JP7114519B2 - Photodeterioration odor masking agent for products containing fruit juice - Google Patents

Description

TECHNICAL FIELD The present invention relates to a photodegradation odor masking agent for fruit juice-containing products and a method of using the same. More specifically, the present invention provides a masking agent for suppressing the deterioration odor caused by deterioration of fruit juice-derived components due to the influence of light, a method for masking the deterioration odor of fruit juice-containing products using the masking agent, and the masking agent. It relates to a fruit juice-containing product and a method for producing the fruit juice-containing product.

Fruit juice-containing products, which are food and drink products containing fruit juice, often undergo a heating step for concentration, sterilization, and the like in the manufacturing process. In addition, these fruit juice-containing products are often placed in showcases at retail stores, etc., and exposed to strong light for a long period of time, for example, in a state of being filled in a light-transmitting container. It is known that the components contained in fruit juice are degraded by heat or light in such a heating process or light exposure process, resulting in various degraded odors (off-flavours) (Non-Patent Documents 1 to 4).

Since such deterioration odors greatly affect the quality of fruit juice-containing products, attempts have been made to suppress the generation of deterioration odors. For example, one or more selected from L-ascorbic acid, rutin, hermanus extract, and chlorogenic acid to prevent generation of unpleasant off-flavours generated during storage of foods and drinks containing grapefruit juice by tea extract (Patent Document 1) Suppression of odor generated during storage of beverages containing white grape juice by a specific antioxidant containing Attempts have been made to suppress the generation of off-flavors due to oxidation (Patent Document 3).

However, among the deterioration of these fruit juice-containing products, there are still many unclear points about what components cause the deterioration odor (photodegradation odor) caused by exposure to light. In addition, when targeting the photodegradation odor among the degradation odors, there is no specific disclosure as to what kind of compound can be used to mask the photodegradation odor of fruit juice-containing products. Therefore, it is eagerly desired to identify components that are not known to be odorous substances caused by photodegradation of fruit juice, and to identify new masking agent components capable of masking odorous substances caused by photodegradation of fruit juice.

JP 2005-304324 JP 2014-168401 WO2012/017984

Journal of Japan Society for Food Science and Technology Vol.58 No.3 81-87 (2011) Soft drink technical data, 3, 257-262 (2000) J Agric Food Chem, 55, 9177-9182 (2007) Journal of the Society of Odor and Fragrant Environment Vol.41 No.4 240-245 (2010)

An object of the present invention is to provide a novel masking agent for photo-deterioration odors of fruit juice-containing products in view of the above-mentioned problems in the prior art. Another object of the present invention is to provide a novel masking method using the novel masking agent, a method for producing a fruit juice-containing product, and a fruit juice-containing product obtained by the production method.

Under such circumstances, the present inventors, as a result of intensive studies, identified an odorant that had not been known to be produced by photodegradation of fruit juice-containing products. The inventors have also identified masking agent ingredients that were not known to have a masking effect on unknown and known odorants produced by photodegradation of fruit juice containing products. Furthermore, the present inventors have confirmed that these masking agent components have the effect of masking the photodegradation odor of fruit juice-containing products, and have completed the present invention.

Accordingly, the present invention provides the following terms:
Section 1. A photodegradation odor masking agent for fruit juice-containing products, containing at least one compound selected from the group consisting of Groups A to G below;
(Group A) heliotropine, ethyl pyruvate, ethyl acetoacetate, and benzyl benzoate (Group B) butyl butyryl lactate, ethyl levulinate, benzyl alcohol, methyl jasmonate, stearic acid, methyl dihydrojasmonate, heliotropin, and Ethyl pyruvate (group C) acetaldehyde, β-damascenone, methyl salicylate, 1,8-cineol, ethyl acetate, δ-hexalactone, 1,4-cineol, menthyl lactate, anethole, rose oxide, and ethyl isovalerate ( Group D) Acetaldehyde, β-damascenone, acetal, 1,8-cineol, γ-valerolactone, p-menthan-3-one, γ-hexalactone, dihydroactinidiolide, ethyl crotonate, 1,4-cineole, Hexanal, anethole, rose oxide, sclareolide, and ethyl isovalerate (group E) diethyl carbonate, 2-pentanone, acetal, methyl salicylate, 1,8-cineol, ethyl acetate, δ-hexalactone, dihydroactinidiolide, 2 - octanone, 1,4-cineole, 2-methyl-2-hepten-6-one, hexanal, γ-heptalactone, anethole, ethyl butyrate, sclareolide and ethyl isovalerate (group F) ethyl lactate, 2-butanone , 2-pentanone, acetal, methyl salicylate, 1,8-cineol, ethyl acetate, p-menthan-3-one, γ-hexalactone, dihydroactinidiolide, 2-octanone, ethyl crotonate, 1,4-cineole , menthyl lactate, 2-methyl-2-hepten-6-one, hexanal, anethole, ethyl butyrate, sclareolide, and ethyl isovalerate (group G) oleic acid, 2-butanone, acetaldehyde, acetal, methyl salicylate, ethyl acetate , p-menthan-3-one, γ-hexalactone, δ-hexalactone, dihydroactinidiolide, ethyl crotonate, menthyl lactate, 2-methyl-2-hepten-6-one, hexanal, γ-heptalactone, Anethole, ethyl butyrate, sclareolide, and ethyl isovalerate.

Section 2. Item 2. The masking agent according to item 1, wherein at least two of the compounds contained in the masking agent are compounds belonging to different groups among the groups A to G.

Item 3. Item 2. The masking agent according to item 1, wherein at least three of the compounds contained in the masking agent are compounds belonging to groups different from each other in the groups A to G.

Item 4-1. Item 4. The masking agent according to any one of items 1 to 3, comprising methional, trans-4,5-epoxy-(E)-2-decenal, 1-octen-3-one, sotolone, (E,E )-2,4-nonadienal, (E,E)-2,4-decadienal and (E)-2-nonenal masking the photodegradation odor of fruit juice-containing products caused by at least five selected from the group consisting of masking agent for

Item 4-2. Item 4. The masking agent according to any one of Items 1 to 3, which contains at least one compound belonging to Group A and is for masking the photodegradation odor of fruit juice-containing products caused by methional.

Item 4-3. Item 4. The masking agent according to any one of Items 1 to 3, which contains at least one compound belonging to Group B and is derived from trans-4,5-epoxy-(E)-2-decenal. Masking agent for masking the photodegradation odor of containing products.

Item 4-4. Item 4. The masking agent according to any one of items 1 to 3, which contains at least one compound belonging to the above-mentioned group C and masks the photodegradation odor of fruit juice-containing products caused by 1-octen-3-one. masking agent for

Item 4-5. Item 4. The masking agent according to any one of Items 1 to 3, which contains at least one compound belonging to Group D and is for masking the photodeterioration odor of fruit juice-containing products caused by sotolone.

Item 4-6. Item 4. The masking agent according to any one of Items 1 to 3, wherein the masking agent contains at least one compound belonging to Group E, and the light of fruit juice-containing products resulting from (E,E)-2,4-nonadienal. A masking agent for masking deterioration odors.

Item 4-7. Item 4. The masking agent according to any one of Items 1 to 3, wherein the masking agent contains at least one compound belonging to the F group, and the light of a fruit juice-containing product caused by (E,E)-2,4-decadienal. A masking agent for masking deterioration odors.

Item 4-8. Item 4. The masking agent according to any one of Items 1 to 3, which contains at least one compound belonging to Group G and masks the photodeterioration odor of fruit juice-containing products caused by (E)-2-nonenal. masking agent for

Item 5. Any one of items 1 to 3, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 4-7 and 4-8 A method of masking the photodegradation odor of a fruit juice containing product comprising adding a masking agent as described to the fruit juice containing product.

Item 6. Any one of items 1 to 3, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 4-7 and 4-8 A method of making a fruit juice-containing product comprising adding a masking agent as described to the fruit juice-containing product.

Item 7. Any one of items 1 to 3, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 4-7 and 4-8 A fruit juice-containing product containing the masking agent described.

According to the present invention, a novel masking agent for photodegradation odor of fruit juice-containing products, a novel masking method using the novel masking agent, a method for producing a fruit juice-containing product, and a fruit juice-containing product obtained by the production method are provided. can be done. INDUSTRIAL APPLICABILITY The present invention can mask the light-degraded odor of a fruit juice-containing product or the raw material of the fruit juice, so that the deterioration of the aroma and/or taste of the fruit juice-containing product can be suppressed, and the fruit juice can be easily and effectively extracted. Containing product quality can be maintained.

As used herein, the phrase "includes" or the phrase "contains" is intended to encompass the phrase "consisting of" and the phrase "consisting only of".
The operations and steps described herein may be performed at room temperature unless otherwise specified.
As used herein, the term “room temperature” is understood according to common general technical knowledge and can mean a temperature within the range of 10° C. to 35° C., for example.

