JPH08103242A - Sustainable flavor/scent imparting agent/modifier - Google Patents
Sustainable flavor/scent imparting agent/modifierInfo
- Publication number
- JPH08103242A JPH08103242A JP6242917A JP24291794A JPH08103242A JP H08103242 A JPH08103242 A JP H08103242A JP 6242917 A JP6242917 A JP 6242917A JP 24291794 A JP24291794 A JP 24291794A JP H08103242 A JPH08103242 A JP H08103242A
- Authority
- JP
- Japan
- Prior art keywords
- flavor
- aroma
- imparting agent
- sustainable
- modifier
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、バター、チーズなどを
想起させる持続性の香気香味特性を有するＮ−プロピオ
ニルロイシン、Ｎ−ブチリルバリンおよびＮ−ブチリル
ロイシン（以下、アルカノイルアミノ酸アミド類という
ことがある）の中から選ばれた少なくとも一種を有効成
分として含有する新規な持続性香気香味賦与乃至変調剤
に関する。FIELD OF THE INVENTION The present invention relates to N-propionyl leucine, N-butyryl valine and N-butyryl leucine (hereinafter referred to as alkanoyl amino acid amides) having a persistent aroma and flavor characteristic reminiscent of butter, cheese and the like. The present invention relates to a novel persistent aroma and flavor imparting or modulating agent containing as an active ingredient at least one selected from the group (1).
【０００２】[0002]
【従来の技術】本発明のアルカノイルアミノ酸アミド類
は、化粧品あるいは治療薬の調製に使用され（フランス
特許；２５０３１４４）、またカルシウムの吸収促進作
用への寄与に関する報告（Ｊ．Ｐｈａｒｍ．ｓｃｉ．，
78(6),499 〜503 ）などが知られ、また、これら化合物
の製造方法についても知られている既知の化合物である
［ＣＡ７０（２５）；１１５５３６］。しかしながら、
本発明の上記化合物が、バター、チーズなどを想起させ
る香気香味特性を有し、各種の飲食品の香気香味賦与乃
至変調剤として利用できることについては記載されてい
ない。2. Description of the Related Art The alkanoylamino acid amides of the present invention are used for the preparation of cosmetics or therapeutic drugs (French Patent; 2503144), and a report on the contribution of calcium to the absorption promoting action (J. Pharm. Sci.,
78 (6), 499-503) and the like, and also known methods for producing these compounds [CA70 (25); 115536]. However,
It is not described that the above compound of the present invention has an aroma and flavor characteristic reminiscent of butter, cheese and the like, and can be used as an aroma and flavor imparting or modulating agent for various foods and drinks.
【０００３】[0003]
【発明が解決しようとする課題】近年、食生活の変化に
より簡便な飲食品の開発が活発に行われ、これに伴い、
種々の香気香味を有する素材のニーズが高まっている。
特にチーズ、バターなどの乳製品の醗酵香味を有する素
材のニーズが高いが、必ずしも満足できる素材は開発さ
れていないのが現状である。In recent years, simple foods and drinks have been actively developed due to changes in eating habits.
There is an increasing need for materials having various flavors and aromas.
In particular, there is a great need for materials having a fermented flavor of dairy products such as cheese and butter, but at present, satisfactory materials have not been developed.
【０００４】[0004]
【課題を解決するための手段】そこで本発明者らは、バ
ター、チーズなどの香気香味を有する素材について鋭意
研究した結果、上記化合物が、上記の香気香味を有し、
しかも優れた持続性を有し、且つ容易に製造ができるこ
とを見出し本発明を完成した。Therefore, as a result of diligent research on materials having an aroma and flavor such as butter and cheese, the present inventors have found that the above compound has the above aroma and flavor.
Moreover, they have found that they have excellent durability and can be easily manufactured, and completed the present invention.
【０００５】従って、本発明の目的は、アルカノイルア
ミノ酸アミド類の中から選ばれた少なくとも一種を有効
成分として含有する持続性香気香味賦与乃至変調剤を提
供するにある。Therefore, an object of the present invention is to provide a persistent aroma and flavor imparting or modulating agent containing at least one selected from alkanoylamino acid amides as an active ingredient.
