JP2019170374A - Masking agent for heat degradation odor of fruit juice-containing products - Google Patents

Abstract

To provide a novel masking agent for heat degradation odor of fruit juice-containing products.SOLUTION: Provided is a heat degradation odor masking agent for fruit juice-containing products containing at least one compound selected from the group consisting of the following groups a to c: (Group a) levulinic acid, linalool oxide, 2-acetylpyrrole, cinnamic acid, and γ-butyrolactone, (Group b) benzyl benzoate, benzyl lactate, geranic acid, isophorone, cyclotenbutyrate, lauric acid, 3-methyl-1-butanol, menthol, and linalool, (Group c) heliotropin, ethyl pyruvate, ethyl acetoacetate, and benzyl benzoate.SELECTED DRAWING: None

Description

  The present invention relates to a heat-degraded odor masking agent for fruit juice-containing products and a method for using the same. More specifically, the present invention includes a masking agent for suppressing a deterioration odor caused by deterioration of a fruit-derived component due to the influence of heat, a method for masking a fruit-containing product deterioration odor by the masking agent, and the masking agent. The present invention relates to a fruit juice-containing product and a method for producing the fruit juice-containing product.

  Fruit juice-containing products, which are foods and drinks containing fruit juice, often undergo a heating step for concentration, sterilization, and the like in the production process. In such a heating step, and during the subsequent storage period, for example, it is known that citrus fruit juice is deteriorated by heat to generate various deteriorated odors (off-flavors) (Non-Patent Documents 1 and 2).

  Since such deteriorated odor greatly affects the quality of fruit juice-containing products, attempts have been made to suppress the generation of deteriorated odor components or to suppress the deteriorated odor with a masking agent. For example, improvement of deterioration odor of fruit juice (orange fruit juice) produced during heat sterilization or storage with xylitol (Patent Document 1), prevention of generation of unpleasant odor caused during storage of grapefruit juice-containing foods and drinks by tea extract ( Patent Document 2), 1 selected from suppression of the generation of deteriorated odor of lemon flavored beverage containing lemon juice by jasmine tea extract (Patent Document 3), L-ascorbic acid, rutin, hermanus extract and chlorogenic acid Suppression of off-flavor generation during storage of beverage containing white grape juice with a specific antioxidant containing at least seeds (Patent Document 4), and the flavor component of citrus fruits by cineol or cis-3-hexenol has deteriorated Attempts have been made to mask off-flavors produced (Patent Document 5).

  However, there are still many unclear points as to what components cause the heat-degraded odor in various fruit juices in general and what components can mask the heat-degraded odor of products containing fruit juice. Therefore, there is an eager desire to identify a compound that constitutes an odor caused by the heat deterioration of fruit juice and a new masking agent component that can mask odor substances due to the heat deterioration of fruit juice.

JP 2000-308476 A JP 2005-304324 A JP2013-005787A JP2014-168401 JP2016-036319A

Journal of Japan Society for Food Science and Technology Vol.58 No.3 81-87 (2011) Journal of Agricultural and Food Chemistry, Vol.56, No.21, 9785-9796 (2008)

  This invention makes it a subject to provide the novel masking agent of the heat deterioration odor of a fruit juice containing product in view of the problem in the said prior art. Moreover, it aims at providing the novel masking method using a novel masking agent, the manufacturing method of a fruit juice containing product, and the fruit juice containing product obtained by the said manufacturing method.

  Under such circumstances, as a result of intensive studies, the present inventors have identified a main odor substance constituting a deteriorated odor caused by thermal deterioration of a fruit juice-containing product. In addition, the present inventors specify a masking agent component that has a masking effect on odorous substances generated by thermal degradation of fruit juice-containing products, and that these masking agent components exhibit a thermal degradation odor masking effect of fruit juice-containing products. By confirming, it came to complete this invention.

Accordingly, the present invention provides the following sections:
Item 1. A heat-degrading odor masking agent for fruit juice-containing products, containing at least one compound selected from the group consisting of the following groups a to c;
(Group a) levulinic acid, linalool oxide, 2-acetylpyrrole, cinnamic acid, and γ-butyrolactone,
(Group b) Benzyl benzoate, benzyl lactate, gellanic acid, isophorone, cyclotenbutyrate, lauric acid, 3-methyl-1-butanol, menthol, and linalool,
(Group c) Heliotropin, ethyl pyruvate, ethyl acetoacetate, and benzyl benzoate.

  Item 2-1. 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 in the groups a to c.

  Item 2-2. Item 2. A masking agent according to Item 1, which contains at least one compound belonging to Group a and masks a heat-degraded odor of a fruit juice-containing product caused by 4-vinyl guaiacol.

  Claim | item 2-3. Item 2. The masking agent according to Item 1, which contains at least one compound belonging to Group b and masks a heat-degraded odor of a fruit juice-containing product caused by furfural.

  Item 2-4. Item 2. The masking agent according to Item 1, which contains at least one compound belonging to Group c and masks a heat-degraded odor of a fruit juice-containing product caused by methional.

  Item 3. Item 1, Item 2-1, Item 2-2, Item 2-3, and Item 2-4, wherein the masking agent according to any one of Items 2 to 4 is added to the fruit juice-containing product. How to mask.

  Item 4. The manufacturing method of a fruit juice containing product including adding the masking agent as described in any one of claim | item 1, the term 2-1, the term 2-2, the term 2-3, and the term 2-4 to a fruit juice containing product.

  Item 5. The fruit juice containing product containing the masking agent as described in any one of claim | item 1, term 2-1, term 2-2, term 2-3, and term 2-4.

