JPH08103243A - Sustainable flavor/scent imparting agent - Google Patents
Sustainable flavor/scent imparting agentInfo
- Publication number
- JPH08103243A JPH08103243A JP6242991A JP24299194A JPH08103243A JP H08103243 A JPH08103243 A JP H08103243A JP 6242991 A JP6242991 A JP 6242991A JP 24299194 A JP24299194 A JP 24299194A JP H08103243 A JPH08103243 A JP H08103243A
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- flavor
- formula
- aroma
- sustainable
- imparting agent
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、チーズ、醤油、味噌、
魚醤油などの醗酵生成物やバター、チーズなどの熟成感
を想起させる持続性の香気香味特性を有するアルカノイ
ルアミノ酸アミドを有効成分として含有する新規な持続
性香気香味賦与剤に関する。更に詳しくは、本発明は、
下記式（１）The present invention relates to cheese, soy sauce, miso,
The present invention relates to a novel persistent aroma and flavor imparting agent containing an alkanoyl amino acid amide having a persistent aroma and flavor characteristic reminiscent of fermentation products such as fish soy sauce and aging of butter and cheese as an active ingredient. More specifically, the present invention provides
The following formula (1)
【化２】 式中Ｒは前記したと同義、で表されるアルカノイルアミ
ノ酸アミド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剤に関する。Embedded image In the formula, R relates to the same meaning as described above, and relates to a persistent aroma and flavor imparting agent containing an alkanoylamino acid amide represented by the above as an active ingredient.
【０００２】[0002]
【従来の技術】本発明の上記式（１）の化合物は、化粧
品、治療薬の調製あるいは酵素による加水分解の機構の
解明の試料として利用されることが知られている［フラ
ンス特許；２５０３１４４、Ｂｕｌｌ．Ｃｈｅｍ．Ｓｏ
ｃ．Ｊｐｎ.,６１（２），５７５−６］。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、本発明の式（１）化合物が、チーズ、醤油、味
噌、魚醤油など醗酵生成物やバター、チーズなどの熟成
感を想起させる香気香味特性を有し、各種の飲食品の香
気香味賦与剤として利用できることについては記載され
ていない。BACKGROUND OF THE INVENTION The compound of the above formula (1) of the present invention is known to be used as a sample for the preparation of cosmetics, therapeutic agents or elucidation of the mechanism of enzymatic hydrolysis [French Patent; 2503144, Bull. Chem. So
c. Jpn., 61 (2), 575-6]. In addition, it is a known compound [CA70 (25); 115536] which is also known for the production method of these compounds. However, the compound of the formula (1) of the present invention has aroma and flavor characteristics that evoke the aging feeling of fermentation products such as cheese, soy sauce, miso, and fish soy sauce, butter, and cheese, and imparts aroma and flavor to various foods and drinks. It does not describe that it can be used as an agent.
【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、あるいは
ハムなどの畜肉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 a material having a fermenting flavor of dairy products such as cheese and butter, or a fermenting flavor of livestock meat such as ham, 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、特
にバター、チーズあるいはハム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、上記式（１）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。The inventors of the present invention have conducted extensive studies as to materials having an aroma and flavor such as butter, cheese or ham. As a result, the compound of the formula (1) has the aroma and flavor described above. 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、式（１）で表さ
れるアルカノイルアミノ酸アミドを有効成分として含有
する持続性香気香味賦与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 agent containing an alkanoylamino acid amide represented by the formula (1) as an active ingredient.
【０００６】本発明の式（１）化合物は、例えば（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 compound of formula (1) of the present invention is, for example, (A)
It can be easily synthesized by the 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；フェニルアラニンを
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式（１）化合物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、一般的にはフェニルアラニンに対して、例えば約等
量〜約１０量倍使用すればよい。また、ＤＭＡＰの使用
量は、フェニルアラニンに対して、０．００１モル〜
０．１モル程度使用すればよい。アルカン酸無水物は、
式（１）化合物のＲに相当する無水酢酸、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、例えばフェニルアラニンに対して、約１〜
約５モル程度用いられる。反応は、約０〜１００℃程度
で、約０．５〜約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式（１）化合物を収率
よく容易に合成することができる。(A) Acid anhydride method: The compound of formula (1) is easily prepared by reacting phenylalanine with an alkanoic acid anhydride in a pyridine solvent in the presence of N, N-dimethylaminopyridine (hereinafter referred to as DMAP). Can be synthesized. The amount of pyridine used may be appropriately selected, and generally, it may be used, for example, in an amount of about equal to about 10 times the amount of phenylalanine. The amount of DMAP used is 0.001 mol to phenylalanine.