【０００６】本発明のアルカノイルアミノ酸アミド類
は、（Ａ）酸無水物法あるいは（Ｂ）酸クロリド法によ
り容易に合成することができる。この（Ａ）法ならびに
（Ｂ）法の合成法を以下に述べる。The alkanoylamino acid amides of the present invention can be easily synthesized by the (A) acid anhydride method or the (B) acid chloride method. The synthesis method of the method (A) and the method (B) will be described below.
【０００７】（Ａ）酸無水物法；ロイシンまたはバリン
（以下、アミノ酸ということがある）をＮ, Ｎ−ジメチ
ルアミノピリジン（以下、ＤＭＡＰという）の存在下、
ピリジン溶媒中でアルカン酸無水物と反応させることに
よりアルカノイルアミノ酸アミド類を容易に合成するこ
とができる。ピリジンの使用量は、適宜に選択すればよ
く、一般的にはアミノ酸に対して、例えば約１倍重量〜
１０倍重量使用すればよい。また、ＤＭＡＰの使用量
は、フエニルアラニンに対して、約０．００１〜０．１
モル程度の範囲で使用される。また、アルカン酸無水物
は、無水プロピオン酸あるいは無水酪酸を用いればよ
い。これら酸無水物の使用量は、例えばアミノ酸に対し
て、約１〜５モル程度が用いられる。反応温度は、約０
°〜１００℃程度で、約０. ５〜２４時間程度の条件で
行われる。反応終了後は、常法に従って処理してアルカ
ノイルアミノ酸アミド類を収率よく容易に合成すること
ができる。(A) Acid anhydride method; leucine or valine (hereinafter sometimes referred to as amino acid) in the presence of N, N-dimethylaminopyridine (hereinafter referred to as DMAP),
The alkanoylamino acid amides can be easily synthesized by reacting with an alkanoic acid anhydride in a pyridine solvent. The amount of pyridine used may be appropriately selected, and is generally about 1-fold by weight to amino acid.
It is sufficient to use 10 times the weight. The amount of DMAP used is about 0.001 to 0.1 with respect to phenylalanine.
It is used in a molar range. As the alkanoic acid anhydride, propionic anhydride or butyric anhydride may be used. The amount of these acid anhydrides used is, for example, about 1 to 5 mol per amino acid. The reaction temperature is about 0
It is carried out under conditions of about 0.5 to 100 ° C. and about 0.5 to 24 hours. After completion of the reaction, alkanoylamino acid amides can be easily synthesized in good yield by treatment according to a conventional method.
【０００８】（Ｂ）酸クロリド法；またアルカノイルア
ミノ酸アミド類は、アミノ酸をピリジンの存在下に、ア
ルカン酸クロリドと反応させることによっても容易に合
成することができる。反応温度は、通常約０°〜１０℃
で約０. ５〜２４時間程度で行われる。この場合、一般
的には有機溶媒中で行うのが好ましく、一般的にはジク
ロルメタン、クロロホルムなどがよく使用される。その
使用量は適宜に選択すればよく、例えばアミノ酸に対し
て、約１〜１０倍重量程度使用すればよい。また、反応
に使用するピリジンその使用量には格別の制限はなく、
例えばアミノ酸に対して、約１〜５倍重量程度を挙げる
ことができる。また、アルカン酸クロリドは、プロピオ
ン酸クロリドあるいは酪酸クロリドを使用すればよく、
その使用量はアミノ酸に対して、一般的には約１〜３モ
ル程度が使用される。反応終了後は、常法により処理し
てアルカノイルアミノ酸を収率よく容易に合成すること
ができる。(B) Acid chloride method; alkanoylamino acid amides can also be easily synthesized by reacting an amino acid with alkanoic acid chloride in the presence of pyridine. The reaction temperature is usually about 0 ° to 10 ° C.
It takes about 0.5 to 24 hours. In this case, it is generally preferable to carry out the reaction in an organic solvent, and dichloromethane, chloroform and the like are generally often used. The amount used may be appropriately selected, for example, about 1 to 10 times the weight of the amino acid may be used. Also, there is no particular limitation on the amount of pyridine used in the reaction,
For example, the amount can be about 1 to 5 times the weight of the amino acid. In addition, as the alkanoic acid chloride, propionic acid chloride or butyric acid chloride may be used,
The amount used is generally about 1 to 3 mol based on the amino acid. After completion of the reaction, the alkanoylamino acid can be easily synthesized in good yield by treatment by a conventional method.
