JP5399083B2 - Milk flavor imparting or enhancing agent and its use in food and drink - Google Patents
Milk flavor imparting or enhancing agent and its use in food and drink Download PDFInfo
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本発明は、バター、チーズ、ミルクなどの乳製品が有する風味、コク味などの乳風味賦与乃至増強剤、および、該乳風味賦与乃至増強剤により乳風味の増強された飲食品に関する。 The present invention relates to a flavor and / or enhancer such as flavor and richness of dairy products such as butter, cheese and milk, and a food or beverage with enhanced milk flavor by the milk flavor or enhancer.
バター、チーズ、牛乳、アイスクリーム、ヨーグルトなどの乳製品は、食事の洋風化に伴って日本人の食生活に浸透し、なくてはならない食品の一つとなっている。 Dairy products such as butter, cheese, milk, ice cream, and yogurt have become one of the essential foods that permeate the Japanese diet along with the westernization of meals.
しかしながら、良質なバターやチーズなどの乳製品は、ごく一部の、高価な国産品、あるいは輸入品に限られており、一般品はその多くが安価で品質の劣る輸入原料を主原料として作られるか、あるいは日本での製造過程において香気、香味の減少または損失が起こるために、乳製品が本来有する芳醇、かつリッチな風味、コク味を消費者が享受する機会が意外と少ないのが実情である。また、最近ではコスト低減あるいはメタボ対策を目的として、乳原料の使用量を減らしても十分な乳風味を有する商品の開発が求められている。 However, dairy products such as high-quality butter and cheese are limited to only a few expensive domestic products or imported products, and many of the general products are made from imported raw materials that are cheap and inferior in quality. As a result, there are surprisingly few opportunities for consumers to enjoy the rich, rich flavor and richness inherent in dairy products because of the reduction or loss of flavor and flavor in the manufacturing process in Japan. is there. In recent years, there has been a demand for the development of a product having a sufficient milk flavor even if the amount of milk raw material is reduced for the purpose of cost reduction or measures against metabolic syndrome.
これまで、バター、チーズなどの乳製品の風味改善、風味増強に関する提案がいくつか行われている。例えば、乳脂肪含有食品材料をリパーゼの存在下に酵素処理する際及び／又は酵素処理して得られる処理物に分枝サイクロデキストリンを配合し、生成物の刺激臭、後味の油っぽい不快臭を除去した嗜好性に優れたバター、チーズ、ミルク等の香気香味を有する乳製品フレーバーの製造法（特許文献１）、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持続性香気香味賦与剤（特許文献２）、飲食品に２−ヒドロキシ−３−メチルペンタン酸とジアセチル及び／又は２−フェニルエチルシンナメートを添加し、マイルドなコク味を有するバター様、果実様、チーズ様、ヨーグルト様などの香気香味特性を賦与、増強できる香料組成物（特許文献３）、乳清蛋白質のプロテアーゼ処理物および乳脂のリパーゼ処理物を各種の飲料、乳製品、焼き菓子類、各種麺類など広範囲な飲食品の異味異臭を除き、風味の付与増強又は改善を図る風味改良材（特許文献４）、（Ｚ）−６−オクテナールを有効成分として含有し、飲食品に乳製品特有の甘いクリーミーな香味を付与することのできる乳風味賦与乃至増強剤（特許文献５）、３−メチルノナン−２，４−ジオンを含有し、乳、乳製品、乳若しくは乳製品を含有する飲食物、又は乳製品代用品に、乳関連製品の香味や「こく」を賦与増強することのできる香味料組成物（特許文献６）、乳又は乳製品のリパーゼ処理及び／又は乳酸菌による発酵処理により得られる処理物を有効成分として含有し、発酵乳にみられる粉っぽい味・においを低減し、かつ呈味（乳感）を増強する、乳飲料又は発酵乳の風味改良剤（特許文献７）、焙煎コーヒーを水、極性有機溶媒又はこれらの混合物で抽出して得られる抽出物を分画して得られた分画分子量１００００以上の画分を乳製品等に添加し、こく、ボリューム感を賦与することのできる香味増強剤（特許文献８）、メチル ２−メチル−３−フリルジスルフィド、ビス（２−メチル−３−フリル）ジスルフィド、メチルフルフリルジスルフィド及びジフルフリルジスルフィドからなる群から選ばれた１種又は2種以上のジスルフィド化合物を含有させる乳、乳製品、乳若しくは乳製品を含有する飲食物、又は乳製品代用品用の香料組成物（特許文献９）、最終飲食品中に、低級脂肪酸をその検知閾値濃度に対して０．０１〜０．５倍濃度添加することで、軽やかで広がりのある香気の増強された飲食品（特許文献１０）
などの提案がある。
