JPWO2019221221A1 - Chicken flavor improver - Google Patents

Abstract

An object of the present invention is to provide a chicken flavor improving agent having a flesh peculiar to chicken, which is useful as a flavor enhancing agent for various foods and drinks, seasonings and the like. The present invention is a chicken flavor improver containing an amino group-substituted aromatic ketone, preferably a chicken flavor improver in which the amino group-substituted aromatic ketone is an aromatic ketone having an amino group at the ortho or para position. More preferably, it relates to a chicken flavor improver in which the amino group-substituted aromatic ketone is ortho-aminoacetophenone.

Description

The present invention relates to a chicken flavor improving agent capable of imparting or enhancing a preferable chicken flesh to various foods.

Conventionally, as a material for improving the flavor of chicken, for example, (1) animal and plant extract, (2) yeast extract, (3) animal and plant protein hydrolyzate, (4) cooked flavor, (5) synthetic flavor and the like can be mentioned. A chicken flavor improver is prepared by appropriately combining one or more of these depending on the intended use (Non-Patent Document 1 (Patent Agency Gazette Well-known and Common Techniques [Fragrance] Part 2 Food Flavors 3.9. 4 Chicken flavor (issued January 14, 2000)). The characteristics required of the chicken flavor improver include the natural flavor and richness peculiar to chicken, the appetizing boiled flavor that is in harmony with the dish, the fried flavor and the roasted flavor, and the peculiar flesh of chicken. ..
Since yeast extract contains a relatively large amount of glutamic acid, which is an umami component, it is mainly used to supplement umami (Patent Document 1 (Japanese Unexamined Patent Publication No. 2005-102549) and Patent Document 2 (International Publication 99 /). See (Patent No. 16860)), and it is being considered to use it with the expectation that it will have an effect on the taste and flavor of meat. For example, Patent Document 3 (Pamphlet of International Publication No. 2008/081519) states that a yeast extract containing 8.0% or more of free amino acid composition can be applied for imparting sweetness peculiar to animal protein hydrolyzate. Is disclosed. However, these are intended to provide a taste component common to many animal foods, and cannot express the flesh peculiar to chicken.

On the other hand, aroma components that affect the richness and flavor of meat have been studied. For example, in Patent Document 4 (Japanese Unexamined Patent Publication No. 11-313635), as a seasoning capable of imparting richness to foods and drinks. , Pyrazine compounds, specifically 2-methylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, 2,3,5-trimethylpyrazine, tetramethylpyrazine, 2,5-diethylpyrazine, 2 , 6-Diethylpyrazine, 2,3-diethyl-5-methylpyrazine, 2-ethyl-3,5-dimethylpyrazine have been proposed as seasonings containing one or more compounds selected from. Further, in Patent Document 5 (Japanese Unexamined Patent Publication No. 2005-15683), as stronger and more preferable meat-based flavor compositions, (A) pyrroles, (B) pyridines, (C) pyrazines, and (D) oxazole , (E) Oxazolines, (F) Amines, (G) Thiazoles, (H) Thiazolins, (I) Thiazolidines, (J) Thiols, (K) Sulfides, (L) Thioethers, A meat-based flavor composition has been proposed, which comprises at least one fragrance selected from the group consisting of (M) sulfur-containing carboxylic acids, (N) quinoxazolines, and (O) furanones. .. However, these also give a flavor common to all meats, and cannot give a flesh peculiar to chicken.

In the preparation of chicken flavors using synthetic flavors, it is common to refer to the aroma analysis data of heat-treated chicken meat and chicken bones. Aroma analysis is usually performed by gas chromatography, and the analytical values are generally arranged in order of retention time or grouped by functional group. Therefore, a formulator who refers to the aroma analysis data often selects various synthetic fragrances with reference to the retention time or selects each functional group to start the formulation. However, it is rare that a chicken flavor prepared by reproducing quantitative analysis data of aroma components as it is can be used as a desired chicken flavor, and it is rare that a satisfactory flavor is obtained. A commonly used synthetic flavored chicken flavor is an image flavor in which a specific aroma component of chicken is found by aroma analysis and the characteristic aroma is emphasized and / or deformed. Therefore, the conventional chicken flavor can recognize the target chicken by using it together with the color and taste in the final product, and it has been possible to reproduce the preferable flesh of chicken only by the flavor. Absent.
As described above, in order to prepare a chicken flavor improver capable of imparting a favorable flesh, (1) animal and plant extract, (2) yeast extract, (3) animal and plant protein hydrolyzate, (4) cooked flavor and the like are used. Often composed of the main material. However, those made of these materials have a problem that the aroma and flavor intensity that can be imparted are not high. Therefore, new materials are desired in the preparation of flavor improvers that can impart a stronger and more favorable chicken flesh.

On the other hand, ortho-aminoacetophenone, which is an amino group-substituted aromatic ketone, is a known compound contained in grapes, wine, beer, corn tortilla, etc. It is known that it can be used as a flavor / flavor as described in Part 2 Food Flavors 3.9.4 Chicken Flavors (issued January 14, 2000). Further, as described in Non-Patent Document 2 (FOOD RESEARCH INTERRNATIONAL 2014, VOL62, 35-42), it has been reported that ortho-aminoacetophenone was detected in the fat of wild boar. Further, Non-Patent Document 3 discloses that ortho-aminoacetophenone is identified from a plant protein enzymatic decomposition product having a meat-like flavor, and that this compound is a compound having a grape-like sweet aroma. .. However, according to Non-Patent Document 3 (JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 2002, VOL50, 2900-2907), ortho-aminoacetophenone is used as a compound that causes undesired flavors in fermented tuna sauce and dairy products. Are listed. Further, Patent Document 6 (Pamphlet of International Publication No. 2017/202893) describes that 2-aminoacetophenone can be used in a beef flavor formulation.

