JP5825787B2 - Amino acid degradation odor prevention agent - Google Patents
Amino acid degradation odor prevention agent Download PDFInfo
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- JP5825787B2 JP5825787B2 JP2010540391A JP2010540391A JP5825787B2 JP 5825787 B2 JP5825787 B2 JP 5825787B2 JP 2010540391 A JP2010540391 A JP 2010540391A JP 2010540391 A JP2010540391 A JP 2010540391A JP 5825787 B2 JP5825787 B2 JP 5825787B2
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
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- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
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- A23L33/17—Amino acids, peptides or proteins
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
- A23L5/27—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption
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Description
本発明は，アミノ酸劣化臭防止剤，アミノ酸含有飲食品及び劣化臭防止方法に関する。より詳しく説明すると，本発明は，所定の短分子エステル化合物を有効成分として含有するアミノ酸劣化臭防止剤，そのアミノ酸劣化臭防止剤を有効量で含むアミノ酸含有飲食品，及び劣化臭防止方法に関する。 The present invention relates to an amino acid degradation odor inhibitor, an amino acid-containing food and drink, and a degradation odor prevention method. More specifically, the present invention relates to an amino acid degradation odor inhibitor containing a predetermined short molecular ester compound as an active ingredient, an amino acid-containing food / beverage product containing the amino acid degradation odor inhibitor in an effective amount, and a degradation odor prevention method.
アミノ酸は，たとえば，栄養成分を強化する目的で飲食品や医薬品に添加されていた。そして，近年，アミノ酸が，疲労回復，筋力強化，成長補助，免疫力増加，美肌促進，及び脂質代謝調節などの機能を有することが明らかになった。これにより，アミノ酸含有飲食品の開発が進められている。 For example, amino acids have been added to foods and drinks and pharmaceuticals for the purpose of strengthening nutritional components. In recent years, it has been clarified that amino acids have functions such as recovery from fatigue, strength strengthening, growth support, increased immunity, promotion of beautiful skin, and regulation of lipid metabolism. As a result, the development of foods and drinks containing amino acids is being promoted.
しかしながら，アミノ酸含有飲食品は，殺菌時や保存中に，アミノ酸特有の風味が劣化臭として発現する場合がある。この劣化臭を抑制するために，いくつかの提案がなされている。 However, in amino acid-containing foods and drinks, a flavor peculiar to amino acids may appear as a deteriorated odor during sterilization or storage. Several proposals have been made to suppress this deterioration odor.
たとえば，特開２０００−４８３６号公報（下記特許文献１）には，酸味料でｐＨを調製した後，非還元糖および甘味料で風味を整えるアミノ酸含有食品の製造法が開示されている。 For example, JP 2000-4836 A (Patent Document 1 below) discloses a method for producing an amino acid-containing food in which the pH is adjusted with an acidulant and then the flavor is adjusted with a non-reducing sugar and a sweetener.
また，特開２００５−３３６０７８号公報（下記特許文献２）には，分岐アミノ酸または分岐アミノ酸を含むペプチドにステビア抽出物を配合して劣化臭をマスキングする方法が開示されている。 Japanese Patent Laid-Open No. 2005-336078 (Patent Document 2 below) discloses a method of masking a deteriorated odor by adding a stevia extract to a branched amino acid or a peptide containing a branched amino acid.
さらに，特開２００７−１８５１６９号公報（下記特許文献３）には，アミノ酸含有食品のメチオニン含量に対して，スレオニン含量が１０倍以上の重量含有比となるように調整し，非還元糖を特定量で配合する方法が開示されている。 Furthermore, JP 2007-185169 A (Patent Document 3 below) specifies a non-reducing sugar by adjusting the threonine content to a weight content ratio of 10 times or more with respect to the methionine content of amino acid-containing foods. A method of blending in quantities is disclosed.
一方，香料を配合することで，アミノ酸の劣化臭を抑制する方法も提案されている。このような方法として，たとえば，特開平２−１２８６７０号公報（下記特許文献４）には，苦味を有するアミノ酸にハーブ系又はフルーツ系の香料を配合する方法が開示されている。 On the other hand, a method for suppressing the deterioration odor of amino acids by blending a fragrance has also been proposed. As such a method, for example, Japanese Patent Application Laid-Open No. 2-128670 (the following Patent Document 4) discloses a method of blending an amino acid having a bitter taste with a herb-based or fruit-based fragrance.
また，特開２００３−２３５５１２号公報（下記特許文献５）には，アミノ酸を含む主原料に果物系フレーバー，チョコレートフレーバー，ミルクフレーバー，ティーフレーバー又はバニラフレーバーを配合する方法が開示されている。 Japanese Patent Laid-Open No. 2003-235512 (Patent Document 5 below) discloses a method of blending a fruit-based flavor, chocolate flavor, milk flavor, tea flavor or vanilla flavor with a main raw material containing amino acids.
さらに，特開２００５−８２４８８号公報（下記特許文献６）には，アミノ酸と，カルボン又はサリチル酸メチルとを配合した口腔用組成物が開示されている。 Furthermore, Japanese Unexamined Patent Application Publication No. 2005-82488 (Patent Document 6 below) discloses an oral composition in which an amino acid and carvone or methyl salicylate are blended.
しかしながら，上記のアミノ酸の劣化臭を防止する方法は，いずれも効果が十分ではなかった。 However, none of the methods for preventing the above-mentioned degradation odors of amino acids was effective.
本発明は，アミノ酸の劣化臭を効果的に防止できるアミノ酸劣化臭防止剤を提供することを目的とする。 An object of the present invention is to provide an amino acid degradation odor inhibitor that can effectively prevent the degradation odor of amino acids.