So far, several proposals have been made regarding flavor improvement and flavor enhancement of dairy products such as butter and cheese. For example, when a milk fat-containing food material is enzymatically treated in the presence of lipase and / or a processed product obtained by enzymatic treatment is blended with a branched cyclodextrin, an irritating odor of the product, an oily unpleasant odor of the aftertaste A method for producing dairy flavors having an aroma and flavor such as butter, cheese, milk, etc. (Patent Document 1), cheese containing alkanoylamino acid amide as an active ingredient, soy sauce, miso, fish soy sauce, etc. Sustained fragrance flavoring agent (Patent Document 2) having a persistent fragrance flavor property reminiscent of the ripening feeling of fermentation products, butter, cheese, etc., and 2-hydroxy-3-methylpentanoic acid and diacetyl and / or Alternatively, 2-phenylethylcinnamate is added to impart aroma-like flavor characteristics such as butter-like, fruit-like, cheese-like, and yogurt-like with a mild body. A strong flavor composition (Patent Document 3), a whey protein protease-treated product and a milk fat lipase-treated product, except for a wide range of foods and beverages such as various beverages, dairy products, baked goods, and various noodles. Flavor improver (Patent Document 4), (Z) -6-octenal as an active ingredient, and imparting a sweet and creamy flavor peculiar to dairy products to foods and drinks Thorough enhancer (Patent Document 5), 3-methylnonane-2,4-dione, milk, dairy products, food or drink containing milk or dairy products, or dairy substitutes, A flavoring composition capable of imparting and enhancing “koku” (Patent Document 6), a processed product obtained by lipase treatment of milk or dairy products and / or fermentation treatment with lactic acid bacteria as an active ingredient, A flavor improver for milk beverages or fermented milk (Patent Document 7) that reduces the powdery taste and smell and enhances the taste (milky feeling), roasted coffee with water, polar organic solvent, or a mixture thereof A flavor enhancer capable of adding a fraction having a molecular weight cut off of 10,000 or more obtained by fractionating an extract obtained by extraction to dairy products, etc. , One or more disulfide compounds selected from the group consisting of methyl 2-methyl-3-furyl disulfide, bis (2-methyl-3-furyl) disulfide, methylfurfuryl disulfide and difurfuryl disulfide Milk, dairy products, milk or food containing dairy products, or perfume composition for dairy products substitutes (Patent Document 9), final food and drink, lower fatty acids relative to their detection threshold concentrations By adding 0.01 to 0.5-fold concentration was enhanced fragrance with light and spread food or beverage (Patent Document 10)
There are suggestions.
これらの提案は、製品の風味、コク味の賦与または増強を目的とした提案であるが、さらに良質な乳製品の風味またはコク味の賦与または増強を行える提案が求められていた。 These proposals are proposals for the purpose of imparting or enhancing the flavor and richness of the product, but there has been a demand for a proposal capable of imparting or enhancing the flavor or richness of higher quality dairy products.
本発明は、１２−メチルトリデカナールを有効成分として含有することを特徴とする乳風味賦与または増強剤、および、該乳風味賦与または増強剤を用いた飲食品の風味改善に関する。 The present invention relates to a milk flavor imparting or enhancing agent characterized by containing 12-methyltridecanal as an active ingredient, and a flavor improvement of foods and drinks using the milk flavor imparting or enhancing agent.
