, beverage, fragrance composition, degradation odor production inhibiting method and aroma degradation inhibiting method
　本発明は、シトラスフレーバー含有製品、飲料、香料組成物、劣化臭生成抑制方法および香気劣化抑制方法に関する。 The present invention relates to a citrus flavor-containing product, a beverage, a fragrance composition, a degradation odor production inhibiting method, and an aroma degradation inhibiting method.
　従来、シトラスフレーバーを飲料に添加することにより、飲料にレモンのような柑橘類特有の風味を加えることが広くなされている。また、このような柑橘類特有の風味を加えることにより、飲用した者にすっきりとした爽快感を与えることができる。
　ここで、このシトラスフレーバーの代表的な香気成分としては、シトラールやリモネン等が挙げられる。 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.
　ここで、このようなシトラスフレーバーに含まれる香気成分は、加熱を行うこと、あるいは長期的に保存することにより他の成分に変換されてしまうことが知られている。また、このような知見に対する対策を行った例として以下のような技術が知られている。 Here, it is known that the aroma component contained in such a citrus flavor is converted to other components by heating or storing for a long time. In addition, the following techniques are known as examples of measures against such knowledge.
　たとえば、特許文献１にはシトラールを加熱等した際に生じる、ｐ－メチルアセトフェノン等の生成を抑制するために、カリン、マンゴー、マンゴスチン、ミロバラン、ザクロまたはカカオからの溶媒抽出された抽出物や、エピカテキン、エピカテキンガレート、エピガロカテキンガレート、酵素処理ルチン、クエルセチン、フェルラ酸、カフェー酸、ロズマリン酸、シリンガ酸または没食子酸を添加する技術が開示されている。 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.
　また、特許文献２には、エリオシトリンまたはエリオシトリン含有物をシトラール等のフレーバー成分の劣化防止剤として用いる技術が開示されている。
　その他、アシタバ、アボカド、オオバコ等の溶媒抽出物を用いてシトラールやシトラール含有製品の劣化臭の生成を抑制する技術（特許文献３参照）や、バンレイシ属植物の果皮の溶媒抽出物を香料劣化抑制剤として用いる技術が知られている（特許文献４参照）。 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).
特開２００２－１８００８１号公報Japanese Patent Laid-Open No. 2002-180081 特開２００１－６１４６１号公報JP 2001-61461 A 特開２００４－１８６１３号公報JP 2004-18613 A 特開２００４－２９２７７８号公報JP 2004-292778 A
　すなわち、特許文献１～４に記載されているように、シトラスフレーバー固有の香気を保つための研究はなお盛んになされているものであり、各種製品を設計する上での技術開拓が望まれている。
　このような事情を鑑み、本発明はシトラスフレーバー固有の香気を保つための劣化臭生成抑制方法を提供することを課題とする。
　また同時に、シトラスフレーバー固有の香気が保たれた製品等を提供することを課題とする。 In other words, 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 technologies 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.
At the same time, it is an object to provide a product or the like in which an aroma unique to citrus flavor is maintained.
　本発明によれば、シトラスフレーバーと、分子内に共役二重結合を有するジカルボン酸又はその金属塩とを含有することを特徴とする、シトラスフレーバー含有製品が提供される。 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.
　また、本発明によれば、シトラスフレーバーと、分子内に共役二重結合を有するジカルボン酸又はその金属塩と、アルコールとを含有する飲料において、
　当該飲料全体における、前記分子内に共役二重結合を有するジカルボン酸又はその金属塩の含有量は、０．５ｐｐｍ以上１５０００ｐｐｍ以下である、飲料が提供される。 Moreover, according to the present invention, in a beverage containing citrus flavor, dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof, and alcohol,
A beverage is provided in which the content of the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof in the whole beverage is 0.5 ppm or more and 15000 ppm or less.
　また、本発明によれば、シトラスフレーバーと、分子内に共役二重結合を有するジカルボン酸又はその金属塩とを含有することを特徴とする、香料組成物が提供される。 Moreover, according to the present invention, there is provided a fragrance composition characterized by containing a citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof.
　また、本発明によれば、シトラスフレーバーを含有する製品に対して、分子内に共役二重結合を有するジカルボン酸又はその金属塩を添加することにより、
　前記シトラスフレーバーを含有する製品中におけるｐ－クレゾール、ｐ－サイメン、ｐ－メチルアセトフェノン、α－テルピネオールおよびテルピノレンからなる群から選ばれる１種又は２種以上の化合物の生成を抑制する、劣化臭生成抑制方法が提供される。 Further, 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 product containing a citrus flavor,
Deteriorated odor generation that suppresses the generation of one or more compounds selected from the group consisting of p-cresol, p-cymene, p-methylacetophenone, α-terpineol, and terpinolene in products containing the citrus flavor A suppression method is provided.
　また、本発明によれば、シトラスフレーバーを含有する製品に対して、分子内に共役二重結合を有するジカルボン酸又はその金属塩を添加することを特徴とする、香気劣化抑制方法が提供される。 In addition, according to the present invention, there is provided a method for suppressing fragrance degradation, characterized by adding a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a product containing a citrus flavor. .
　本発明の劣化臭生成抑制方法では、シトラスフレーバーを含有する製品に対して、分子内に共役二重結合を有するジカルボン酸又はその金属塩を添加することにより、劣化臭の原因となりうる特定の化合物群の生成を抑制することができる。
　これにより、シトラスフレーバー固有の香気が保たれた製品等を提供することができる。 In the degradation odor production inhibiting method of the present invention, a specific compound that can cause a degradation odor by adding a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a product containing a citrus flavor. Generation of groups can be suppressed.
Thereby, the product etc. in which the fragrance peculiar to citrus flavor was maintained can be provided.
　以下、本発明を実施の形態に基づいて説明する。 Hereinafter, the present invention will be described based on embodiments.
（劣化臭生成抑制方法、香気劣化抑制方法）
　まず、本実施形態に係る劣化臭生成抑制方法と香気劣化抑制方法について説明する。
　本実施形態の劣化臭生成抑制方法は、シトラスフレーバーを含有する製品に対して、分子内に共役二重結合を有するジカルボン酸又はその金属塩を添加することにより、前記シトラスフレーバーを含有する製品中におけるｐ－クレゾール、ｐ－サイメン、ｐ－メチルアセトフェノン、α－テルピネオールおよびテルピノレンからなる群から選ばれる１種又は２種以上の化合物の生成を抑制する、劣化臭生成抑制方法である。 (Deterioration odor generation suppression method, aroma deterioration suppression method)
First, the degradation odor production | generation suppression method and fragrance degradation suppression method which concern on this embodiment are demonstrated.
The degradation odor production suppressing method of the present embodiment adds a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a product containing a citrus flavor, thereby adding the citrus flavor to the product. In this method, the production of a deteriorated odor is suppressed by suppressing the production of one or more compounds selected from the group consisting of p-cresol, p-cymene, p-methylacetophenone, α-terpineol and terpinolene.
