JP7292971B2 - Fish surimi degradation odor masking agent - Google Patents

Description

TECHNICAL FIELD The present invention relates to a fish surimi deterioration odor masking agent and a method for using the same. More particularly, the present invention relates to a fish surimi deterioration odor masking agent, a method for masking fish surimi deterioration odor using the masking agent, a fish surimi product containing the masking agent, and a method for producing the fish surimi product.

Fish surimi, which is made by grinding the meat of seafood (fish meat), has been consumed not only in Japan but also in countries around the world against the background of health consciousness. However, surimi of fish with reduced freshness has a problem in that it has a strong odor (off-flavour) compared to surimi using fish with high freshness, and thus has a lower commercial value.

For this reason, various methods have conventionally been proposed for masking the off-flavours of fish meat or fish paste. Specifically, a method of adding monk fruit extract (Patent Document 1), a method of using a furanone derivative having a specific structure as an additive (Patent Document 2), a method of using shallot and / or onion extract (Patent Document 3) A method of immersing whole fish and shellfish meat in a mixed aqueous solution of salt water and tea (including tea dry distillation components or tea extraction components) has been proposed (Patent Document 4).

However, it is not easy to mask off-flavours with a strong fishy odor, and development of a new, more effective masking method has been desired.

JP 2012-223138 Special table 2010-528673 JP 2004-357648 JP 2003-334035 Japanese Patent Laid-Open No. 07-000151

An object of the present invention is to provide a novel masking agent for the deterioration odor of minced fish in view of the 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 minced fish product, and a minced fish product obtained by the production method. In the present invention, in the product obtained by using minced fish as at least a part of the raw material, the odor that occurs as the freshness of the fish meat declines and requires masking is collectively referred to as the odor of deteriorated minced fish. The fish surimi deteriorated odor is typically caused by products using second-grade frozen pollock surimi described in paragraph [0006] of Patent Document 5 (Japanese Patent Application Laid-Open No. 07-000151) shown in the examples of the present application. However, in the present invention, the fish surimi deterioration odor includes the same odors as described above originating from fish and shellfish surimi other than walleye pollock.

Under such circumstances, the present inventors, as a result of intensive studies, identified components that constitute the fish surimi deterioration odor. Based on this, the present inventors identified a masking agent component that was not known to have a masking effect on the degraded odor of fish surimi. Furthermore, the present inventors have confirmed that these masking agent components have the effect of masking the degraded odor of minced fish in minced fish products, and have completed the present invention.

Accordingly, the present invention provides the following terms:
Section 1. A fish surimi degradation odor masking agent containing at least one compound selected from the group consisting of Groups A to C below;
(Group A) 2-pentanone, 1,1-diethoxyethane, and β-damascenone (Group B) isoamyl lactate, 1,4-cineole, and hexyl butyrate (Group C) linalyl acetate, methyl laurate, butyl nonanoate , and geranyl propionate.

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 in the groups A to C.

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 C.

Section 4. Item 4. A method for masking the deterioration odor of ground fish, comprising adding the masking agent according to any one of items 1 to 3 to a ground fish product.

Item 5. Item 4. A method for producing a fish paste product, comprising adding the masking agent according to any one of items 1 to 3 to the fish paste product.

Item 6. A fish surimi product containing the masking agent according to any one of Items 1 to 3.

According to the present invention, there are provided a novel masking agent for fish surimi deterioration odor in a fish surimi product, a novel masking method using the novel masking agent, a method for producing a surimi product, and a surimi fish product obtained by the production method. be able to.

In the present invention, "suppressing the deterioration odor of minced fish" or "masking the deteriorated odor of minced fish" means that the masking compound of the present invention is added to the composition having the deteriorated odor of minced fish. It means that the fish surimi deteriorated odor is reduced or eliminated compared to before the addition of the masking compound. Moreover, the present invention can also be applied to a composition that develops the fish surimi degraded odor over time or by a predetermined treatment such as heating. It means that the addition of the compound suppresses (reduces) the deterioration odor of the minced fish even after a predetermined treatment (heating, storage, etc.) compared to when the masking compound is not added. .

As used herein, the phrase "includes" or the phrase "contains" is intended to encompass the phrase "consisting of" and the phrase "consisting only of".