本発明者らは、乳製品の香気、香味を形成する重要な成分である乳脂肪を高濃度で含有するバターに着目した。バターは未加熱のものはフレッシュバター、あるいは３０℃程度で溶解した溶かしバターで使用される一方、ソテー、焼き菓子その他の料理で頻繁に使用される場合には、未加熱あるいは低温で溶解する場合に比べ、高温での加熱を経ることにより非常に複雑で強い香気香味を生じることが一般に知られている。そこで、バターを１００〜２００℃で加熱したとき生ずる香気物質を分析し、その中に乳製品の香味および乳製品が有するコク味を増強する成分の探索を鋭意検討したところ、１２−メチルトリデカナールは乳製品が有する風味またはコク味を増強する効果があることを見出した。 The present inventors have focused on butter containing milk fat, which is an important component for forming the aroma and flavor of dairy products, at a high concentration. When the butter is unheated, it is used as fresh butter or melted butter melted at about 30 ° C. When it is frequently used in saute, baked goods and other dishes, it is unheated or melts at a low temperature. It is generally known that a very complex and strong aroma is produced by heating at a high temperature. Then, the aromatic substance produced when the butter was heated at 100 to 200 ° C. was analyzed, and when the search for the ingredient that enhances the flavor of the dairy product and the rich taste of the dairy product was conducted, 12-methyltridecanal was analyzed. Has found that it has the effect of enhancing the flavor or richness of dairy products.
なお、１２−メチルトリデカナールの香気に関する報告がわずかながら存在する。例えば、煮込んだ牛肉から得られるエキスに存在し、獣脂様（ｔａｌｌｏｗｙ）、あるいは牛肉様（ｂｅｅｆ−ｌｉｋｅ）の香気を有することが報告されている（Ｃｏｌｌｏｑｕｅｓ（７５）、Ｂｉｏｆｌａｖｏｕｒ９５、２０１−２０５、１９９５）。また、微粉砕のミルクパウダーは保蔵により、異臭を発生し、その一つとして１２−メチルトリデカナールが獣脂様（ｔａｌｌｏｗｙ）の香気を有することが報告されている（ＡＣＳ.Ｓｙｍｐ．Ｓｅｒ.７８２，Ｇａｓ Ｃｈｒｏｍａｔｏｇｈｒａｐｈｙ Ｏｌｆａｃｔｏｍｅｔｒｙ，ｐ４６−６１、２００１）。しかしながら、バター、チーズなどの良好な香気成分として報告はこれまでなかった。そのため、１２−メチルトリデカナールは、肉のフレーバーなどごく一部の香料素材として使用されるのみで、乳系香料の香料素材として使用されたことはなかった。 There are a few reports on the aroma of 12-methyltridecanal. For example, it has been reported that it is present in extracts obtained from stewed beef and has a tallow-like or beef-like aroma (Colloques (75), Bioflavour 95, 201-205, 1995). ). In addition, it is reported that finely pulverized milk powder generates off-flavor due to storage, and as one of them, 12-methyltridecanal has a tallow-like aroma (ACS. Symp. Ser. 782, Gas Chromatography Olfactory, p46-61, 2001). However, there has been no report so far as a good aroma component such as butter and cheese. Therefore, 12-methyltridecanal is only used as a part of a fragrance material such as a flavor of meat, and has never been used as a fragrance material for a milk-based fragrance.
なお、１２−メチルトリデカナールの構造式は［化１］で示される。 The structural formula of 12-methyltridecanal is represented by [Chemical Formula 1].
本発明者らが検討した結果、１２−メチルトリデカナールをバター、チーズ、牛乳などの乳製品に１ｐｐｔ〜１００ｐｐｍの濃度で含有させたところ、乳製品の香味および乳製品が有する風味またはコク味を増強することを見いだし、本発明を完成するに至った。 As a result of the study by the present inventors, when 12-methyltridecanal was added to dairy products such as butter, cheese, and milk at a concentration of 1 ppt to 100 ppm, the flavor of the dairy product and the flavor or richness of the dairy product were obtained. As a result, the present invention has been completed.
かくして、本発明は、１２−メチルトリデカナールからなる乳風味賦与乃至増強剤を提供するものである。 Thus, the present invention provides a milk flavor enhancer or enhancer comprising 12-methyltridecanal.