【０００９】かくして得られたアルカノイルアミノ酸ア
ミド類のそれぞれの香気香味特性は、以下のように表す
ことができる。 化合物名 香気香味 Ｎ−プロピオニルロイシン ；甘酸っぱい醸造臭を有し、マイルドな酸味 Ｎ−ブチリルバリン ；チーズ様香気香味を有し、まろやかな酸味 Ｎ−ブチリルロイシン ；完熟果実様、バター様香気香味The aroma and flavor characteristics of the alkanoyl amino acid amides thus obtained can be expressed as follows. Compound name Aroma flavor N-propionyl leucine; Sweet and sour brewing odor, mild acidity N-butyryl valine; Cheese-like aroma, mellow acidity N-butyryl leucine; Ripe fruit-like, butter-like aroma
【００１０】アルカノイルアミノ酸アミド類は、上記の
ようにそれぞれの香気香味特性を有し、それ自体持続性
香気香味賦与乃至変調剤として、好ましくは他の例えば
レモン油、オレンジ油、アニス油、クロ−ブ油、カプシ
カム油、シンナモン油などのごとき天然香料；リモネ
ン、ピネン、カリオフィレンのごとき炭化水素類、リナ
ロール、ゲラニオール、シトロネロール、ミルセノー
ル、フアルネソール、ヘキセノール、ベンジルアルコー
ル、フェニルエチルアルコール、アニスアルコール、シ
ンナミックアルコール、アネトール、オイゲノールのご
ときアルコール類、オクチルアルデヒド、ウンデシルア
ルデヒド、ノナジエナール、シトラール、ペリラアルデ
ヒド、フェニルアルデヒド、シンナミックアルデヒド、
バニリン、ジアセチル、Ｌ−カルボン、アセトフェノ
ン、ヨノン、メチルヘプチルケトン、メチルデシルケト
ンのごときアルデヒドおよひケトン類、酢酸エチル、酢
酸ブチル、酢酸シトロネリル、プロピオン酸エチル、プ
ロピオン酸イソアミル、プロピオン酸ゲラニル、酪酸イ
ソアミル、イソ吉草酸エチルなどのごときエステル類、
δ−デカラクトン、γ−ウンデカラクトンなどのラクト
ン類、酢酸、プロピオン酸などの酸類などの合成香料；
の一種以上と適宜に混合して、持続性香気香味賦与乃至
変調剤として利用することができる。これら香料に対す
るアルカノイルアミノ酸アミド類の使用量は、通常約
０. ００１〜１０重量％程度で調製される。The alkanoyl amino acid amides have their respective aroma and flavor characteristics as described above, and as themselves, as a persistent aroma and flavor imparting or modulating agent, preferably other ones such as lemon oil, orange oil, anise oil, and chloro-acetic acid. Natural fragrances such as bubu oil, capsicum oil and cinnamon oil; hydrocarbons such as limonene, pinene and caryophyllene, linalool, geraniol, citronellol, myrcenol, farnesol, hexenol, benzyl alcohol, phenylethyl alcohol, anis alcohol, cinnamic alcohol , Alcohols such as anethole, eugenol, octyl aldehyde, undecyl aldehyde, nonadienal, citral, perilla aldehyde, phenyl aldehyde, cinnamic aldehyde,
Aldehydes and ketones such as vanillin, diacetyl, L-carvone, acetophenone, yonone, methylheptyl ketone, and methyldecyl ketone, ethyl acetate, butyl acetate, citronellyl acetate, ethyl propionate, isoamyl propionate, geranyl propionate, butyric acid Esters such as isoamyl and ethyl isovalerate,
Synthetic perfumes such as lactones such as δ-decalactone and γ-undecalactone, acids such as acetic acid and propionic acid;
It can be used as a persistent aroma and flavor imparting or modulating agent by appropriately mixing with one or more of the above. The amount of alkanoylamino acid amides used relative to these flavors is usually adjusted to about 0.001 to 10% by weight.