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.
Fruit juice-containing products targeted by the present invention include a wide range of foods containing fruit juice, such as fruit juice itself, fruit juice-containing soft drinks prepared by diluting fruit juice with water or sugar solution, fruit juice-containing mixed drinks, and fruit juice. Various beverages such as carbonated drinks containing fruit juice, milk drinks containing fruit juice, fruit drinks, and thick syrups containing fruit juice; alcoholic beverages such as liqueur containing fruit juice; jelly and mousse containing fruit juice; Confectionery such as Fruit-containing foods broadly include foods containing pulp or foods in general produced from fruits, such as pulp drinks such as fruit purees and nectars, fruit cocktails, cakes containing fruits, jellies, mousses and other sweets. , frozen desserts such as ice cream and sherbet, canned or bottled fruit containing fruit, fruit sauce, fruit butter, fruit wine, fruit vinegar, and the like.

In addition, the kind of the fruit used as the raw material of fruit juice is not specifically limited, Any fruit can be mentioned. For example, citrus fruits such as oranges, grapefruits, lemons and mandarin oranges; berries such as strawberries, blueberries and raspberries; , mango, cherry, watermelon, etc., but are not limited to these.

As described in the Examples below, the present inventors have identified the major odorants in the photodegradation odor of fruit juice-containing products in relation to the present invention.
Briefly, the inventors determined that the main odorants that make up the photodegradation odor of fruit juice-containing products are:
(1) Analyze the odor components of the fruit juice-containing product that produced a degraded odor by irradiating light and the fruit juice-containing product that was not photodegraded by a gas chromatography olfactometer (hereinafter abbreviated as GC/O). and (2) photo-generated odor components (i.e., newly generated odor components or increased odor in the photo-irradiated fruit juice-containing product compared to the non-photodegraded fruit juice-containing product). components), the main substances constituting the deterioration odor were identified.

Suitable specific examples of such major odorants are methional, trans-4,5-epoxy-(E)-2-decenal, 1-octen-3-one, sotolone, (E,E)-2,4 -nonadienal, (E,E)-2,4-decadienal, and (E)-2-nonenal.

The photodegradation odor masking agent for the fruit juice-containing product of the present invention (in this specification, it may be referred to as "deterioration odor masking agent" or "masking agent") is selected from the following groups A to G: (In this specification, this may be referred to as a masking agent compound.) One or more kinds of compounds are used as active ingredients;
(Group A) heliotropine, ethyl pyruvate, ethyl acetoacetate, and benzyl benzoate (Group B) butyl butyryl lactate, ethyl levulinate, benzyl alcohol, methyl jasmonate, stearic acid, methyl dihydrojasmonate, heliotropin, and Ethyl pyruvate (group C) acetaldehyde, β-damascenone, methyl salicylate, 1,8-cineol, ethyl acetate, δ-hexalactone, 1,4-cineol, menthyl lactate, anethole, rose oxide, and ethyl isovalerate ( Group D) Acetaldehyde, β-damascenone, acetal, 1,8-cineol, γ-valerolactone, p-menthan-3-one, γ-hexalactone, dihydroactinidiolide, ethyl crotonate, 1,4-cineole, Hexanal, anethole, rose oxide, sclareolide, and ethyl isovalerate (group E) diethyl carbonate, 2-pentanone, acetal, methyl salicylate, 1,8-cineol, ethyl acetate, δ-hexalactone, dihydroactinidiolide, 2 - octanone, 1,4-cineole, 2-methyl-2-hepten-6-one, hexanal, γ-heptalactone, anethole, ethyl butyrate, sclareolide and ethyl isovalerate (group F) ethyl lactate, 2-butanone , 2-pentanone, acetal, methyl salicylate, 1,8-cineol, ethyl acetate, p-menthan-3-one, γ-hexalactone, dihydroactinidiolide, 2-octanone, ethyl crotonate, 1,4-cineole , menthyl lactate, 2-methyl-2-hepten-6-one, hexanal, anethole, ethyl butyrate, sclareolide, and ethyl isovalerate (group G) oleic acid, 2-butanone, acetaldehyde, acetal, methyl salicylate, ethyl acetate , p-menthan-3-one, γ-hexalactone, δ-hexalactone, dihydroactinidiolide, ethyl crotonate, menthyl lactate, 2-methyl-2-hepten-6-one, hexanal, γ-heptalactone, Anethole, ethyl butyrate, sclareolide, and ethyl isovalerate.

All of the compounds of Groups A to G are known aroma ingredients.
In the present invention, as the compound, purified products from natural fragrances or synthesized products by chemical reaction can be used without limitation. For convenience, these commercially available products can be suitably used in the present invention.
In addition, a natural fragrance containing the compound can be used as the masking agent of the present invention as long as it does not impair the effect of the present invention. Examples of such natural flavors include, but are not limited to: natural flavors containing heliotropin, such as vanilla oil; natural flavors containing benzyl benzoate, such as benzoin oil; and benzyl alcohol. Natural fragrances containing clove oil, perilla oil, and vanilla oil; natural fragrances containing β-damascenone, such as rose oil; natural fragrances containing methyl salicylate, such as clove oil; 1,8-cineole natural flavors such as cardamom oil, spearmint oil, sage oil, marjoram oil, eucalyptus oil, rosemary oil, laurel oil, lime oil, allspice oil, Japanese pepper oil, ginger oil, thyme oil, and tarragon oil; Natural flavors containing ethyl include grape lees oil and the like; natural flavors containing anethole include star anise oil, fennel oil and caraway oil; natural flavors containing dihydroactinidiolide include melissa oil and the like. be able to.

Heliotropin, ethyl pyruvate, ethyl acetoacetate, and benzyl benzoate, which are the compounds described in Group A, are compounds that each effectively function as photodegradation odor masking agents for fruit juice-containing products. It effectively functions as a masking agent for methional, which is one of the main odorous substances of deterioration odors. Therefore, when a compound belonging to Group A is used, the masking agent of the present invention can be used to mask the photodegradation odor of fruit juice-containing products by suppressing the methional-induced deterioration odor. Methional is an odorant that was not previously known to be produced by photodegradation of fruit juice-containing products. In a preferred embodiment of the present invention, at least one selected from the group consisting of ethyl acetoacetate and benzyl benzoate can be used. These compounds described in Group A can be used singly or in combination of two or more.

The compounds listed in Group B, butyl butyryl lactate, ethyl levulinate, benzyl alcohol, methyl jasmonate, stearic acid, methyl dihydrojasmonate, heliotropine, and ethyl pyruvate, each contribute to photodegradation of fruit juice-containing products. It is a compound that functions effectively as an odor masking agent, and is particularly effective as a masking agent for trans-4,5-epoxy-(E)-2-decenal, which is one of the main odorous substances of the deterioration odor described above. Function. Therefore, when a compound belonging to Group B is used, the masking agent of the present invention suppresses the deterioration odor caused by trans-4,5-epoxy-(E)-2-decenal. can be used to mask the In addition, trans-4,5-epoxy-(E)-2-decenal is an odorant that was not previously known to be produced by photodegradation of fruit juice-containing products. In a preferred embodiment of the present invention, at least one selected from the group consisting of butyl butyryllactate, methyl jasmonate, stearic acid, and heliotropine can be used. These compounds described in Group B can be used singly or in combination of two or more.

Acetaldehyde, β-damascenone, methyl salicylate, 1,8-cineole, ethyl acetate, δ-hexalactone, 1,4-cineol, menthyl lactate, anethole, rose oxide, and isokichi, which are compounds described in Group C. Ethyl herbate is a compound that functions effectively as a masking agent for the photodegradation odor of fruit juice-containing products, and in particular, it is a masking agent for 1-octen-3-one, which is one of the main odorous substances of the above-described degradation odor. function effectively as Therefore, when a compound belonging to Group C is used, the masking agent of the present invention can be used to mask the photodeterioration odor of fruit juice-containing products by suppressing the odor of deterioration caused by 1-octen-3-one. can. In a preferred embodiment of the present invention, at least one selected from the group consisting of β-damascenone, ethyl acetate, δ-hexalactone, 1,4-cineole, menthyl lactate, anethole, rose oxide, and ethyl isovalerate is used. can be These compounds described in Group C can be used singly or in combination of two or more.

Acetaldehyde, β-damascenone, acetal, 1,8-cineol, γ-valerolactone, p-menthan-3-one, γ-hexalactone, dihydroactinidiolide, ethyl crotonate, which are compounds described in Group D , 1,4-cineol, hexanal, anethole, rose oxide, sclareolide, and ethyl isovalerate are compounds that effectively function as masking agents for photo-degradation odors in fruit juice-containing products, and in particular, the above-described degradation odors. It functions effectively as a masking agent for sotolone, one of the major odorants. Therefore, when a compound belonging to Group D is used, the masking agent of the present invention can be used to mask the photodegradation odor of fruit juice-containing products by suppressing the degradation odor caused by sotolone. It should be noted that sotolon is an odorant that was not known to be produced by photodegradation of fruit juice-containing products. These compounds described in Group D can be used singly or in combination of two or more.