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.
The fish paste products targeted by the present invention include a wide range of general foods that use fish paste as at least a part of the raw material, and examples thereof include boiled fish paste, fish paste, fish paste, fish sausage, and the like. Therefore, fish paste products in the present invention include fish paste products. Fish paste products also include crab-flavored kamaboko, scallop-flavored kamaboko, lobster-flavored kamaboko, and the like. Seafood used as raw materials for producing surimi is not particularly limited, but examples include walleye pollock, atka mackerel, golden threadbream, sea bream, horse mackerel, white-winged pollack, crocodile, lizardfish, hairtail, conger eel, squid, sea bass, kiss, abalone, and barracuda. , tilefish, flounder, goby, mullet, salmon, shrimp, and sharks. Among these, fish are preferable, and walleye pollack, atka mackerel, golden threadbream, sea bream, horse mackerel, white-ganed pollack and the like are more preferable.

As described in the examples below, the present inventors have identified the major odorants in the fish surimi degraded odor of surimi products related to the present invention.
Briefly, the present inventors have determined that the main odorants that make up the fish surimi deterioration odor of fish surimi products are (1) a fish surimi product using special-grade frozen surimi as a raw material (standard product) and a relatively low-freshness fish surimi product. Analyze the odor components of fish surimi products (deteriorated odor products) using second-grade frozen surimi as raw materials by solid-phase microextraction-gas chromatograph mass spectrometry (hereinafter abbreviated as SPME-GC-MS). and (2) among the odor components increased in the deteriorated odor product compared to the standard product, the main substances constituting the deteriorated odor were identified. In the above description, the special grade frozen surimi and the second grade frozen surimi refer to surimi equivalent to that described in paragraph number [0006] of Patent Document 5 (JP-A-07-000151).

Suitable examples of such primary odorants include trimethylamine, (Z)-4-heptenal, dimethyltrisulfide.

The masking agent for the degraded odor of fish surimi of the present invention (which may be referred to herein as a "masking agent") is a compound selected from the group consisting of Groups A to C below (in this specification, this may be referred to as a masking agent compound.) as an active ingredient;
(Group A) 2-pentanone, 1,1-diethoxyethane, and β-damascenone (Group B) isoamyl lactate, 1,4-cineole, and hexyl butyrate (Group C) linalyl acetate, methyl laurate, butyl nonanoate , and geranyl propionate.

All of the compounds of Groups A to C are known fragrance 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: 2-pentanone-containing natural flavors such as coffee flavor; 1,1-diethoxyethane-containing natural flavors such as Joryu Natural fragrances containing β-damascenone, such as rose fragrances; Natural fragrances containing isoamyl lactate, such as Joryush fragrances; Natural fragrances containing 1,4-cineol, such as lime fragrances Natural flavors containing hexyl butyrate, such as yuzu flavor; Natural flavors containing linalyl acetate, such as clary sage flavor and bergamot flavor; Natural flavors containing methyl laurate, such as vanilla flavor; Nonanoic acid Examples of natural flavors containing butyl include cherry flavor, and examples of natural flavors containing geranyl propionate include wormwood flavor and hop flavor.

2-pentanone, 1,1-diethoxyethane, and β-damascenone, which are the compounds described in Group A, are compounds that function effectively as masking agents for degraded odors of fish surimi. It effectively functions as a masking agent for trimethylamine, which is one of the main odorous substances of the deteriorated surimi odor. Therefore, when a compound belonging to Group A is used, the masking agent of the present invention can be used to mask the odor of deteriorated fish surimi by suppressing the odor caused by trimethylamine. In a preferred embodiment of the invention 1,1-diethoxyethane may be used. These compounds described in Group A can be used singly or in combination of two or more.

Isoamyl lactate, 1,4-cineole, and hexyl butyrate, which are the compounds described in Group B, are compounds that each effectively function as a masking agent for the fish surimi deterioration odor, and in particular, the fish surimi deterioration odor masking agent. It functions effectively as a masking agent for (Z)-4-heptenal, one of the major odorants. Therefore, when a compound belonging to Group B is used, the masking agent of the present invention can be used to mask the odor of deteriorated fish surimi by suppressing the odor caused by (Z)-4-heptenal. In a preferred embodiment of the present invention, at least one selected from the group consisting of isoamyl lactate and hexyl butyrate can be used. These compounds described in Group B can be used singly or in combination of two or more.