  According to the present invention, a novel masking agent for a heat-degrading odor of a fruit juice-containing product, 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 do. The present invention can mask the heat-degraded odor of the fruit juice-containing product or the fruit juice used as the raw material, and therefore can suppress the deterioration of the aroma and / or taste of the fruit juice-containing product, and easily and effectively. The quality of the contained product can be maintained.

  In this specification, the phrase “comprising” or the phrase “containing” is intended to encompass the phrase “consisting of” and the phrase “consisting of only”.

  The operations and processes described herein can be performed at room temperature unless otherwise specified.

  In the present specification, the term “room temperature” is understood according to common general technical knowledge, and can mean a temperature in the range of 10 ° C. to 35 ° C., for example.

Hereinafter, the present invention will be described in detail.
Fruit juice-containing products targeted by the present invention include a wide range of foods containing fruit juices. For example, fruit juices themselves, fruit juice soft drinks prepared by diluting fruit juice with water, sugar liquid, etc., fruit juice mixed drinks, fruit juices Various drinks such as carbonated drinks, milk drinks with fruit juice, fruit drinks, concentrated syrup with fruit juices; alcohols such as liqueurs with fruit juices; jelly and mousse with fruit juices; frozen desserts such as ice cream and sorbets; gummy, candy, gum with fruit juices And other confectionery. In addition, fruit-containing foods widely include foods containing pulp or foods produced using fruits as raw materials. For example, fruit purees, fruit drinks such as nectar, fruit cocktails, fruit cakes, jelly, mousse and other confectionery , Frozen desserts such as ice cream and sherbet, canned and bottled fruits, fruit sauce, fruit butter, fruit liquor, fruit vinegar and the like.

  In addition, the kind in particular of the fruit used as the raw material of fruit juice is not restrict | limited, All the fruits can be mentioned. For example, citrus fruits such as orange, grapefruit, lemon and tangerine, berries such as strawberry, blueberry and tree strawberry, banana, pineapple, peach, grape, muscat, apple, none, melon, kiwifruit, guava, passion fruit , Mango, cherry, watermelon, etc., but are not limited thereto.

  As described in Examples below, the present inventors have identified the main odorous substances in the heat-degraded odor of fruit juice-containing products in relation to the present invention.

Briefly stated, the present inventors made (1) a fruit juice-containing product in which a deteriorated odor was generated by heat deterioration treatment, and a fruit juice-containing product that was not thermally deteriorated. Analyzing the odor component of the product with a gas chromatography olfactometer (hereinafter abbreviated as GC / O), and (2) the odor component generated by the heat deterioration treatment (that is, containing fruit juice that has not been heat deteriorated) In fruit-containing products that have been heat-degraded as compared to the product, among the newly generated odor components or increasing odor components), the main substances constituting the deteriorated odor were identified.

  Suitable examples of such major odorants include 4-vinyl guaiacol, furfural, and methional.

The heat-degraded odor masking agent of the fruit juice-containing product of the present invention (in the present specification, this is sometimes referred to as “degraded odor masking agent” or “masking agent”) is from the following groups a, b and c: One or more compounds selected from the group consisting of these compounds (in the present specification, they may be referred to as masking agent compounds) are used as active ingredients;
(Group a) levulinic acid, linalool oxide, 2-acetylpyrrole, cinnamic acid, and γ-butyrolactone,
(Group b) Benzyl benzoate, benzyl lactate, gellanic acid, isophorone, cyclotenbutyrate, lauric acid, 3-methyl-1-butanol, menthol, and linalool,
(Group c) Heliotropin, ethyl pyruvate, ethyl acetoacetate, and benzyl benzoate.

The compounds of group a, b and c are all known fragrance components.
In the present invention, as the compound, a purified product from a natural fragrance or a synthetic product by chemical reaction can be used without limitation. For convenience, in the present invention, these commercially available products can be suitably used.

  Moreover, the natural fragrance | flavor containing the said compound can be used as a masking agent of this invention in the range which does not impair the effect of this invention. Such natural flavors include, but are not limited to, for example: natural fragrances containing linalool oxide, beeswax oil, salamander oil, grape wine oil, etc .; natural fragrances containing cinnamic acid Cinnamon oil, etc .; natural fragrance containing 3-methyl-1-butanol, camomil oil, and grape wine oil, etc .; natural fragrance containing menthol, mint oil, peppermint oil, etc .; natural containing linalool As perfumes, ylang ylang oil, orange flower oil, jasmine oil, osmanthus oil, nutmeg oil, mace oil, lemon oil, geranium oil, clari sage oil, coriander oil, basil oil, petit grain oil, bergamot oil Marjoram oil, lavender oil, orange oil, grapefruit oil, and lime oil, and the like; as a natural flavor containing heliotropin, vanilla oil and the like; as a natural flavor containing benzyl benzoate, may be mentioned benzoin oil.

  The compounds described in group a, levulinic acid, linalool oxide, 2-acetylpyrrole, cinnamic acid, and γ-butyrolactone are compounds that function effectively as masking agents for thermal degradation of fruit juice-containing products. In particular, it effectively functions as a masking agent for 4-vinyl guaiacol, which is one of the main odor substances of the above-mentioned deteriorated odor. Therefore, when using the compound which belongs to a group, the masking agent of this invention can be used in order to mask the heat-degraded odor of fruit juice containing products by suppressing the deodorized odor resulting from 4-vinyl guaiacol. These compounds described in group a can be used singly or in combination of two or more.