About 0.1 mol may be used. The alkanoic anhydride is
Acetic anhydride, propionic anhydride or butyric anhydride corresponding to R of the compound of formula (1) may be used. The amount of these acid anhydrides used is, for example, about 1 to phenylalanine.
About 5 mol is used. The reaction is performed at about 0 to 100 ° C. for about 0.5 to about 24 hours. After completion of the reaction, the compound of the formula (1) can be easily synthesized in good yield by treatment according to a conventional method.
【０００８】（Ｂ）酸クロリド法；また式（１）化合物
は、フェニルアラニンを塩基性溶媒の存在下に、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。反応は、通常約０℃〜１００℃で約
０．５〜２４時間程度で行われる。この場合、通常は有
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、トルエン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、例えばフェニルアラ
ニンに対して、約１〜約２０倍重量程度使用すればよ
い。また、反応に使用するアルカリとしては、例えば、
ピリジンなどを挙げることができる。その使用量には格
別の制限はなく、例えばフェニルアラニンに対して、約
等量〜約２０倍重量程度が使用される。また、アルカン
酸クロリドは、式（１）化合物のＲに相当する酢酸クロ
リド、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、その使用量はフエニルアラニンに対し
て、一般的には約１〜約３モル程度使用される。反応終
了後は、常法により処理して式（１）化合物を収率よく
容易に合成することができる。(B) Acid chloride method: The compound of formula (1) can also be easily synthesized by reacting phenylalanine with alkanoic acid chloride in the presence of a basic solvent. The reaction is usually performed at about 0 ° C to 100 ° C for about 0.5 to 24 hours. In this case, it is usually preferable to carry out in an organic solvent, and in general, dichloromethane, chloroform, toluene and the like are often used. The amount used may be appropriately selected, and for example, it may be used in an amount of about 1 to about 20 times the weight of phenylalanine. Further, as the alkali used in the reaction, for example,
Pyridine and the like can be mentioned. There is no particular limitation on the amount used, and for example, about the equivalent amount to about 20 times the weight of phenylalanine is used. As the alkanoic acid chloride, acetic acid chloride, propionic acid chloride or butyric acid chloride corresponding to R of the compound of the formula (1) may be used, and the amount thereof is generally about 1 to 1 with respect to phenylalanine. About 3 mol is used. After completion of the reaction, the compound of the formula (1) can be easily synthesized in good yield by treatment by a conventional method.
【０００９】かくして得られた式（１）化合物のそれぞ
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−アセチルフエニルアラニン ；酢酸様の香味を伴ったマイルドな醗酵臭 Ｎ−プロピオニルフエニルアラニン；強いハニー様、マイルドな醸造酢様 Ｎ−ブチリルフエニルアラニン ；チーズ様で甘い香味The aroma and flavor characteristics of each of the compounds of formula (1) thus obtained can be expressed as follows. Compound name Aroma flavor N-acetylphenylalanine; Mild fermentation odor with acetic acid-like flavor N-propionylphenylalanine; Strong honey-like, mild vinegar-like N-butyrylphenylalanine; Cheese-like sweet flavor
【００１０】式（１）化合物は、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、クローブ油、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
トンなどのごときアルデヒド、ケトン類、δ−デカラク
トン、γ−デカラクトンのごときラクトン類、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、酢酸、プロピオン酸、酪酸などのごとき酸類など
の合成香料；の一種以上と適宜に混合して、持続性香気
香味賦与剤として利用することができる。これら香料に
対する前記式（１）化合物の使用量は、通常約０．００
１〜１０重量％程度で使用される。The compounds of formula (1) have their respective aroma and flavor properties as described above, and as a long-lasting aroma and flavor imparting agent, preferably other compounds such as lemon oil, orange oil,
Natural flavors such as anise oil, clove oil, capsicum oil, cinnamon oil, etc .; hydrocarbons such as limonene, pinene, caryophyllene, linalool, geraniol, citronellol, myrcenol, farnesol, hexenol, benzyl alcohol, phenylethyl alcohol, anis alcohol, Alcohols such as cinnamic alcohol, anethole, eugenol, octyl aldehyde, undecyl aldehyde, nonadienal,
Citral, perilaldehyde, phenylaldehyde,
Cinnamic aldehyde, vanillin, diacetyl, L-
Carboxyl, acetophenone, yonone, aldehydes such as methylheptyl ketone, ketones, lactones such as δ-decalactone, γ-decalactone, ethyl acetate, butyl acetate, citronellyl acetate, ethyl propionate, isoamyl propionate, geranyl propionate,
It can be used as a persistent flavor enhancer by appropriately mixing with one or more of synthetic flavorings such as esters such as isoamyl butyrate and ethyl isovalerate, and acids such as acetic acid, propionic acid, butyric acid and the like. . The amount of the compound of the formula (1) used for these flavors is usually about 0.00
It is used at about 1 to 10% by weight.