The compounds described in Group C, linalyl acetate, methyl laurate, butyl nonanoate, and geranyl propionate, are compounds that each function effectively as a masking agent for the deterioration odor of fish surimi. It effectively functions as a masking agent for dimethyltrisulfide, which is one of the major odorous substances of deterioration odor. Therefore, when a compound belonging to Group C is used, the masking agent of the present invention can be used to mask the deterioration odor of fish surimi by suppressing the odor caused by dimethyltrisulfide. Incidentally, dimethyltrisulfide is an odorant that has not been known as a constituent of the deteriorated odor of minced fish. In a preferred embodiment of the present invention, at least one selected from the group consisting of linalyl acetate and methyl laurate can be used. These compounds described in Group C can be used singly or in combination of two or more.

The masking agent of the present invention is one or two compounds selected from the group consisting of Groups A to C (that is, a compound group including all compounds belonging to Group A, compounds belonging to Group B, and compounds belonging to Group C). It is characterized by containing more than seeds. In the present invention, "two or more compounds selected from the group consisting of Groups A to C" 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 (two or more in total) each selected from two or more groups of Groups A to C,
It is particularly preferable to use a combination of one or more compounds (three or more in total) each selected from all groups A to C.

In its preferred embodiment, the masking agent of the present invention comprises one or more (preferably two or more, more preferably all three) of the three odorants of trimethylamine, (Z)-4-heptenal and dimethyltrisulfide. contains a masking agent compound that has a masking effect on In some preferred embodiments of the present invention, the masking agent of the present invention is characterized in that the fish surimi deterioration odor is caused by at least one selected from the group consisting of trimethylamine, (Z)-4-heptenal and dimethyltrisulfide. At least one type (preferably at least two types, more preferably three types) selected from the above group, which are odors and mask the fish surimi deterioration odor.

The amount of the masking compound used in the present invention (for example, the content of the masking agent of the present invention in the fish surimi product) may be any amount as long as it exhibits the effect of masking the fish surimi deterioration odor. The concentration for the entire surimi product is
It is preferable to use within the range of 0.00001 ppm to 50 ppm,
It is more preferably used within the range of 0.0001 ppm to 10 ppm, and more preferably within the range of 0.001 ppm to 5 ppm.
From the viewpoint of obtaining a sufficient masking effect on the deteriorated fish surimi odor and suppressing the aroma and/or taste of the masking agent compound itself from undesirably affecting the aroma and/or taste of the fish surimi product, the above range is is preferred.

In the present invention, the total mass (or total concentration) of each group of compounds in Groups A to C 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., trimethylamine for compounds described in Group A, (Z)-4-heptenal for compounds described in Group B, and dimethyltrisulfide for compounds described in Group C) for example, a ratio in the range of 1:10000 to 10000:1, a ratio in the range of 1:1000 to 1000:1, a ratio in the range of 1:500 to 500:1, a ratio of 1:100 to 100:1 A ratio within the range, a ratio within the range of 1:50 to 50:1, or a ratio within the range of 1:10 to 10:1 is preferred.

In the present invention, by using one or more compounds selected from the group consisting of Groups A to C, the fish surimi deterioration odor possessed by fish surimi products (manufacturing, distribution, storage, and (Including degraded odor of minced fish produced at each stage of sales, etc.) can be easily and safely masked without affecting the aroma and/or taste of the final product.

The masking agent of the present invention may contain compounds other than the masking agent compound. The form of the 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 masking agent of the present invention.

The masking agent of the present invention may consist of the masking agent compound alone, or may contain a suitable diluent (thickener) or carrier in addition to the masking agent compound. In this case, the ratio of the masking agent compound in the masking agent is appropriately from the range of 0.00000001 to 99% by mass (0.0001 to 990000 ppm) so that the masking agent exhibits the effect of suppressing the fish surimi deterioration odor. Settings can be adjusted.

