WO2016098515A1 - Produit contenant un arôme d'agrume, boisson, composition de parfum, procédé de suppression de génération d'odeur de dégradation, et procédé de suppression de dégradation d'arôme - Google Patents

Produit contenant un arôme d'agrume, boisson, composition de parfum, procédé de suppression de génération d'odeur de dégradation, et procédé de suppression de dégradation d'arôme 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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English (en)
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/fr

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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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  • Chemical Kinetics & Catalysis (AREA)
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  • Wood Science & Technology (AREA)
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Abstract

Un produit contenant un arôme d'agrume selon la présente invention est caractérisé par le fait qu'il contient un arôme d'agrume et d'un acide dicarboxylique ou un sel métallique de celui-ci qui a une double liaison conjuguée intramoléculaire.
PCT/JP2015/082358 2014-12-19 2015-11-18 Produit contenant un arôme d'agrume, boisson, composition de parfum, procédé de suppression de génération d'odeur de dégradation, et procédé de suppression de dégradation d'arôme WO2016098515A1 (fr)

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JP6198907B1 (ja) * 2016-08-17 2017-09-20 アサヒビール株式会社 シトラールの残存量を向上させた、柑橘類果実様香味組成物及びそれを含有した製品
TWI670015B (zh) * 2016-12-19 2019-09-01 統一企業股份有限公司 檸檬茶飲料的篩選方法
JP2020203958A (ja) * 2017-08-18 2020-12-24 ライオン株式会社 シソ科メンタ属植物由来の抽出物とその製造方法
JP7311964B2 (ja) * 2018-12-21 2023-07-20 アサヒビール株式会社 シトラール由来オフフレーバーの抑制方法

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JPH01254619A (ja) * 1988-04-01 1989-10-11 Kao Corp 入浴剤
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JP2003231894A (ja) * 2002-02-08 2003-08-19 Nagaoka Koryo Kk 柑橘系香味の劣化抑制剤、柑橘系香料、食品およびシトラールの環化抑制剤
WO2009011271A1 (fr) * 2007-07-13 2009-01-22 Ogawa & Co., Ltd. Inhibiteur de dégradation d'une flaveur ou d'un arôme
JP2012167061A (ja) * 2011-02-15 2012-09-06 Kao Corp 血行促進用身体化粧料

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