  The compounds described in group b, benzyl benzoate, benzyl lactate, gellanic acid, isophorone, cyclotenbutyrate, lauric acid, 3-methyl-1-butanol, menthol, and linalool are each a fruit juice-containing product. It is a compound that effectively functions as a heat-degraded odor masking agent, and in particular, effectively functions as a masking agent for furfural, which is one of the main odor substances of the above-mentioned deteriorating odor. Therefore, when using the compound which belongs to b group, the masking agent of this invention can be used in order to mask the heat deterioration odor of a fruit juice containing product by suppressing the deterioration odor resulting from a furfural. These compounds described in group b can be used singly or in combination of two or more.

  Heliotropin, ethyl pyruvate, ethyl acetoacetate, and benzyl benzoate, which are compounds described in group c, are compounds that effectively function as masks for thermal degradation of fruit juice-containing products. It effectively functions as a masking agent for methional, which is one of the main odor substances of the deteriorated odor. In preferable embodiment, the masking agent etc. in which the compound described in the c group contains at least 1 sort (s) of ethyl acetoacetate and benzyl benzoate are mentioned. Therefore, when using the compound which belongs to c group, the masking agent of this invention can be used in order to mask the heat deterioration odor of a fruit juice containing product by suppressing the deterioration odor resulting from methional. These compounds described in group c can be used singly or in combination of two or more. As described above, the masking agent of the present invention masks the heat deterioration odor of fruit juice-containing products by suppressing deterioration odor caused by at least one selected from the group consisting of 4-vinyl guaiacol, furfural, and methional. Can be used to

  The deteriorated odor masking agent of the present invention is a compound selected from the group consisting of the a group, the b group and the c group (that is, a compound group comprising all compounds belonging to the group a, compounds belonging to the group b and compounds belonging to the group c). 1) or 2 types or more. In the present invention, the compound “two or more compounds selected from the group consisting of the group a, b and c” includes compounds belonging to different groups unless otherwise specified 2 The case where not only a compound of two or more species but also two or more compounds belonging to the same group is 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.

In the present invention, from the point of the good masking effect,
It is preferable to use a combination of one or more compounds (two or more in total) selected from two groups out of group a, group b and group c,
It is more preferable to use a combination of one or more (total of three or more) compounds selected from all three groups of the a group, the b group, and the c group.

  Among the masking agent compounds, benzyl benzoate belongs to both b group and c group. In the present invention, by adding benzyl benzoate to the masking agent, the masking agent includes both compounds belonging to group b and compounds belonging to group c. Therefore, in the present invention, the masking agent containing benzyl benzoate is It is included in “a masking agent including a combination of one or more (two or more in total) selected from two groups out of group a, b and c”. In the present invention, when benzyl benzoate is used as the masking agent compound, benzyl benzoate may be used alone, but a masking agent compound other than benzyl benzoate (for example, belonging to group b and / or c, A combination of at least one masking agent compound other than benzyl benzoate may be used.

In a preferred embodiment, the present invention provides a heat-degraded odor masking agent for fruit juice-containing products, which contains at least one compound selected from the group consisting of the following groups a to c:
(Group a) levulinic acid, linalool oxide, 2-acetylpyrrole, cinnamic acid, and γ-butyrolactone,
(Group b) Benzyl benzoate, benzyl lactate, gellanic acid, isophorone, cyclotenbutyrate, lauric acid, 3-methyl-1-butanol, menthol, and linalool,
(Group c) Ethyl acetoacetate and benzyl benzoate.

The amount of use of the deteriorated odor masking compound in the present invention (for example, the content of the deteriorated odor masking agent of the present invention relative to the fruit juice-containing product) may be any amount that exhibits the effect of masking the deteriorated odor. The concentration of the whole juice-containing product is
It is preferable to use it in the range of 0.0000025 ppb to 100,000 ppb,
It is more preferable to use so that it may become in the range of 0.000025ppb-10000ppb, and it is still more preferable to use it so that it may exist in the range of 0.00025ppb-1000ppb.
From the viewpoint of sufficiently obtaining the masking effect of the deteriorated odor and suppressing the scent and / or taste of the masking agent compound itself from undesirably affecting the scent and / or taste of the fruit juice-containing product, in the above range. It is preferable to use it.

  In a preferred embodiment of the present invention, the total mass (or total concentration) of each group of compounds in groups a, b and c is effective as a masking agent suitable for each group (ie, effectively as a masking agent). The mass (or concentration) of the odorous substance that is the functional target) (ie, 4-vinyl guaiacol for the compound described in group a, furfural for the compound described in group b, methional for the compound described in group c) On the other hand, for example, a ratio in the range of 1: 1000 to 1000: 1, a ratio in the range of 1: 100 to 100: 1, or a ratio in the range of 1:10 to 10: 1 is preferable. In the present invention, when benzyl benzoate is used as the masking agent compound, in the calculation of the above ratio, benzyl benzoate is calculated as both a compound of group b and a compound of group c.

  Surprisingly, not only when there are few masking agent compounds, but also when there are too many, the masking effect with respect to the target odor substance may weaken.

  The present invention uses one or more compounds selected from the group consisting of the a group, b group and c group at each stage of production, distribution, storage and sale of fruit juice-containing products, Masking of degraded odors (for example, heat-degraded odors of fruit-containing products produced by heat) simply and safely, without affecting the scent and / or taste of the final product can do.

  The deteriorated odor masking agent of the present invention may contain a compound 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 use mode of the deteriorated odor masking agent of the present invention.

  The deteriorated odor masking agent of the present invention may consist only of the masking agent compound, or may contain an appropriate diluent (thickening agent) 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) so that the deteriorated odor masking agent exhibits the effect of suppressing the heat deterioration odor derived from fruit juice. It can be set and adjusted as appropriate from the above range.