また、本発明は、前記の乳風味賦与乃至増強剤を１２−メチルトリデカナール濃度として１ｐｐｂ〜１０４ｐｐｍ含有させることを特徴とする乳系香料組成物を提供するものである。 In addition, the present invention provides a milk-based fragrance composition characterized by containing 1 ppb to 10 4 ppm of the above-mentioned milk flavor imparting or enhancing agent as a 12-methyltridecanal concentration.
さらに、本発明は、前記の乳風味賦与乃至増強剤または乳系香料組成物を１２−メチルトリデカナール濃度として１ｐｐｔ〜１００ｐｐｍ含有させることを特徴とする飲食品を提供するものである。 Furthermore, the present invention provides a food or drink characterized by containing 1 ppt to 100 ppm of the above-described milk flavor imparting or enhancing agent or milk-based fragrance composition as a 12-methyltridecanal concentration.
本発明によれば、１２−メチルトリデカナールを含有させることにより乳風味の賦与または増強を行うことができる。さらに、１２−メチルトリデカナール濃度として１ｐｐｂ〜１０４ｐｐｍ含有させた乳系香料組成物を飲食品に添加することにより、乳製品が有する風味またはコク味を顕著に賦与または増強し、飲食品の品質を著しく向上させることが出来る。 According to the present invention, milk flavor can be given or enhanced by containing 12-methyltridecanal. Furthermore, by adding a milk-based fragrance composition containing 1 ppb to 10 4 ppm as a 12-methyltridecanal concentration to a food or drink, the flavor or richness of the dairy product is remarkably imparted or enhanced. The quality can be significantly improved.
以下、本発明についてさらに詳細に説明する。 Hereinafter, the present invention will be described in more detail.
本発明の方法において原料で使用しうる乳風味賦与乃至増強剤の有効成分である１２−メチルトリデカナールは、一般的な方法にしたがって合成されたものまたは市販品のいずれでも良い。市販品としては、例えば、１２−メチルトリデカナール（Ｇｉｖａｕｄａｎ社製）、１２−メチルトリデカナール（ＴＲＥＡＴ社製）などを挙げることができる。 12-methyltridecanal, which is an active ingredient of a milk flavor enhancer or enhancer that can be used as a raw material in the method of the present invention, may be either synthesized according to a general method or a commercially available product. As a commercial item, 12-methyl tridecanal (made by Givaudan), 12-methyl tridecanal (made by TREAT) etc. can be mentioned, for example.
本発明の乳風味賦与乃至増強剤は、そのまま飲食品、香粧品、保健・衛生・医薬品にごく微量配合して乳風味を付与又は増強することができるが他の成分と混合して乳系香料組成物を調製し、該香料組成物を用いて飲食品、香粧品、保健・衛生・医薬品に乳風味を付与又は増強することもできる。該香料組成物の１２−メチルトリデカナールと共に含有しうる他の香料成分としては、各種の合成香料、天然香料、天然精油、植物エキスなどを挙げることができる。例えば、「特許庁、周知慣用技術集（香料）第ＩＩ部食品香料、Ｐ８８−１３１、平成１２年１月１４日発行」に記載されている天然精油、天然香料、合成香料を挙げることができる。 The milk flavor imparting or enhancing agent of the present invention can be added or enhanced as it is in foods and beverages, cosmetics, health / hygiene / pharmaceuticals as it is, but it is mixed with other ingredients to give a milk flavor. A composition can be prepared, and the flavor composition can be used to impart or enhance milk flavor to foods, drinks, cosmetics, health / hygiene / pharmaceuticals. Examples of other fragrance components that can be contained together with 12-methyltridecanal of the fragrance composition include various synthetic fragrances, natural fragrances, natural essential oils, plant extracts, and the like. For example, natural essential oils, natural fragrances, and synthetic fragrances described in "Patent Office, Well-known and commonly used technology (fragrance) Part II food fragrance, P88-131, issued on January 14, 2000" can be mentioned. .