As described above, a new material is desired in the preparation of a flavor improving agent capable of imparting a preferable chicken flesh. Therefore, an object of the present invention is to provide a chicken flavor improving agent having a flesh peculiar to chicken, which is useful as a flavor enhancing agent for various foods and drinks, seasonings and the like.

As a result of diligent studies to solve the above problems, the present inventors have made an amino group-substituted aromatic ketone, preferably an aromatic ketone in which the amino group-substituted aromatic ketone has an amino group at the ortho or para position, more preferably amino. The present invention has been completed by finding that a chicken flavor improver in which a group-substituted aromatic ketone contains ortho-aminoacetophenone is surprisingly excellent in the effect of imparting or enhancing the flesh peculiar to chicken.

That is, the present invention relates to the following [1] to [7].
[1] A chicken flavor improver containing an amino group-substituted aromatic ketone.
[2] The chicken flavor improving agent according to the above [1], wherein the amino group-substituted aromatic ketone is an aromatic ketone having an amino group at the ortho or para position.
[3] The chicken flavor improving agent according to the above [1], wherein the amino group-substituted aromatic ketone is ortho-aminoacetophenone.
[4] A method for producing a chicken flavored food, which comprises a step of adding the chicken flavor improving agent according to any one of the above [1] to [3] to the food for which the chicken flavor is to be improved.
[5] The above-mentioned [4], wherein the chicken flavor improving agent is added in an amount such that the concentration of the amino group-substituted aromatic ketone contained in the chicken flavored food for which the flavor is to be improved is 0.01 ppt to 100 ppt. How to make chicken flavored foods.
[6] A flavor composition containing the chicken flavor improving agent according to any one of [1] to [3] in an amount of 0.01 ppb to 100 ppb.
[7] A method for improving the flavor of chicken using an amino group-substituted aromatic ketone.

When the chicken flavor enhancer of the present invention is added to various foods and drinks, seasonings and the like, the flesh peculiar to chicken can be imparted or enhanced, and at the same time, the palatability can be improved.

（１）
（式中、ｎ₁は１〜３の整数を示し、ｎ₂は０〜２の整数を示す）
また、アミノ基置換芳香族ケトンは、オルトまたはパラ位にアミノ基を有することが好ましく、オルト−アミノアセトフェノンであることがより好ましい。
上記アミノ基置換芳香族ケトンは、天然物から抽出して得られたものを用いてもよいし、化学合成して得られたものを用いてもよいし、または天然物から得られたものと化学合成により得られたものを併用してもよい。<Chicken flavor improver>
The chicken flavor improving agent of the present invention contains an amino group-substituted aromatic ketone. In the present invention, the amino group-substituted aromatic ketone has, for example, the structure represented by the following formula (1).

(1)
(In the formula, n ₁ indicates an integer of _{1 to 3 and n 2} indicates an integer of 0 to 2)
Further, the amino group-substituted aromatic ketone preferably has an amino group at the ortho or para position, and more preferably ortho-aminoacetophenone.
As the amino group-substituted aromatic ketone, one obtained by extracting from a natural product may be used, one obtained by chemical synthesis may be used, or one obtained from a natural product. Those obtained by chemical synthesis may be used in combination.

The chicken flavor improving agent of the present invention can specifically further impart or enhance the flesh of chicken in foods and drinks having a chicken flavor. Here, the "chicken flesh" in the present specification refers to, for example, a firm and dry flesh in chicken breast, and is not juicy like chicken breast but firm like trimne meat. Means flavor. To further exemplify the "chicken flesh", it has a less greasy and tasty flavor like chicken breast rather than chicken breast, a protein-like taste like chicken breast or chicken breast, and becomes white when heated. The flavor of meat and the fibrous texture of chicken breast can be mentioned.
What is important here is that there have been no reports of amino group-substituted aromatic ketones such as ortho-aminoacetophenone being discovered in chicken, and it was not known that they could be used to impart or enhance the favorable sensation of chicken. It is a point. As mentioned above, for example, ortho-acetophenone itself is known as a compound having a sweet grape-like aroma, but its own aroma is not reminiscent of the flesh of chicken. Nevertheless, the chicken flavor improver containing an amino group-substituted aromatic ketone such as ortho-acetophenone according to the present invention balances the flavor and aroma of chicken meat, and makes the meat feel more like meat. It has a function to bring it closer to, and can improve the flavor of chicken.
Further, the "chicken flesh" is a flavor different from other types of flesh, for example, beef flesh. For example, "beef flesh" is required to have juiciness reminiscent of lean meat, moderate animal odor, and body sensation reminiscent of brown, and these are different types of flavors that are preferably required for "chicken flesh". It is a flavor. As described above, the sensation required for "flesh feeling" differs depending on the type of meat, and the chicken flavor improving agent of the present invention exerts an effect specially for imparting or enhancing the flesh feeling of chicken. It is something that can be done.

Further, in order to enhance the flesh of the chicken flavored food by the chicken flavor improving agent of the present invention, it is preferable that the chicken flavored food contains 2-methyl-3-franthiol. This is because the chicken flavor improving agent of the present invention gives a more preferable flesh and palatability to a chicken flavored food by a synergistic effect with 2-methyl-3-franthiol.
As will be described later, the chicken flavor improving agent may be contained in a liquid (flavor) composition, a solid (flavor) composition, etc., and added to foods or beverages in any dosage form depending on the purpose of use. It is possible. However, in the present invention, "ppt" means "mass ppt" regardless of the mode (for example, liquid or solid) of the composition containing the added food or the like and the chicken flavor improving agent. To do.