Diethyl carbonate, 2-pentanone, acetal, methyl salicylate, 1,8-cineol, ethyl acetate, δ-hexalactone, dihydroactinidiolide, 2-octanone, 1,4-cineole, which are compounds described in group E , 2-methyl-2-hepten-6-one, hexanal, γ-heptalactone, anethole, ethyl butyrate, sclareolide, and ethyl isovalerate each function effectively as photodegradation odor masking agents in fruit juice-containing products. In particular, it functions effectively as a masking agent for (E,E)-2,4-nonadienal, which is the main odorant of the deterioration odor described above. Therefore, when a compound belonging to Group E is used, the masking agent of the present invention suppresses the deterioration odor caused by (E,E)-2,4-nonadienal, thereby masking the photodeterioration odor of fruit juice-containing products. can be used for (E,E)-2,4-nonadienal is an odorant that was not previously known to be produced by photodegradation of fruit juice-containing products. These compounds described in Group E can be used singly or in combination of two or more.

Ethyl lactate, 2-butanone, 2-pentanone, acetal, methyl salicylate, 1,8-cineol, ethyl acetate, p-menthan-3-one, γ-hexalactone, dihydroactinone, which are compounds described in group F Nidiolide, 2-octanone, ethyl crotonate, 1,4-cineole, menthyl lactate, 2-methyl-2-hepten-6-one, hexanal, anethole, ethyl butyrate, sclareolide, and ethyl isovalerate, respectively, It is a compound that effectively functions as a masking agent for photodeterioration odor of fruit juice-containing products, and in particular, it functions effectively as a masking agent for (E,E)-2,4-decadienal, which is the main odorant of the above-described deterioration odor. do. Therefore, when a compound belonging to Group F is used, the masking agent of the present invention suppresses the deterioration odor caused by (E,E)-2,4-decadienal, thereby masking the photodegradation odor of fruit juice-containing products. can be used for These compounds described in Group F can be used singly or in combination of two or more.

Oleic acid, 2-butanone, acetaldehyde, acetal, methyl salicylate, ethyl acetate, p-menthan-3-one, γ-hexalactone, δ-hexalactone, dihydroactinidiolide, which are compounds described in Group G, Ethyl crotonate, menthyl lactate, 2-methyl-2-hepten-6-one, hexanal, γ-heptalactone, anethole, ethyl butyrate, sclareolide, and ethyl isovalerate each mask photodegradation odor of fruit juice-containing products. In particular, it functions effectively as a masking agent for (E)-2-nonenal, which is the main odor substance of the deterioration odor described above. Therefore, when a compound belonging to Group G is used, the masking agent of the present invention can be used to mask the photodegradation odor of fruit juice-containing products by suppressing the degradation odor caused by (E)-2-nonenal. can. (E)-2-nonenal is an odorant that was not previously known to be produced by photodegradation of fruit juice-containing products. In a preferred embodiment of the invention, oleic acid, 2-butanone, acetaldehyde, acetal, methyl salicylate, ethyl acetate, p-menthan-3-one, δ-hexalactone, dihydroactinidiolide, ethyl crotonate, menthyl lactate, At least one selected from the group consisting of 2-methyl-2-hepten-6-one, γ-heptalactone, anethole, ethyl butyrate, sclareolide, and ethyl isovalerate can be used. These compounds described in Group G can be used singly or in combination of two or more. As described above, the masking agent of the present invention includes methional, trans-4,5-epoxy-(E)-2-decenal, 1-octen-3-one, sotolone, (E,E)-2,4- By suppressing the deterioration odor caused by at least one selected from the group consisting of nonadienal, (E,E)-2,4-decadienal, and (E)-2-nonenal, the photodegradation odor of fruit juice-containing products is suppressed. Can be used for masking.

The deteriorated odor masking agent of the present invention is a compound selected from the group consisting of Groups A to G (that is, a compound belonging to Group A, a compound belonging to Group B, a compound belonging to Group C, a compound belonging to Group D, a compound belonging to Group E compound group including all compounds belonging to group F, compounds belonging to group F, and compounds belonging to group G). In the present invention, "two or more compounds selected from the group consisting of Groups A to G" includes two or more compounds, including compounds belonging to different groups, unless otherwise specified. In addition, cases in which two or more compounds belonging to the same group are included are also included.
The masking effect can be obtained by using only one of the compounds, a better effect can be obtained by using two or more of the compounds, and three or more of the compounds can be used. A better effect can be obtained with

In the present invention, from the viewpoint of the good masking effect,
It is preferable to use in combination one or more compounds each selected from two or more groups of Groups A to G (total of two or more compounds),
It is more preferable to use in combination one or more compounds (three or more in total) each selected from three or more groups of Groups A to G,
It is even more preferable to use a combination of one or more compounds each selected from four or more groups of A to G (total of four or more),
It is even more preferable to use in combination one or more compounds each selected from five or more groups of A to G (five or more in total),
It is even more preferable to use a combination of one or more compounds (6 or more in total) each selected from six or more of Groups A to G,
It is particularly preferable to use a combination of one or more compounds (7 or more in total) each selected from all seven groups A to G.
Among the above masking agent compounds, for example, heliotripin, acetaldehyde, ethyl acetate, etc. belong to at least two groups among groups A to G, respectively. In the present invention, by blending a compound belonging to a plurality of these groups into the masking agent, the masking agent will be blended with compounds belonging to a plurality of groups to which the compound belongs. A masking agent containing a compound belonging to a plurality of groups (n groups) is defined as "a masking agent containing a combination of one or more compounds (a total of n or more) each selected from n groups of Groups A to G. ”. For example, when heliotropin is added to a masking agent, the masking agent contains compounds belonging to two groups, Group A and Group B. Masking agent containing a combination of one or more compounds (two or more in total) selected from each of the two groups of Similarly, a masking agent containing acetaldehyde belonging to the three groups C, D and E alone is "one or more of each selected from three groups of A to G (three or more in total). A masking agent containing a combination of compounds” and belonging to the four groups of C group, E group, F group and G group. Masking agent containing a combination of one or more compounds (four or more in total) each selected from
Further, in the present invention, when a compound belonging to a plurality of groups is used as a masking agent compound, the compound may be used alone, or a masking agent compound other than the compound may be used in combination.

The masking agent of the present invention includes a plurality of compounds (for example, 2 or more, preferably 3 or more, more preferably 4 or more, more preferably 4 or more, more preferably 5 or more, more preferably 6 or more, more preferably 7 or more) combinations. Here, "the groups to which they belong do not match each other (belong to different groups)" refers to both cases in which the groups to which these compounds belong do not overlap, and cases in which some of the groups that belong to the compounds do not overlap, but some of them do not match. include. Therefore, in the present invention, the combination of compounds "whose groups do not match each other (belongs to different groups)" includes a combination of ethyl pyruvate (groups A and B) and rose oxide (groups C and D). β-damascenone (C group, D group) and ethyl crotonate (D group, F group, G group), β-damascenone (C group, D group), not only when the groups do not overlap as in and 1,4-cineole (C group, D group, E group, F group), which partially overlap but do not partially match.

In its preferred embodiments, the masking agent of the present invention is methional, trans-4,5-epoxy-(E)-2-decenal, 1-octen-3-one, sotolone, (E,E)-2,4 -nonadienal, (E,E)-2,4-decadienal, and (E)-2-nonenal one or more of the seven odorants (preferably two or more, more preferably three or more, more preferably 4 or more, more preferably 5 or more, more preferably 6 or more, more preferably all 7). In some preferred embodiments of the present invention, the masking agent of the present invention is methional, trans-4,5-epoxy-(E)-2-decenal, 1-octene-3, and the photodegradation odor of fruit juice-containing products. - odor caused by at least one selected from the group consisting of one, sotolone, (E,E)-2,4-nonadienal, (E,E)-2,4-decadienal and (E)-2-nonenal Masking at least one (preferably at least two, more preferably at least three, more preferably at least four, more preferably at least five) photodegradation odors selected from the above group mentioned.

The amount of the deterioration odor masking compound used in the present invention (for example, the content of the deterioration odor masking agent of the present invention in the fruit juice-containing product) may be any amount as long as it exhibits the effect of masking the deterioration odor. The concentration of the total juice-containing product in
It is preferable to use it within the range of 0.0000025 ppb to 100000 ppb,
It is more preferably used within the range of 0.000025 ppb to 10000 ppb, and more preferably within the range of 0.00025 ppb to 1000 ppb.
From the viewpoint of sufficiently obtaining the effect of masking the deteriorated odor and suppressing the aroma and/or taste of the masking agent compound from undesirably affecting the aroma and/or taste of the fruit juice-containing product, the above range is It is preferred to use

In the present invention, the total mass (or total concentration) of each group of compounds in Groups A to G is an odorant that is a suitable target for masking of each group (that is, a target that effectively functions as a masking agent). (i.e., methional for compounds described in Group A, trans-4,5-epoxy-(E)-2-decenal for compounds described in Group B, 1-octene-3 for compounds described in Group C -one, sotolone for compounds listed in group D, (E,E)-2,4-nonadienal for compounds listed in group E, (E,E)-2,4 for compounds listed in group F -decadienal, relative to the mass (or concentration) of (E)-2-nonenal) to the compounds listed in Group G, for example in a ratio within the range 1:1000 to 1000:1, 1:100 to 100:1 or in the range 1:10 to 10:1. In the present invention, when a compound belonging to a plurality of groups is used as the masking agent compound, in calculating the above ratio, the compound belonging to the plurality of groups is assumed to be a compound of any group to which the compound belongs (for example, β- Damascenone is both a Group C compound and a Group D compound).
Surprisingly, not only too little masking agent compound but also too much can weaken the masking effect on the odorant of interest.