例えば、γ−カプロラクトン、γ−ヘプタラクトン、γ−オクタラクトン、γ−ノナラクトン、γ−デカラクトン、７−デセン−４−オリド、３−メチル−４−デセン−４−オリド、３−メチル−５−デセン−４−オリド、γ−ウンデカラクトン、γ−ドデカラクトン、γ−トリデカラクトン、γ−テトラデカラクトン、δ−カプロラクトン、２−ヘキセン−５−オリド、２−ヘプテン−５−オリド、δ−オクタラクトン、２−オクテン−５−オリド、４−メチル−５−オクタノリド、δ−ノナラクトン、２−ノネン−５−オリド、４−メチル−５−ノナノリド、δ−デカラクトン、２−デセン−５−オリド、４−メチル−５−デカノリド、δ−ウンデカラクトン、２−ウンデセン−５−オリド、４−メチル−５−ウンデカノリド、δ−ドデカラクトン、２−ドデセン−５−オリド、４−メチル−５−ドデカノリド、δ−トリデカラクトン、２−トリデセン−５−オリド、４−メチル−５−トリデカノリド、δ−テトラデカラクトン、２−テトラデセン−５−オリド、２−ペンタデセン−５−オリド、２−ヘキサデセン−５−オリド、２−ヘプタデセン−５−オリド、２−オクタデセン−５−オリド、２−ノナデセン−５−オリド、２−エイコセン−５−オリド、ε−デカラクトンなどのラクトン類；プロピオン酸、酪酸、吉草酸、イソ吉草酸、カプロン酸、トランス−２−ヘキセン酸、ヘプタン酸、カプリル酸、ノナン酸、５−ヒドロキシノナン酸、カプリン酸、２−デセン酸、４−デセン酸、５−デセン酸、６−デセン酸、９−デセン酸、５−ヒドロキシデセン酸、５−ヒドロキシウンデカン酸、ラウリン酸、５−ヒドロキシドデカン酸、ミリスチン酸、ペンタデカン酸、イソペンタデカン酸、パルミチン酸、ヘプタデカン酸、ステアリン酸、オレイン酸、リノール酸、リノレン酸などの脂肪酸類；アセトアルデヒド、プロパナール、ブタナール、２−ブテナール、ヘキサナール、オクタナール、４−ヘプテナール、２，４−オクタジエナール、ノナナール、２−ノネナール、２，４−ノナジエナール、２，６−ノナジエナール、デカナール、２，４−デカジエナール、ウンデカナール、２，４−ウンデカジエナール、ドデカナール、ベンズアルデヒド、バニリン、エチルバニリン、フルフラール、ヘリオトロピンジエチルアセタールなどのアルデヒド類；蟻酸エチル、酢酸エチル、酢酸ブチル、酢酸イソアミル、酢酸デシル、酢酸ドデシル、酢酸フェネチル、乳酸エチル、酪酸エチル、２−メチル酪酸エチル、３−エチル酪酸エチル、吉草酸メチル、カプロン酸メチル、カプロン酸エチル、ヘプタン酸メチル、ヘプタン酸エチル、カプリル酸エチル、カプリル酸イソアミル、カプリル酸ヘプチル、ノナン酸メチル、ノナン酸エチル、カプリン酸メチル、カプリン酸エチル、ウンデカン酸エチル、ラウリン酸メチル、ラウリン酸エチル、ミリスチン酸エチル、パルミチン酸エチル、サリチル酸メチル、コハク酸ジエチル、セバシン酸ジエチル、５−ヒドロキシヘキサン酸エチル、５−ヒドロキシデカン酸エチル、５−ヒドロキシウンデカン酸エチル、５−ヒドロキシデカン酸プロピル、５−ヒドロキシデカン酸イソプロピル、５−ヒドロキシオクタン酸２−メチルプロピル、５−ヒドロキシ−９−メチルデカン酸エチルなどのエステル類；エタノール、プロパノール、ブタノール、ペンタノール、ヘキサノール、ヘプタノール、オクタノール、ノナノール、デカノール、ベンジルアルコール、フェニルエチルアルコール、フルフリルアルコールなどのアルコール類；２−ヘプタノン、２−オクタノン、３−オクタノン、１−オクテン−３−オン、２−ノナノン、３−ノナノン、８−ノネン−２−オン、２−ウンデカノン、２−トリデカノン、アセトイン、５−ヒドロキシ−４−オクタノン、ジアセチル、２，３−ペンタジオン、２，３−ヘキサジオン、２，３−ヘプタジオン、アセチルイソバレリル、ｐ−メトキシアセトフェノン、ベンゾフェノン、マルトールなどのケトン類；フェニルエチルアンスラニレート、トリメチルアミン、インドール、スカトール、ピリジン、イソキノリン、ピラジン、メチルピラジンなどの含窒素化合物類；メチルメルカプタン、イソブチルメルカプタン、２，４−ジチアペンタン、ジメチルスルフィド、ジメチルジスルフィド、２，４−ジチアペンタン、ジメチルトリスルフィド、ジメチルスルフォキシド、ジメチルスルフォン、メタンチオール、メチルスルフォニルメタン、メチルイソチオシアネート、エチルイソチオシアネート、アリルイソチオシアネート、２−メチル−３−ブタンチオール、メチオナール、チオ酢酸