<Fragrance composition>
The flavor composition of the present invention refers to a composition containing the above-mentioned chicken flavor improving agent, which can improve the flavor of chicken and particularly impart or enhance the flesh of chicken. The flavor composition of the present invention is added to chicken-flavored foods and drinks to not only impart or enhance chicken flavor, especially chicken flesh, but also to various foods and drinks having no chicken flavor at all. It is possible to provide food and drink with a chicken flavor. The flavor composition may contain various flavor-imparting materials in addition to the chicken flavor improving agent. Examples of various taste materials include salts, sugars, acidulants, amino acids, nucleic acids, organic acids, sweeteners, bitterness agents, yeast extracts, animal and plant protein hydrolysates, and heat-reacted products thereof. Be done. In addition, the fragrance composition of the present invention may contain various natural and synthetic flavors and aroma components.
Further, the fragrance composition of the present invention may be in a liquid form or in a powder form (solid state), and the form thereof is not particularly limited. For example, the flavor composition comprises a suitable solvent for dissolving the chicken flavor improver, a flavor-imparting material, a flavor and aroma components, and the like, for example, water, ethyl alcohol, glycerin, propylene glycol, triacetin, and medium chain. Natural pigments, vitamins, and vegetable oils that can be dissolved in edible vegetable oils such as fatty acid glycerin ester or edible vegetable oils (eg rice salad oil) and edible animal fats and oils (eg chicken oil) and used in foods and drinks as needed. It may be in a liquid form to which resins or the like are added, or it may be in a powdery (solid) form containing excipients such as lactose, dextrin, arabic gum and cyclodextrin. Furthermore, the flavor composition of the present invention may be emulsified using various emulsifiers that can be used in foods and drinks, or may be in any dosage form such as paste, granules, microcapsules, etc. Can be prepared and used.
In addition, the flavor composition of the present invention contains the chicken flavor improving agent at a concentration of 0.01 ppb to 100 ppb, preferably 0.1 ppb to 50 ppb, and more preferably 1 ppb to 10 ppb. If the content of the chicken flavor improving agent in the flavor composition is less than 0.01 ppb, the effect is not sufficiently exhibited when added to food, and if it is more than 100 ppb, the flavor is different from the chicken flavor. It is not preferable to be. Further, in the flavor composition of the present invention, in order to provide a richer flesh to the added food and enhance the palatability, a chicken flavor improving agent and 2-methyl-3-franthiol are added. It is preferable to include it. The ratio of 2-methyl-3-franthiol to the chicken flavor improver is more preferably 10 to 10,000, and particularly preferably 100 to 1,000.
In addition, the flavor composition of the present invention further adds the chicken flavor improver of the present invention to a flavor package containing flavors and aroma components other than the chicken flavor improver prepared in advance to improve the chicken flavor. (Hereinafter, the composition is also referred to as a fragrance premix). The composition of the flavor premix can be appropriately adjusted according to the type of food to which it is added, but for reasons such as adding complexity to the flavor, the composition is derived from chicken such as chicken oil and chicken extract. It is preferable to use the above-mentioned food raw materials, and from the viewpoint of enhancing the palatability, it is preferable to contain flavors and aroma components such as spices, seasonings, roasted feelings and fried feelings.

Here, the flavor and aroma components that may be contained in the perfume composition of the present invention will be described in more detail. As such an ingredient, any commonly used fragrance such as an essential oil, a natural fragrance, or a synthetic fragrance can be used. Specifically, synthetic fragrances and natural fragrances such as esters, alcohols, aldehydes, ketones, acetals, phenols, ethers, lactones, furans, hydrocarbons, acids, sulfur-containing / nitrogen compounds, etc. And so on. These fragrances may be used alone, or may be a so-called mixed fragrance in which two or more kinds of fragrances are mixed.

Examples of the esters in the above synthetic fragrances include acrylic acid esters (methyl, ethyl, etc.), acetoacetic acid esters (methyl, ethyl, etc.), anis acid esters (methyl, ethyl, etc.), and benzoic acid esters (allyl, isoamyl, etc.). Ethyl, geranyl, linaryl, phenylethyl, hexyl, cis-3-hexenyl, benzyl, methyl, etc.), anthranyl ester (cinnamyl, cis-3-hexenyl, methyl, ethyl, linaryl, isobutyl, etc.), N-methylanthranyl acid Esters (methyl, ethyl, etc.), Isovaleric acid esters (Amil, allyl, isoamyl, isobutyl, isopropyl, ethyl, octyl, geranyl, cyclohexyl, citronellyl, terpenyl, linaryl, cinnamyl, phenylethyl, butyl, propyl, hexyl, benzyl, Methyl, rosinyl, etc.), Isobutyric acid esters (isoamyl, geranyl, citroneryl, terpenyl, cinnamyl, octyl, neryl, phenylethyl, phenylpropyl, phenixethyl, butyl, propyl, isopropyl, hexyl, benzyl, methyl, ethyl, linaryl, Loginyl, etc.), Undecylene acid ester (allyl, isoamyl, butyl, ethyl, methyl, etc.), Octanoic acid ester (allyl, isoamyl, ethyl, octyl, hexyl, butyl, methyl, linaryl, etc.), Octenoic acid ester (methyl, ethyl, etc.) Etc.), Octincarboxylic acid ester (methyl, ethyl, etc.), Caproic acid ester (allyl, amyl, isoamyl, methyl, ethyl, isobutyl, propyl, hexyl, cis-3-hexenyl, trans-2-hexenyl, linaryl, geranyl, etc.) Cyclohexyl, etc.), hexenoic acid ester (methyl, ethyl, etc.), valerate ester (amyl, isopropyl, isobutyl, ethyl, cis-3-hexenyl, trans-2-hexenyl, cinnamyl, phenylethyl, methyl, etc.), formic acid ester (, etc.) Anisyl, isoamyl, isopropyl, ethyl, octyl, geranyl, citronellyl, cinnamyl, cyclohexyl, terpinyl, phenylethyl, butyl, propyl, hexyl, cis-3-hexenyl, benzyl, linaryl, rosinyl, etc.), crotonic acid esters (isobutyl, ethyl) , Cyclohexyl, etc.),