The diluent or carrier used in combination with the masking agent compound is not particularly limited as long as it does not impair the inhibitory effect of the masking agent compound on the deterioration odor of minced fish. Examples include solid diluents or carriers such as gum arabic, dextrin, cyclodextrin, glucose and sucrose; Carriers can be mentioned. These diluents or carriers may contain additives such as excipients, binders, disintegrants, emulsifiers, solubilizers, and thickeners used to prepare the masking agent of the present invention into a desired shape (dosage form). Viscous agents, lubricants, flavoring agents, coloring agents, and the like are included. Among them, emulsifiers can be suitably used to disperse the masking agent compound in a liquid diluent to prepare an aqueous solution (dispersion, suspension) or emulsion 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 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 masking agent of the present invention can be appropriately set according to the type and shape of the object to suppress the deterioration odor of minced fish.

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

The masking agent of the present invention may be a perfume composition containing one or two or more masking agent compounds described above as perfume components, or one or two or more masking agent compounds in addition to the masking agent compound. A perfume composition containing other perfume ingredients (fragrance ingredients other than the masking agent compound) may be used.

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 flavor of the minced fish product containing the masking agent. preferable. 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. Perfume, synthetic perfume and the like 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/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.) (pp. 837-907) 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 0.00000001 to 99% by mass of one or more of the above masking agent compounds 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 0.00000001 to 99% by mass, preferably 0.0000001 to 0.0000001. A ratio of 10% by mass can be exemplified.

The timing and method of adding or applying the masking agent of the present invention or a formulation containing it to the surimi product is not particularly limited, and it may be added or applied at any stage during the production of the surimi product.
For example, after previously adding or applying the masking agent of the present invention or a preparation containing the masking agent of the present invention to a raw material of a fish surimi product, the masking agent of the present invention is added or applied to the fish surimi product, whereby the masking agent of the present invention is applied to the fish surimi product. May be added or applied to the product.

The masking agent of the present invention can also be used for fish paste products containing various food materials commonly used in fish paste products.
Examples of such food materials include sugars, sweeteners, seasonings, thickeners, emulsifiers, vitamins, milk, dairy products, oils and fats, acidulants, marine extracts, flavors, protein hydrolysates, soybean proteins, Examples include starch, dextrin, glycerin, eggs, and pigments.
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;
Seasonings such as salt, soy sauce, mirin, vinegar, amino acids, and nucleic acids;
thickening agents 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 such as palm oil and coconut oil;
Acidulants such as citric acid, malic acid, tartaric acid, and lactic acid;
marine extracts such as crab extract and shrimp extract;
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 minced fish product of the present invention, the method for producing the minced fish product of the present invention, and the minced fish product of the present invention are described in the above masking agent for the minced fish product of the present invention. etc.

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 Components of Deterioration Odor of Fish Surimi According to the procedure described below, main odorants in the odor of deterioration of fish surimi products were identified.

<Preparation of product containing fish paste>
70 parts of special grade frozen surimi (Alaska pollock surimi) was placed in a cutter and roughly ground, then salt ground while adding 1 part of salt, ice was added and finish grinding was performed, and the product was ground to a final product temperature of 8°C. A standard product was obtained by filling the ground surimi in an impermeable casing and heating (after sitting at 40°C for 20 minutes, room temperature (around 25°C) for 30 minutes, boiling at 90°C for 40 minutes). A degraded odor product was obtained in the same manner as described above, except that second grade frozen surimi (walleye pollock surimi) was used in place of the special grade frozen surimi. The compositions of the standard product and the deteriorated odor product are shown in Table 1 below.

<Identification of major odorants of fish surimi deterioration odor>
The aroma of the standard product and the deteriorated odor product was analyzed by solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS), and the difference in odorants due to the difference in fish surimi grade was measured.

<Solid-phase microextraction conditions>
Weigh 3 g of the sample into a 20 mL headspace vial, adsorb the aromatic components for 30 minutes at room temperature by solid-phase microextraction (SPME), desorb at the GC injection port (250 ° C.), and perform GC-MS measurement. rice field.
SPME fiber: Sigma-Aldrich film thickness 65 μm, adsorbent divinylbenzene-dispersed polydimethylsiloxane (PDMS-DVB).

<GC-MS analysis conditions>
GC: Agilent Technologies 7890A GC
MS: Agilent Technologies 5975C Inert XL MSD
Capillary column: Agilent Technologies DB-WAX length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm
Temperature program: Hold at 50° C. for 2 minutes, then increase temperature from 50 to 220° C. at 3° C./minute Carrier gas: Helium.