　また、本実施形態の香気劣化抑制方法は以下に示す通りである。
　シトラスフレーバーを含有する製品に対して、分子内に共役二重結合を有するジカルボン酸又はその金属塩を添加することを特徴とする、香気劣化抑制方法。 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 a molecule or a metal salt thereof to a product containing a citrus flavor.
　すなわち、本実施形態に係る劣化臭生成抑制方法および香気劣化抑制方法は、シトラスフレーバー含有製品に対して、特定の構造を備えるジカルボン酸又はその金属塩を添加するものであり、これによって、シトラスフレーバーに対して加熱や長期保存を行った際に生じる特定の化合物の生成を抑制することができ、結果として、香気の劣化を抑制することができる。 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. 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.
（シトラスフレーバー含有製品）
　本実施形態に係る劣化臭生成抑制方法および香気劣化抑制方法は、シトラスフレーバーを含ませることが慣用的になされている製品であれば、いずれの製品であっても適用することができる。
　このような製品としては、飲料をはじめ、アイスクリームや飴、ガム等の菓子類、ドレッシング等の調味料類等の食料品が挙げられる。また、食用以外では、香水や化粧品、入浴剤や、芳香剤、洗剤、洗口剤等の香粧品にも適用することができる。
　このなかでも、本実施形態の方法は、製品が飲料である場合に好ましく用いられる。 (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.
（シトラスフレーバー）
　本実施形態の劣化臭生成抑制方法に係るシトラスフレーバーとしては、加熱時や保存時において、上述のｐ－クレゾール、ｐ－サイメン、ｐ－メチルアセトフェノン、α－テルピネオールおよびテルピノレンからなる群から選ばれる化合物群のうち、少なくとも一種の化合物が生成しうる成分を含むフレーバーから選ばれる。
　その代表的な例としては、加熱時や保存時にｐ－クレゾール、ｐ－サイメンおよびｐ－メチルアセトフェノンが生成しうるシトラールを含むフレーバーや、加熱時や保存時にｐ－クレゾール、ｐ－サイメン、α－テルピネオールおよびテルピノレンが生成しうるリモネンを含むフレーバーが挙げられる。 (Citrus flavor)
As the citrus flavor according to the method for suppressing the generation of deteriorated odor of this 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 include flavors containing citral, which 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.
　ここで、シトラスフレーバーを加熱や長期保存した場合においては、上記の化合物群として示した化合物以外にも雑多な化合物が生成するが、本発明者は飲料等を作製するにあたって、上記の五つの化合物の生成を抑制、管理することがシトラスフレーバー固有の風味等を担保する上で効果的であることを見出した。
　すなわち、本実施形態に係るフレーバーとしては、上述のシトラールやリモネン以外の香気成分を含むシトラスフレーバーであっても、上記五つの成分のいずれかを生成しうるフレーバーであれば適用することができる。 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.
　また、本実施形態において、例えばシトラスフレーバーがシトラールを含む場合は、生成しうるｐ－クレゾール、ｐ－サイメンおよびｐ－メチルアセトフェノンの全ての化合物の生成が抑制されることが好ましく、また、シトラスフレーバーがリモネンを含む場合は、生成しうるｐ－クレゾール、ｐ－サイメン、α－テルピネオールおよびテルピノレンの全ての化合物の生成が抑制されることが好ましい。これにより、製品として、シトラスフレーバー特有の香気を十分にもたせることができる。
　この効果を達成するための具体的な手法としては、たとえば、製品の組成を調整することや、分子内に共役二重結合を有するジカルボン酸またはその金属塩の添加量を調整すること等が挙げられ、適宜スクリーニングを行うことで、上記のような効果を発現することができる。 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.
　本実施形態において、製品全体におけるシトラスフレーバーの含有量は、設計する製品に合わせて適宜設定することができる。
　このシトラスフレーバーを構成する成分のうち、ｐ－クレゾール、ｐ－サイメン、ｐ－メチルアセトフェノン、α－テルピネオールおよびテルピノレンからなる群から選ばれる化合物群が生成しうる成分の含有量の下限値としては、たとえば１ｐｐｍ以上であり、好ましくは３ｐｐｍ以上であり、より好ましくは５ｐｐｍ以上である。
　また、当該成分の製品全体における含有量の上限値は、たとえば１０００ｐｐｍ以下であり、好ましくは５００ｐｐｍ以下であり、より好ましくは３００ｐｐｍ以下である。
　また、製品全体におけるシトラスフレーバー全体の含有量は、設計する製品に合わせて適宜設定することができるが、その下限値としては、たとえば５ｐｐｍ以上であり、好ましくは２０ｐｐｍ以上であり、より好ましくは５０ｐｐｍ以上である。
　また、製品全体におけるシトラスフレーバー全体の含有量の上限値は、たとえば１００００ｐｐｍ以下であり、好ましくは５０００ｐｐｍ以下であり、より好ましくは３０００ｐｐｍ以下である。 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.
（分子内に共役二重結合を有するジカルボン酸又はその金属塩）
　本実施形態の劣化臭生成抑制方法および香気劣化抑制方法においては、上記の化合物の生成を抑制するために、製品に対して、分子内に共役二重結合を有するジカルボン酸又はその金属塩を添加することを特徴とする。
　ここで、この「分子内に共役二重結合を有するジカルボン酸またはその金属塩」は、ここで規定する化合物としての特徴を満足し、また、製品として添加することのできる材料の中から適宜選択すればよい。
　ここで、分子内における共役二重結合が、製品中に含まれるシトラスフレーバーに対して還元作用をもたらし、加熱時や長期保存時における劣化臭の生成を効果的に抑制することができるものと考えられる。 (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.
　なお、共役二重結合は分子内のカルボキシル基から隔離された部位に複数の二重結合が備えられ、これらが共役する関係にあるものでもよいが、分子内のカルボキシル基が有するＣ＝Ｏ二重結合に対して共役する態様が好ましい。
　また、共役二重結合に寄与する二重結合は炭素－炭素二重結合に限られるものではなく、炭素原子とヘテロ原子との二重結合であってもよい。また、例えば芳香族化合物のように二重結合を介して環を構成していてもよい。
　ここで、共役に寄与する原子数が増えることにより、劣化臭生成抑制の効果はより顕著となり、より具体的には、分子の有する二つのカルボン酸が分子内に備えられる二重結合によって、共役する関係にあることが好ましい。 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
　ここで、このようなジカルボン酸又はその金属塩の例としては、フマル酸やイタコン酸又はこれらの金属塩が挙げられる。特に、入手容易性の高さや劣化臭生成抑制の効果の高さからフマル酸が好ましく用いられる。
　なお、フマル酸のような分子内に共役二重結合を有するジカルボン酸は、一般に食品用途における添加物として用いられており、それにより、抗酸化作用を発現させる試みがなされている。しかしながら、従来技術として、シトラスフレーバー含有製品に対して、添加を行い、上述の劣化臭をもたらす化合物の生成を抑制するという知見は見出されていなかった。
　これに対し、本発明者は、鋭意検討の結果、この特定の構造を備えるジカルボン酸等を、シトラスフレーバーを含有する製品に添加することで、劣化臭の生成を抑制し、香気の劣化を抑制できることを見出した。 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.