By using one or more of the compounds selected from the group consisting of Groups A to G, the present invention reduces deterioration odor ( For example, it is possible to easily and safely mask the degraded odor of fruit juice-containing products produced by light, without affecting the aroma and/or taste of the final product. can.

The deteriorated odor masking agent of the present invention may contain compounds other than the masking agent compound. The form of the deteriorated odor masking agent of the present invention and the type and amount of the other compound can be appropriately set according to the mode of use of the deteriorated odor masking agent of the present invention.
The deteriorated odor masking agent of the present invention may consist of the masking agent compound alone, or may contain an appropriate diluent (thickener) or carrier in addition to the masking agent compound. good. In this case, the ratio of the masking agent compound in the deteriorated odor masking agent is 0.000001 to 99% by mass (0.01 to 990000 ppm).

The diluent or carrier used in combination with the masking agent compound is not particularly limited as long as it does not impair the effect of the masking agent compound on suppressing the photodegradation odor derived from fruit juice. Examples include solid diluents or carriers such as gum arabic, dextrin, cyclodextrin, glucose and sucrose; Carriers can be mentioned. Additives such as excipients, binders, disintegrants, emulsifiers, and solubilizers used to prepare the deteriorated odor masking agent of the present invention into a desired shape (dosage form) may be added to these diluents or carriers. , thickeners, lubricants, flavoring agents, coloring agents, antioxidants, and the like. Among them, emulsifiers can be suitably used for dispersing the masking agent compound in a liquid diluent to prepare an aqueous solution (dispersion, suspension) or emulsion-like deteriorated odor masking agent. Examples of such emulsifiers include, but are not limited to, sucrose fatty acid esters, glycerin fatty acid esters, sorbitan fatty acid esters, lecithin, enzymatically degraded lecithin, quillaya extract, saponin, polysorbate, gum arabic, and gum ghatti. By using such a diluent or carrier, the deteriorated odor masking agent of the present invention can be made into any dosage form such as liquid, suspension, emulsion, paste, powder, granules, and others. The dosage form of the deteriorated odor masking agent of the present invention can be appropriately set according to the type and shape of the object to suppress the fruit juice-derived photo-degraded odor.

The deteriorated odor masking agent of the present invention is prepared as a powder formulation by adding an excipient such as dextrin to an aqueous solution in which the masking agent compound described above is dissolved or dispersed, and pulverizing the agent according to a conventional method such as spray drying or freeze drying. Alternatively, it may be further granulated to prepare a granule formulation.

The deteriorated odor masking agent of the present invention may be a perfume composition containing, as a perfume component, one or two or more masking agent compounds described above. The perfume composition may contain more than one perfume component (perfume component other than the masking agent compound).
Such other perfume ingredients should not impair the effect of the present invention when used in combination with the masking agent compound described above, and should not adversely affect the fragrance of the fruit juice-containing product containing the deteriorated odor masking agent. is preferred. Examples of such flavor components include, for example, natural ingredients described in "Patent Office Gazette, Collection of Well-known and Commonly Used Techniques (Fragrance), Part II Food Flavors" (published January 14, 2000) edited by the Japan Patent Office. Fragrances and synthetic fragrances can be mentioned. Specifically, citrus flavors (pages 88 to 135) having the scent of citrus fruits (orange, lemon, lime, grapefruit, yuzu, sudachi, etc.), fruits other than citrus fruits (apple, grape, strawberry, banana , peach, melon, apricot, plum, cherry, berries, etc.) fruit flavor (pages 136-257), milk flavor with dairy product flavor (milk flavor, butter flavor, cheese flavor, cream flavor , Yogurt flavor, etc.) (pages 258-347), vanilla flavor with the scent of vanilla beans (pages 348-366), tea flavor with the scent of green tea, oolong tea, black tea (pages 367-426), cocoa and Cocoa and chocolate flavors with chocolate aroma (pages 427-446), coffee flavors with coffee aroma (pages 447-475), mint flavors with aromas such as peppermint and spearmint (pages 476-495), spices Fragrant spice flavors (pages 496-580), nut flavors with almond and other nut flavors (pages 581-608), Western liquors (e.g. wine, whiskey, brandy, rum, gin, liqueur, etc.) Fragrance of western liquor (pages 759-825), fragrance of flowers (pages 826-836), fragrance of vegetables (e.g. onion, garlic, green onion, carrot, burdock, shiitake mushroom, matsutake mushroom, trefoil, etc.) (837-907 pages) and the like can be exemplified. Citrus flavor, fruit flavor, milk flavor, cocoa/chocolate flavor, mint flavor, and vegetable flavor are preferred.
The perfume composition of the present invention may contain 0.000001 to 99% by mass of one or more of the masking agent compounds described above as long as the effects of the present invention are exhibited. When the perfume composition of the present invention contains other perfume ingredients in addition to the masking agent compound, the mixing ratio of the other perfume ingredients is not limited, but is 0.000001 to 99% by mass, preferably 0.00001 to 0.00001. A ratio of 10% by mass can be exemplified.

The timing and method of adding or applying the deteriorated odor masking agent of the present invention or the preparation containing the same to the fruit juice-containing product is not particularly limited, and it can be added or applied at any stage during the production of the fruit juice-containing product. good.
For example, after previously adding or applying the deterioration odor masking agent of the present invention or a formulation containing the same to the raw material of the fruit juice-containing product, the deterioration odor masking of the present invention is performed by adding or applying this raw material to the fruit juice-containing product. Agents may be added or applied to the juice-containing product.

The deteriorated odor masking agent of the present invention can also be used for fruit juice-containing products containing various food materials that are commonly used in fruit juice-containing products.
Examples of such food materials include sugars, sweeteners, thickeners, emulsifiers, vitamins, milk, dairy products, oils and fats, acidulants, flavors, starches, dextrin, glycerin, eggs, and pigments. can.
As the food material, more specifically, for example,
Sugars such as sucrose, glucose, fructose, palatinose, xylose, starch syrup and maltose;
Sugar alcohols such as sorbitol, xylitol, erythritol, palatinit, and reduced starch syrup;
high intensity sweeteners such as aspartame, thaumatin, sucralose, acesulfame potassium, and stevia;
Thickeners such as agar, gelatin, carrageenan, guar gum, xanthan gum, pectin, locust bean gum, galactomannan, glucomannan and gellan gum;
emulsifiers such as sucrose fatty acid esters, glycerin fatty acid esters, sorbitan fatty acid esters, and lecithin;
vitamins such as vitamin A, vitamin B, vitamin C, and vitamin E;
Milk such as raw milk, cow milk, skimmed milk and processed milk;
Dairy products such as fermented milk, concentrated milk, condensed milk, whole milk powder, skimmed milk powder, cream, cheese and butter;
Oils and fats such as palm oil and coconut oil;
Acidulants such as citric acid, malic acid, tartaric acid, lactic acid;
Perfume and the like exemplified in the above "other perfume ingredients" can be mentioned.

In addition, the method for masking the deterioration odor of the fruit juice-containing product of the present invention, the method for producing the fruit juice-containing product of the present invention, and the fruit juice-containing product of the present invention are the above-described deterioration odor masking agent for the fruit juice-containing product of the present invention. It is understood from the explanation of

EXAMPLES The present invention will be specifically described below using the following examples, but the present invention is not limited to these.
In the following examples, numerical values indicating amounts and concentrations can be based on mass unless otherwise specified.

Experimental example 1
(Identification of major odorants)
The following procedure was followed to identify the major odorants in the photodegradation odor of fruit juice-containing products.

(Preparation of fruit juice-containing products)
A 100% fruit juice solution was prepared by adding deionized water to commercially available 5-fold concentrated orange juice.
After sterilization by filling this liquid with a hot pack at a temperature of 93° C., it was filled and sealed in a 200 ml PET bottle to prepare an orange juice drink.
In addition, an apple juice drink or a grape juice drink was prepared in the same manner as the above orange juice drink, using a commercially available 4-fold concentrated apple juice or 5-fold concentrated grape juice.

(Photodegradation treatment)
Photodegradation-treated fruit juice beverages were prepared by storing the packaged orange juice beverage, apple juice beverage, and grape juice beverage prepared above at 10° C. for 5 days under irradiation with a fluorescent lamp (20000 lux). Separately, a packaged orange juice beverage, an apple juice beverage, and a grape juice beverage were stored in the dark at 5°C for 5 days to prepare fruit juice beverages not subjected to photodegradation treatment.

(Identification of main odorant of photodegradation odor)
The three types of fruit juice beverages subjected to the photodegradation treatment and the three types of fruit juice beverages not subjected to the photodegradation treatment were analyzed by GC/O. Major odorants in the photodegradation odor common to apple juice and grape juice include methional, trans-4,5-epoxy-(E)-2-decenal, 1-octen-3-one, sotolone, (E,E )-2,4-nonadienal, (E,E)-2,4-decadienal, and (E)-2-nonenal were identified.
In addition, the measurement conditions of GC/O are shown below.
・ GC / O device: 6890N (manufactured by Agilent Technologies) / CharmAnalysis (TM) (manufactured by Datu)
・ Column: DB-WAX / length 15 m, inner diameter 0.32 mm (manufactured by Agilent Technologies)
・Column temperature conditions: 40 to 220°C, temperature rise of 6°C/min. ・Carrier gas: helium.