<Analysis results>
Compared to the standard product, the peak areas of the deteriorated odor product were twice as large for trimethylamine, 1.5 times for (Z)-4-heptenal, and twice as large for dimethyltrisulfide.
From the above results, the deteriorated odor product using frozen surimi (second grade) contains more trimethylamine, (Z)-4-heptenal, and dimethyltrisulfide than the standard product using frozen surimi (special grade). It turned out to be

Experimental Example 2 Verification of fish surimi deterioration odor <Preparation of product containing fish surimi deterioration odor (preparation of simulated deterioration odor product)>
70 parts of special-grade frozen surimi was placed in a cutter and roughly ground, salt-ground while adding 1 part of salt, ice was added and finish-grinding was performed, and the mixture was ground to a final product temperature of 8°C.
After adding and mixing the degraded odor liquid having the composition shown in Table 3 below, the mixture is filled into a non-air-permeable casing and heated (after sitting at 40°C for 20 minutes, room temperature (around 25°C) for 30 minutes, boiling at 90°C for 40 minutes). By doing so, a product with a pseudo-deteriorated odor was obtained. Table 2 below shows the composition of the simulated deterioration odor products.

<Sensory evaluation of pseudo-deteriorated odor product>
Using the deteriorated odor product prepared in Experimental Example 1 as a standard sample, seven panelists well trained in sensory evaluation of odor evaluated the odor of the simulated deteriorated odor product prepared above according to the following evaluation criteria:
<Evaluation Criteria>
Equivalent odor to deteriorated odor product: 5 points Odor similar to deteriorated odor product: 4 points Mixed odor similar to deteriorated odor product and different odor: 3 points Different odor from deteriorated odor product Yes: 2 points Odor completely different from deteriorated odor product: 1 point <Evaluation result>
The average score was 4.0.
The result of the above evaluation of the off-flavor-containing simulated beverage (average value of 7 people) was 4.0, and the three main odorants successfully reproduced an odor equivalent to the deteriorated odor of fish paste. I was sure that.

Experimental Example 3 Masking Effect of Group A Compounds on Trimethylamine To 950 g of deionized water, 50 g of soy protein powder (Fujipro-CL manufactured by Fuji Oil Co., Ltd.) was added and stirred to prepare a 5% soy protein solution. A solution of trimethylamine dissolved in 95% ethanol was added to the 5% soy protein solution so that the concentration of trimethylamine was 5 ppm. A group A compound (2-pentanone, 1,1-diethoxyethane or β-damascenone) was dissolved in 95% ethanol in the solution thus prepared. Each was added so as to obtain a medium amount.
In the sensory evaluation, the soybean protein solution containing 5 ppm of trimethylamine was evaluated as "strongly feeling the odor of trimethylamine: 4 points", and the soybean protein solution was evaluated as "not feeling the odor of trimethylamine at all: 0 points". The following evaluation criteria were set, and five panelists (skill level of the panelists is the same as above/same hereafter) performed by assigning evaluation points. The average rating points are shown in Table 4:
<Evaluation Criteria>
Strong trimethylamine odor: 4 points Trimethylamine odor is sensed: 3 points Trimethylamine odor is sensed slightly: 2 points Trimethylamine odor is hardly sensed: 1 point Trimethylamine odor is not sensed at all: 0 points <Evaluation of Group A compounds>

<Evaluation of added concentration of Group A compound (1,1-diethoxyethane)>
Also, the relationship between the concentration of the group A compound relative to trimethylamine and the masking effect was examined.
1,1-diethoxyethane was added to the soybean protein solution having a trimethylamine concentration of 5 ppm so as to have the concentration shown in Table 5, and the relationship between the amount of 1,1-diethoxyethane and the masking effect on trimethylamine was examined. was evaluated by the same method as described above. Table 5 shows the evaluation results.

From the above results, it was found that the masking effect of the group A compounds tended to increase as the ratio of the concentration of the masking agent compound to the concentration of the odorant approached 0.1 to 0.2.