  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 suppressing the thermal deterioration odor derived from the fruit juice of the masking agent compound. For example, for example, a solid diluent or carrier such as gum arabic, dextrin, cyclodextrin, glucose, sucrose; or a liquid diluent such as water, ethanol, propylene glycol, glycerin, glycerin fatty acid ester, edible oil or fat, or A carrier can be mentioned. For these diluents or carriers, additives used to prepare the deteriorated odor masking agent of the present invention in a desired shape (drug form), such as excipients, binders, disintegrants, emulsifiers, and solubilizers. , Thickeners, lubricants, flavoring agents, coloring agents, antioxidants and the like. Among them, the emulsifier can be suitably used for preparing an aqueous solution (dispersion liquid, suspension) or an emulsion deterioration odor masking agent by dispersing a masking agent compound in a liquid diluent. Examples of the emulsifier include, but are not limited to, sucrose fatty acid ester, glycerin fatty acid ester, sorbitan fatty acid ester, lecithin, enzymatically decomposed lecithin, quilla extract, saponin, polysorbate, gum arabic, and gati gum. By using such a diluent or carrier, the deteriorated odor masking agent of the present invention can be made into a liquid, suspension, emulsion, paste, powder, granule, or any other dosage form. The dosage form of the degradation odor masking agent of the present invention can be appropriately set according to the type and shape of the object that suppresses the heat degradation odor derived from fruit juice.

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

  The deteriorated odor masking agent of the present invention may be a fragrance composition containing one or more masking agent compounds described above as a fragrance component, and, in addition to the masking agent compound, one or two. It is good also as a fragrance | flavor composition containing the other fragrance | flavor components (fragrance | flavor components other than the said masking agent compound) of a seed or more.

  Such other perfume ingredients may be used in combination with the above-described masking agent compound as long as they do not impair the effects of the present invention, and do not adversely affect the aroma of the fruit juice-containing product containing the deteriorated odor masking agent. It is preferable. As such a fragrance component, for example, a natural substance described in “Patent Office Gazette of Known and Conventional Techniques (Fragrance) Part II Food Fragrance” edited by the Japan Patent Office (issued on January 14, 2000) A fragrance | flavor, a synthetic | combination fragrance | flavor, etc. can be mentioned. Specifically, citrus flavors (p. 88-135) that have the scent of citrus fruits (orange, lemon, lime, grapefruit, yuzu sudachi, etc.) and fruits other than citrus fruits (apple, grape, strawberry, banana) , Peaches, melons, apricots, ume, cherries, berries, etc.) Fruit flavors (p. 136-257), milk flavors with dairy flavors (milk flavor, butter flavor, cheese flavor, cream flavor) , Yogurt flavor, etc.) (pages 258-347), vanilla fragrance with vanilla beans fragrance (pages 348-366), tea fragrance with fragrance such as green tea, oolong tea, black tea (pages 367-426), cocoa and Cocoa chocolate flavor with chocolate scent (pages 427-446), coffee flavor with coffee scent (pages 447-475), -Mint-based fragrances with scents such as mint and spearmint (pages 476-495), spice-based fragrances with spices scents (pages 496-580), and nut-based fragrances with the scent of nuts such as almonds (pages 581-608) ), Western liquor-based fragrances (for example, wine, whiskey, brandy, rum, gin, liqueur, etc.) (759-825 pages), flower-based fragrances with floral fragrance (pages 826-836), vegetables ( Examples thereof include vegetable flavors (pages 837 to 907) having the scent of onion, garlic, leek, carrot, burdock, shiitake mushroom, matsutake mushroom, trefoil, and the like. Preferred examples include citrus flavors, fruit flavors, milk flavors, cocoa / chocolate flavors, mint flavors, and vegetable flavors.

  The fragrance composition of the present invention may be one containing one or two or more masking agent compounds described above in a proportion of 0.000001 to 99% by mass, as long as the effects of the present invention are exhibited. When the fragrance composition of the present invention contains other fragrance components in addition to the masking agent compound, the blending ratio of the other fragrance components is not limited, but is 0.000001 to 99% by mass, preferably 0.00001 to A proportion of 10% by mass can be exemplified.

  The timing and method for adding or applying the deteriorated odor masking agent of the present invention or the preparation containing the same to the juice-containing product are not particularly limited, and if it is added or applied at any stage during the production of the juice-containing product. Good.

  For example, the degradation odor masking agent of the present invention is added to or applied to the fruit juice-containing product after the degradation odor masking agent of the present invention or a preparation containing the same is added or applied to the raw material of the fruit juice-containing product in advance. The agent may be added or applied to the fruit juice-containing product.

  In addition, the deterioration odor masking agent of this invention can be used also with respect to the fruit juice containing product containing the various food raw materials used for a normal fruit juice containing product.

Examples of the food material include carbohydrates, sweeteners, thickeners, emulsifiers, vitamins, milk, dairy products, fats and oils, acidulants, fragrances, starches, dextrins, glycerin, eggs, and pigments. it can. More specifically, as the food material, for example,
Sugars such as sucrose, glucose, fructose, palatinose, xylose, 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 ester, glycerin fatty acid ester, sorbitan fatty acid ester, and lecithin;
Vitamins such as vitamin A, vitamin B, vitamin C and vitamin E;
Milk such as raw milk, milk, skim milk, and processed milk;
Dairy products such as fermented milk, concentrated milk, condensed milk, whole milk powder, skim milk powder, cream, cheese and butter;
Fats and oils such as palm oil and palm oil;
Acidulants such as citric acid, malic acid, tartaric acid, lactic acid;
The fragrance | flavor etc. which were illustrated by said "other fragrance | flavor component" can be mentioned.