Silica ester (allyl, ethyl, methyl, isopropyl, propyl, 3-phenylpropyl, benzyl, cyclohexyl, methyl, etc.), succinic acid ester (monomentyl, diethyl, dimethyl, etc.), acetate ester (anisyl, amyl, α-amylcinnamyl, etc.) , Isoamyl, isobutyl, isopropyl, isobornyl, isoeugenyl, eugenyl, 2-ethylbutyl, ethyl, 3-octyl, p-credyl, o-credyl, geranyl, α- or β-santalyl, cyclohexyl, cycloneryl, dihydrocuminyl, dimethylbenzyl Carvinyl, cinnamyl, styralyl, decyl, dodecyl, terpinyl, guainyl, neryl, nonyl, phenylethyl, phenylpropyl, butyl, furfuryl, propyl, hexyl, cis-3-hexenyl, trans-2-hexenyl, cis-3-nonenyl , Sis-6-nonenyl, cis-3, cis-6-nonazienyl, 3-methyl-2-butenyl, heptyl, benzyl, bornyl, myrsenyl, dihydromyrsenyl, myrtenyl, methyl, 2-methylbutyl, menthyl, linaryl, Loginyl, etc.), salicylates (allyl, isoamyl, phenyl, phenylethyl, benzyl, ethyl, methyl, etc.), cyclohexylalkanoic acid esters (ethylcyclohexylacetate, allylcyclohexylpropionate, allylcyclohexylbutyrate, allylcyclohexylsenoate, cyclohexyldecanoic acid) Allyl, allyl cyclohexyl valerate, etc.), stearic acid ester (ethyl, propyl, butyl, etc.), sebatic acid ester (diethyl, dimethyl, etc.), decanoic acid ester (isoamyl, ethyl, butyl, methyl, etc.), dodecanoic acid ester (isoamyl, etc.) , Ethyl, butyl, etc.),

Lactic acid ester (isoamyl, ethyl, butyl, etc.), nonanoic acid ester (ethyl, phenylethyl, methyl, etc.), nonenoic acid ester (allyl, ethyl, methyl, etc.), hydroxyhexanoic acid ester (ethyl, methyl, etc.), phenylacetic acid ester (Isoamyl, isobutyl, ethyl, geranyl, citronellyl, cis-3-hexenyl, methyl, etc.), phenoxyacetic acid ester (allyl, ethyl, methyl, etc.), furancarboxylic acid ester (ethyl furancarboxylate, methyl furancarboxylate, furancarbonate, etc.) Hexyl acid, isobutyl furanpropionate, etc.), propionate (anisyl, allyl, ethyl, amyl, isoamyl, propyl, butyl, isobutyl, isopropyl, benzyl, geranyl, cyclohexyl, citronellyl, cinnamyl, tetrahydrofurfuryl, tricyclodece Nyl, heptyl, bornyl, methyl, menthyl, linaryl, terpinyl, α-methylpropionyl, β-methylpropionyl, etc.), heptanic acid esters (allyl, ethyl, octyl, propyl, methyl, etc.), heptincarboxylic acid esters (allyl, Ethyl, propyl, methyl, etc.), myricitic acid ester (isopropyl, ethyl, methyl, etc.), phenylglycidate ester (ethyl phenylglycidate, ethyl 3-methylphenylglycidate, p-methyl-β-phenylglycid) Ethyl acid acid, etc.), 2-methylbutyric acid ester (methyl, ethyl, octyl, phenylethyl, butyl, hexyl, benzyl, etc.), 3-methylbutyric acid ester (methyl, ethyl, etc.), butyric acid ester (anicil, amyl, allyl, isoamyl, etc.) , Methyl, ethyl, propyl, octyl, guainyl, linaryl, geranyl, cyclohexyl, citronellyl, cinnamyl, neryl, terpenyl, phenylpropyl, β-phenylethyl, butyl, hexyl, cis-3-hexenyl, trans-2-hexenyl, benzyl , Loginyl, etc.), hydroxybutyric acid ester (methyl, ethyl, menthyl, etc. of 3-hydroxybutyric acid) and the like are used.

Examples of alcohols include aliphatic alcohols (isoamyl alcohol, 2-ethylhexanol, 1-octanol, 3-octanol, 1-octen-3-ol, 1-decanol, 1-dodecanol, 2,6-nonazienol, nonanol. , 2-Nonanol, cis-6-nonenol, trans-2, cis-6-nonadienol, cis-3, cis-6-nonazienol, butanol, hexanol, cis-3-hexenol, trans-2-hexenol, 1-undecanol , Heptanol, 2-heptanol, 3-methyl-1-pentanol, etc.), terpen alcohols (bornol, isobornol, carbeol, geraniol, α- or β-santalol, citronellol, 4-thyanol, terpineol, 4-terpineol, Nerol, Milsenol, Miltenol, Dihydromilsenol, Tetrahydromilsenol, Nerolidel, Hydroxycitronerol, Farnesol, Perilla alcohol, Loginol, Linarol, etc.), Aromatic alcohols (anis alcohol, α-amyl cinnamic alcohol, isopropyl pen) Zylcarbinol, carbachlor, cumin alcohol, dimethylpenzylcarbinol, synamic alcohol, phenylallyl alcohol, phenylethylcarbinol, β-phenylethyl alcohol, 3-phenylpropyl alcohol, penzyl alcohol, etc.) can be exemplified. ..