Experimental example 2
(Verification of major odorants)
(Preparation of photodegraded fruit juice drink 1)
A photo-degraded orange juice drink was prepared by filling 200 ml of a commercially available 100% orange juice drink into a 200 ml PET bottle, sealing it, and storing it at 10° C. for 5 days under irradiation with a fluorescent lamp (20000 lux). Separately, a packaged orange juice beverage was stored in the dark at 5° C. for 5 days to prepare an orange juice beverage that had not undergone photodegradation treatment.
In addition, after filling and sealing a PET bottle with a 100% apple juice drink or a grape juice drink prepared from commercially available apple 4-fold concentrated juice or grape 5-fold concentrated juice, in the same manner as the orange juice drink, the same A photodegraded fruit juice drink and a fruit juice drink not subjected to the photodegradation treatment were prepared by performing the photodegradation treatment under the conditions.

(Preparation of simulated photodegraded fruit juice drink)
methional, trans-4,5-epoxy-(E)-2-decenal, 1-octen-3-one, sotolone in packaged orange juice beverages, apple juice beverages, and grape juice beverages that have not undergone photodegradation treatment , (E,E)-2,4-nonadienal, (E,E)-2,4-decadienal, and (E)-2-nonenal were all added to prepare a simulated photodegraded fruit juice drink. did.
Specifically, a solution in which methional is dissolved in 95% ethanol at a concentration of 0.0001% by mass, and trans-4,5-epoxy-(E)-2-decenal is dissolved in 95% ethanol at 0.00001% by mass. A solution in which 1-octen-3-one was dissolved in 95% ethanol to a concentration of 0.0005% by mass, and a solution in which sotolone was dissolved in 95% ethanol to a concentration of 0.0003% by mass. A solution in which (E,E)-2,4-nonadienal was dissolved in 95% ethanol to a concentration of 0.0001% by mass, (E,E)-2,4- A solution in which decadienal was dissolved in 95% ethanol to a concentration of 0.0001% by mass, and a solution in which (E)-2-nonenal was dissolved in 95% ethanol to a concentration of 0.00001% by mass, respectively. It was prepared and added to packaged orange juice beverages, apple juice beverages, and grape juice beverages that had not been subjected to photodegradation treatment so that the concentrations of each component were as shown in Table 1.

The odor of the simulated photodegraded fruit juice beverage prepared by adding the compound in the above (Preparation of simulated photodegraded fruit juice drink) was evaluated by seven panelists who had been engaged in flavor development for more than 3 years and were well trained in sensory evaluation of odor. It was evaluated in comparison with the photodegraded fruit juice drink obtained in (Preparation of Photodegraded Fruit Juice Beverage 1). Evaluation criteria were as follows:
<Evaluation Criteria>
Odor equivalent to photodegraded fruit juice beverage: 5 points Odor similar to photodegraded fruit juice beverage: 4 points Odor similar to photodegraded fruit juice beverage mixed with a different odor: 3 points Odor different from photodegradation-treated fruit juice beverage: 2 points Odor completely different from photodegradation-treated fruit juice beverage: 1 point (evaluation result)
The results of the above evaluation of the simulated photodegraded fruit juice drink (average value of 7 people) were 4.29 for the orange juice drink, 4.29 for the apple juice drink, and 4.57 for the grape juice drink. It was confirmed that an odor equivalent to the degraded odor generated in photo-degraded fruit juice beverages can be reproduced satisfactorily by the odorant.

Experimental example 3
(Masking effect of group A compounds on methional)
Methional was dissolved in 95% ethanol to a concentration of 0.0001% by mass, and this solution was added to deionized water so that the concentration of methional was 1 ppb. A solution obtained by dissolving each of the compounds of Group A (heliotropin, ethyl pyruvate, ethyl acetoacetate, benzyl benzoate) in 95% ethanol was added to the methional-containing aqueous solution thus prepared at the concentrations shown in Table 2. The masking effect against methional was confirmed by sensory evaluation.
In the sensory evaluation, the ion-exchanged water containing 1 ppb of methional was evaluated as "a strong methional odor: 4 points", and the ion-exchanged water was evaluated as "no methional odor was felt at all: 0 points". were set, and five panelists (skill level of the panelists was the same as above/same hereafter) gave evaluation points. Table 2 shows the average score.
<Evaluation Criteria>
Stronger methional odor: 5 points Strong methional odor: 4 points Methional odor: 3 points Slightly methional odor: 2 points Almost no methional odor: 1 point No methional odor: 0 points

In addition, the relationship between the concentration of group A compounds relative to methional and the masking effect was examined.
Ethyl pyruvate was added to the aqueous solution having a methional concentration of 1 ppb so as to have the concentration shown in Table 3, and the relationship between the amount of ethyl pyruvate and the masking effect on methional was evaluated by the same method as described above. . Table 3 shows the evaluation results.

上記結果からＡ群の化合物のマスキング効果は、臭気物質の濃度に対する、マスキング剤化合物の濃度の比が０．１～１０に近づく程高い傾向があることがわかった。

From the above results, it was found that the masking effect of the compounds of Group A tends to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorant approaches 0.1-10.

Experimental example 4
(Masking effect of group B compounds on trans-4,5-epoxy-(E)-2-decenal)
In Experimental Example 3, Group A compounds were converted to Group B compounds (butyl butyryl lactate, ethyl levulinate, benzyl alcohol, methyl jasmonate, stearic acid, methyl dihydrojasmonate, heliotropine, or ethyl pyruvate), and methional was converted to trans- 4,5-epoxy-(E)-2-decenal and trans-4,5-epoxy-(E)-2-decenal at a concentration of 0.00001% by mass in 95% ethanol, Group B compound trans-4,5-epoxy-( E) The masking effect on -2-decenal and the masking effect on the added amount of benzyl alcohol were evaluated.
<Evaluation Criteria>
Strong sense of trans-4,5-epoxy-(E)-2-decenal odor: 5 points Strong sense of trans-4,5-epoxy-(E)-2-decenal odor: 4 points trans-4,5 -Epoxy-(E)-2-decenal smell: 3 points trans-4,5-epoxy-(E)-2-Decenal smell slightly: 2 points trans-4,5-epoxy-(E)- Almost no smell of 2-decenal: 1 point No smell of trans-4,5-epoxy-(E)-2-decenal: 0 point *The above trans-4,5-epoxy-(E)-2 The ion-exchanged water containing 0.1 ppb of -decenal was evaluated as "strong smell of trans-4,5-epoxy-(E)-2-decenal: 4 points".
The evaluation results are shown in Tables 4 and 5.

上記結果からＢ群の化合物のマスキング効果は、臭気物質の濃度に対する、マスキング剤化合物の濃度の比が１００に近づく程高い傾向があることがわかった。

From the above results, it was found that the masking effect of the group B compounds tended to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorant approached 100.

Experimental example 5
(Masking effect of group C compounds on 1-octen-3-one)
In Experimental Example 3, Group A compounds were replaced with Group C compounds (acetaldehyde, β-damascenone, methyl salicylate, 1,8-cineole, ethyl acetate, δ-hexalactone, 1,4-cineol, menthyl lactate, anethole, rose oxide and ethyl isovalerate), methional to 1-octen-3-one, and the concentration of 1-octen-3-one in 95% ethanol to 0.0005% by mass, and 1-octene- The masking effect of the group C compound on 1-octen-3-one and the amount of anethole added were evaluated in the same manner as in Experimental Example 3, except that the concentration of 3-one was changed to 5 ppb.
<Evaluation Criteria>
Sense 1-octen-3-one odor more strongly: 5 points Sense 1-octen-3-one odor strongly: 4 points Sense 1-octen-3-one odor: 3 points 1-octen-3-one odor Slightly felt: 2 points 1-octen-3-one almost no odor: 1 point 1-octen-3-one no odor felt: 0 points *Contains 5 ppb of the above 1-octen-3-one The ion-exchanged water was evaluated as "strong smell of 1-octen-3-one: 4 points".
The evaluation results are shown in Tables 6 and 7.

上記結果からＣ群の化合物のマスキング効果は、臭気物質の濃度に対する、マスキング剤化合物の濃度の比が０．０２～０．２に近づく程高い傾向があることがわかった。

From the above results, it was found that the masking effect of the group C compounds tended to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorant approached 0.02 to 0.2.

Experimental example 6
(Masking effect of group D compounds on sotolone)
In Experimental Example 3, Group A compounds were replaced with Group D compounds (acetaldehyde, β-damascenone, acetal, 1,8-cineole, γ-valerolactone, p-menthan-3-one, γ-hexalactone, dihydroactinidiolide, ethyl crotonate, 1,4-cineole, hexanal, anethole, rose oxide, sclareolide or ethyl isovalerate), methional was changed to sotolone, and the concentration of sotolone in 95% ethanol was changed to 0.0003% by mass. The masking effect of the group D compounds on sotolone and the amount of sclareolide added were evaluated in the same manner as in Experimental Example 3, except that the concentration of sotolone in the test solution was changed to 3 ppb.
<Evaluation Criteria>
Smell of sotolone is felt more strongly: 5 points Smell of sotolone is felt strongly: 4 points Smell of sotolone is felt: 3 points Smell of sotolone is felt slightly: 2 points Smell of sotolone is hardly felt: 1 point Smell of sotolone is not felt at all: 0 points *Evaluation of the ion-exchanged water containing 3 ppb of sotolon was given as "strong smell of sotolon: 4 points".
The evaluation results are shown in Tables 8 and 9.