　ここで、先述の特許文献１～４に記載される技術はいずれも、シトラール等の香気成分以外の第三成分を加えることで、シトラスフレーバーの劣化を抑制するものである。そのため、たとえばシトラスフレーバーを含有する飲料を作製する際に、この第三成分を加えることによって飲料の風味が左右されてしまうという点で改善する余地があった。
　これに対し、上記のようなジカルボン酸は、一般に、飲料等について「酸味」を付与するために用いられる。その一方で、適用させるシトラスフレーバーも通常はレモンのようなスッキリとした香気を付与する効果をもたらすため、これらを添加する目的は相反するものではない。
　そのため、たとえば飲料に適用したとしても、シトラスフレーバー固有の香気・風味を損なうことなく、劣化臭の生成を抑制することができることがいえる。また、このような観点から、飲料のみならず、シトラスフレーバーを含有する製品の開発の幅を飛躍的に拡充することができる。 Here, any of the techniques described in Patent Documents 1 to 4 described above suppresses 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.
　ここで、本実施形態に係る金属塩は、ジカルボン酸の備える二つのカルボキシル基のうち、片方のカルボキシル基に対するアニオンについて、対応する金属カチオンが存在するものであってもよいし、ジカルボン酸の備える双方のカルボキシル基に対するアニオンについて、対応する金属カチオンが存在するものであってもよい。
　ここで、金属カチオンの例としては、１価のカチオンのものと、２価のカチオンのものが挙げられ、１価のカチオンとしてはナトリウムイオン、カリウムイオン等を採用することができる。また、２価のカチオンとしては、カルシウムイオン、マグネシウムイオン等を採用することができる。 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.
　本実施形態において、上記のジカルボン酸を製品に添加するか、あるいはジカルボン酸の金属塩を製品に添加するかは、設計する製品に合わせて適宜選択すればよい。
　たとえば、飲料に適用した場合、ジカルボン酸をそのまま添加した場合は、飲用した際に速やかこのジカルボン酸に由来する風味が消え、全体としてキレのある風味となる傾向があり、また、ジカルボン酸の金属塩を添加した場合は、この風味が後まで残る傾向がある。 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.
　本実施形態の劣化臭生成抑制方法および香気劣化抑制方法に係る、上記分子内に共役二重結合を有するジカルボン酸又はその金属塩の飲料に対する添加量は、目的に合わせて適宜調整することができる。
　たとえば、シトラスフレーバー含有製品中における、分子内に共役二重結合を有するジカルボン酸又はその金属塩の添加量の下限値としては、０．５ｐｐｍ以上とすることが好ましく、より好ましくは１０ｐｐｍ以上であり、さらに好ましくは１００ｐｐｍ以上であり、特に好ましくは２５０ｐｐｍ以上である。
　また、シトラスフレーバー含有製品中における、分子内に共役二重結合を有するジカルボン酸又はその金属塩の添加量の上限値としては、たとえば１５０００ｐｐｍ以下である。 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.
　より具体的には、シトラスフレーバーとして、シトラールを含むフレーバーを用いる場合は、製品全体に対する分子内に共役二重結合を有するジカルボン酸又はその金属塩の添加量を０．５ｐｐｍ以上とすることが好ましく、このようにすることにより、ｐ－クレゾールとｐ－メチルアセトフェノンの生成を抑制しやすくなる。
　また、ｐ－クレゾールとｐ－メチルアセトフェノンのみならず、ｐ－サイメンの生成も効果的に抑制できる観点から、製品全体に対する分子内に共役二重結合を有するジカルボン酸又はその金属塩の添加量を１０ｐｐｍ以上とすることがより好ましい。
　なお、上記のようにシトラスフレーバーとしてシトラールを含むフレーバーを用いる場合、製品中に含ませることのできる分子内に共役二重結合を有するジカルボン酸又はその金属塩の量の上限値は特に限定されるものでなく、製品の設計に合わせて適宜選択できるが、例えば、１５０００ｐｐｍ以下である。 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. This makes it easier to suppress the formation of p-cresol and p-methylacetophenone.
From the viewpoint of effectively suppressing not only p-cresol and p-methylacetophenone but also 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.
　また、シトラスフレーバーとして、リモネンを含むフレーバーを用いる場合は、製品全体に対する分子内に共役二重結合を有するジカルボン酸又はその金属塩の添加量を０．５ｐｐｍ以上とすることが好ましく、このようにすることにより、ｐ－クレゾールの生成を抑制しやすくなる。
　また、ｐ－クレゾールのみならず、ｐ－サイメン、α－テルピネオール及びテルピノレンの生成も効果的に抑制できる観点から、製品全体に対する分子内に共役二重結合を有するジカルボン酸又はその金属塩の添加量を１０ｐｐｍ以上とすることがより好ましく、１００ｐｐｍ以上とすることがさらに好ましく、２５０ｐｐｍ以上とすることが特に好ましい。
　なお、シトラスフレーバーとしてリモネンを含むフレーバーを用いる場合、製品中に含ませることのできる分子内に共役二重結合を有するジカルボン酸又はその金属塩の量の上限値は特に限定されるものでなく、製品の設計に合わせて適宜選択できるが、例えば、１５０００ｐｐｍ以下である。 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 so, it becomes easy to suppress the formation of p-cresol.
From the viewpoint of effectively suppressing not only p-cresol but also p-cymene, α-terpineol and terpinolene, the amount of dicarboxylic acid having a conjugated double bond in the molecule or the metal salt thereof in the whole 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.
　また、本実施形態において、分子内に共役二重結合を有するジカルボン酸又はその金属塩の種類と添加量を適宜設定することにより、効果的にシトラスフレーバーの劣化を抑制し、ジカルボン酸又はその金属塩を加えなかった場合に比べて、製品中におけるシトラスフレーバーにおける香気成分の量（残存量）を増加させることができる。
　すなわち、本実施形態に係る分子内に共役二重結合を有するジカルボン酸又はその金属塩は、シトラスフレーバーを含む製品に対しての香気劣化抑制剤として用いることができる。
　ジカルボン酸又はその金属塩の種類としては、フマル酸又はその金属塩が、この効果を顕著に発現させ、また、このフマル酸を添加する場合の添加量としては、製品全体に対するフマル酸又はその金属塩の添加量を０．５ｐｐｍ以上に設定することで、係る効果が発現されやすくなる。
　このような効果から、シトラスフレーバーを含む製品を、加熱や長期保存を行った場合であっても、その香気を十分に保持することができる。 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.