【００１１】かくして、上述のようにして得られた持続
性香気香味賦与剤は、例えば、各種菓子類、各種キャン
ディ類、各種飲料類などの飲食品に添加して、チーズ、
バター、醤油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０．０００１〜０．１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 agent obtained as described above is added to foods and drinks such as various confectionery, various candy and various beverages, and cheese,
An excellent and persistent aroma and flavor reminiscent of butter and soy sauce can be imparted. The amount of the persistent aroma and flavoring agent added to these foods is generally in the range of about 0.0001 to 0.1% 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−アセチルフェニルアラニンの合成 フェニルアラニン３３ｇ、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
水酢酸２５ｇ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４８０ｍｌを加える。不溶物を酢酸エチルで除去し、
水層に稀塩酸を加え酸性にし酢酸エチルで抽出する。水
洗後溶媒を回収し粗製物を得た。これを酢酸エチルで再
結晶を行い、目的物２２ｇを得た（収率；５０％）。Reference Example 1 Synthesis of N-Acetylphenylalanine 25 g of acetic anhydride was gradually injected into a mixture of 33 g of phenylalanine, 100 g of pyridine and 0.1 g of dimethylaminopyridine at room temperature for 10 hours at room temperature. After completion of the reaction, 50 ml of water is added to the reaction solution, pyridine and water are removed under reduced pressure, and 480 ml of a 5% aqueous sodium hydroxide solution of caustic soda is added to the residual solution. Insoluble matter was removed with ethyl acetate,
The aqueous layer is acidified with diluted hydrochloric acid and extracted with ethyl acetate. After washing with water, the solvent was recovered to obtain a crude product. This was recrystallized from ethyl acetate to obtain 22 g of the desired product (yield: 50%).
【００１３】（参考例２） Ｎ−プロピオニルフェニルアラニンの合成 無水酢酸の代わりに、無水プロピオン酸２８ｇを用い、
参考例１と同様の反応操作を行うことにより、目的物３
０ｇ（収率；６０％）を得た。(Reference Example 2) Synthesis of N-propionylphenylalanine 28 g of propionic anhydride was used instead of acetic anhydride.
By performing the same reaction operation as in Reference Example 1, the target compound 3 was obtained.
0 g (yield; 60%) was obtained.
【００１４】（参考例３） Ｎ−ブチリルフェニルアラニンの合成 参考例１の無水酢酸に代え、酪酸クロリド２０ｇを用
い、同様に反応した。反応終了後、メタノール１０m ｌ
を加えた後、ピリジンを留去する。残渣に酢酸エチルを
加え、続いて食塩水で洗浄する。更に稀塩酸水で洗浄
し、更に食塩水で洗浄する。溶剤を留去し粗製物３７ｇ
を得た。酢酸エチルで再結晶し目的物１４ｇを得た（収
率；２８％）。Reference Example 3 Synthesis of N-butyrylphenylalanine The same reaction was carried out using 20 g of butyric acid chloride instead of the acetic anhydride of Reference Example 1. After the reaction, methanol 10 ml
After adding, pyridine is distilled off. Ethyl acetate is added to the residue, followed by washing with brine. Further, it is washed with diluted hydrochloric acid water, and further washed with saline. 37 g of crude product after distilling off the solvent
I got Recrystallization from ethyl acetate gave 14 g of the desired product (yield: 28%).
【００１５】（実施例１）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−ブチリルフェニルアラニンを１．５ｇ
加えた。これらの組成物について、専門パネラー１０人
により官能検査を行った結果、パネラーの全員がＮ−ブ
チリルフェニルアラニンを加えた組成物は、バター様の
香気香味が優れていると判定した。また持続性も優れて
いると判定した。(Example 1) The following components (parts by weight) were mixed as a buttery persistent aroma and flavor imparting agent. 1.5 g of N-butyrylphenylalanine was added to the above composition.
added. As a result of a sensory test conducted by 10 expert panelists on these compositions, it was determined that all the panelists added N-butyrylphenylalanine to the composition having excellent buttery aroma and flavor. It was also determined that the durability was excellent.
【００１６】（実施例２）実施例１において、Ｎ−ブチ
リルフェニルアラニンの代わりにＮ−プロピオニルフェ
ニルアラニンを用いた他は、実施例１と同様にして組成
物を調製した。その結果、専門パネラーの全員が、バタ
ー様の香気香味が強く、持続性に優れていると判定し
た。Example 2 A composition was prepared in the same manner as in Example 1 except that N-propionylphenylalanine was used instead of N-butyrylphenylalanine. As a result, all the expert panelists judged that the buttery aroma and flavor were strong and the durability was excellent.