上記結果からＤ群の化合物のマスキング効果は、臭気物質の濃度に対する、マスキング剤化合物の濃度の比が３．３に近づく程高い傾向があることがわかった。

From the above results, it was found that the masking effect of the group D compounds tended to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorant approached 3.3.

Experimental example 7
(Masking effect of group E compounds on (E,E)-2,4-nonadienal)
In Experimental Example 3, Group A compounds were replaced with Group E compounds (diethyl carbonate, 2-pentanone, acetal, methyl salicylate, 1,8-cineole, ethyl acetate, δ-hexalactone, dihydroactinidiolide, 2-octanone, 1, 4-cineole, 2-methyl-2-hepten-6-one, hexanal, γ-heptalactone, anethole, ethyl butyrate, sclareolide or ethyl isovalerate), and methional to (E,E)-2,4- The masking effect of the group E compound on (E,E)-2,4-nonadienal and the amount of methyl salicylate added were evaluated in the same manner as in Experimental Example 3, except that nonadienal was used.
<Evaluation Criteria>
Feel the (E, E)-2,4-nonadienal odor more strongly: 5 points Feel the (E, E)-2,4-nonadienal odor strongly: 4 points Feel the (E, E)-2,4-nonadienal odor Perceived: 3 points (E, E)-2,4-nonadienal odor slightly felt: 2 points (E, E)-2,4-nonadienal odor hardly felt: 1 point (E, E)-2,4 - No nonadienal odor at all: 0 points : 4 points".
The evaluation results are shown in Tables 10 and 11.

上記結果からＥ群の化合物のマスキング効果は、臭気物質の濃度に対する、マスキング剤化合物の濃度の比が０．１～１０に近づく程高い傾向があることがわかった。

From the above results, it was found that the masking effect of the group E compounds tended to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorant approached 0.1-10.

Experimental example 8
(Masking effect of group F compounds on (E,E)-2,4-decadienal)
In Experimental Example 3, Group A compounds were replaced with Group F compounds (ethyl lactate, 2-butanone, 2-pentanone, acetal, methyl salicylate, 1,8-cineole, ethyl acetate, p-menthan-3-one, γ-hexalactone , dihydroactinidiolide, 2-octanone, ethyl crotonate, 1,4-cineole, menthyl lactate, 2-methyl-2-hepten-6-one, hexanal, anethole, ethyl butyrate, sclareolide or ethyl isovalerate) , Also, in the same manner as in Experimental Example 3, except that methional was changed to (E, E)-2,4-decadienal, the masking effect of the group F compound on (E, E)-2,4-decadienal, and The masking effect was evaluated with respect to the amount of 1,8-cineole added.
<Evaluation Criteria>
Feel the (E, E)-2,4-decadienal odor more strongly: 5 points Feel the (E, E)-2,4-decadienal odor strongly: 4 points Feel the (E, E)-2,4-decadienal odor Smell: 3 points (E, E)-2,4-decadienal odor slightly felt: 2 points (E, E)-2,4-decadienal odor hardly felt: 1 point (E, E)-2,4 - No decadienal odor at all: 0 points : 4 points".
The evaluation results are shown in Tables 12 and 13.

上記結果からＦ群の化合物のマスキング効果は、臭気物質の濃度に対する、マスキング剤化合物の濃度の比が０．１～１０に近づく程高い傾向があることがわかった。

From the above results, it was found that the masking effect of the compounds of group F tends to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorant approaches 0.1-10.

Experimental example 9
(Masking effect of group G compounds on (E)-2-nonenal)
In Experimental Example 3, Group A compounds were replaced with Group G compounds (oleic acid, 2-butanone, acetaldehyde, acetal, methyl salicylate, ethyl acetate, p-menthan-3-one, γ-hexalactone, δ-hexalactone, dihydroactin nidiolid, ethyl crotonate, menthyl lactate, 2-methyl-2-hepten-6-one, hexanal, γ-heptalactone, anethole, ethyl butyrate, sclareolide or ethyl isovalerate), and methional (E)- 2-nonenal, the concentration of (E)-2-nonenal in 95% ethanol was changed to 0.00001% by mass, and the concentration of (E)-2-nonenal in the test solution was changed to 0.1 ppb. evaluated the masking effect of the G group compound on (E)-2-nonenal and the masking effect on the amount of acetaldehyde added in the same manner as in Experimental Example 3.
<Evaluation Criteria>
(E)-2-nonenal smell stronger: 5 points (E)-2-nonenal smell stronger: 4 points (E)-2-nonenal smell: 3 points (E)-2-nonenal smell slightly felt: 2 points (E)-2-nonenal hardly felt: 1 point (E)-2-nonenal odor not felt at all: 0 points * 0.1 ppb of the above (E)-2-nonenal The contained ion-exchanged water was evaluated as "strong smell of (E)-2-nonenal: 4 points".
The evaluation results are shown in Tables 14 and 15.

上記結果からＧ群の化合物のマスキング効果は、臭気物質の濃度に対する、マスキング剤化合物の濃度の比が１～１００に近づく程高い傾向があることがわかった。

From the above results, it was found that the masking effect of the compounds of Group G tends to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorant approaches 1-100.

From the results in Tables 2 to 15, the masking agent compounds of Groups A to G are methional, trans-4,5-epoxy-(E)-2-decenal, 1-octen-3-one, sotolone, ( It was found to be an effective masking agent for E,E)-2,4-nonadienal, (E,E)-2,4-decadienal and (E)-2-nonenal. Surprisingly, not only too little masking agent compound but also too much tended to weaken the masking effect on the odorant of interest.

Experimental example 10
(Masking effect 1 of degraded odor masking agent for simulated photodegraded fruit juice beverage in which major odor substances are added to fruit juice beverage)
The masking agent compound described in Table 16 was added in the amount described in the table to the simulated photodegraded orange juice beverage prepared in "(Preparation of simulated photodegraded fruit juice drink)", and their masking effects were evaluated. It was confirmed by sensory evaluation.
For the sensory evaluation, the above simulated photodegraded orange juice beverage was evaluated as having a strong offensive odor: 4 points. -Orange juice without addition of one, sotolone, (E,E)-2,4-nonadienal, (E,E)-2,4-decadienal, and (E)-2-nonenal and without photodegradation treatment The evaluation of the beverage (that is, the orange juice beverage that was not subjected to photodegradation treatment) was evaluated by 7 panelists based on the following evaluation criteria, with the following evaluation criteria: "no offensive odor: 0 points". The average sensory scores are shown in Table 16:
Abnormal smell is felt more strongly: 5 Abnormal smell is strongly felt: 4 Abnormal smell is felt: 3 Abnormal smell is felt a little: 2 Abnormal smell is hardly felt: 1 Abnormal smell is not felt at all: 0 points

Experimental example 11
(Masking effect of deteriorated odor masking agent for simulated photo-degraded fruit juice beverage containing major odor substances added to fruit juice beverage 2)
In Experimental Example 10, the same as Experimental Example 10 except that the simulated photodegraded orange juice drink was changed to a simulated photodegraded apple juice drink, and the masking agent compounds listed in Table 16 were changed to the masking agent compounds listed in Table 17. The masking effect of the deteriorated odor masking agent compound on the simulated photodegraded fruit juice drink was confirmed by the method of .

Experimental example 12
(Masking effect of degraded odor masking agent for simulated photodegraded fruit juice beverage with major odor substances added to fruit juice beverage 3)
In Experimental Example 10, the procedure was the same as in Experimental Example 10, except that the simulated photodegraded orange juice drink was changed to the simulated photodegraded grape juice drink, and the masking agent compounds listed in Table 16 were changed to the masking agent compounds listed in Table 18. The masking effect of the deteriorated odor masking agent compound on the simulated photodegraded fruit juice drink was confirmed by the method of .

From the results in Tables 16 to 18, Group A (ethyl acetoacetate, heliotropin, ethyl pyruvate), Group B (methyl dihydrojasmonate, butyl butyryl lactate), Group C (1,4-cineol, rose oxide, acetic acid ethyl, anethole, 1,8-cineole, methyl salicylate, ethyl isovalerate), group D (1,4-cineole, rose oxide, dihydroactinidiolide, anethole, hexanal, sclareolide, 1,8-cineol, acetal, γ-hexalactone, ethyl isovalerate), group E (1,4-cineole, dihydroactinidiolide, ethyl butyrate, ethyl acetate, anethole, hexanal, sclareolide, 1,8-cineol, acetal, methyl salicylate, 2- methyl-2-hepten-6-one, ethyl isovalerate), F group (1,4-cineole, dihydroactinidiolide, ethyl butyrate, ethyl acetate, anethole, hexanal, sclareolide, 1,8-cineol, acetal, methyl salicylate, 2-methyl-2-hepten-6-one, γ-hexalactone, ethyl isovalerate) and group G (dihydroactinidiolide, ethyl butyrate, ethyl acetate, anethole, hexanal, sclareolide, acetal, methyl salicylate) , 2-methyl-2-hepten-6-one, γ-hexalactone, and ethyl isovalerate). It was found that deterioration odor can be effectively masked (Experimental Examples 10-1 to 10-7, Experimental Examples 11-1 to 11-7, and Experimental Examples 12-1 to 12-7). Further, in Experimental Examples using two compounds (Experimental Examples 10-8 to 10-10, Experimental Examples 11-8 to 11-9, and Experimental Example 12-8), only one compound was added. It was found that the photodegradation odor masking effect was superior to that of the case. Furthermore, in Experimental Examples using three or four compounds (Experimental Examples 10-11 to 10-13, Example 11-10, and Experimental Example 12-9), an even better photodegradation odor masking effect was obtained. was found to perform.