Examples of aldehydes include acetoaldehyde, n-hexanal, n-heptanal, n-octanal, n-nonanal, 2-methyloctanal, 3,5,5-trimethylhexanal, decanal, undecal and 2-methyldecalal. , Dodecanal, Tridecaneal, Tetradecaneal, Trans-2-hexenal, Trans-4-Desenal, Sis-4-Desenal, Trans-2-Desenal, 10-Undecenal, Trans-2-Undecenal, Trans-2-Dodecenal, 3-dodecenal, trans-2-trideceneal, 2,4-hexadienal, 2,4-decadienal, 2,4-dodecadienal, 5,9-dimethyl-4,8-decadienal, citral, dimethyloctanal, α- Methylene citroneral, citroneryl oxyacetaldehyde, myrutenal, neral, α- or β-sinensal, mylacaldehyde, phenylacetaldehyde, octanal dimethyl acetal, nonanal dimethyl acetal, decanal dimethyl acetal, decanal diethyl acetal, 2- Methylundecalal dimethyl acetal, citral dimethyl acetal, citral diethyl acetal, citral propylene glycol acetal, n-barrel aldehyde, isobarrel aldehyde, 2-methylbutanal, 2-pentenal, trans-2-heptenal, trans-2-nonenal, 2,6-dimethyl-5-peptenal, 2,4-undecadienal, trimethyldecadienal, citroneral, hydroxycitroneral, safranal, bernaldehyde, benzaldehyde, p-isopropylphenylacetaldehyde, p-methylhydrotropa Aldehyde, phenylpropionaldehyde, 2-methyl-3- (4-methylphenyl) propanal, cyclamenaldehyde, synamic aldehyde, salicylaldehyde, anisaldehyde, p-methylphenoxyacetaldehyde, acetaldehyde diethylacetal, citronellylmethylacetal, acetaldehyde 2-Phenyl-2,4-pentanediol acetylate, 2-hexenal diethylacetal, cis-3-hexenal diethylacetal, heptanaldiethylacetal, 2-hexyl-5-methyl-1,3-dioxolane, citronellarsi Examples thereof include clomonoglycol acetal, hydroxycitronellal dimethyl acetal, and phenylacetaldehyde dimethyl acetal.

Examples of the ketones include cyclic ketones (1-acetyl-3,3-dimethyl-1-cyclohexene, cis-jasmon, α-, β- or γ-iron, ethylmaltor, cycloten, dihydronutocatone, 3,4. -Dimethyl-1,2-cyclopentadione, α-, β-, γ- or δ- damascon, α-, β- or γ-damasenone, nutkaton, 2-sec-ptylcyclohexanone, maltor, α-, β- Or γ-yonone, α-, β- or γ-methylyonone, α-one, β- or γ-isomethylyonone, flaneol, kanfa, etc.), aromatic ketones (acetonaphthone, acetophenone, anicylideneacetone, raspberry ketone, p-methylacetophenone, Anisylacetone, p-methoxyacetophenone, etc.) Chain ketones (diacetyl, 2-nonanone, diacetyl, 2-hebutanone, 2,3-heptandione, 2-pentanone, methylamylketone, methylnonylketone, β-methylnaphthyl) Ketone, methylheptanone, 3-heptanone, 4-heptanone, 3-octanone, 2,3-hexanedione, 2-undecanone, dimethyloctenone, 61-methyl-5-heptin-3-one, etc.) ..

Examples of acetals include acetaldehyde diethyl acetal, acetaldehyde diamil acetal, acetaldehyde dihexyl acetal, acetaldehyde propiresiglycol acetal, acetaldehyde ethyl cis-3-hexenyl acetal, benzaldehyde glycerin acetal, benzaldehyde propylene glycol acetal, citral dimethyl acetal, and citral diethyl. Acetal, Citral Propropylene Glycol Acetal, Citral Ethylene Glycol Acetal, Phenylacetaldehyde Dimethyl Acetal, Citronellyl Methyl Acetal, Acetaldehyde phenylethylpropyl Acetal, Hexanal Dimethyl Acetal, Hexanal Dihexyl Acetal, Hexanal Proxyl Glycol Acetal, Trans-2-hexenal Diethyl Acetal -2-Hexenal propylene glycol acetal, cis-3-hexenal diethyl acetal, heptanal diethyl acetal, heptanal ethylene glycol acetal, octanal dimethyl acetal, nonanal dimethyl acetal, decanal dimethyl acetal, decanal diethyl acetal, 2-methyl Examples thereof include undecanal dimethyl acetal, citronellal dimethyl acetal, amber sage (manufactured by Givaudan), ethyl acetate ethylene glycol acetal and 2-phenylpropanal dimethyl acetal.

Examples of the phenols include eugenol, isoeugenol, 2-methoxy-4-vinylphenol, thymol, carvacrol, guaiacol and chabicol.

Examples of ethers include anetol, 1,4-cineole, dibenzyl ether, linalol oxide, limonene oxide, nerol oxide, rose oxide, methylisooigenol, methylchabicol, isoamylphenylethyl ether, β-naphthylmethyl ether. , Phenylpropyl ether, p-credyl methyl ether, vanillyl ptyl ether, α-terpinyl methyl ether, citronellyl ethyl ether, geranyl ethyl ether, rose furan, theaspirane, decyl methyl ether and methyl phenyl methyl ether. ..
Examples of lactones include γ- or δ-decalactone, γ-heptalactone, γ-nonalactone, γ- or δ-hexalactone, γ- or δ-octalactone, γ- or δ-undecalactone, δ-. Dodecalactone, δ-2-decenolactone, methyllactone, 5-hydroxy-8-undecenoic acid δ-lactone, jasmine lactone, mentalactone, dihydrocmarin, octahydrocmarin and 6-methylcoumarin and the like can be mentioned.

Examples of furans include furan, 2-methylfuran, 3-methylfuran, 2-ethylfuran, 2,5-diethyltetrafuran, 3-hydroxy-2-methyltetratransferase, 2- (methoxymethyl) furan, 2, 3-Dihydrofuran, furfuran, 5-methylfurfuran, 3- (2-furyl) -2-methyl-2-propenal, 5- (hydroxymethyl) furfuran, 2,5-dimethyl-4-hydroxy-3 (2H) -Franone (Franeol), 4,5-dimethyl-3-hydroxy-2 (5H) -Flanon (Sotron), 2-Ethyl-4-hydroxy-5-Methyl-3 (2H) -Flanon (Homofuranool), 5-Ethyl-3-hydroxy-4-methyl-2 (5H) furanone (homosotron), 3-methyl-2-hydroxycyclopentan-2-one (cycloten), 2 (5H) -furanone, 4-methyl-2 (5H) -furanone, 5-methyl-2 (5H) -furanone, 2-methyl-3 (2H) -furanone, 5-methyl-3 (2H) -furanone, 2-acetylfuranone, 2-acetyl-5- Examples include methylfuran, furfuryl alcohol, methyl 2-furancarboxylate, ethyl 2-furancarboxylate and frifryl acetate.