That is, the dicarboxylic acid or a metal salt thereof having a conjugated double bond in the molecule according to the present embodiment can be used as an aroma deterioration inhibitor for products containing citrus flavor.
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.
（飲料）
　本実施形態の劣化臭生成抑制方法および香気劣化抑制方法は好ましくは飲料に対して適用することができる。係る飲料は、先述のシトラスフレーバーと、分子内に共役二重結合を有するジカルボン酸又はその金属塩とを含有するものであり、それ以外の組成等は適宜設定することができる。
　また、当該飲料はアルコール飲料であってもよく、またノンアルコール飲料であってもよい。なお、アルコール飲料としてのアルコール濃度の下限値は、たとえば１％以上であり、好ましくは２％以上であり、より好ましくは３％以上である。
　また、アルコール飲料としてのアルコール濃度の上限値は、たとえば１５％以下であり、好ましくは１２％以下である、より好ましくは１０％以下である。
　本実施形態においては、係る飲料に先述の分子内に共役二重結合を有するジカルボン酸又はその金属塩を添加することにより、加熱時や長期保存時においても劣化臭の生成が抑制され、結果として、香気の劣化が抑制された飲料を提供することができる。 (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.
　本実施形態に係る飲料のｐＨに関して、シトラスフレーバーは、飲料のｐＨが低くなるほど、変性を起こしやすくなり、結果として、劣化臭を招く化合物を生成しやすくなる傾向がある。
　このことから、本実施形態に係る劣化臭生成抑制方法及び香気劣化抑制方法においては、飲料が酸性、すなわち、飲料のｐＨが７未満である場合に、その効果が顕著なものとなる。同様の観点から、飲料のｐＨを６未満とすることもできるし、ｐＨが５未満とすることもできる。
　なお、飲料のｐＨは公知の方法に従って測定することができ、例えば、東亜ディーケーケー社製のｐＨメーター　ＨＭ－３０Ｒ等を用いて測定することができる。 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.
The pH of the beverage can be measured according to a known method. For example, it can be measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
　また、上記のようなｐＨに調整するために、適宜、飲料に対してｐＨ調整剤を添加することもできる。このｐＨ調整剤としては、設計する製品に合わせて適宜選択すればよいが、例えばクエン酸のようなカルボン酸やクエン酸ナトリウムのようなカルボン酸塩等が挙げられる。
　また、このｐＨ調整剤は、飲料のｐＨを逐次観測しながら、添加量を調整すればよい。 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.
（香料組成物）
　上述の劣化臭生成抑制方法等においては、シトラスフレーバー含有製品に対して、分子内に共役二重結合を有するジカルボン酸又はその金属塩を添加する態様を示したが、他の実施形態として、事前にシトラスフレーバーと、分子内に共役二重結合を有するジカルボン酸又はその金属塩とを含有する香料組成物を調製しておき、この香料組成物を製品に添加することで所望の効果を発現することができる。 (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.
　このような香料組成物は、例えば、シトラスフレーバー１００質量部に対して、分子内に共役二重結合を有するジカルボン酸又はその金属塩を０．０１質量部以上含むものであり、より好ましくは０．１質量部以上含むものであり、さらに好ましくは１質量部以上、特に好ましくは５質量部以上含むものである。
　なお、本実施形態に係る香料組成物は、必ずしも全体として均一である必要はなく、分子内に共役二重結合を有するジカルボン酸又はその金属塩が固体状で混合されていてもよい。
　また、本実施形態に係る香料組成物に含まれる分子内に共役二重結合を有するジカルボン酸又はその金属塩の上限値は、例えば、シトラスフレーバー１００質量部に対して、５０質量部以下である。 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. .
　ここで、先述の通り、シトラスフレーバーは加熱時や長期保存時、また、ｐＨの低い環境におかれることにより、変性を招きやすくなる。これに対し、本実施形態の香料組成物においては、保管する環境を適切に管理することにより上述の添加量であっても十分にシトラスフレーバー固有の香気を保つことができる。
　より具体的には、香料組成物を不活性ガスとともに容器に収容した上で密閉し、冷暗所に保管することが、シトラスフレーバー固有の香気を保つ観点から好ましい態様である。 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.
　本実施形態に係る香料組成物は、飲料に添加することができるのは勿論のこと、アイスクリームや飴、ガム等の菓子類、ドレッシング等の調味料類等の食料品に添加することができる。また、食品以外であっても、香水や化粧品、入浴剤や、芳香剤、洗剤、洗口剤等の香粧品にも添加することができる。 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, an aromatic agent, a detergent, and a mouthwash.
　以上、本発明の実施形態について述べたが、これらは本発明の例示であり、上記以外の様々な構成を採用することもできる。
　本発明は以下の内容を含む。
（Ａ１）　シトラスフレーバーと、分子内に共役二重結合を有するジカルボン酸又はその金属塩とを含有することを特徴とする、シトラスフレーバー含有製品。
（Ａ２）　アルコール飲料である、（Ａ１）に記載のシトラスフレーバー含有製品。
（Ａ３）　前記分子内に共役二重結合を有するジカルボン酸又はその金属塩は、フマル酸あるいはイタコン酸又はこれらの金属塩である、（Ａ１）または（Ａ２）に記載のシトラスフレーバー含有製品。
（Ａ４）　前記シトラスフレーバーはシトラールを含む、（Ａ１）乃至（Ａ３）のいずれか１つに記載のシトラスフレーバー含有製品。
（Ａ５）　前記シトラスフレーバーはリモネンを含む、（Ａ１）乃至（Ａ３）のいずれか１つに記載のシトラスフレーバー含有製品。
（Ａ６）　前記シトラスフレーバー含有製品中における、前記分子内に共役二重結合を有するジカルボン酸又はその金属塩の含有量は、０．５ｐｐｍ以上１５０００ｐｐｍ以下である、（Ａ１）乃至（Ａ５）のいずれか１つに記載のシトラスフレーバー含有製品。
（Ａ７）　シトラスフレーバーと、分子内に共役二重結合を有するジカルボン酸又はその金属塩と、アルコールとを含有する飲料において、
　当該飲料全体における、前記分子内に共役二重結合を有するジカルボン酸又はその金属塩の含有量は、０．５ｐｐｍ以上１５０００ｐｐｍ以下である、飲料。
（Ａ８）　前記分子内に共役二重結合を有するジカルボン酸又はその金属塩は、フマル酸あるいはイタコン酸又はこれらの金属塩である、（Ａ７）に記載の飲料。
（Ａ９）　前記シトラスフレーバーはシトラールを含む、（Ａ７）または（Ａ８）に記載の飲料。
（Ａ１０）　前記シトラスフレーバーはリモネンを含む、（Ａ７）または（Ａ８）に記載の飲料。
（Ａ１１）　シトラスフレーバーと、分子内に共役二重結合を有するジカルボン酸又はその金属塩とを含有することを特徴とする、香料組成物。
（Ａ１２）　シトラスフレーバーを含有する製品に対して、分子内に共役二重結合を有するジカルボン酸又はその金属塩を添加することにより、
　前記シトラスフレーバーを含有する製品中におけるｐ－クレゾール、ｐ－サイメン、ｐ－メチルアセトフェノン、α－テルピネオールおよびテルピノレンからなる群から選ばれる１種又は２種以上の化合物の生成を抑制する、劣化臭生成抑制方法。
（Ａ１３）　前記シトラスフレーバーを含有する製品がアルコール飲料である、（Ａ１２）に記載の劣化臭生成抑制方法。
（Ａ１４）　前記アルコール飲料のｐＨが７未満である、（Ａ１３）に記載の劣化臭生成抑制方法。
（Ａ１５）　前記分子内に共役二重結合を有するジカルボン酸又はその金属塩は、フマル酸あるいはイタコン酸又はこれらの金属塩であることを特徴とする、（Ａ１２）乃至（Ａ１４）のいずれか１つに記載の劣化臭生成抑制方法。
（Ａ１６）　前記シトラスフレーバーを含有する製品中における、前記分子内に共役二重結合を有するジカルボン酸又はその金属塩の添加量は、０．５ｐｐｍ以上１５０００ｐｐｍ以下であることを特徴とする、（Ａ１２）乃至（Ａ１５）のいずれか１つに記載の劣化臭生成抑制方法。
（Ａ１７）　前記シトラスフレーバーはシトラールを含む、（Ａ１２）乃至（Ａ１６）のいずれか一つに記載の劣化臭生成抑制方法。
（Ａ１８）　ｐ－クレゾール、ｐ－サイメンおよびｐ－メチルアセトフェノンの全ての化合物の生成が抑制されることを特徴とする、（Ａ１７）に記載の劣化臭生成抑制方法。
（Ａ１９）　前記シトラスフレーバーはリモネンを含む、（Ａ１２）乃至（Ａ１６）のいずれか１つに記載の劣化臭生成抑制方法。
（Ａ２０）　ｐ－クレゾール、ｐ－サイメン、α－テルピネオールおよびテルピノレンの全ての化合物の生成が抑制されることを特徴とする、（Ａ１９）に記載の劣化臭生成抑制方法。
（Ａ２１）　シトラスフレーバーを含有する製品に対して、分子内に共役二重結合を有するジカルボン酸又はその金属塩を添加することを特徴とする、香気劣化抑制方法。