また，本発明は，アミノ酸の劣化臭を効果的に防止できるアミノ酸含有飲食品を提供することを目的とする。 Moreover, an object of this invention is to provide the amino acid containing food / beverage products which can prevent the degradation odor of an amino acid effectively.
さらに，本発明は，アミノ酸の劣化臭を効果的に防止できる劣化臭防止方法を提供することを目的とする。 Furthermore, this invention aims at providing the degradation odor prevention method which can prevent the degradation odor of an amino acid effectively.
本発明は，基本的には，所定の低分子エステル化合物を用いることで，アミノ酸の劣化臭を効果的に防止できるという知見に基づくものである。 The present invention is basically based on the knowledge that the use of a predetermined low molecular weight ester compound can effectively prevent the deterioration odor of amino acids.
本発明の第１の側面は，下記式（Ｉ）で示されるエステル化合物（本発明のエステル化合物）を有効成分として含有するアミノ酸の劣化臭防止剤に関する。
Ｒ１がメチル基の場合，
Ｒ２は，Ｃ４〜Ｃ７アルケニル基であり，
Ｒ１がエチル基の場合，
Ｒ２は，Ｃ２〜Ｃ３アルキル基であるか，又はＣ４〜Ｃ７アルケニル基である。）The 1st side surface of this invention is related with the degradation odor prevention agent of the amino acid which contains the ester compound (ester compound of this invention) shown by following formula (I) as an active ingredient.
When R 1 is a methyl group,
R 2 is a C 4 to C 7 alkenyl group,
When R 1 is an ethyl group,
R 2 is a C 2 -C 3 alkyl group or a C 4 -C 7 alkenyl group. )
後述する実施例により実証されたとおり，所定の低分子エステル化合物を配合することで，アミノ酸の劣化臭を効果的に防止することができた。すなわち，上記のエステル化合物は，アミノ酸の劣化臭を防止するために有効に用いることができる。 As demonstrated by the examples described later, the deterioration odor of amino acids could be effectively prevented by blending a predetermined low molecular weight ester compound. That is, the above ester compound can be used effectively in order to prevent the deterioration odor of amino acids.
また，実施例により実証されたとおり，本発明のエステル化合物として好ましいものは，式（Ｉ）において，
Ｒ１がメチル基の場合，
Ｒ２は，シス体のＣ５〜Ｃ７アルケニル基であり，
Ｒ１がエチル基の場合，
Ｒ２は，Ｃ２〜Ｃ３アルキル基であるか，又はシス体のＣ５〜Ｃ７アルケニル基である。Also, as demonstrated by the examples, preferred as the ester compounds of the present invention are those represented by the formula (I):
When R 1 is a methyl group,
R 2 is a cis-C 5 -C 7 alkenyl group,
When R 1 is an ethyl group,
R 2 is a C 2 to C 3 alkyl group or a cis isomer of a C 5 to C 7 alkenyl group.
なお，後述する実施例によりアミノ酸の劣化臭を防止することが実証された化合物は，「エチル ブチレート，エチル プロピオネート，メチル ２−ヘキセノエート，エチル ２−ヘキセノエート，メチル ３−ヘキセノエート，エチル ３−ヘキセノエート，メチル ２−オクテノエート，エチル ２−オクテノエート，メチル ３−オクテノエート，およびエチル ３−オクテノエート」である。よって，これらのエステル化合物からなる群から選択される１種のエステル化合物又は２種以上の混合物は，アミノ酸の劣化臭防止剤として確実に有効である。 In addition, the compounds that have been demonstrated to prevent the degradation odor of amino acids in the examples described later are “ethyl butyrate, ethyl propionate, methyl 2-hexenoate, ethyl 2-hexenoate, methyl 3-hexenoate, ethyl 3-hexenoate, methyl 2-octenoate, ethyl 2-octenoate, methyl 3-octenoate, and ethyl 3-octenoate ”. Therefore, one type of ester compound selected from the group consisting of these ester compounds or a mixture of two or more types is surely effective as a deodorizing agent for amino acids.
なお，後述する実施例により実証されたとおり，本発明のエステル化合物は，メチオニン，イソロイシン，ロイシン，フェニルアラニンおよびトリプトファン由来の劣化臭を効果的に防止できる。 In addition, as demonstrated by the examples described later, the ester compound of the present invention can effectively prevent a deterioration odor derived from methionine, isoleucine, leucine, phenylalanine and tryptophan.
本発明の第２の側面は，アミノ酸を含有するアミノ酸含有飲食品に関する。そして，アミノ酸は，アミノ酸含有飲食品に，１重量％以上で含まれる。また，このアミノ酸含有飲食品は，本発明のエステル化合物を０．１ｐｐｍ以上２００ｐｐｍ以下で含有する。 The 2nd side surface of this invention is related with the amino acid containing food / beverage products containing an amino acid. The amino acid is contained in the amino acid-containing food or drink at 1% by weight or more. Moreover, this amino acid containing food / beverage products contain the ester compound of this invention in 0.1 ppm or more and 200 ppm or less.
本発明の第２の側面の好ましい態様は，アミノ酸含有飲料，又はアミノ酸含有ゼリー飲料に関する。 A preferred embodiment of the second aspect of the present invention relates to an amino acid-containing beverage or an amino acid-containing jelly beverage.