Hydrocarbons include, for example, α- or β-visaborene, β-caryophyllene, p-cymen, terpinene, terpinene, cadinene, farnesene, limonene, ocimene, myrcene, α- or β-pinene, 1,3,5-. Examples include Undecatorien and Valencene.
Examples of acids include acetic acid, propionic acid, butyric acid, isobutyric acid, 2-methylbutyric acid, valeric acid, isovaleric acid, caproic acid, enanthic acid, capric acid, pelargonic acid, capric acid, geranoic acid and dodecanoic acid. , Myristic acid, stearic acid, lactic acid, phenylacetic acid, pyruvate, trans-2-methyl-2-pentenoic acid, 2-methyl-cis-3-pentenoic acid, 2-methyl-4-pentenoic acid and cyclohexanecarboxylic acid, etc. Can be exemplified.
Examples of sulfur / nitrogen compounds include dimethyl disulfide, dimethyl sulfide, methyl 3- (methyl thio) propionate, ethyl 3- (methyl thio) propionate, limonene thiol, thioterpineol, thiogeraniol, 2-flufuryl disulfide, and 8-mercaptomentone. , 5-Methyl-2-thiophene carboxylaldehyde, furfuryl monosulfide, furfuryl mercaptan, methionol, methional, bis (2-furyl) sulfide or disulfide, 4,5-dihydro-3 (2H) thiophene, ethyl thioacetate, 3-Mercaptopropionic acid, allyl isothiocyanate, 2,6-dimethylthiophenol, ethyl 3- (furfurylthio) propionate, ethyl 4- (methylthio) butyrate, 3-methyl-1,2,4-trithian, 2-pentanthiol , 3,7-Dimethyl-2,6-nonadiennitrile, geranylnitrile, citronellylnitrile, tridecenenitrile, phenylmethylpentanonitrile, indol, 2-methyl-6-ethoxypyrazine, 2-isobutyl-3-methoxy Examples thereof include pyrazine, 4-methyl-5-thiazole ethanol or acetate and 4-methylthiazole.

<Chicken flavored food and its manufacturing method>
The chicken flavor improving agent or flavor composition of the present invention can be added to or sprinkled on foods and drinks to produce foods and drinks having enhanced chicken flavor, particularly flesh. The food or drink to which the chicken flavor improving agent or fragrance composition of the present invention is applied is not particularly limited, but is not limited to snacks such as potato chips, confectionery such as rice confectionery, and bakery products such as bread, biscuits, pretzels, and donut cakes. , Chicken meat paste products, seasoned seaweed, processed marine products such as Tokoten, dairy products such as butter and processed cheese, dried noodles such as soba, instant noodles, prepared foods, microwave foods, curry, pasta sauce and other retort foods, frozen foods , Instant foods such as cooked and processed foods, processed soybeans such as tofu, miso soup, buoy base, chowder, chicken soup, onion soup, santori hot water, acid hot water and other soups, seasonings such as margarine and mayonnaise, Examples include liquid seasonings such as dressings, soups, sauces, and ponzu, powdered seasonings such as flavor seasonings, sprinkles, and Ochazuke-no-moto, and foods such as tsukubuki, pickles, konjac, and delicacies.

In the present invention, the food and drink includes not only food and drink as it is, but also raw materials for food and drink. For example, some potato chips are given a chicken consomme taste by a consomme flavor, but by adding the chicken flavor improving agent or flavor composition of the present invention to the consomme flavor used as a raw material, this is used. It is possible to produce a flavor in which the flesh of chicken is enhanced in the produced product. Similarly, in the production of other foods and drinks, the chicken flavor improving agent or flavor composition of the present invention may be added to the raw materials of the foods and drinks and used, or the present invention may be used in the process of producing the foods and drinks. A chicken flavor improving agent or a flavor composition may be added, or it may be applied to the manufactured food or drink by adding or sprinkling it. As described above, the method of adding and applying the chicken flavor improving agent or flavor composition of the present invention is not particularly limited, and may be added by any known means. It may be added and mixed so that it is uniformly contained in the product, it may be applied so that it is contained only in a specific material of the product, or it may be sprinkled on the finished product.
The chicken flavor improving agent of the present invention is added to a chicken flavored food for which the flavor is to be improved so that the concentration is 0.01 ppt to 100 ppt, preferably 0.1 ppt to 50 ppt, and more preferably 1 ppt to 10 ppt. This is good. If the content of the chicken flavor improving agent is less than 0.01 ppt, the effect of enhancing the flesh is not sufficiently exhibited, and if it is more than 100 ppt, a flavor different from the chicken flavor may be imparted, so that the chicken flavor balance is balanced. It may be spoiled and the flavor may be spoiled.
Further, in order to enhance the flesh of the chicken flavored food by the chicken flavor improving agent of the present invention, it is preferable that the food or drink contains 2-methyl-3-franthiol. This is because the chicken flavor improving agent of the present invention can give a more preferable flesh and palatability to a chicken flavored food by a synergistic effect with 2-methyl-3-franthiol.

Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited thereto, and various changes and modifications are made without departing from the scope of the present invention. May be good. Unless otherwise specified, the units of the formulation described below mean "%" and "ppt", respectively, and the composition ratio represents the mass ratio.