  Moreover, the method for masking the heat-degraded 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 heat-degraded odor masking agent for the fruit juice-containing product of the present invention. It is understood from the explanation etc.

  Hereinafter, the present invention will be specifically described with reference to the following examples, but the present invention is not limited thereto.

  In the following examples, the numerical values indicating the amount and concentration can be based on mass unless otherwise specified.

Experimental example 1
(Identification of major odor substances)
In accordance with the procedure shown below, the main odor substances in the heat-degraded odor of the fruit juice-containing product were identified.

(Preparation of fruit juice-containing products)
Ion-exchange water was added to commercially available orange 5-fold concentrated fruit juice to prepare a fruit juice 100% solution. This liquid was sterilized by hot pack filling at a temperature reaching 93 ° C., and then filled and sealed in a 200 ml capacity PET bottle to prepare an orange juice drink.
Moreover, the apple juice drink or the grape juice drink was prepared by the method similar to the said orange juice drink using the commercially available apple 4 times concentrated fruit juice or the grape 5 times concentrated fruit juice.

(Heat degradation treatment)
By storing the container-packed orange juice drink, apple juice drink, and grape juice drink prepared above in a thermostatic bath at 40 ° C. for 1 week, a heat-degraded fruit juice drink was prepared. Separately, the fruit juice drink which was not heat-degraded was prepared by storing the container-packed orange juice drink, the apple juice drink, and the grape juice drink in a refrigerator at 5 ° C. for 1 week.

(Identification of major odorous substances of heat-degraded odor)
The three types of fruit juice beverages subjected to the thermal degradation treatment and the three types of fruit juice beverages not subjected to the thermal degradation treatment were analyzed by GC / O, and the orange juice, Three compounds of 4-vinyl guaiacol, furfural, and methional were identified as main odor substances in the heat-degraded odor common to apple juice and grape juice.
The measurement conditions for GC / O are shown below.
GC / O device: 6890N (manufactured by Agilent Technologies) / Charm Analysis (TM) (manufactured by Data)
Column: DB-WAX / length 15 m, inner diameter 0.32 mm (manufactured by Agilent Technologies)
Column temperature conditions: 40 to 220 ° C., 6 ° C./minute temperature increase Carrier gas: helium

Experimental example 2
(Verification of major odor substances)
(Preparation of heat-degraded fruit juice beverage 1)
A commercially available fruit juice 100% orange juice drink was filled and sealed in a 200 ml capacity plastic bottle, and stored in a constant temperature bath at 40 ° C. for one week to prepare a heat-degraded orange juice drink. Separately, an orange juice drink not subjected to heat deterioration treatment was prepared by storing the packaged orange juice drink in a refrigerator at 5 ° C. for 1 week instead of a constant temperature bath at 40 ° C.

  Also, after filling and sealing a plastic bottle with 100% apple juice drink or grape juice drink prepared from commercially available apple 4-fold concentrated fruit juice or grape 5-fold concentrated fruit juice in the same manner as the above-mentioned orange juice drink, By performing the heat deterioration treatment under conditions, a heat deterioration fruit juice drink and a fruit juice drink not subjected to the heat deterioration treatment were prepared.

(Preparation of simulated heat-degraded fruit juice beverage)
All the three compounds of 4-vinyl guaiacol, furfural, and methional were added to a container-packed orange juice drink, apple juice drink, and grape juice drink that had not been subjected to heat deterioration treatment to prepare a pseudo heat deterioration fruit juice drink. .

  Specifically, a solution in which 4-vinyl guaiacol is dissolved in 95% ethanol to a concentration of 0.01% by mass, a solution in which furfural is dissolved in 95% ethanol to a concentration of 0.1% by mass, And methional dissolved in 95% ethanol to a concentration of 0.0001% by mass, respectively, and a container-packed orange that has not been subjected to thermal deterioration treatment so that the concentration of each component is the amount shown in Table 1 Added to fruit juice drinks, apple fruit juice drinks, and grape juice drinks.

The above-mentioned (preparation of simulated heat-degraded fruit juice drink), the odor of the simulated heat-degraded fruit juice drink prepared by adding the compounds, was engaged in the development of fragrances for more than 3 years, and was trained by seven panelists who were well trained in sensory evaluation of odor. Evaluation was made in comparison with the heat-degraded fruit juice drink obtained in (Preparation 1 of heat-degraded fruit juice drink). The evaluation criteria are as follows:
<Evaluation criteria>
Odor equivalent to heat-degraded fruit juice: 5-point odor similar to heat-degraded fruit juice: 4-point odor similar to heat-degraded fruit juice and heterogeneous odor: 3 points Heat-degraded fruit juice drink has a different odor: 2-point heat-degraded fruit juice drink has a completely different odor: 1 point (evaluation result)
The results of the above evaluation of the simulated heat-degraded fruit juice drink (average value of seven persons) were 4.71 for the orange juice drink, 4.57 for the apple juice drink, and 4.71 for the grape juice drink. It was confirmed that the odor equivalent to the deteriorated odor generated in the heat-degraded fruit juice beverage was reproduced well by the odor substance.