本発明の第３の側面は，本発明のエステル化合物を添加する工程を含む，アミノ酸含有飲食品の劣化臭防止方法に関する。本発明のエステル化合物をアミノ酸含有飲食品の製造工程において添加してもよいし，製造されたアミノ酸含有飲食品にエステル化合物を添加してもよい。 The 3rd side surface of this invention is related with the degradation odor prevention method of amino acid containing food / beverage products including the process of adding the ester compound of this invention. The ester compound of this invention may be added in the manufacturing process of amino acid containing food / beverage products, and an ester compound may be added to the manufactured amino acid containing food / beverage products.
本発明によれば，本発明のエステル化合物を有効成分として含有することで，アミノ酸の劣化臭を効果的に防止できるアミノ酸劣化臭防止剤を提供できる。 ADVANTAGE OF THE INVENTION According to this invention, the amino acid degradation odor inhibitor which can prevent the degradation odor of an amino acid effectively can be provided by containing the ester compound of this invention as an active ingredient.
また，本発明によれば，有効量のアミノ酸劣化臭防止剤を有効成分として含有することで，アミノ酸の劣化臭を効果的に防止できるアミノ酸含有飲食品を提供できる。 Moreover, according to this invention, the amino acid containing food-drinks which can prevent the degradation odor of an amino acid effectively can be provided by containing an effective amount of an amino acid degradation odor prevention agent as an active ingredient.
さらに，本発明によれば，本発明のエステル化合物を有効量で添加することで，アミノ酸の劣化臭を効果的に防止できる劣化臭防止方法を提供できる。 Furthermore, according to this invention, the degradation odor prevention method which can prevent the degradation odor of an amino acid effectively can be provided by adding the ester compound of this invention in an effective amount.
以下，発明を実施するための最良の形態について説明する。 The best mode for carrying out the invention will be described below.
本発明の第１の側面は，下記式（Ｉ）で示されるエステル化合物（本発明のエステル化合物）を有効成分として含有するアミノ酸の劣化臭防止剤に関する。
Ｒ１がメチル基の場合，
Ｒ２は，Ｃ４〜Ｃ７アルケニル基であり，
Ｒ１がエチル基の場合，
Ｒ２は，Ｃ２〜Ｃ３アルキル基であるか，又はＣ４〜Ｃ７アルケニル基である。）The 1st side surface of this invention is related with the degradation odor prevention agent of the amino acid which contains the ester compound (ester compound of this invention) shown by following formula (I) as an active ingredient.
When R 1 is a methyl group,
R 2 is a C 4 to C 7 alkenyl group,
When R 1 is an ethyl group,
R 2 is a C 2 -C 3 alkyl group or a C 4 -C 7 alkenyl group. )
上記式（Ｉ）に含まれるエステル化合物は，全て低分子エステル化合物である。そして，これらの低分子エステル化合物は，公知であり，市販されている。よって，本発明のエステル化合物自体は，市販されているものを購入することができる。 All the ester compounds contained in the above formula (I) are low molecular weight ester compounds. These low molecular ester compounds are known and are commercially available. Therefore, the ester compound of the present invention can be purchased commercially.
Ｃ４〜Ｃ７アルケニル基とは，炭素数が４個以上７個以下のアルケニル基を意味する。Ｃ４〜Ｃ７アルケニル基には，二重結合が２つのジアルケニル基も含まれる。しかしながら，実施例において実証されたとおり，Ｃ４〜Ｃ７アルケニル基として二重結合が１つ含まれる（モノ）アルケニル基が好ましい。さらに，Ｃ４〜Ｃ７アルケニル基には，分枝したＣ４〜Ｃ７アルケニル基も含まれる。しかしながら，実施例において実証されたとおり，Ｃ４〜Ｃ７アルケニル基は，直鎖のＣ４〜Ｃ７アルケニル基が好ましい。アルケニル基は二重結合を有するため，シス体とトランス体が存在する。実施例において実証されたとおり，アルケニル基の中では，シス体が好ましい。さらに，実施例において実証されたとおり，本発明のエステル化合物におけるＣ４〜Ｃ７アルケニル基は，Ｃ５〜Ｃ７アルケニル基が好ましい。The C 4 to C 7 alkenyl group means an alkenyl group having 4 to 7 carbon atoms. C 4 -C 7 alkenyl groups also include dialkenyl groups with two double bonds. However, as demonstrated in the examples, (mono) alkenyl groups containing one double bond as the C 4 -C 7 alkenyl group are preferred. In addition, the C 4 -C 7 alkenyl group, C 4 -C 7 alkenyl groups branched also included. However, as demonstrated in Example, C 4 -C 7 alkenyl groups, C 4 -C 7 alkenyl group is preferably linear. Since an alkenyl group has a double bond, there are cis and trans forms. As demonstrated in the examples, among the alkenyl groups, the cis isomer is preferred. Furthermore, as demonstrated in the examples, the C 4 to C 7 alkenyl group in the ester compound of the present invention is preferably a C 5 to C 7 alkenyl group.
Ｃ２〜Ｃ３アルキル基とは，炭素数が２個又は３個のアルキル基を意味する。具体的な，Ｃ２〜Ｃ３アルキル基は，エチル基，又はプロピル基である。The C 2 -C 3 alkyl group, carbon number means a two or three alkyl groups. A specific C 2 -C 3 alkyl group is an ethyl group or a propyl group.