【００１１】かくして、上述のようにして得られた持続
性香気香味賦与乃至変調剤は、例えば、各種菓子類、キ
ャンディ類、各種冷菓類、各種乳製品類、各種飲料類な
どの食品に添加して、チーズ、バターなどを想起させる
優れた持続性のある香気香味を賦与することができる。
これらの食品に添加される持続性香気香味賦与乃至変調
剤の使用量は、例えば上記食品類に対して、一般的には
約０．００１〜１０重量％程度の範囲で使用される。以
下、実施例を挙げて本発明の態様につき更に詳細に説明
する。Thus, the persistent aroma and flavor imparting or modulating agent obtained as described above is added to foods such as various kinds of confectionery, candies, various frozen desserts, various dairy products and various beverages. As a result, an excellent and persistent aroma and flavor reminiscent of cheese and butter can be imparted.
The amount of the persistent aroma and flavor imparting or modulating agent added to these foods is generally in the range of about 0.001 to 10% by weight based on the above foods. Hereinafter, the embodiments of the present invention will be described in more detail with reference to Examples.
【００１２】[0012]
（参考例１） Ｎ−プロピオニルロイシンの合成 ロイシン２６ｇ、ピリジン１００ｇおよびジメチルアミ
ノピリジン０. １ｇの混合物中に、室温下、無水プロピ
オン酸３０ｇを徐々に注入、１０時間、室温下に反応を
行う。反応終了後、反応液に水５０ｍｌを加え、ピリジ
ン、水を減圧下に除去し、残液に５％苛性ソーダ氷水溶
液６４０ｍｌを加え、不溶物を酢酸エチルを加え除き、
酢酸エチルで抽出する。洗浄処理後、減圧下に軽沸部を
除き粗製物１８ｇを得た。これを酢酸エチルで再結晶を
行い、目的物９. ５ｇ（収率；２５％）を得た。Reference Example 1 Synthesis of N-propionylleucine A mixture of 26 g of leucine, 100 g of pyridine and 0.1 g of dimethylaminopyridine was gradually injected with 30 g of propionic anhydride at room temperature, and the reaction was carried out for 10 hours at room temperature. After completion of the reaction, 50 ml of water was added to the reaction solution, pyridine and water were removed under reduced pressure, 640 ml of 5% caustic soda ice water solution was added to the residual liquid, and ethyl acetate was added to remove insoluble matter.
Extract with ethyl acetate. After the washing treatment, the light boiling portion was removed under reduced pressure to obtain 18 g of a crude product. This was recrystallized from ethyl acetate to obtain 9.5 g of the desired product (yield: 25%).
【００１３】（参考例２） Ｎ−ブチリルバリンの合成 参考例１において、ロイシンの代わりにバリン、無水プ
ロピオン酸の代わりに無水酪酸を用いた他は、参考例１
と同様に反応してＮ−ブチリルバリン１２ｇ（収率；３
０％）を得た。Reference Example 2 Synthesis of N-butyrylvaline Reference Example 1 except that valine was used instead of leucine and butyric anhydride was used instead of propionic anhydride in Reference Example 1.
12 g of N-butyrylvaline (yield: 3
0%).
【００１４】（参考例３） Ｎ−ブチリルロイシンの合成 参考例１において、無水酢酸プロピオン酸の代わりに酪
酸クロリドを用い参考例１と同様に反応して、目的物１
３ｇ（収率；３２％）を得た。Reference Example 3 Synthesis of N-Butyrylleucine In Reference Example 1, butyric acid chloride was used instead of acetic anhydride propionic acid, and the reaction was performed in the same manner as in Reference Example 1 to obtain the target compound 1
3 g (yield; 32%) was obtained.
【００１５】（実施例１）チーズ様の持続性香気香味賦
与剤として下記の各成分（重量部）を混合した。 上記組成物にＮ−ブチリルロイシン０．５ｇを加えて新
規組成物を調製した。これらについて１０名の専門パネ
ラーにより官能テストを行った。その結果、パネラーの
全員が新規組成物は、チーズ様香気香味および香気香味
の持続性の点で優れていると判定した。Example 1 The following components (parts by weight) were mixed as a cheese-like persistent flavor and flavor imparting agent. A novel composition was prepared by adding 0.5 g of N-butyryl leucine to the above composition. A sensory test was performed on these by 10 professional panelists. As a result, all of the panelists judged that the novel composition was excellent in terms of cheese-like aroma and persistence of aroma and aroma.