【００１７】醤油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−アセチルフェニルアラニン０．５ｇを
加えた。これらの組成物について、専門パネラー１０人
により官能検査を行った。その結果、パネラーの全員が
Ｎ−アセチルフエニルアラニンを加えた組成物は、こげ
臭の強調された醤油様の香気香味を有し、また、持続性
においても優れていると判定した。The following components (parts by weight) were mixed as a soy sauce-like persistent aroma and flavor imparting agent. 0.5 g of N-acetylphenylalanine was added to the above composition. A sensory test was conducted by 10 professional panelists on these compositions. As a result, all the panelists judged that the composition to which N-acetylphenylalanine was added had a soy sauce-like aroma with an emphasized dark odor and was also excellent in durability.
【００１８】[0018]
【発明の効果】本発明によれば、バター、チーズ、ハ
ム、醤油などを想起させる優れた持続性香気香味を有す
る前記式（１）で表されるアルカノイルアミノ酸アミド
を有効成分とする持続性香気香味賦与剤が提供される。
前記式（１）化合物は、各種の飲食品などに用いる香気
香味賦与剤の素材として有用である。INDUSTRIAL APPLICABILITY According to the present invention, a persistent aroma containing an alkanoylamino acid amide represented by the above formula (1) as an active ingredient, which has an excellent persistent aroma and flavor reminiscent of butter, cheese, ham, soy sauce, etc. A flavor enhancer is provided.
The compound of the formula (1) is useful as a material for an aroma and flavor imparting 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)
す、で表されるアルカノイルアミノ酸アミドを有効成分
として含有することを特徴とする持続性香気香味賦与
剤。1. The following formula (1): In the formula, R represents a methyl group, an ethyl group, or a propyl group, and the alkanoylamino acid amide represented by the formula is contained as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6242991A JPH08103243A (en) | 1994-10-06 | 1994-10-06 | Sustainable flavor/scent imparting agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6242991A JPH08103243A (en) | 1994-10-06 | 1994-10-06 | Sustainable flavor/scent imparting agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08103243A true JPH08103243A (en) | 1996-04-23 |
Family
ID=17097273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6242991A Pending JPH08103243A (en) | 1994-10-06 | 1994-10-06 | Sustainable flavor/scent imparting agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH08103243A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005041684A3 (en) * | 2003-08-06 | 2009-04-09 | Senomyx Inc | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| JP2014523950A (en) * | 2011-07-15 | 2014-09-18 | ジボダン エス エー | Flavor modifying compounds |
| US9072313B2 (en) | 2006-04-21 | 2015-07-07 | Senomyx, Inc. | Comestible compositions comprising high potency savory flavorants, and processes for producing them |
| JP2015519298A (en) * | 2012-03-30 | 2015-07-09 | ジボダン エス エー | N-acyl-amino acid derivatives as food flavoring compounds |
| AU2014202646B2 (en) * | 2003-08-06 | 2016-04-21 | Senomyx, Inc. | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
-
1994
- 1994-10-06 JP JP6242991A patent/JPH08103243A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005041684A3 (en) * | 2003-08-06 | 2009-04-09 | Senomyx Inc | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| AU2004285410B2 (en) * | 2003-08-06 | 2011-04-14 | Senomyx, Inc. | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| US8124121B2 (en) | 2003-08-06 | 2012-02-28 | Senomyx, Inc. | Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| CN103275058A (en) * | 2003-08-06 | 2013-09-04 | 西诺米克斯公司 | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| US8895050B2 (en) | 2003-08-06 | 2014-11-25 | Senomyx, Inc. | Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| AU2014202646B2 (en) * | 2003-08-06 | 2016-04-21 | Senomyx, Inc. | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| US10060909B2 (en) | 2003-08-06 | 2018-08-28 | Senomyx, Inc. | Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| US10557845B2 (en) | 2003-08-06 | 2020-02-11 | Firmenich Incorporated | Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| US11268952B2 (en) | 2003-08-06 | 2022-03-08 | Firmenich Incorporated | Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| US9072313B2 (en) | 2006-04-21 | 2015-07-07 | Senomyx, Inc. | Comestible compositions comprising high potency savory flavorants, and processes for producing them |
| JP2014523950A (en) * | 2011-07-15 | 2014-09-18 | ジボダン エス エー | Flavor modifying compounds |
| JP2015519298A (en) * | 2012-03-30 | 2015-07-09 | ジボダン エス エー | N-acyl-amino acid derivatives as food flavoring compounds |
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