本発明のエステル化合物の例は，「エチル ブチレート，エチル プロピオネート，メチル ２−ヘキセノエート，エチル ２−ヘキセノエート，メチル ３−ヘキセノエート，エチル ３−ヘキセノエート，メチル ２−オクテノエート，エチル ２−オクテノエート，メチル ３−オクテノエート，およびエチル ３−オクテノエート」である。 Examples of ester compounds of the present invention are “ethyl butyrate, ethyl propionate, methyl 2-hexenoate, ethyl 2-hexenoate, methyl 3-hexenoate, ethyl 3-hexenoate, methyl 2-octenoate, ethyl 2-octenoate, methyl 3-octenoate. , And ethyl 3-octenoate ".
アミノ酸の劣化臭防止剤とは，アミノ酸含有食品などにおけるアミノ酸の殺菌時，保存時，又は経時変化により発生するアミノ酸特有の劣化臭を防止するための剤を意味する。 An amino acid degradation odor preventive agent means an agent for preventing amino acid-specific degradation odors caused by sterilization, storage, or change over time of amino acids in foods containing amino acids.
本発明のアミノ酸の劣化臭防止剤は，上記のとおり本発明のエステルを，アミノ酸の劣化臭を防止するための有効成分として含有する。本発明のアミノ酸の劣化臭防止剤は，本発明のエステルそのものであってもよいし，公知の希釈剤，又は担体を含んだ組成物であってもよい。本発明のアミノ酸の劣化臭防止剤は，希釈剤，及び担体以外にも公知の成分を含んでもよい。本発明のアミノ酸の劣化臭防止剤の剤型として，公知の剤型を適宜採用できる。剤型の例は，液剤，錠剤，粉末剤，顆粒剤，ペースト状の剤型，乳液状の剤型，及びゼリー状の剤型である。 As described above, the amino acid degradation odor inhibitor of the present invention contains the ester of the present invention as an active ingredient for preventing the degradation odor of amino acids. The degradation odor preventing agent for amino acids of the present invention may be the ester of the present invention, or a composition containing a known diluent or carrier. The amino acid degradation odor preventive agent of the present invention may contain known components in addition to the diluent and the carrier. As the dosage form of the amino acid degradation odor preventing agent of the present invention, known dosage forms can be appropriately employed. Examples of dosage forms are liquids, tablets, powders, granules, pastes, emulsions, and jellys.
希釈剤の例は，水，エタノール，プロピレングリコール，グリセリン，及び界面活性剤である。担体の例は，アラビアガム，デキストリン，グルコース，シクロデキストリン，及びスクロースである。 Examples of diluents are water, ethanol, propylene glycol, glycerin, and surfactants. Examples of carriers are gum arabic, dextrin, glucose, cyclodextrin, and sucrose.
アミノ酸特有の劣化臭は，アミノ酸と糖類との相互作用によって引き起こされるアミノカルボニル反応に起因すると考えられる。したがって，本発明のアミノ酸の劣化臭防止剤は，アミノ酸と糖類が存在するアミノ酸含有飲食品におけるアミノ酸の劣化臭を防止するために，効果的に用いることができる。後述する実施例により実証されたとおり，本発明のエステル化合物は，メチオニン，イソロイシン，ロイシン，フェニルアラニンおよびトリプトファン由来の劣化臭を効果的に防止できる。これらのアミノ酸は，特に劣化臭の原因となると考えられる。このため，本発明のアミノ酸の劣化臭防止剤は，これらのアミノ酸を含有するアミノ酸含有飲食品におけるアミノ酸の劣化臭を防止するために有効に利用されうる。 Deterioration odor peculiar to amino acids is thought to be caused by aminocarbonyl reaction caused by the interaction between amino acids and sugars. Therefore, the degradation odor preventing agent for amino acids of the present invention can be effectively used to prevent the degradation odor of amino acids in an amino acid-containing food or drink containing amino acids and saccharides. As demonstrated by the examples described later, the ester compound of the present invention can effectively prevent the deterioration odor derived from methionine, isoleucine, leucine, phenylalanine and tryptophan. These amino acids are thought to cause a particularly deteriorated odor. For this reason, the deterioration odor preventing agent for amino acids of the present invention can be effectively used to prevent the deterioration odor of amino acids in an amino acid-containing food or drink containing these amino acids.
本発明の第２の側面は，アミノ酸を含有するアミノ酸含有飲食品に関する。アミノ酸含有飲食品とは，アミノ酸が所定量以上で含まれる飲食品を意味する。アミノ酸含有飲食品の例は，アミノ酸成分を添加して，アミノ酸の含有量を高めた飲食物である。具体的なアミノ酸含有飲食品の例は，飲料，ゼリー飲料，ゼリー，食品である。好ましいアミノ酸含有飲食品は，アミノ酸含有飲料，又はアミノ酸含有ゼリー飲料である。アミノ酸含有飲食品におけるアミノ酸は，遊離アミノ酸やアミノ酸の塩であってもよい。アミノ酸の塩の例は，ナトリウム塩，塩酸塩，および酢酸塩である。 The 2nd side surface of this invention is related with the amino acid containing food / beverage products containing an amino acid. An amino acid-containing food or drink means a food or drink containing an amino acid in a predetermined amount or more. The example of an amino acid containing food / beverage is food / beverage which added the amino acid component and raised content of an amino acid. Specific examples of amino acid-containing foods and beverages are beverages, jelly beverages, jelly, and foods. A preferred amino acid-containing food or drink is an amino acid-containing beverage or an amino acid-containing jelly beverage. The amino acid in the amino acid-containing food or drink may be a free amino acid or an amino acid salt. Examples of amino acid salts are sodium, hydrochloride, and acetate.