Experimental example 13
(Masking effect 1 of deteriorated odor masking agent compound in fruit juice beverage)
A 100% fruit juice solution was prepared by adding deionized water to commercially available 5-fold concentrated orange juice. This liquid was sterilized by filling it with a hot pack at a temperature of 93° C., and then filled and sealed in a 200 ml PET bottle to prepare an orange juice drink. A portion of the packaged orange juice beverage prepared above was stored at 10° C. for 5 days under irradiation with a fluorescent lamp (20000 lux) to prepare a photo-degraded orange juice beverage. Separately, the rest of the above packaged orange juice beverage is stored under fluorescent light (20000 lux) irradiation at 10°C for 5 days, but a part of it is stored at 5°C under light shielding to obtain orange juice that has not undergone photodegradation treatment. A beverage was prepared.

To the photodegraded orange juice beverage prepared above, the masking agent compound shown in Table 19, which had been dissolved in 95% ethanol in advance, was added in the amount shown in the table.

マスキング剤を添加していない前記光劣化オレンジ果汁飲料を「異臭を強く感じる：４点」とし、光劣化処理をしていないオレンジ果汁飲料を「異臭を全く感じない：０点」として、以下の評価基準を設定し、マスキング剤を添加した果汁飲料の劣化臭マスキング効果について官能評価を実施した。官能評価は、パネラー７名により行い、評価点の平均を表２０に示した：
＜評価基準＞
異臭をより強く感じる：５点
異臭を強く感じる：４点
異臭を感じる：３点
異臭を少し感じる：２点
異臭を殆ど感じない：１点
異臭を全く感じない：０点

The photodegraded orange juice beverage to which no masking agent was added was set as "strongly smelling offensive odor: 4 points", and the orange juice beverage not subjected to photodegradation treatment was set to "no offensive odor at all: 0 points", and the following was performed. Evaluation criteria were set, and a sensory evaluation was carried out on the effect of masking the deterioration odor of fruit juice beverages containing masking agents. Sensory evaluation was performed by 7 panelists, and the average evaluation points are shown in Table 20:
<Evaluation Criteria>
Abnormal smell is felt more strongly: 5 Abnormal smell is strongly felt: 4 Abnormal smell is felt: 3 Abnormal smell is felt a little: 2 Abnormal smell is hardly felt: 1 Abnormal smell is not felt at all: 0 points

Experimental example 14
(Masking effect 2 of deteriorated odor masking agent compound in fruit juice beverage)
A 100% juice solution prepared by adding ion-exchanged water to commercially available 4-fold concentrated apple juice is sterilized by filling it with a hot pack at a temperature of 93 ° C., and then dissolved in 95% ethanol in advance. After adding the masking agent compound shown in Table 21 in the amount shown in the table, the mixture was filled in a 200 ml PET bottle and sealed to prepare a packaged apple juice drink. By storing the masking agent-added apple juice beverage prepared above together with a packaged apple juice beverage separately prepared without adding a masking agent compound at 10° C. under irradiation with a fluorescent lamp (20000 lux) for 5 days, A photodegraded apple juice drink was prepared. Separately, a packaged apple juice beverage prepared without adding a masking agent compound was stored at 5° C. under light shielding for 5 days to prepare an apple juice beverage without photodegradation treatment.

The masking effect of the masking agent compound was confirmed by the same evaluation method as in Experimental Example 13 for the photodegradation-treated apple juice beverage to which the masking agent was added, prepared as described above. The results are shown in Table 21.

Experimental example 15
(Masking effect 3 of deteriorated odor masking agent compound in fruit juice beverage)
In Experimental Example 14, using the same method as in Experimental Example 14, except that 4-fold concentrated apple juice was changed to 5-fold concentrated grape juice, and the masking agent compounds listed in Table 21 were changed to the masking agent compounds listed in Table 22. The masking effect of the masking agent compound was confirmed, and the evaluation results are shown in Table 22.

Experimental example 16
(Masking effect of deteriorated odor masking agent compound in fruit juice-containing jelly)
<Preparation of grape juice-containing jelly>
(1) Raw materials 1, 2 and 7 to 9 shown in Table 23 below were added to water at the blending ratio (parts by mass) shown in Table 23, stirred at room temperature for 10 minutes, and then heated and dissolved at 80°C for 10 minutes with stirring.
(2) Raw materials 3 to 6 and 10 shown in Table 23 below were added to the solution obtained in step (1) at the blending ratio (parts by mass) shown in Table 23, and the total amount was corrected with water while stirring.
(3) Fill a polypropylene bag (10 cm x 8 cm x about 1.5 cm) with 100 g of the solution obtained in step (2), heat sterilize at 85°C for 30 minutes, cool to 5°C or less, and add a masking agent compound. Jelly and jelly without added masking agent compound were prepared.

<Photodegradation treatment>
A masking agent compound-added jelly and a masking agent compound-free jelly were stored at 10° C. for 5 days under irradiation with a fluorescent lamp (20000 lux) to prepare photo-degraded jelly.
Separately, the jelly without the addition of the masking agent was stored at 5° C. for 5 days under light shielding to prepare the jelly without the photodegradation treatment.
<Sensory evaluation>
A sensory evaluation of the masking agent compound-added jelly that had undergone the photodegradation treatment was performed by seven panelists who had been well trained in sensory evaluation of odor. In the sensory evaluation, the jelly with no added masking agent compound that was subjected to the photodegradation treatment was evaluated as "strongly smelling offensive: 4 points", and the jelly without the addition of the masking agent compound that was not subjected to photodegradation was evaluated as " Absolutely no offensive odor: 0 points” was set according to the following evaluation criteria.
Abnormal smell strongly sensed: 4 Strange smell felt: 3 Strange smell felt a little: 2 Strange smell hardly felt: 1 Strange smell felt at all: 0 points

<Evaluation results>
The score (average) of the masking agent compound-added jelly after photodegradation treatment was 2.0.

Experimental example 17
(Masking effect of deteriorated odor masking agent compound in fruit juice-containing jam)
<Preparation of jam containing strawberry juice>
(1) Raw materials 1 to 3 shown in Table 25 below were mixed in advance at the mixing ratio (parts by mass) shown in Table 25, and added to raw material 4 shown in Table 25 below in the proportion shown in the table, and dissolved by boiling.
(2) Raw materials 5 and 6 shown in Table 25 below were added to the solution obtained in step (1) at the mixing ratio (parts by mass) shown in Table 25, and the mixture was boiled down to 99.15 parts by mass.
(3) Raw materials 7 and 8 shown in Table 25 below were added to the solution obtained in step (2) at the mixing ratio (parts by mass) shown in Table 25 and mixed.
(4) A portion of the solution obtained in step (3) is placed in a separate container, and 0.05 part by mass of a 95% ethanol solution of a masking agent compound is added to 100 parts by mass of the solution. It was added and mixed so that it might become the compounding quantity of 26 description.
(5) Fill a polypropylene bag (10 cm x 8 cm x about 1.5 cm) with 100 g of the solution obtained in step (4), heat sterilize at 94°C for 10 minutes, cool to 5°C or less, and add masking agent. Prepared jam. A jam without masking agent was prepared according to the above steps, except that 100 g of the solution obtained in step (3) was used in place of the solution obtained in step (4).

<Photodegradation treatment>
The masking agent compound-added jam and the masking agent compound-free jam were stored at 10° C. for 5 days under irradiation with a fluorescent lamp (20000 lux) to prepare a photodegradation-treated jam.
Separately, the jam without the addition of the masking agent compound was stored at 5° C. for 5 days under light shielding to prepare the jam without photodegradation treatment.

<Sensory evaluation>
A sensory evaluation of the masking agent compound-added jam that had undergone the photodegradation treatment was performed by seven panelists who had been well trained in sensory evaluation of odor. In the sensory evaluation, the evaluation of the jam without the addition of the masking agent compound, which was subjected to the photodegradation treatment, was given as "Strong smell: 4 points", and the evaluation of the jam without the addition of the masking agent compound, which was not subjected to the photodegradation treatment, was " Absolutely no offensive odor: 0 points” was set according to the following evaluation criteria.
Abnormal smell strongly sensed: 4 Strange smell felt: 3 Strange smell felt a little: 2 Strange smell hardly felt: 1 Strange smell felt at all: 0 points

<Evaluation results>
The score (average) of the masking agent-added jam after photodegradation treatment was 2.14.