Experimental example 3
(Masking effect of group a compounds on 4-vinyl guaiacol)
4-vinyl guaiacol was dissolved in 95% ethanol to a concentration of 0.01% by mass, and this solution was added to ion-exchanged water so that the concentration of 4-vinyl guaiacol was 100 ppb. A solution obtained by dissolving each of the compounds of group a (levulinic acid, linalool oxide, 2-acetylpyrrole, cinnamic acid, and γ-butyrolactone) in 95% ethanol in the aqueous solution containing 4-vinylguaiacol thus prepared. These were added so as to have the concentrations shown in Table 2, and the masking effect on 4-vinyl guaiacol was confirmed by sensory evaluation.

In sensory evaluation, the evaluation of ion-exchanged water containing 100 ppb of 4-vinyl guaiacol described above was “4-vinyl guaiacol odor strongly felt: 4 points”, and the evaluation of ion-exchanged water was “no 4-vinyl guaiacol odor at all” The following evaluation criteria were set as “I don't feel: 0 points”, and the evaluation score was given by 5 panelists (the panelists' skill level is the same as above / the same applies thereafter). The average evaluation points are shown in Table 2.
<Evaluation criteria>
4-Vinyl Guaiaol odor more strongly: 5 points 4-Vinyl Guaiaol odor strongly felt: 4 points 4-Vinyl Guaiaol odors felt: 3 points 4-Vinyl Guaiaol odor slightly felt: 2 points 4-Vinyl Guaiaol odors Almost no feeling: 1 point 4-Vinyl guaiacol no odor at all: 0 points

  Moreover, the relationship between the density | concentration of a group compound with respect to 4-vinyl guaiacol, and a masking effect was examined.

  To the aqueous solution having a 4-vinyl guaiacol concentration of 100 ppb, 2-acetylpyrrole was added so as to have the concentration shown in Table 3, and the relationship between the amount of 2-acetylpyrrole and the masking effect on 4-vinyl guaiacol was determined. Evaluation was performed in the same manner as described above. The evaluation results are shown in Table 3.

From the above results, it was found that the masking effect of the group a compound tends to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorous substance approaches 0.01 to 0.1.

Experimental Example 4
(Masking effect of group b compounds on furfural)
In Experimental Example 3, the group a compound was changed to the group b compound (benzyl benzoate, benzyl lactate, gellanic acid, isophorone, cyclotenbutyrate, lauric acid, 3-methyl-1-butanol, menthol, or linalool), and 4- Except that vinyl guaiacol was changed to furfural, the concentration of furfural in 95% ethanol to 0.1% by mass, and the concentration of furfural in the test solution was changed to 1000 ppb, the same procedure as in Experimental Example 3 was repeated. The masking effect with respect to the furfural of a compound and the masking effect with respect to the addition amount of menthol were evaluated.
<Evaluation criteria>
Feel the furfural odor more strongly: 5 points Feel the furfural odor strongly: 4 points Feel the furfural odor: 3 points Feel a little furfural odor: 2 points Feel almost no furfural odor: 1 point Feel no furfural odor: 0 * Evaluation of ion-exchanged water containing 1000 ppb of the above-mentioned furfural was set to “feel furfural odor strongly: 4 points”.
The evaluation results are shown in Tables 4 and 5.

From the above results, it was found that the masking effect of the group b compound tends to be higher as the ratio of the concentration of the masking agent compound to the concentration of the odorous substance approaches 0.01.

Experimental Example 5
(Masking effect of c group compound on methional)
In Experimental Example 3, the concentration of the group a compound in the group c compound (heliotropin, ethyl pyruvate, ethyl acetoacetate, or benzyl benzoate), 4-vinyl guaiacol in methional, and methional in 95% ethanol Except that the concentration of methional in the test solution was changed to 0.0001% by mass and the concentration of methional in the test solution was changed to 1 ppb, the masking effect on the methional of the group c compound and the masking amount on the addition amount of ethyl pyruvate were performed in the same manner as in Experimental Example 3. The effect was evaluated.
<Evaluation criteria>
Feel the methional odor more strongly: 5 points Feel the methional odor strongly: 4 points * Evaluation of ion-exchanged water containing 1 ppb of methional as described above was made to “feel methional odor strongly: 4 points”.
The evaluation results are shown in Tables 6 and 7.

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

  From the results of Tables 2 to 7, it was found that the masking agent compounds of group a, b and c were effective masking agents for 4-vinyl guaiacol, furfural and methional, respectively. Surprisingly, not only when the amount of the masking agent compound is small, but also when the amount is too large, the masking effect on the target odor substance tends to be weakened.

Experimental Example 6
(Masking effect 1 of masked odor masking agent for pseudo-heat-degraded fruit juice with main odor substance added to fruit juice)
The masking agent compounds listed in Table 8 are added in the amounts shown in the table to the simulated heat-degraded orange juice drink prepared in “(Preparation of simulated heat-degraded fruit juice beverage)”, and the masking effect thereof is obtained. It confirmed by sensory evaluation.

In sensory evaluation, the above-mentioned pseudo heat-degraded orange juice drink was evaluated as “I feel a strong odor: 4 points”, and the addition of 4-vinyl guaiacol, furfural and methional, and no heat-degradation treatment ( That is, the evaluation of the orange juice drink that has not been heat-degraded was set to “I don't feel a strange odor at all: 0 points”, and the following evaluation criteria were set and evaluated by 7 panelists. The average sensory evaluation points are shown in Table 8:
I feel a strong odor: 5 points I feel a strong odor: 4 points I feel a bad odor: 3 points I feel a little odor: 2 points I hardly feel a bad odor: 1 point I don't feel a bad odor at all: 0 points

Experimental Example 7
(Masking effect 2 of masked odor masking agent for pseudo-heat-degraded fruit juice with main odor substance added to fruit juice)
In Experimental Example 6, the simulated heat-degraded orange juice drink was changed to a pseudo-heat-degraded apple juice drink, and the masking agent compound described in Table 8 was changed to the masking agent compound described in Table 9, as in Experimental Example 6. By this method, the masking effect of the deteriorated odor masking agent compound on the simulated heat-degraded fruit juice drink was confirmed.