本発明におけるアミノ酸含有飲食品は，アミノ酸を１重量％以上で含む。なお，アミノ酸がアミノ酸含有飲食品に１．５重量％以上で含有されるものは，特にアミノ酸由来の劣化臭が生じ易い。このため，本発明のアミノ酸含有飲食品として，アミノ酸がアミノ酸含有飲食品に１．５重量％以上で含有されるものである場合，アミノ酸の有益な機能を享受しつつ，アミノ酸の劣化臭を防止できるため特に好ましい。なお，メチオニン，イソロイシン，ロイシン，フェニルアラニンおよびトリプトファンの合計量が，アミノ酸含有飲食品の１重量％以上（好ましくは１．５重量％以上）で含まれる場合，本発明のアミノ酸含有食品は，効果的にアミノ酸の劣化臭を防止できる。 The amino acid-containing food / beverage products in the present invention contain 1% by weight or more of amino acids. In addition, when the amino acid is contained in the amino acid-containing food or drink at 1.5% by weight or more, a deteriorated odor derived from the amino acid is particularly likely to occur. For this reason, as an amino acid-containing food / beverage product of the present invention, when the amino acid is contained in the amino acid-containing food / beverage product by 1.5% by weight or more, the amino acid-containing food / beverage product enjoys the beneficial function of the amino acid and prevents the amino acid from deteriorating odor. This is particularly preferable because it can be performed. In addition, when the total amount of methionine, isoleucine, leucine, phenylalanine and tryptophan is contained in 1% by weight or more (preferably 1.5% by weight or more) of the amino acid-containing food or drink, the amino acid-containing food of the present invention is effective. In addition, the degradation odor of amino acids can be prevented.
本発明のアミノ酸含有飲食品は，本発明のエステル化合物を０．１ｐｐｍ以上２００ｐｐｍ以下で含有する。本発明のエステル化合物が０．１ｐｐｍ未満ではアミノ酸含有飲食品の劣化臭を十分に抑制することができない。一方，本発明のエステル化合物を，２００ｐｐｍを越えて配合すると，エステル化合物の香気が強くなりすぎてアミノ酸含有飲食品の風味に悪影響を及ぼす。なお，本発明のエステル化合物の好ましい含有量は，本発明のアミノ酸含有飲食品中に１ｐｐｍ以上１００ｐｐｍ以下である。また，本発明のエステル化合物をアミノ酸含有飲食品に配合する方法は，特に限定されない。本発明のエステル化合物をアミノ酸含有飲食品に配合する方法の例は，原材料を混合する際に本発明のエステル化合物を添加する方法；および原材料を混合し，殺菌した後，本発明のエステル化合物を添加する方法があげられる。 The amino acid-containing food or drink of the present invention contains the ester compound of the present invention at 0.1 ppm or more and 200 ppm or less. If the ester compound of the present invention is less than 0.1 ppm, the deterioration odor of the amino acid-containing food or drink cannot be sufficiently suppressed. On the other hand, when the ester compound of the present invention is blended in excess of 200 ppm, the aroma of the ester compound becomes too strong and adversely affects the flavor of the amino acid-containing food or drink. In addition, the preferable content of the ester compound of this invention is 1 ppm or more and 100 ppm or less in the amino acid containing food / beverage products of this invention. Moreover, the method of mix | blending the ester compound of this invention with an amino acid containing food / beverage products is not specifically limited. An example of a method of blending the ester compound of the present invention into an amino acid-containing food or drink is a method of adding the ester compound of the present invention when mixing raw materials; and, after mixing and sterilizing the raw materials, The method of adding is mention | raise | lifted.
本発明のアミノ酸含有飲食品には，アミノ酸含有飲食品の風味に悪影響を及ぼさない範囲で香料を配合してもよい。 You may mix | blend a fragrance | flavor with the amino acid containing food / beverage products of this invention in the range which does not have a bad influence on the flavor of amino acid containing food / beverage products.
アミノ酸含有飲食品は，必要に応じて，飲食品で通常使用されている糖類，甘味料，酸味料，着色料，保存剤，防かび剤，酸化防止剤，増粘安定剤，乳化剤，ゲル化剤を配合してもよい。 Amino acid-containing foods and drinks are sugars, sweeteners, acidulants, colorants, preservatives, fungicides, antioxidants, thickening stabilizers, emulsifiers, and gels that are commonly used in foods and drinks as needed. An agent may be blended.
本発明の第３の側面は，本発明のエステル化合物を添加する工程を含む，アミノ酸含有飲食品の劣化臭防止方法に関する。アミノ酸含有飲食品を製造する過程で，本発明のエステル化合物又は本発明のアミノ酸の劣化臭防止剤を添加し，これによりアミノ酸含有飲食品の劣化臭を防止してもよい。また，アミノ酸含有飲食品を製造した後に，本発明のエステル化合物又は本発明のアミノ酸の劣化臭防止剤を添加し，これによりアミノ酸含有飲食品の劣化臭を防止してもよい。 The 3rd side surface of this invention is related with the degradation odor prevention method of amino acid containing food / beverage products including the process of adding the ester compound of this invention. In the process of producing an amino acid-containing food / beverage product, the ester compound of the present invention or the amino acid-containing food / drink preventive agent of the present invention may be added to thereby prevent the deterioration odor of the amino acid-containing food / beverage product. Moreover, after manufacturing an amino acid containing food / beverage product, the deterioration odor of an amino acid containing food / beverage product may be prevented by adding the ester compound of this invention, or the degradation odor inhibitor of the amino acid of this invention.
以下，実施例を用いて本発明を具体的に説明する。しかしながら，本発明は以下の実施例に限定されず，当業者に自明な範囲で適宜変更を加えることができる。 Hereinafter, the present invention will be specifically described with reference to examples. However, the present invention is not limited to the following examples, and modifications can be made as appropriate within the scope obvious to those skilled in the art.