（Ａ２２）　前記シトラスフレーバーを含有する製品がアルコール飲料である、（Ａ２１）に記載の香気劣化抑制方法。
（Ａ２３）　前記分子内に共役二重結合を有するジカルボン酸又はその金属塩は、フマル酸あるいはイタコン酸又はこれらの金属塩であることを特徴とする、（Ａ２１）または（Ａ２２）に記載の香気劣化抑制方法。
（Ｂ１）　シトラールを含む飲料又は食料品に対して、フマル酸又はその金属塩を添加することを特徴とする、香気劣化抑制方法であって、
　シトラールを含む前記飲料又は前記食料品全体に対して、前記フマル酸又はその金属塩を０．５ｐｐｍ以上１５０００ｐｐｍ以下添加することを特徴とする、香気劣化抑制方法。
（Ｂ２）　シトラールを含む前記飲料又は前記食料品は、シトラールを含む飲料である、（Ｂ１）に記載の香気劣化抑制方法。
（Ｂ３）　シトラールを含む前記飲料のｐＨが７未満であることを特徴とする、（Ｂ２）に記載の香気劣化抑制方法。
（Ｂ４）　フマル酸又はその金属塩からなる香気劣化抑制剤であって、
　シトラールを含む飲料又は食料品全体に対して、０．５ｐｐｍ以上１５０００ｐｐｍ以下添加されることを特徴とする、香気劣化抑制剤。 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.
The present invention includes the following contents.
(A1) 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.
(A2) The citrus flavor-containing product according to (A1), which is an alcoholic beverage.
(A3) The citrus flavor-containing 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, itaconic acid, or a metal salt thereof.
(A4) The citrus flavor-containing product according to any one of (A1) to (A3), wherein the citrus flavor includes citral.
(A5) The citrus flavor-containing product according to any one of (A1) to (A3), wherein the citrus flavor includes limonene.
(A6) The content 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 or more and 15000 ppm or less, and any of (A1) to (A5) The citrus flavor containing product as described in any one.
(A7) In a beverage containing citrus flavor, dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof, and alcohol,
Content of the dicarboxylic acid which has a conjugated double bond in the said molecule | numerator in the whole said drink, or its metal salt is a drink which is 0.5 ppm or more and 15000 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, itaconic acid or a metal salt thereof.
(A9) The beverage according to (A7) or (A8), wherein the citrus flavor includes citral.
(A10) The beverage according to (A7) or (A8), wherein the citrus flavor contains limonene.
(A11) A fragrance composition comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof.
(A12) By adding a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a product containing a citrus flavor,
Deteriorated odor generation that suppresses the generation of one or more compounds selected from the group consisting of p-cresol, p-cymene, p-methylacetophenone, α-terpineol, and terpinolene in products containing the citrus flavor Suppression method.
(A13) The degradation odor production | generation suppression method as described in (A12) whose product containing the said citrus flavor is an alcoholic beverage.
(A14) The degradation odor production | generation suppression method as described in (A13) whose pH of the said alcoholic beverage is less than 7.
(A15) Any one of (A12) to (A14), 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. Deterioration odor production suppression method as described in one.
(A16) In the product containing the citrus flavor, 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, (A12 ) To (A15) The degradation odor production suppressing method according to any one of the above.
(A17) The degradation odor production | generation suppression method as described in any one of (A12) thru | or (A16) in which the said citrus flavor contains citral.
(A18) The degradation odor production inhibiting method according to (A17), wherein the production of all compounds of p-cresol, p-cymene and p-methylacetophenone is inhibited.
(A19) The degradation odor production | generation suppression method as described in any one of (A12) thru | or (A16) in which the said citrus flavor contains limonene.
(A20) The method for inhibiting degradation odor production according to (A19), wherein the production of all compounds of p-cresol, p-cymene, α-terpineol and terpinolene is inhibited.
(A21) 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 product containing a citrus flavor.
(A22) The fragrance deterioration suppressing method according to (A21), wherein the product containing the citrus flavor is an alcoholic beverage.
(A23) The fragrance 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, itaconic acid or a metal salt thereof. Deterioration suppression method.
(B1) To a beverage or food containing citral, fumaric acid or a metal salt thereof is added.
A method for suppressing aroma degradation, comprising adding 0.5 ppm or more and 15000 ppm or less of the fumaric acid or a metal salt thereof to the beverage or the entire food containing citral.