Experimental Example 8
(Masking effect 3 of masked odor masking agent for simulated heat-degraded fruit juice beverages with main odor substances added to fruit juice beverages)
Experimental Example 6 was the same as Experimental Example 6 except that the pseudo heat-degraded orange juice drink was changed to a pseudo heat-degraded grape juice drink and the masking agent compound shown in Table 8 was changed to the masking agent compound shown in Table 10. By this method, the masking effect of the deteriorated odor masking agent on the pseudo heat deteriorated fruit juice drink was confirmed.

  From the results of Tables 8 to 10, group a (levulinic acid, linalool oxide, or 2-acetylpyrrole), group b (cyclotenbutyrate, menthol, gellanic acid, benzyl benzoate, or 3-methyl-1-butanol ) And c group (heliotropin, benzyl benzoate, or ethyl acetoacetate), one compound selected from the group consisting of a simulated heat-degraded fruit juice drink that reproduces the heat-degraded state effectively (Experimental examples 6-1 to 6-4, Experimental examples 7-1 to 7-3, and Experimental examples 8-1 to 8-3). In addition, Experimental Examples 6-5 to 6-8, Experimental Example 7-4, and Experimental Example 8-4 in which two kinds of compounds were selected from different groups of the a group, the b group, and the c group, As compared with the case where the compound was added, it was found that the thermal deterioration odor masking effect was more excellent.

Experimental Example 9
(Masking Effect 1 of Degraded Odor Masking Agent Compound in Fruit Drinks)
Ion-exchange water was added to commercially available orange 5-fold concentrated fruit juice to prepare a fruit juice 100% solution. This liquid was sterilized by hot pack filling at a temperature reaching 93 ° C., and then filled and sealed in a 200 ml capacity PET bottle to prepare an orange juice drink. A heat-degraded orange juice drink was prepared by storing the container-packed orange juice drink prepared above in a constant temperature bath at 40 ° C. for 1 week. Separately, an orange juice drink not subjected to heat deterioration treatment was prepared by storing the packaged orange juice drink in a refrigerator at 5 ° C. for 1 week instead of a constant temperature bath at 40 ° C.

  The masking agent compound shown in Table 11 previously dissolved in 95% ethanol was added to the heat-degraded orange juice drink prepared above so as to have the amount in the table.

The heat-degraded orange juice drink without the masking agent is defined as “I feel a strong odor: 4 points”, and the orange juice drink that has not been heat-degraded as “I do not feel any odor: 0 points” Evaluation criteria were set and sensory evaluation was performed about the masking effect of the deterioration smell of the fruit juice drink which added the masking agent. The sensory evaluation was performed by 7 panelists, and the average evaluation score is shown in Table 12:
<Evaluation criteria>
I feel a strange smell more strongly: 5 points I feel a strange smell strongly: 4 points I feel a strange smell: 3 points I feel a little strange smell: 2 points I hardly feel a strange smell: 1 point I don't feel a strange smell at all: 0 points

Experimental Example 10
(Masking effect 2 of masking agent compound for deterioration odor in fruit juice drink)
The fruit juice 100% liquid prepared by adding ion-exchanged water to commercially available apple 4-fold concentrated fruit juice is sterilized by hot-pack filling at 93 ° C. and then dissolved in 95% ethanol in advance. After adding the masking agent compound described in Table 13 so as to have the amount in the table, it was filled and sealed in a 200 ml capacity plastic bottle to prepare a container-packed apple juice drink. The apple fruit juice that has been heat-deteriorated by storing the apple juice drink with the masking agent prepared above together with the container-packed apple juice drink separately prepared without adding the masking agent compound in a thermostatic bath at 40 ° C. for one week. A beverage was prepared. Separately, an apple juice drink that has not been subjected to heat degradation treatment is stored in a refrigerator at 5 ° C. for 1 week instead of a constant temperature bath at 40 ° C. Prepared.

  The masking effect of the masking agent compound was confirmed by the same evaluation method as in Experimental Example 9 for the heat-degraded apple juice drink prepared by adding the masking agent. The results are shown in Table 13.

Experimental Example 11
(Masking effect 3 of the masking compound for odor deterioration in fruit juice drinks)
In Experimental Example 10, except that apple 4 times concentrated fruit juice was changed to grape 5 times concentrated fruit juice, and the masking agent compound shown in Table 13 was changed to the masking agent compound shown in Table 14, the same method as in Experimental Example 10, The masking effect of the masking agent compound was confirmed, and the evaluation results are shown in Table 14.

Experimental Example 12
(Masking effect of deteriorated odor masking compound in fruit juice-containing jelly)
<Preparation of grape juice-containing jelly>
(1) Raw materials 1, 2 and 7 to 9 shown in Table 15 below were added to water at the blending ratios (parts by mass) shown in Table 15 and stirred at room temperature for 10 minutes, and then dissolved by stirring at 80 ° C. for 10 minutes.
(2) The raw materials 3 to 6 and 10 shown in the following Table 15 were added to the solution obtained in the step (1) at the blending ratio (parts by mass) shown in Table 15, and the whole amount was corrected with water while stirring.
(3) Fill a polypropylene bag (10 cm × 8 cm × 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 masking compound addition were prepared.