In Examples and Comparative Examples, Knorr (registered trademark) chicken consomme (manufactured by Ajinomoto Co., Inc.) or Knorr (registered trademark) beef consomme (manufactured by Ajinomoto Co., Inc.) was added to hot water so as to have a concentration of 1.8% by mass. The melted soup (50-60 ° C.) was used as a chicken standard soup or a beef standard soup.
In Examples 1 to 3, Reference Examples 1 to 3 and Comparative Examples 1 to 3, the chicken standard soup or beef standard soup is referred to as "a flavor premix for chicken (composite system of a single flavor)" or "a composite system of a single flavor" described later. "Beef flavor premix (composite system of single flavor)" was added in an amount of 0.1% by mass, and sensory evaluation was performed by eight specialized panelists. Further, in Example 4 and Comparative Example 4, orthoacetophenone was added at a predetermined concentration (10 ppt) to the chicken standard soup and the beef standard soup, respectively, and sensory evaluation was performed by eight specialized panelists. The "control" in the sensory evaluation in a series of experiments is "a flavor premix for chicken (complex system of a single flavor)" that does not contain a flavor improver and "a flavor improver (orthoaminoacetophenone or methyl anthranilate)" that does not contain. The beef flavor premix (composite system of a single flavor) was added to the chicken standard soup and the beef standard soup by 0.1% by mass, respectively.
The “chicken flavoring premix” and the “beef flavoring premix” were prepared with the compositions shown in Table 1 below. In Table 1, the flavor improving agent was added in a predetermined amount to the chicken standard soup or the beef standard soup so as to have the concentrations shown in Tables 3 to 5 in the whole soup.
In Table 1, the composition of CK-1, which is a “chicken flavor premix”, and BF-1, which is a “beef flavor premix”, is different because CK-1 sets the optimum conditions for chicken. This is because the composition of BF-1 was obtained as a result of examining the conditions for beef corresponding to this optimum condition. Since chicken and beef originally have different flavors, it can be easily understood by those skilled in the art that the composition of the premix used as a base is different.

In addition, the sensory evaluation by eight specialized panelists was evaluated according to the criteria shown in Table 2 for the three evaluation targets of flesh, offensive odor, and palatability, and the average scores are shown in Tables 3 to 5. It was the evaluation result. In addition, in Tables 3 to 5, the standard deviation is also shown in order to support the small variation in each score of each specialized panelist.

In Tables 2 to 5, "flesh" in chicken is evaluated based on the image of proteininess and fibrousness (reminiscent of chicken breast and chicken breast), cooked chicken soup, and heated white meat. Was done. In addition, the "flesh feeling" in beef was evaluated based on the juiciness and moderate animal odor reminiscent of lean meat, the meat that turned brown when cooked, and the image of blood. Then, in Tables 3 to 5, those having an average sensation score of 4 or more are evaluated as A, those having an average sensation score of 3.5 or more and less than 4 are evaluated as B, and those having an average score of 3.0 or more and less than 3.5 are evaluated as C. 5 or more and less than 3.0 was evaluated as D, and less than 2.5 was evaluated as E.
In Tables 2 to 5, "unpleasant taste and offensive odor" is based on a flavor that brings about a flavor completely different from the original taste of chicken or beef, that is, a flavor that can bring about a negative factor with respect to the so-called expected taste. It was evaluated. Then, in Tables 3 to 5, those having an average score of less than 2.5 for off-flavors and off-flavors are evaluated as A, those with 2.5 or more and less than 3 are evaluated as B, and those with 3 or more and less than 3.5 are evaluated as C. .5 or more and less than 4 was evaluated as D, and 4 or more was evaluated as E.
In Tables 2 to 5, "preference" is not evaluated with an emphasis on the personal taste and taste of each specialized panelist, but whether or not it is generally preferable as the taste of chicken or beef. Evaluated on the basis. Then, in Tables 3 to 5, those having an average preference score of 4 or more are evaluated as A, those having a palatability of 3.5 or more and less than 4 are evaluated as B, and those having an average preference score of 3.0 or more and less than 3.5 are evaluated as C. A rating of 5.5 or more and less than 3.0 was given a D rating, and a rating of less than 2.5 was given an E rating.
Then, those having an evaluation of flesh feeling of any of A to C and an evaluation of off-flavor and off-flavor and palatability of A or B were accepted.

<Example 1>
Ortho-aminoacetophenone, which is an amine group-substituted aromatic ketone, was selected as the flavor improving agent. This flavor improving agent was contained in chicken CK-1, which is a flavor premix for chicken shown in Table 1, at a concentration of 10 ppb. Then, the CK-1 was added to the chicken standard soup at a concentration of 0.1% by mass, and a sensory evaluation was performed. Therefore, the soup of Example 1 contained 10 ppt of ortho-aminoacetophenone.
<Comparative example 1>
A sensory evaluation was carried out in the same manner as in Example 1 except that methyl anthranilate, which is an aroma component contained in grapes and jasmine and has a structure similar to that of ortho-aminoacetophenone, was selected as the flavor improving agent.
Table 3 shows the results of comparing Example 1 and Comparative Example 1. The controls in Table 3 are chicken CK-1, which does not contain a flavor improving agent, added to chicken standard soup at a concentration of 0.1% by mass.

As can be seen from Table 3, in the case of Example 1, the evaluation A was the most excellent in all of the flesh, the offensive odor, and the palatability. On the other hand, when methyl anthranilate, which has a structure similar to that of ortho-aminoacetophenone, is used as a flavor improving agent as in Comparative Example 1, almost no flesh is imparted, an offensive odor is strengthened, and the palatability is controlled. A completely different result from that of Example 1 was obtained.

<Example 2>
Ortho-aminoacetophenone, which is an amine group-substituted aromatic ketone, was selected as the flavor improving agent. This flavor improving agent was contained in chicken CK-1, which is a flavor premix for chicken shown in Table 1, at a concentration of 100 ppb. Then, the CK-1 was added to the chicken standard soup at a concentration of 0.1% by mass, and a sensory evaluation was performed. Therefore, the soup of Example 2 contained 100 ppt of ortho-aminoacetophenone.
<Example 3>
The same flavor improving agent as in Example 2 was contained in chicken CK-1, which is a flavor premix for chicken shown in Table 1, at a concentration of 0.01 ppb. Then, the CK-1 was added to the chicken standard soup at a concentration of 0.1% by mass, and a sensory evaluation was performed. Therefore, the soup of Example 3 contained 0.01 ppt of ortho-aminoacetophenone.