実施例１：官能基別香料成分のマスキング効果の検討
検討方法
表１に示すアミノ酸バランス組成物を１．６重量％，クエン酸を０．７重量％，トレハロースを１．０重量％およびショ糖を３．０重量％で溶解した水溶液（模擬液）を調製した。この模擬液を５５℃，７日間で保存した後に，以下に示す各種の官能基別香料成分（酸パート，アルコールパート，エステルパート１および２，ラクトンパート，含硫黄化合物パート）を０．５ｐｐｍ，５ｐｐｍ，５０ｐｐｍのそれぞれの濃度で添加して飲料を調製した。それぞれの飲料をよく訓練されたパネラー５名により官能評価を行い，各パートのマスキング効果を比較した。パネラー５名の平均的な評価を表２に示す。なお，評価基準を以下に示す。Example 1: Examination of masking effect of perfume component by functional group Examination method 1.6% by weight of amino acid balance composition shown in Table 1, 0.7% by weight of citric acid, 1.0% by weight of trehalose and sucrose An aqueous solution (simulated liquid) in which 3.0% by weight was dissolved was prepared. After storing this simulated solution at 55 ° C. for 7 days, 0.5 ppm of various functional group-based perfume ingredients (acid part, alcohol part, ester part 1 and 2, lactone part, sulfur-containing compound part) shown below. Beverages were prepared by adding them at respective concentrations of 5 ppm and 50 ppm. Sensory evaluation was conducted by five panelists who were well trained in each beverage, and the masking effect of each part was compared. Table 2 shows the average evaluation of five panelists. The evaluation criteria are shown below.
官能基別香料成分
酸パート：７０％エタノール水溶液に，酢酸，プロピオン酸，酪酸，ヘキサン酸，イソ吉草酸，オクタン酸およびデカン酸を等量ずつ混合溶解し，それらの酸の合計量が上記の濃度となるように飲料に添加した。
アルコールパート：７０％エタノール水溶液に，ヘキサノール，シス−３−ヘキセノール，オクタノール，デカノール，リナロール，ゲラニオール，メントールおよびβ−フェニルエチルアルコールを等量ずつ混合溶解し，それらのアルコールの合計量が上記の濃度となるように飲料に添加した。
エステルパート１：７０％エタノール水溶液に，エチル アセテート，エチル ブチレート，エチル プロピオネート，エチル バレレート，プロピル アセテート，ブチル アセテートおよびイソアミル アセテートを等量ずつ混合溶解し，それらのエステル化合物の合計量が上記の濃度となるように飲料に添加した。エステルパート２：７０％エタノール水溶液に，エチル ヘキサノエート，メチル ２−ヘキセノエート，エチル ２−ヘキセノエート，メチル ３−ヘキセノエート，エチル ３−ヘキセノエート，エチル ヘプタノエート，エチル オクタノエート，メチル ２−オクテノエート，エチル ２−オクテノエート，メチル ３−オクテノエート，エチル ３−オクテノエート，エチル ノナノエート，エチル デカノエート，ヘキシル アセテート，イソアミル ブチレート，オクチル アセテート，メチル ２−デセノエート，エチル ２−デセノエートおよびメチル ３−ノナノエートを等量ずつ混合溶解し，それらのエステル化合物の合計量が上記の濃度となるように飲料に添加した。
ラクトンパート：γ−ヘキサラクトン，γ−オクタラクトン，γ−ノナラクトン，γ−デカラクトン，γ−ウンデカラクトン，γ−ドデカラクトン，δ−デカラクトン，δ−ウンデカラクトンおよびδ−ドデカラクトンを等量ずつ混合溶解し，それらのラクトンの合計量が上記の濃度となるように飲料に添加した。Perfume ingredients by functional group Acid part: Acetic acid, propionic acid, butyric acid, hexanoic acid, isovaleric acid, octanoic acid and decanoic acid are mixed and dissolved in equal amounts in 70% ethanol aqueous solution. It added to the drink so that it might become a concentration.
Alcohol part: In 70% ethanol aqueous solution, hexanol, cis-3-hexenol, octanol, decanol, linalool, geraniol, menthol and β-phenylethyl alcohol are mixed and dissolved in equal amounts, and the total amount of these alcohols is the above concentration. It added to the drink so that it might become.
Ester part 1: Ethyl acetate, ethyl butyrate, ethyl propionate, ethyl valerate, propyl acetate, butyl acetate and isoamyl acetate are mixed and dissolved in equal amounts in a 70% aqueous ethanol solution, and the total amount of these ester compounds is the above concentration. So that it was added to the beverage. Ester part 2: 70% aqueous ethanol solution with ethyl hexanoate, methyl 2-hexenoate, ethyl 2-hexenoate, methyl 3-hexenoate, ethyl 3-hexenoate, ethyl heptanoate, ethyl octanoate, methyl 2-octenoate, ethyl 2-octenoate, methyl 3-octenoate, ethyl 3-octenoate, ethyl nonanoate, ethyl decanoate, hexyl acetate, isoamyl butyrate, octyl acetate, methyl 2-decenoate, ethyl 2-decenoate and methyl 3-nonanoate are mixed and dissolved in equal amounts, and their ester compounds Was added to the beverage so that the total amount of
Lactone part: γ-hexalactone, γ-octalactone, γ-nonalactone, γ-decalactone, γ-undecalactone, γ-dodecalactone, δ-decalactone, δ-undecalactone and δ-dodecalactone The mixture was dissolved and added to the beverage so that the total amount of these lactones was the above concentration.