From the results of Experimental Examples 13 to 17, ethyl pyruvate (A group, B group), ethyl acetoacetate (A group), benzyl benzoate (A group), heliotropine (A group, B group), benzyl alcohol (B group), methyl dihydrojasmonate (group B), methyl jasmonate (group B), stearic acid (group B), ethyl levulinate (group B), butyl butyryl lactate (group B), 1,4-cineole (C group, D group, E group, F group), γ-valerolactone (D group), γ-hexalactone (D group, F group, G group), p-menthan-3-one (D group, F group, G group), ethyl isovalerate (C group, D group, E group, F group, G group), ethyl acetate (C group, E group, F group, G group), rose oxide (C group, D group) , β-damascenone (C group, D group), anethole (C group, D group, E group, F group, G group), acetaldehyde (C group, D group, G group), methyl salicylate (C group, E group , F group, G group), 1,8-cineol (C group, D group, E group, F group), dihydroactinidiolide (D group, E group, F group, G group), menthyl lactate (C group , F group, G group), hexanal (D group, E group, F group, G group), 2-octanone (E group, F group), δ-hexalactone (C group, E group, G group), γ - heptalactone (group E, group G), ethyl butyrate (group E, group F, group G), 2-pentanone (group E, group F), 2-methyl-2-hepten-6-one (group E, F group, G group), acetal (D group, E group, F group, G group), sclareolide (D group, E group, F group, G group), diethyl carbonate (E group), ethyl lactate (F group) , 2-butanone (F group, G group), oleic acid (G group), ethyl crotonate (D group, F group, G group), orange juice drink, apple juice drink, grape juice drink, grape juice-containing jelly And it was found that the photodegradation odor generated by photodegradation in jam containing strawberry juice can be effectively masked. It was also confirmed that a good masking effect was obtained when natural fragrances such as star anise oil containing anethole and eucalyptus oil containing 1,8-cineol were used as masking agents. In Experimental Examples 2 to 17 above, the range of evaluation points given by the panelists to the same sample (the difference between the maximum value and the minimum value) was 0 or 1 for many samples, and 0 to 1 for all samples. 2.

Claims (7)

A fruit juice-derived photodegradation odor masking agent for a fruit juice-containing product, containing at least one compound selected from the group consisting of Groups A to G below;
(Group A) heliotropine, ethyl pyruvate, ethyl acetoacetate, and benzyl benzoate (Group B) butyl butyryl lactate, ethyl levulinate, benzyl alcohol, methyl jasmonate, stearic acid, methyl dihydrojasmonate, heliotropin, and Ethyl pyruvate (group C) acetaldehyde, β-damascenone, methyl salicylate, 1,8-cineol, ethyl acetate, δ-hexalactone, 1,4-cineol, menthyl lactate, anethole, rose oxide, and ethyl isovalerate ( Group D) Acetaldehyde, β-damascenone, acetal, 1,8-cineol, γ-valerolactone, p-menthan-3-one, γ-hexalactone, dihydroactinidiolide, ethyl crotonate, 1,4-cineole, Hexanal, anethole, rose oxide, sclareolide, and ethyl isovalerate (group E) diethyl carbonate, 2-pentanone, acetal, methyl salicylate, 1,8-cineol, ethyl acetate, δ-hexalactone, dihydroactinidiolide, 2 - octanone, 1,4-cineole, 2-methyl-2-hepten-6-one, hexanal, γ-heptalactone, anethole, ethyl butyrate, sclareolide and ethyl isovalerate (group F) ethyl lactate, 2-butanone , 2-pentanone, acetal, methyl salicylate, 1,8-cineol, ethyl acetate, p-menthan-3-one, γ-hexalactone, dihydroactinidiolide, 2-octanone, ethyl crotonate, 1,4-cineole , menthyl lactate, 2-methyl-2-hepten-6-one, hexanal, anethole, ethyl butyrate, sclareolide, and ethyl isovalerate (group G) oleic acid, 2-butanone, acetaldehyde, acetal, methyl salicylate, ethyl acetate , p-menthan-3-one, γ-hexalactone, δ-hexalactone, dihydroactinidiolide, ethyl crotonate, menthyl lactate, 2-methyl-2-hepten-6-one, hexanal, γ-heptalactone, Anethole, ethyl butyrate, sclareolide, and ethyl isovalerate. 2. The masking agent according to claim 1, wherein at least two of the compounds contained in said masking agent are compounds belonging to different groups in said Groups A to G. 2. The masking agent according to claim 1, wherein at least three of the compounds contained in said masking agent are compounds belonging to groups different from each other in said Groups A to G. The masking agent according to any one of claims 1 to 3, comprising methional, trans-4,5-epoxy-(E)-2-decenal, 1-octen-3-one, sotolone, (E, Masking the photodegradation odor of fruit juice-containing products caused by at least five selected from the group consisting of E)-2,4-nonadienal, (E,E)-2,4-decadienal and (E)-2-nonenal masking agent for A method for masking a fruit juice-derived photodegradation odor of a fruit juice-containing product, comprising adding the masking agent according to any one of claims 1 to 4 to the fruit juice-containing product. A method for producing a fruit juice-containing product, comprising adding at least one compound selected from the group consisting of Groups A to G below to a fruit juice-containing product, wherein the added amount of these compounds is is in the range of 0.00001 ppb to 1000 ppb, respectively, the method includes a step of producing a fruit juice-derived photodegradation odor, and/or the fruit juice-containing product obtained by the method is exposed to light to produce a fruit juice-derived light The manufacturing method, which is a product that can produce a deterioration odor:
(Group A) heliotropine, ethyl acetoacetate, and benzyl benzoate (Group B) butyl butyryl lactate, ethyl levulinate, benzyl alcohol, stearic acid, and heliotropine (Group C) acetaldehyde, β-damascenone, methyl salicylate, 1 ,8-cineole, ethyl acetate, δ-hexalactone, 1,4-cineol, menthyl lactate, anethole, rose oxide, and ethyl isovalerate (group D) acetaldehyde, β-damascenone, acetal, 1,8-cineole, γ-valerolactone, p-menthan-3-one, γ-hexalactone, dihydroactinidiolide, ethyl crotonate, 1,4-cineole, hexanal, anethole, rose oxide, sclareolide, and ethyl isovalerate (group E ) diethyl carbonate, 2-pentanone, acetal, methyl salicylate, 1,8-cineol, ethyl acetate, δ-hexalactone, dihydroactinidiolide, 2-octanone, 1,4-cineol, 2-methyl-2-heptene- 6-one, hexanal, γ-heptalactone, anethole, ethyl butyrate, sclareolide, and ethyl isovalerate (Group F) ethyl lactate, 2-butanone, 2-pentanone, acetal, methyl salicylate, 1,8-cineol, acetic acid Ethyl, p-menthan-3-one, γ-hexalactone, dihydroactinidiolide, 2-octanone, ethyl crotonate, 1,4-cineol, menthyl lactate, 2-methyl-2-hepten-6-one, hexanal , anethole, ethyl butyrate, sclareolide, and ethyl isovalerate (group G) oleic acid, 2-butanone, acetaldehyde, acetal, methyl salicylate, ethyl acetate, p-menthan-3-one, γ-hexalactone, δ-hexa Lactones, dihydroactinidiolide, ethyl crotonate, menthyl lactate, 2-methyl-2-hepten-6-one, hexanal, γ-heptalactone, anethole, ethyl butyrate, sclareolide, and ethyl isovalerate. A fruit juice-containing product containing at least one compound selected from the group consisting of Groups A to G below, wherein the content of each of these compounds is 0.00001 ppb to 1000 ppb relative to the fruit juice-containing product. The product within the scope and capable of producing a fruit juice-derived photodegradation odor upon exposure to light:
(Group A) heliotropine, ethyl acetoacetate, and benzyl benzoate (Group B) butyl butyryl lactate, ethyl levulinate, benzyl alcohol, stearic acid, and heliotropine (Group C) methyl salicylate, 1,8-cineol, delta - hexalactone, 1,4-cineole, menthyl lactate, anethole, rose oxide and ethyl isovalerate (group D) acetal, 1,8-cineole, γ-valerolactone, p-menthan-3-one, γ- Hexalactone, dihydroactinidiolide, ethyl crotonate, 1,4-cineol, anethole, rose oxide, sclareolide, and ethyl isovalerate (group E) diethyl carbonate, 2-pentanone, acetal, methyl salicylate, 1,8- Cineol, δ-hexalactone, dihydroactinidiolide, 2-octanone, 1,4-cineole, γ-heptalactone, anethole, sclareolide, and ethyl isovalerate (F group) ethyl lactate, 2-butanone, 2-pentanone , acetal, methyl salicylate, 1,8-cineol, p-menthan-3-one, γ-hexalactone, dihydroactinidiolide, 2-octanone, ethyl crotonate, 1,4-cineole, menthyl lactate, anethole, sclareolide , and ethyl isovalerate (group G) oleic acid, 2-butanone, acetal, methyl salicylate, p-menthan-3-one, γ-hexalactone, δ-hexalactone, dihydroactinidiolide, ethyl crotonate, lactic acid Menthyl, gamma-heptalactone, anethole, sclareolide, and ethyl isovalerate.