(B2) The fragrance deterioration suppression method according to (B1), wherein the beverage or food product containing citral is a beverage containing citral.
(B3) The method of inhibiting fragrance deterioration according to (B2), wherein the beverage containing citral has a pH of less than 7.
(B4) A fragrance degradation inhibitor comprising fumaric acid or a metal salt thereof,
A fragrance degradation inhibitor 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.
　以下、実施例を用いて本発明を詳細に説明するが、本発明はこれらの実施例の記載に何ら限定されるものではない。 Hereinafter, the present invention will be described in detail using examples, but the present invention is not limited to the description of these examples.
　まず、本実施例項において、飲料中に含まれる各成分の量はガスクロマトグラフィ（ＧＣ）分析を用いて定量を行っている。この分析の手順は以下に示す通りである。
（サンプル作製方法）
　試料を５０．０ｇ秤量し、内部標準として２－オクタノールを１００μＬ添加した上で、５０ｍＬの水で希釈を行う。これとは別にジクロロメタン（５ｍＬ）、エタノール（５ｍＬ）、水（２０ｍＬ）にて順次コンディショニングを行った固相（Ｗａｔｅｒｓ社製Ｏａｓｉｓ　ＨＬＢ　２００ｍｇ／６ｃｃ）を準備し、上で得られた希釈試料に含まれる有機成分を全量吸着させる。その後、ジクロロメタン５ｍＬにて溶出を行い、この溶出液を無水硫酸ナトリウムで脱水し、その上清をスピッツ管に移注して窒素パージにて２００μＬまで濃縮し、分析用のサンプルを作製する。
（定量方法）
　この分析用のサンプルは以下に示す条件にて、ガスクロマトグラフィ（ＧＣ）分析を行う。試料中の成分量は内部標準として用いた２－オクタノールのピークとの面積比から計算する。また、同一試料についてＧＣ分析を二度行い、その平均値として試料中の成分量であるものとして定量を行う。
（ＧＣ条件）
機器名：Ａｇｉｌｅｎｔ　Ｔｅｃｈｎｏｌｏｇｉｅｓ社製　５９７３ｉｎｅｒｔ　Ｍａｓｓ　Ｓｅｌｅｃｔｉｖｅ　Ｄｅｔｅｃｔｏｒ
カラム：ＤＢ－ＷＡＸ（６０ｍ×０．２５ｍｍ×０．２５μｍ）
オーブン温度：４０℃（１ｍｉｎ）－（３℃／ｍｉｎ）－２１０℃（３ｍｉｎ）
流量：１ｍｌ／ｍｉｎ
インジェクション温度：２５０℃
インジェクション量：１μＬ
スプリット比：１０：１ 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 components 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
（実施例１）
　モデル液Ａとして、アルコール濃度５％、シトラール１０ｐｐｍを含む飲料を用意し、この飲料のｐＨを、ｐＨ調整剤であるクエン酸三ナトリウムを用いてｐＨが３．１となるように調整した。なお、ここでｐＨは東亜ディーケーケー社製のｐＨメーター　ＨＭ－３０Ｒを用いて測定した。
　この飲料に対し、フマル酸一ナトリウムを、飲料全体の２５０ｐｐｍとなるように添加し、密栓した上で、３７℃の温度にて７日間静置した。静置後、飲料に含まれるシトラールの量、ｐ－クレゾールの量、ｐ－サイメンの量、ｐ－メチルアセトフェノンの量を定量した。
　この含有量について、後述する比較例１における各成分の含有量との比として表１に示した。 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.
（実施例２、３）
　実施例１の方法において、フマル酸一ナトリウムの添加量を表１に記載の通りに調整する以外は、実施例１と同様の方法で静置を行い、飲料中に含まれる各成分の量を定量した。結果は表１に示す。 (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.
（実施例４）
　実施例１の方法において、フマル酸一ナトリウムの代わりに、フマル酸を２１０ｐｐｍとなるように添加した以外は、実施例１と同様の方法で静置を行い、飲料中に含まれる各成分の量を定量した。結果は表１に示した。 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.
（比較例１）
　実施例１の方法において、フマル酸一ナトリウムを加えなかった以外は、実施例１と同様の方法で静置を行い、飲料中に含まれる各成分の量を定量した。この比較例１の結果を対照（１００．０％）として表１に示した。 (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%).
　ここで、これらの実施例１－４においては、「シトラス感」、「劣化香」、「美味しさ」の項目について、官能評価を行った。
　官能評価は３名の専門パネラーが行い、比較例１と比較して良い印象を持ったものを＋１、悪い印象を持ったものを－１、印象として変わらないものを０として、３名のパネラーの平均点を評点として表１に示した。
　なお、「劣化香」については、シトラールの劣化した香気がより感じられないものを良い場合として評価を行っている。 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.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
（実施例５）
　モデル液Ａとして、アルコール濃度５％、シトラール１０ｐｐｍ、を含む飲料を用意し、この飲料のｐＨを、ｐＨ調整剤であるクエン酸三ナトリウムを用いてｐＨが３．３となるように調整した。なお、ここでｐＨは東亜ディーケーケー社製のｐＨメーター　ＨＭ－３０Ｒを用いて測定した。
　この飲料に対し、フマル酸一ナトリウムを、飲料全体の２５０ｐｐｍとなるように添加し、密栓した上で、３７℃の温度にて７日間静置した。静置後、飲料に含まれるシトラールの量、ｐ－クレゾールの量、ｐ－サイメンの量、ｐ－メチルアセトフェノンの量を定量した。
　この含有量について、後述する比較例２における各成分の含有量との比として表２に示した。 (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.
（実施例６、７）
　実施例５の方法において、フマル酸一ナトリウムの添加量を表２に記載の通りに調整する以外は、実施例５と同様の方法で静置を行い、飲料中に含まれる各成分の量を定量した。結果は表２に示した。 (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.
（比較例２）
　実施例５の方法において、フマル酸一ナトリウムを加えなかった以外は、実施例５と同様の方法で静置を行い、飲料中に含まれる各成分の量を定量した。この比較例２の結果を対照（１００．０％）として表２に示した。 (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%).
（実施例８）
　モデル液Ａとして、アルコール濃度５％、シトラール１０ｐｐｍ、を含む飲料を用意し、この飲料のｐＨを、ｐＨ調整剤であるクエン酸三ナトリウムを用いてｐＨが３．５となるように調整した。なお、ここでｐＨは東亜ディーケーケー社製のｐＨメーター　ＨＭ－３０Ｒを用いて測定した。
　この飲料に対し、フマル酸一ナトリウムを、飲料全体の２５０ｐｐｍとなるように添加し、密栓した上で、３７℃の温度にて７日間静置した。静置後、飲料に含まれるシトラールの量、ｐ－クレゾールの量、ｐ－サイメンの量、ｐ－メチルアセトフェノンの量を定量した。
　この含有量について、後述する比較例３における各成分の含有量との比として表２に示した。 (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.