<Reference example 1>
The same flavor improving agent as in Example 2 was contained in chicken CK-1, which is a flavor premix for chicken shown in Table 1, at a concentration of 0.001 ppb. Then, the CK-1 was added to the chicken standard soup at a concentration of 0.1% by mass, and a sensory evaluation was performed. Therefore, the soup of Reference Example 1 contained 0.001 ppt of ortho-aminoacetophenone.
<Reference example 2>
The same flavor improving agent as in Example 2 was contained in chicken CK-1, which is a flavor premix for chicken shown in Table 1, at a concentration of 1,000 ppb. Then, the CK-1 was added to the chicken standard soup at a concentration of 0.1% by mass, and a sensory evaluation was performed. Therefore, the soup of Reference Example 2 contained 1,000 ppt of ortho-aminoacetophenone.
Table 4 shows the results of comparing Examples 1 to 3 with Reference Examples 1 and 2. The controls in Table 4 are chicken CK-1, which does not contain a flavor improving agent, added to chicken standard soup at a concentration of 0.1% by mass.

By comparing Examples 1 to 3 with Reference Examples 1 and 2 in Table 4, the flavor improving agent according to the present invention is preferably contained in the entire food in the range of 0.01 ppt to 100 ppt. Therefore, it was found that the palatability can be improved while improving the sensation of flesh. Further, as shown in Reference Example 2, not only the food containing the flavor improving agent according to the present invention at a high concentration does not necessarily improve the flesh, but also only the off-flavor and off-flavor are improved, and the palatability is remarkably lowered. I also found out.

<Comparative example 2>
Ortho-aminoacetophenone, which is an amine group-substituted aromatic ketone, was selected as the flavor improving agent. This flavor improving agent was contained in beef BF-1, which is a premix of beef flavors shown in Table 1, at a concentration of 10 ppb. Then, the BF-1 was added to the beef standard soup at a concentration of 0.1% by mass, and a sensory evaluation was performed. Therefore, the soup of Comparative Example 2 contained 10 ppt of ortho-aminoacetophenone.
<Comparative example 3>
The same flavor improving agent as in Comparative Example 2 was contained in beef BF-1, which is a premix of beef flavors shown in Table 1, at a concentration of 0.01 ppb. Then, the BF-1 was added to the beef standard soup at a concentration of 0.1% by mass, and a sensory evaluation was performed. Therefore, the soup of Comparative Example 3 contained 0.01 ppt of ortho-aminoacetophenone.

<Example 4>
Ortho-aminoacetophenone, which is an amine group-substituted aromatic ketone, was selected as a flavor improving agent, and this ortho-aminoacetophenone was added to a chicken standard soup to a concentration of 10 ppt (the soup of Example 4 was a fragrance pre-scented product). Does not include mix).
<Comparative example 4>
Ortho-aminoacetophenone, which is an amine group-substituted aromatic ketone, was selected as a flavor improving agent, and this ortho-aminoacetophenone was added to the beef standard soup at a concentration of 10 ppt (the soup of Comparative Example 4 was a fragrance pre. Does not include mix).

<Reference example 3>
The same flavor improving agent as in Example 2 was contained in chicken CK-2, which is a flavor premix for chicken shown in Table 1, at a concentration of 10 ppb. Then, the CK-2 was added to the chicken standard soup at a concentration of 0.1% by mass, and a sensory evaluation was performed. Therefore, the soup of Reference Example 3 contained chicken CK-2 and 10 ppt of ortho-aminoacetophenone.

Table 5 shows the results of comparing Examples 1 and 3 with Comparative Examples 2 and 3, and Example 4 with Comparative Example 4 and Reference Example 3. In addition, control 1 in Table 5 is chicken CK-1 containing no flavor improving agent added to chicken standard soup at a concentration of 0.1% by mass, and control 2 is beef containing no flavor improving agent. BF-1 is added to beef standard soup at a concentration of 0.1% by mass.

Comparing Examples 1 and 3 with Comparative Examples 2 and 3, respectively, in the results of Table 5, the flavor improving agent according to the present invention can greatly improve the flesh of chicken, but has almost an effect on the flesh of beef. It turned out that it could not exert. Furthermore, in Comparative Examples 2 and 3, it was shown that the palatability could be lowered more than the control, and it was found that the flavor improving agent according to the present invention could specifically affect the flesh of chicken among meats. Chicken.
Further, when comparing Example 4 and Comparative Example 4, it was found that the flavor improving agent according to the present invention can give a higher evaluation to chicken even when the flavor premix is not used. Further, comparing Example 4 and Reference Example 3, even when the fragrance premix is used, if it is not in an appropriate composition, the fragrance premix is not used in Example 4. Was found to be able to give a higher rating.
Further, in Table 5, by comparing Example 1 and Reference Example 3, the flesh and palatability were remarkably improved by using 2-methyl-3-franthiol and the flavor improving agent according to the present invention in combination. I found out that I would do it.

Claims (7)

A chicken flavor improver containing an amino group-substituted aromatic ketone. The chicken flavor improving agent according to claim 1, wherein the amino group-substituted aromatic ketone is an aromatic ketone having an amino group at the ortho or para position. The chicken flavor improving agent according to claim 1, wherein the amino group-substituted aromatic ketone is ortho-aminoacetophenone. A method for producing a chicken-flavored food, which comprises a step of adding the chicken flavor-improving agent according to any one of claims 1 to 3 to a food for which the chicken flavor is to be improved. The chicken flavor improving agent according to claim 4, wherein the chicken flavor improving agent is added in an amount such that the concentration of the amino group-substituted aromatic ketone contained in the chicken flavored food for which the flavor is to be improved is 0.01 ppt to 100 ppt. Production method. A flavor composition containing the chicken flavor improving agent according to any one of claims 1 to 3 in an amount of 0.01 ppb to 100 ppb. A method for improving the flavor of chicken using an amino group-substituted aromatic ketone.