<Heat degradation treatment>
Masking agent compound added jelly and masking agent compound added jelly were stored in a constant temperature bath at 40 ° C. for 7 days to prepare a heat-degraded jam. Separately, the jelly without adding a masking agent was stored in a refrigerator at 5 ° C. for 7 days to prepare a jelly without heat deterioration treatment.

<Sensory evaluation>
The sensory evaluation of the masking agent compound-added jelly subjected to the above heat deterioration treatment was carried out by seven panelists who were well trained in the sensory evaluation of odor. In the sensory evaluation, the evaluation of the jelly without the addition of the masking agent compound subjected to the above-described heat deterioration treatment was set to “strongly feel a bad odor: 4 points”, and the evaluation of the jelly without the addition of the masking agent compound subjected to the heat deterioration treatment The following evaluation criteria were set as “no odor at all: 0 points”.
Strongly feel the bad odor: 4 points Feel the bad odor: 3 points Feel a little bad smell: 2 points Feel almost no bad odor: 1 point Feel no bad odor: 0 points.

<Evaluation results>
The evaluation score (average) of the masking agent compound-added jelly after the thermal deterioration treatment was 1.00.

Experimental Example 13
(Masking effect of deteriorated odor masking compound in fruit juice-containing jam)
<Preparation of jam containing strawberry juice>
(1) Raw materials 1 to 3 shown in Table 17 below were mixed in advance at the blending ratio (parts by mass) shown in Table 17 and added to the raw material 4 shown in Table 17 below, and dissolved by boiling.
(2) The raw materials 5 and 6 shown in the following Table 17 were added to the solution obtained in the step (1) at a blending ratio (parts by mass) shown in Table 23 and boiled to 99.15 parts by mass.
(3) The raw materials 7 and 8 shown in the following Table 17 were added to the solution obtained in the step (2) at the blending ratio (parts by mass) shown in Table 23 and mixed.
(4) A part of the solution obtained in step (3) is placed in a separate container, and with respect to 100 parts by mass, 0.05 part by mass of a 95% ethanol solution of the masking agent compound, It added and mixed so that it might become the compounding quantity of 18 description.
(5) Fill a polypropylene bag (10 cm × 8 cm × about 1.5 cm) with 100 g of the solution obtained in step (4), heat sterilize at 94 ° C. for 10 minutes, and cool to 5 ° C. or less to prepare a jam. did. A jam without adding a masking agent was prepared according to the above steps except that 100 g of the solution obtained in the step (3) was used instead of the solution obtained in the step (4).

<Heat degradation treatment>
Masking agent compound added jam and masking agent compound added jam were stored in a constant temperature bath at 40 ° C. for 7 days to prepare a heat-degraded jam. Separately, a jam without addition of a masking agent compound was stored in a refrigerator at 5 ° C. for 7 days to prepare a jam without heat deterioration treatment.

<Sensory evaluation>
Sensory evaluation of the masking agent compound-added jam subjected to the above-described heat deterioration treatment was carried out by seven panelists who were well trained in sensory evaluation of odor. In the sensory evaluation, the evaluation of the jam without the masking agent compound added with the above-described heat deterioration treatment was “strongly feels an odor: 4 points”, and the evaluation of the jam without the masking agent compound added without the heat deterioration treatment was “ The following evaluation criteria were set as “no odor at all: 0 points”.
Strongly feel a bad odor: 4 points Feel a bad odor: 3 points Feel a little bad odor: 2 points Feel almost no bad odor: 1 point Do not feel bad odors: 0 points.

<Evaluation results>
Sensory evaluation was performed by seven panelists who were well trained in sensory evaluation of odor.
The evaluation score (average) of the jamming agent added with the masking agent after the thermal deterioration treatment was 1.14.

  From the results of Experimental Examples 9 to 13, group a (linalool oxide, 2-acetylpyrrole, levulinic acid, γ-butyrolactone, or cinnamic acid), group b (menthol, linalool, benzyl lactate, benzyl benzoate, lauric acid, One or more compounds selected from the group consisting of 3-methyl-1-butanol or isophorone), group c (ethyl pyruvate, ethyl acetoacetate, heliotropin, or benzyl benzoate) are orange juice It was found that the heat deterioration odor generated by heat deterioration can be effectively masked in beverages, apple juice drinks, grape juice drinks, grape juice containing jelly and strawberry juice containing jams. Further, it was confirmed that a good masking effect was exhibited even when orange flower oil (natural fragrance) containing linalool was used as a masking agent. In Experimental Examples 2 to 13, the range of evaluation points (difference between the maximum value and the minimum value) given by the paneler for the same sample is 0 or 1 for many samples, and 0 to 1 for all samples. It was in the range of 2.

Claims (5)

A heat-degrading odor masking agent for fruit juice-containing products, containing at least one compound selected from the group consisting of the following groups a to c;
(Group a) levulinic acid, linalool oxide, 2-acetylpyrrole, cinnamic acid, and γ-butyrolactone,
(Group b) Benzyl benzoate, benzyl lactate, gellanic acid, isophorone, cyclotenbutyrate, lauric acid, 3-methyl-1-butanol, menthol, and linalool,
(Group c) Heliotropin, ethyl pyruvate, ethyl acetoacetate, and benzyl benzoate. 2. The masking agent according to claim 1, wherein at least two of the compounds contained in the masking agent are compounds belonging to different groups in the groups a to c. A method for masking a heat-degraded odor of a fruit juice-containing product, comprising adding the masking agent according to claim 1 or 2 to the fruit juice-containing product. The manufacturing method of a fruit juice containing product including adding the masking agent of Claim 1 or 2 to a fruit juice containing product. A fruit juice-containing product containing the masking agent according to claim 1 or 2.