（実施例９）
　実施例８の方法において、フマル酸一ナトリウムの添加量を表２に記載の通りに調整する以外は、実施例８と同様の方法で静置を行い、飲料中に含まれる各成分の量を定量した。結果は表２に示した。 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.
（比較例３）
　実施例８の方法において、フマル酸一ナトリウムを加えなかった以外は、実施例８と同様の方法で静置を行い、飲料中に含まれる各成分の量を定量した。この比較例３の結果を対照（１００．０％）として表２に示した。 (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%).
　ここで、これらの実施例５－９においては、「シトラス感」、「劣化香」、「美味しさ」の項目に従い、官能評価を行った。
　具体的な手法は実施例１－４で行ったものに準じるものであり、実施例５－７は比較例２に対して、実施例８、９は比較例３に対して、各項目における印象を統計している。結果は表２に示した通りである。 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.
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
（実施例１０）
　モデル液Ｂとして、アルコールを含まず、シトラール１０ｐｐｍ、を含む飲料を用意し、この飲料のｐＨを、ｐＨ調整剤であるクエン酸三ナトリウムを用いてｐＨが３．０となるように調整した。なお、ここでｐＨは東亜ディーケーケー社製のｐＨメーター　ＨＭ－３０Ｒを用いて測定した。
　この飲料に対し、フマル酸一ナトリウムを、飲料全体の２５０ｐｐｍとなるように添加し、密栓した上で、３７℃の温度にて７日間静置した。静置後、飲料に含まれるシトラールの量、ｐ－クレゾールの量、ｐ－サイメンの量、ｐ－メチルアセトフェノンの量を定量した。
　この含有量について、後述する比較例４における各成分の含有量との比として表３に示した。 (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.
（比較例４）
　実施例１０の方法において、フマル酸一ナトリウムを加えなかった以外は、実施例１０と同様の方法で静置を行い、飲料中に含まれる各成分の量を定量した。この比較例４の結果を対照（１００．０％）として表３に示した。 (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%).
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
（実施例１１）
　モデル液Ｃとして、アルコール濃度５％、リモネン１０ｐｐｍ、を含む飲料を用意し、この飲料のｐＨを、ｐＨ調整剤であるクエン酸三ナトリウムを用いてｐＨが３．３となるように調整した。なお、ここでｐＨは東亜ディーケーケー社製のｐＨメーター　ＨＭ－３０Ｒを用いて測定した。
　この飲料に対し、フマル酸一ナトリウムを、飲料全体の２５０ｐｐｍとなるように添加し、密栓した上で、３７℃の温度にて７日間静置した。静置後、飲料に含まれるリモネンの量、ｐ－クレゾールの量、ｐ－サイメンの量、α－テルピネオール、テルピノレンの量を定量した。
　この含有量について、後述する比較例５における各成分の含有量との比として表４に示した。 (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.
（比較例５）
　実施例１１の方法において、フマル酸一ナトリウムを加えなかった以外は、実施例１１と同様の方法で静置を行い、飲料中に含まれる各成分の量を定量した。この比較例５の結果を対照（１００．０％）として表４に示した。 (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%).
Figure JPOXMLDOC01-appb-T000004
Figure JPOXMLDOC01-appb-T000004
（実施例１２）
　モデル液Ａとして、アルコール濃度５％、シトラール１０ｐｐｍ、を含む飲料を用意し、この飲料のｐＨをｐＨ調整剤であるクエン酸三ナトリウムを用いてｐＨが３．０となるように調整した。なお、ここでｐＨは東亜ディーケーケー社製のｐＨメーター　ＨＭ－３０Ｒを用いて測定した。
　この飲料に対し、フマル酸一ナトリウムを、飲料全体の１０ｐｐｍとなるように添加し、密栓した上で、３７℃の温度にて７日間静置した。静置後、飲料に含まれるシトラールの量、ｐ－クレゾールの量、ｐ－サイメンの量、ｐ－メチルアセトフェノンの量を定量した。
　この含有量について、後述する比較例６における各成分の含有量との比として表５に示した。 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.
（実施例１３）
　実施例１２の方法において、フマル酸一ナトリウムの添加量を表５に記載の通りに調整する以外は、実施例１２と同様の方法で静置を行い、飲料中に含まれる各成分の量を定量した。結果は表５に示した。 (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.
（実施例１４）
　実施例１２の方法において、フマル酸一ナトリウムの代わりにイタコン酸を用い、含有量を２５０ｐｐｍに設定した以外は、実施例１２と同様の方法で静置を行い、飲料中に含まれる各成分の量を定量した。結果は表５に示した。 (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.
（比較例６）
　実施例１２の方法において、フマル酸一ナトリウムを加えなかった以外は、実施例１２と同様の方法で静置を行い、飲料中に含まれる各成分の量を定量した。この比較例６の結果を対照（１００．０％）として表５に示した。 (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%).
Figure JPOXMLDOC01-appb-T000005
Figure JPOXMLDOC01-appb-T000005
　各実施例に示されるように、シトラスフレーバーを有する飲料に対して、特定のジカルボン酸又はその金属塩を添加することにより、劣化臭をもたらす成分の生成が抑制された。
　また、このように劣化臭をもたらす成分の生成を抑制することにより、飲用した者に心地よいシトラス感や美味しさをもたらすことができた。 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.
　本発明の劣化臭生成抑制方法は、効果的にシトラスフレーバー固有の香気を保つことができる。このことから、シトラスフレーバーを有する製品の開発の幅を飛躍的に拡充することができる。
　また、これにより、シトラスフレーバー固有の香気が保たれた製品等を提供することができる。 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.
In addition, this makes it possible to provide a product or the like in which an aroma unique to citrus flavor is maintained.
　この出願は、２０１４年１２月１９日に出願された日本出願特願２０１４－２５８０５２号を基礎とする優先権を主張し、その開示の全てをここに取り込む。 This application claims priority based on Japanese Patent Application No. 2014-258052 filed on December 19, 2014, the entire disclosure of which is incorporated herein.

Claims (23)

  1. 　シトラスフレーバーと、分子内に共役二重結合を有するジカルボン酸又はその金属塩とを含有することを特徴とする、シトラスフレーバー含有製品。 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.
  2. 　アルコール飲料である、請求項１に記載のシトラスフレーバー含有製品。 The citrus flavor-containing product according to claim 1, which is an alcoholic beverage.
  3. 　前記分子内に共役二重結合を有するジカルボン酸又はその金属塩は、フマル酸あるいはイタコン酸又はこれらの金属塩である、請求項１または２に記載のシトラスフレーバー含有製品。 The citrus flavor-containing 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, itaconic acid or a metal salt thereof.