評価基準
◎：アミノ酸由来の劣化臭が非常に良くマスキングされている。
○：アミノ酸由来の劣化臭が良くマスキングされている。
△：アミノ酸由来の劣化臭がややマスキングされている。
×：アミノ酸由来の劣化臭がマスキングされていない。Evaluation criteria A: Degradation odor derived from amino acid is masked very well.
○: Degraded odor derived from amino acids is well masked.
Δ: Degraded odor derived from amino acids is slightly masked.
X: Degradation odor derived from amino acids is not masked.
表２に示すように，官能基別の香料成分の中ではエステルパートがアミノ酸由来の劣化臭をよくマスキングしていた。 As shown in Table 2, among the perfume ingredients by functional group, the ester part masked the deteriorated odor derived from amino acids well.
実施例２：各エステル化合物のマスキング効果の検討
実施例１において検討したエステルパート１および２の各エステル化合物のマスキング効果について，実施例１と同様に模擬液に添加して，それぞれの飲料をよく訓練されたパネラー５名により官能評価を行い，各エステル化合物のマスキング効果を比較した。パネラー５名の平均的な評価を表３に示す。なお，評価基準は実施例１と同様である。Example 2: Examination of the masking effect of each ester compound The masking effect of each ester compound of the ester parts 1 and 2 examined in Example 1 was added to the simulated solution in the same manner as in Example 1, and the respective beverages were thoroughly used. Sensory evaluation was performed by five trained panelists, and the masking effects of each ester compound were compared. Table 3 shows the average evaluation of five panelists. The evaluation criteria are the same as in Example 1.
表３の結果から，エチル ブチレート，エチル プロピオネート，メチル ２−ヘキセノエート，エチル ２−ヘキセノエート，メチル ３−ヘキセノエート，エチル ３−ヘキセノエート，メチル ２−オクテノエート，エチル ２−オクテノエート，メチル ３−オクテノエートおよびエチル ３−オクテノエートがアミノ酸に由来する劣化臭をよくマスキングしていた。 From the results in Table 3, ethyl butyrate, ethyl propionate, methyl 2-hexenoate, ethyl 2-hexenoate, methyl 3-hexenoate, ethyl 3-hexenoate, methyl 2-octenoate, ethyl 2-octenoate, methyl 3-octenoate and ethyl 3- Octenoate masked the bad smell derived from amino acids well.
実施例３：エステル化合物の添加濃度の検討
実施例２でマスキング効果のあった５品のエステル化合物を使用して表４に示すマスキングフレーバーＡを調製した。Example 3 Examination of Addition Concentration of Ester Compound Masking flavor A shown in Table 4 was prepared using the five ester compounds having a masking effect in Example 2.
実施例１の模擬液に対して，このマスキングフレーバーＡを，エステル化合物５品の合計量が無添加（比較品１），０．０５ｐｐｍ（比較品２），０．１ｐｐｍ（本発明品１），１０ｐｐｍ（本発明品２），１００ｐｐｍ（本発明品３），２００ｐｐｍ（本発明品４），３００ｐｐｍ（比較品３）となるように添加して飲料を調製した。それぞれの飲料をよく訓練されたパネラー５名により官能評価を行い，アミノ酸由来の劣化臭およびマスキングフレーバーＡの風味について，以下に示す評価基準により評価した。パネラー５名の平均的な評価結果を表５に示す。 With respect to the simulated liquid of Example 1, this masking flavor A was added in a total amount of 5 ester compounds (Comparative product 1), 0.05 ppm (Comparative product 2), 0.1 ppm (Invention product 1). , 10 ppm (Invention product 2), 100 ppm (Invention product 3), 200 ppm (Invention product 4), and 300 ppm (Comparative product 3). Each beverage was subjected to sensory evaluation by five well-trained panelists, and the deterioration odor derived from amino acids and the flavor of masking flavor A were evaluated according to the following evaluation criteria. Table 5 shows the average evaluation results of five panelists.
評価基準
（アミノ酸由来の劣化臭）
×：アミノ酸由来の劣化臭を強く感じる。
○：アミノ酸由来の劣化臭をやや感じるが，ほとんど気にならない。
◎：アミノ酸由来の劣化臭は全く感じられない。
（マスキングフレーバーＡの風味）
×：マスキングフレーバーＡの風味が強く出すぎている。
○：マスキングフレーバーＡの風味がやや強いが，ほとんど気にならない。
◎：マスキングフレーバーＡの風味はほとんど気にならない。Evaluation criteria (degraded odor derived from amino acids)
X: Deterioration odor derived from amino acids is strongly felt.
○: A slight deterioration odor derived from amino acids is felt, but it is hardly noticed.
A: Deterioration odor derived from amino acids is not felt at all.
(Mask flavor A flavor)
X: The flavor of the masking flavor A is too strong.
○: The flavor of masking flavor A is slightly strong, but it is hardly anxious.
A: The flavor of the masking flavor A is hardly a concern.