Experimental Example 4 Masking effect of group B compounds on (Z)-4-heptenal A solution of (Z)-4-heptenal dissolved in 95% ethanol was ionized so that the concentration of (Z)-4-heptenal was 2 ppb. Added to exchanged water. A group B compound (isoamyl lactate, 1,4-cineol or hexyl butyrate) was dissolved in 95% ethanol in the aqueous solution thus prepared, and the concentration of each compound was the amount shown in Table 6. were added respectively.
In the sensory evaluation, the ion-exchanged water containing the (Z)-4-heptenal concentration of 2 ppb was evaluated as "strongly smelling (Z)-4-heptenal", and the ion-exchanged water was evaluated as "trimethylamine odor. Absolutely no feeling: 0 points”, and the following evaluation criteria were set, and evaluation was performed by five panelists. The average rating points are shown in Table 6:
<Evaluation Criteria>
(Z) -4-heptenal smell strongly: 4 points (Z) -4-heptenal smell: 3 points (Z) -4-heptenal smell slightly: 2 points (Z) -4-heptenal smell Hardly sensed: 1 point (Z)-4-heptenal odor not sensed at all: 0 points <Evaluation of Group B compounds>

<Evaluation of addition concentration of group B compound (isoamyl lactate)>
In addition, the relationship between the concentration of group B compounds for (Z)-4-heptenal and the masking effect was examined.
Isoamyl lactate was added to the above aqueous solution with a (Z)-4-heptenal concentration of 2 ppb so as to have the concentration shown in Table 7, and the relationship between the amount of isoamyl lactate and the masking effect on (Z)-4-heptenal. was evaluated by the same method as described above. Table 7 shows the evaluation results.

From the above results, it was found that the compounds of group B exhibited a good masking effect on (Z)-4-heptenal.

Experimental Example 5 Masking Effect of Group C Compound on Dimethyltrisulfide A solution of dimethyltrisulfide dissolved in 95% ethanol was added to deionized water so that the concentration of dimethyltrisulfide was 2 ppb. In the aqueous solution thus prepared, a solution was prepared by dissolving each of the C group compounds (linalyl acetate, methyl laurate, butyl nonanoate or geranyl propionate) in 95% ethanol, and the concentration of each compound was as shown in Table 8. Each was added so that the amount of
In the sensory evaluation, the ion-exchanged water containing 2 ppb of dimethyltrisulfide was evaluated as "strongly smelling dimethyltrisulfide: 4 points", and the ion-exchanged water was evaluated as "not smelling dimethyltrisulfide at all: The following evaluation criteria were set as "0 point", and evaluation points were given by five panelists. The average rating points are shown in Table 8:
<Evaluation Criteria>
Strong odor of dimethyltrisulfide: 4 points Smell of dimethyltrisulfide: 3 points Slight odor of dimethyltrisulfide: 2 points Almost no odor of dimethyltrisulfide: 1 point No odor of dimethyltrisulfide: 0 Points <Evaluation of Group C compounds>

<Evaluation of added concentration of group C compound (methyl laurate)>
In addition, the relationship between the concentration of the group C compound for dimethyltrisulfide and the masking effect was examined.
Methyl laurate was added to the aqueous solution having a dimethyltrisulfide concentration of 2 ppb so as to have the concentration shown in Table 9, and the relationship between the amount of methyl laurate and the masking effect on dimethyltrisulfide was evaluated in the same manner as described above. evaluated by the method. Table 9 shows the evaluation results.

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 100-250.

Experimental Example 6 Masking effect in fish paste product <Preparation of fish paste product>
A "standard product" and a "deteriorated odor product" were prepared in the same manner as in "Experimental Example 1 Identification of Degraded Odor Components of Fish Surimi". A "masking agent additive" was prepared according to the following procedure:
70 parts of second-grade frozen surimi was placed in a cutter and roughly ground, salted while adding 1 part of salt, ice was added, and the ground was finished to a final product temperature of 8°C. After adding and mixing the masking agent solution described later, the non-air-permeable casing is filled and heated (after sitting at 40 ° C. for 20 minutes, room temperature (around 25 ° C.) for 30 minutes, boiling at 90 ° C. for 40 minutes). Additives” were obtained. The composition of each fish paste product is shown in Table 10 below.