  4. 　前記シトラスフレーバーはシトラールを含む、請求項１乃至３のいずれか１項に記載のシトラスフレーバー含有製品。 The citrus flavor-containing product according to any one of claims 1 to 3, wherein the citrus flavor includes citral.
  5. 　前記シトラスフレーバーはリモネンを含む、請求項１乃至３のいずれか１項に記載のシトラスフレーバー含有製品。 The citrus flavor-containing product according to any one of claims 1 to 3, wherein the citrus flavor includes limonene.
  6. 　前記シトラスフレーバー含有製品中における、前記分子内に共役二重結合を有するジカルボン酸又はその金属塩の含有量は、０．５ｐｐｍ以上１５０００ｐｐｍ以下である、請求項１乃至５のいずれか１項に記載のシトラスフレーバー含有製品。 6. The content 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 or more and 15000 ppm or less. 6. Citrus flavored products.
  7. 　シトラスフレーバーと、分子内に共役二重結合を有するジカルボン酸又はその金属塩と、アルコールとを含有する飲料において、
    　当該飲料全体における、前記分子内に共役二重結合を有するジカルボン酸又はその金属塩の含有量は、０．５ｐｐｍ以上１５０００ｐｐｍ以下である、飲料。     In a beverage containing a citrus flavor, a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof, and an alcohol,
    Content of the dicarboxylic acid which has a conjugated double bond in the said molecule | numerator in the whole said drink, or its metal salt is a drink which is 0.5 ppm or more and 15000 ppm or less.
  8. 　前記分子内に共役二重結合を有するジカルボン酸又はその金属塩は、フマル酸あるいはイタコン酸又はこれらの金属塩である、請求項７に記載の飲料。 The beverage according to claim 7, wherein the dicarboxylic acid or a metal salt thereof having a conjugated double bond in the molecule is fumaric acid, itaconic acid or a metal salt thereof.
  9. 　前記シトラスフレーバーはシトラールを含む、請求項７または８に記載の飲料。 The beverage according to claim 7 or 8, wherein the citrus flavor includes citral.
  10. 　前記シトラスフレーバーはリモネンを含む、請求項７または８に記載の飲料。 The beverage according to claim 7 or 8, wherein the citrus flavor contains limonene.
  11. 　シトラスフレーバーと、分子内に共役二重結合を有するジカルボン酸又はその金属塩とを含有することを特徴とする、香料組成物。 A fragrance composition comprising a citrus flavor and a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof.
  12. 　シトラスフレーバーを含有する製品に対して、分子内に共役二重結合を有するジカルボン酸又はその金属塩を添加することにより、
    　前記シトラスフレーバーを含有する製品中におけるｐ－クレゾール、ｐ－サイメン、ｐ－メチルアセトフェノン、α－テルピネオールおよびテルピノレンからなる群から選ばれる１種又は２種以上の化合物の生成を抑制する、劣化臭生成抑制方法。     By adding a dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof to a product containing a citrus flavor,
    Deteriorated odor generation that suppresses the generation of one or more compounds selected from the group consisting of p-cresol, p-cymene, p-methylacetophenone, α-terpineol, and terpinolene in products containing the citrus flavor Suppression method.
  13. 　前記シトラスフレーバーを含有する製品がアルコール飲料である、請求項１２に記載の劣化臭生成抑制方法。 The method for suppressing deterioration odor production according to claim 12, wherein the product containing the citrus flavor is an alcoholic beverage.
  14. 　前記アルコール飲料のｐＨが７未満である、請求項１３に記載の劣化臭生成抑制方法。 The method for suppressing the generation of a deteriorated odor according to claim 13, wherein the pH of the alcoholic beverage is less than 7.
  15. 　前記分子内に共役二重結合を有するジカルボン酸又はその金属塩は、フマル酸あるいはイタコン酸又はこれらの金属塩であることを特徴とする、請求項１２乃至１４のいずれか１項に記載の劣化臭生成抑制方法。 The deterioration according to any one of claims 12 to 14, 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. Odor generation suppression method.
  16. 　前記シトラスフレーバーを含有する製品中における、前記分子内に共役二重結合を有するジカルボン酸又はその金属塩の添加量は、０．５ｐｐｍ以上１５０００ｐｐｍ以下であることを特徴とする、請求項１２乃至１５のいずれか１項に記載の劣化臭生成抑制方法。 The addition amount of the dicarboxylic acid having a conjugated double bond in the molecule or a metal salt thereof in the product containing the citrus flavor is 0.5 ppm or more and 15000 ppm or less. The degradation odor production | generation suppression method of any one of these.
  17. 　前記シトラスフレーバーはシトラールを含む、請求項１２乃至１６のいずれか１項に記載の劣化臭生成抑制方法。 The method for suppressing generation of a deteriorated odor according to any one of claims 12 to 16, wherein the citrus flavor includes citral.
  18. 　ｐ－クレゾール、ｐ－サイメンおよびｐ－メチルアセトフェノンの全ての化合物の生成が抑制されることを特徴とする、請求項１７に記載の劣化臭生成抑制方法。 18. The method for inhibiting the generation of deteriorated odor according to claim 17, wherein the production of all compounds of p-cresol, p-cymene and p-methylacetophenone is inhibited.
  19. 　前記シトラスフレーバーはリモネンを含む、請求項１２乃至１６のいずれか１項に記載の劣化臭生成抑制方法。 The method for suppressing deterioration odor generation according to any one of claims 12 to 16, wherein the citrus flavor contains limonene.
  20. 　ｐ－クレゾール、ｐ－サイメン、α－テルピネオールおよびテルピノレンの全ての化合物の生成が抑制されることを特徴とする、請求項１９に記載の劣化臭生成抑制方法。 20. The method for inhibiting the generation of degraded odor according to claim 19, wherein the production of all compounds of p-cresol, p-cymene, α-terpineol and terpinolene is inhibited.
  21. 　シトラスフレーバーを含有する製品に対して、分子内に共役二重結合を有するジカルボン酸又はその金属塩を添加することを特徴とする、香気劣化抑制方法。 A method for suppressing fragrance degradation, comprising adding a dicarboxylic acid having a conjugated double bond in its molecule or a metal salt thereof to a product containing a citrus flavor.
  22. 　前記シトラスフレーバーを含有する製品がアルコール飲料である、請求項２１に記載の香気劣化抑制方法。 The method for suppressing aroma deterioration according to claim 21, wherein the product containing the citrus flavor is an alcoholic beverage.
  23. 　前記分子内に共役二重結合を有するジカルボン酸又はその金属塩は、フマル酸あるいはイタコン酸又はこれらの金属塩であることを特徴とする、請求項２１または２２に記載の香気劣化抑制方法。 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, itaconic acid or a metal salt thereof.
PCT/JP2015/082358 2014-12-19 2015-11-18 Citrus flavor containing product, beverage, perfume composition, method for suppressing generation of degradation odor, and method for suppressing aroma degradation WO2016098515A1 (en)

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