表５の結果より，エステル化合物の添加濃度が無添加（比較品１）および０．０５ｐｐｍではアミノ酸由来の劣化臭が強く感じられ，０．１ｐｐｍ（本発明品１），１０ｐｐｍ（本発明品２），１００ｐｐｍ（本発明品３）および２００ｐｐｍ（本発明品４）では，アミノ酸由来の劣化臭はほとんど感じられなかった。一方，添加濃度が３００ｐｐｍ（比較品３）では，アミノ酸由来の劣化臭は感じられなかったが，マスキングフレーバーＡ自体の風味が強く出すぎていた。 From the results of Table 5, when the additive concentration of the ester compound is not added (Comparative product 1) and 0.05 ppm, a deteriorated odor derived from amino acids is strongly felt, and 0.1 ppm (Invention product 1), 10 ppm (Invention product 2) ), 100 ppm (Invention product 3) and 200 ppm (Invention product 4), the amino acid-derived deterioration odor was hardly felt. On the other hand, when the added concentration was 300 ppm (Comparative product 3), the deterioration odor derived from amino acids was not felt, but the flavor of the masking flavor A itself was too strong.
実施例４．シス体とトランス体との比較
次に，アルケニル基を有するエステル化合物におけるシス体とトランス体とで，アミノ酸の劣化臭を防止する能力に差があるかどうかを検証した。以下の化合物を用いて実施例２と同様に評価を行った。その結果を表６に示す。Example 4 Comparison between cis and trans isomers Next, we examined whether there is a difference in the ability to prevent the degradation odor of amino acids between cis and trans isomers in ester compounds having an alkenyl group. Evaluation was performed in the same manner as in Example 2 using the following compounds. The results are shown in Table 6.
表６に示されるとおり，式（１）で示される化合物のうち，Ｒ２にアルケニル基を有するものは，シス体のものの方がトランス体に比べて，アミノ酸の劣化臭をより効果的に防止することがわかる。As shown in Table 6, among compounds represented by the formula (1), those having an alkenyl group at R 2 are more effective in preventing the degradation odor of amino acids in the cis isomer than in the trans isomer. I understand that
本発明は，食品産業の分野で利用されうる。 The present invention can be used in the field of the food industry.
Claims (2)
Ｒ１がメチル基の場合，
Ｒ２は，シス体のＣ ５ アルケニル基又はシス体のＣ ７ アルケニル基であり，
Ｒ１がエチル基の場合，
Ｒ２は，Ｃ２〜Ｃ３アルキル基であるか，又はシス体のＣ ５ アルケニル基である。） An amino acid degradation odor inhibitor comprising an ester compound represented by the following formula (I) as an active ingredient , wherein the amino acid degradation odor prevention agent is an amino acid degradation odor in an amino acid-containing food or drink containing amino acids and sugars. An anti-degradation odor for amino acids .
When R 1 is a methyl group,
R 2 is a cis isomer of a C 5 alkenyl group or a cis isomer of a C 7 alkenyl group ,
When R 1 is an ethyl group,
R 2 is a C 2 -C 3 alkyl group or a cis isomer of a C 5 alkenyl group . )
請求項１に記載のアミノ酸の劣化臭防止剤。
One or more amino acids selected from methionine, isoleucine, leucine, phenylalanine and tryptophan are used to prevent amino acid degradation odors in amino acid-containing foods and beverages containing saccharides .
The amino acid degradation odor inhibitor according to claim 1.
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| JP7265846B2 (en) * | 2018-08-17 | 2023-04-27 | アサヒ飲料株式会社 | Red grape-flavored beverage, display method for transparent container packed beverage, masking agent for photo-deterioration odor of red grape-flavored beverage, method for masking photo-deterioration odor of red grape-flavored beverage |
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| JPH02128670A (en) * | 1988-11-08 | 1990-05-17 | Ajinomoto Co Inc | Amino acid-containing food composition |
| JP2003192585A (en) * | 2001-12-27 | 2003-07-09 | Lion Corp | Oral composition |
| JP2003235512A (en) * | 2002-02-22 | 2003-08-26 | Ajinomoto Co Inc | Amino acid-containing composition improved in taste |
| JP2005015686A (en) * | 2003-06-27 | 2005-01-20 | Kiyomitsu Kawasaki | Fruit-like flavor composition |
| JP2005160402A (en) * | 2003-12-03 | 2005-06-23 | Kiyomitsu Kawasaki | Method for producing flavor of crustacean |
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| JPS60186261A (en) * | 1984-03-06 | 1985-09-21 | Ajinomoto Co Inc | Solid food composition |
| JPH01285157A (en) * | 1988-05-11 | 1989-11-16 | Sanwa Kagaku Kenkyusho Co Ltd | Raw material for amino acid food |
| JP2004203892A (en) * | 2004-03-05 | 2004-07-22 | Asahi Soft Drinks Co Ltd | Hangover and liver dysfunction preventative containing glycine |
| JP4526467B2 (en) * | 2005-10-26 | 2010-08-18 | アサヒビール株式会社 | Nourishing tonic beverage |
| JP4847829B2 (en) * | 2006-09-25 | 2011-12-28 | 協和発酵バイオ株式会社 | Vinegar corner control method |
| JP5360368B2 (en) * | 2008-09-05 | 2013-12-04 | 味の素株式会社 | Amino acid preparation for oral use with improved dosage |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH02128670A (en) * | 1988-11-08 | 1990-05-17 | Ajinomoto Co Inc | Amino acid-containing food composition |
| JP2003192585A (en) * | 2001-12-27 | 2003-07-09 | Lion Corp | Oral composition |
| JP2003235512A (en) * | 2002-02-22 | 2003-08-26 | Ajinomoto Co Inc | Amino acid-containing composition improved in taste |
| JP2005015686A (en) * | 2003-06-27 | 2005-01-20 | Kiyomitsu Kawasaki | Fruit-like flavor composition |
| JP2005160402A (en) * | 2003-12-03 | 2005-06-23 | Kiyomitsu Kawasaki | Method for producing flavor of crustacean |
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| CN102164509A (en) | 2011-08-24 |
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