<Preparation of masking agent solution>
Based on the weight of the fish paste product after adding the masking agent solution, the masking agent component was dissolved in 95% ethanol so that the amount (ppm) of the masking agent component added was as shown in Table 11 below. A masking agent solution” was prepared.

<Sensory evaluation>
In the sensory evaluation, the evaluation of the same odor as the deteriorated odor product was "strongly sensed deterioration odor: 4 points", and the evaluation equivalent to the standard product was defined as "no deterioration odor: 0 points". Evaluation criteria were set, and seven panelists (skill level of the panelists is the same as above/same hereafter) performed by assigning evaluation points. The average rating points are shown in Table 11:
<Evaluation Criteria>
Strong smell of deterioration: 4 points Slightly strong smell of deterioration: 3 points Feeling of deterioration smell: 2 points Slight deterioration smell: 1 point No deterioration smell: 0 points

Experimental Example 7 Masking effect in kamaboko products <Preparation of kamaboko products>
A kamaboko product was prepared by the method described in steps (1) to (7) below. The raw materials indicated by alphanumeric characters in each step mean the raw materials of the types and mass parts described with the corresponding alphanumeric characters in Table 12.
(1) Add the raw material 1a to the cutter and grind it roughly.
(2) Ingredient 2 is added to the ground surimi ground in step (1) and salted.
(3) 1/3 of the mass of raw material 12 shown in Table 12 is added to the ground surimi salted in step (2) and ground.
(4) Ingredient 3 is added to the surimi ground in step (3), and ground further.
(5) Ingredients 6 to 10 and 12, which is 1/3 of the mass shown in Table 12, are added to the surimi ground in step (4), and ground.
(6) Ingredients 4, 5, and remaining 12 are added to the ground surimi ground in step (5), and ground to a final product temperature of 8°C.
(7) After adding raw material 11 to the surimi ground in step (6) and mixing, fill the non-air-permeable casing, heat (after sitting at 40 ° C. for 20 minutes, room temperature (around 25 ° C.) for 30 minutes, boil at 90 ° C. 40 minutes) to obtain a kamaboko product containing a masking agent.

A kamaboko product with a deteriorated odor was obtained according to the method described in steps (1) to (7) above, except that raw material 11 (masking agent solution) was not added.

In addition, according to the method described in the above steps (1) to (7), except that frozen surimi (special grade) is used instead of frozen surimi (second grade) and raw material 11 (masking agent solution) is not added, the standard product A kamaboko product was obtained.

The masking agent solution is prepared by dissolving the masking agent component in 95% ethanol so that the amount (ppm) of the masking agent component added is shown in Table 13 below, based on the weight after addition of the masking agent solution. (masking agent solutions 1 and 2) were prepared.

<Sensory evaluation>
For the sensory evaluation, the following evaluation criteria are set, with the evaluation of the same odor as the above-mentioned deteriorated odor product as "strong deterioration odor: 4 points" and the standard product as "no deterioration odor: 0 points". , and evaluation points were given by seven panelists. The average rating points are shown in Table 13:
<Evaluation Criteria>
Strong smell of deterioration: 4 points Slightly strong smell of deterioration: 3 points Feeling of deterioration smell: 2 points Slight deterioration smell: 1 point No deterioration smell: 0 points

From the results in Tables 11 and 13, it was found that the masking compounds belonging to Groups A to C above can effectively mask the odor of deterioration of minced fish. In Experimental Examples 2 to 7 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 (5)

A masking agent for the odor of deterioration of fish surimi containing at least two compounds selected from the following groups A to C , wherein at least two of the compounds contained in the masking agent are selected from the group A A fish surimi deterioration odor masking agent, which is a compound belonging to a different group in Group C ;
(Group A) 2-pentanone, 1,1-diethoxyethane, and β-damascenone (Group B) isoamyl lactate, 1,4-cineole, and hexyl butyrate (Group C) linalyl acetate, methyl laurate, butyl nonanoate , and geranyl propionate. 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 C. 3. A method for masking fish surimi deterioration odor, comprising adding the masking agent according to claim 1 or 2 to a fish surimi product. A method for producing a surimi fish product, comprising adding the masking agent according to claim 1 or 2 to a surimi fish product. A fish surimi product containing the masking agent according to claim 1 or 2 .