【００１６】（実施例２）バター様の持続性香気香味賦
与剤として下記の各成分（重量部）を混合した。 上記組成物にＮ−ブチリルバリン１. ０ｇを加えて新規
組成物を製造した。これらについて１０名の専門パネラ
ーにより官能テストを行った結果、パネラーの全員がこ
の新規組成物は、強いバター様香気香味を有し、バター
様香気香味の持続性の点でも優れているとした。(Example 2) The following components (parts by weight) were mixed as a buttery persistent aroma and flavor imparting agent. A novel composition was prepared by adding 1.0 g of N-butyrylvaline to the above composition. As a result of a sensory test conducted by 10 expert panelists, all of the panelists found that the novel composition had a strong butter-like aroma and was excellent in the persistence of the butter-like aroma and aroma.
【００１７】（実施例３）実施例１の組成物に、Ｎ−プ
ロピオニルロイシン２ｇを加え、新規組成物を製造し
た。これらについて専門パネラー１０名により官能テス
トを行った。その結果、パネラーの全員がこの新規組成
物は、独特のバター風味を有し、マイルドで優れた持続
性を有していると判定した。(Example 3) To the composition of Example 1 was added 2 g of N-propionyl leucine to prepare a new composition. A sensory test was conducted on these by 10 professional panelists. As a result, all panelists determined that the new composition had a unique buttery flavor and had mild and excellent persistence.
【００１８】[0018]
【発明の効果】本発明によれば、バター、チーズなどを
想起させる優れた持続性香気香味を有するアルカノイル
アミノ酸アミド類を有効成分とする持続性香気香味賦与
乃至変調剤が提供される。アルカノイルアミノ酸アミド
類は、各種の飲食品などに用いる香気香味賦与乃至変調
剤の素材として有用である。INDUSTRIAL APPLICABILITY According to the present invention, there is provided a persistent aroma and flavor imparting or modulating agent containing alkanoyl amino acid amides having an excellent persistent aroma and flavor reminiscent of butter, cheese and the like as an active ingredient. The alkanoyl amino acid amides are useful as a material for an aroma and flavor imparting or modulating agent used in various foods and drinks.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 千田 直 東京都中央区日本橋本町４−４−14 長谷 川香料株式会社フレーバー研究所内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Nao Senda 4-4-14 Nihonbashihonmachi, Chuo-ku, Tokyo Hasegawa Koryo Co., Ltd.
Claims (1)
バリンおよびＮ−ブチリルロイシンの中から選ばれた少
なくとも一種を有効成分として含有することを特徴とす
る持続性香気香味賦与乃至変調剤。1. A continuous aroma-flavor imparting or modulating agent, comprising at least one selected from N-propionylleucine, N-butyrylvaline and N-butyrylleucine as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6242917A JPH08103242A (en) | 1994-10-06 | 1994-10-06 | Sustainable flavor/scent imparting agent/modifier |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6242917A JPH08103242A (en) | 1994-10-06 | 1994-10-06 | Sustainable flavor/scent imparting agent/modifier |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08103242A true JPH08103242A (en) | 1996-04-23 |
Family
ID=17096139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6242917A Pending JPH08103242A (en) | 1994-10-06 | 1994-10-06 | Sustainable flavor/scent imparting agent/modifier |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH08103242A (en) |
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| WO2013010991A1 (en) * | 2011-07-15 | 2013-01-24 | Givaudan Sa | Flavour modifying compounds |
| WO2013149012A1 (en) * | 2012-03-30 | 2013-10-03 | Givaudan S.A. | N-acyl amino acid derivatives as food flavouring compounds |
| US10201175B2 (en) | 2012-03-30 | 2019-02-12 | Givaudan Sa | N-acylated 1-aminocycloalkyl carboxylic acids as food flavouring compounds |
| US10537127B2 (en) | 2013-10-02 | 2020-01-21 | Givaudan S.A. | Organic compounds |
| US10582715B2 (en) | 2012-03-30 | 2020-03-10 | Givaudan Sa | Powder flavour composition |
| US10645955B2 (en) | 2012-03-30 | 2020-05-12 | Givaudan Sa | N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds |
| US10674755B2 (en) | 2013-10-02 | 2020-06-09 | Givaudan S.A. | Organic Compounds |
| US10711230B2 (en) | 2012-03-30 | 2020-07-14 | Givaudan Sa | N-acyl proline derivatives as food flavoring compounds |
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-
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