エチル、チオ酪酸メチル、３−ブテニルイソチオシアネート、２−メチルチオフェン、ベンゾチアゾール、スルフロール、アセチル乳酸チオメチルエステル、プロピオニル乳酸チオメチルエステル、ブチリル乳酸チオメチルエステル、バレリル乳酸チオメチルエステル、２−メチルブチリル乳酸チオメチルエステル、デシリル乳酸チオメチルエステル、アセチル乳酸チオエチルエステル、プロピオニル乳酸チオエチルエステル、ブチリル乳酸チオエチルエステル、バレリル乳酸チオエチルエステル、イソカプロイル乳酸チオプロピルエステルなどの含硫化合物類など公知の香料化合物；乳脂のリパーゼ分解物；乳タンパク質のプロテアーゼ分解物；乳、濃縮乳、粉乳、ミルクホエイ、バター、チーズ、ヨーグルトもしくはこれらの混合物からの乳または乳加工品の分画物などを挙げることができる。 For example, γ-caprolactone, γ-heptalactone, γ-octalactone, γ-nonalactone, γ-decalactone, 7-decen-4-olide, 3-methyl-4-decen-4-olide, 3-methyl-5- Decene-4-olide, γ-undecalactone, γ-dodecalactone, γ-tridecalactone, γ-tetradecalactone, δ-caprolactone, 2-hexene-5-olide, 2-heptene-5-olide, δ -Octalactone, 2-octene-5-olide, 4-methyl-5-octanolide, δ-nonalactone, 2-nonene-5-olide, 4-methyl-5-nonanolide, δ-decalactone, 2-decene-5 Orido, 4-methyl-5-decanolide, δ-undecalactone, 2-undecen-5-olide, 4-methyl-5-undecanolide, δ-dodecalactone 2-dodecene-5-olide, 4-methyl-5-dodecanolide, δ-tridecalactone, 2-tridecen-5-olide, 4-methyl-5-tridecanolide, δ-tetradecalactone, 2-tetradecene-5 Orido, 2-Pentadecene-5-Olide, 2-Hexadecene-5-Olide, 2-Heptadecene-5-Olide, 2-Octadecene-5-Olide, 2-Nonadecene-5-Olide, 2-Eicocene-5-Olide, Lactones such as ε-decalactone; propionic acid, butyric acid, valeric acid, isovaleric acid, caproic acid, trans-2-hexenoic acid, heptanoic acid, caprylic acid, nonanoic acid, 5-hydroxynonanoic acid, capric acid, 2- Decenoic acid, 4-decenoic acid, 5-decenoic acid, 6-decenoic acid, 9-decenoic acid, 5-hydroxydecenoic acid, 5-hydroxyundeca Fatty acids such as acid, lauric acid, 5-hydroxydodecanoic acid, myristic acid, pentadecanoic acid, isopentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, oleic acid, linoleic acid, linolenic acid; acetaldehyde, propanal, butanal, 2-butenal, hexanal, octanal, 4-heptenal, 2,4-octadienal, nonanal, 2-nonenal, 2,4-nonadienal, 2,6-nonadienal, decanal, 2,4-decadienal, undecanal, 2 , 4-Undecadienal, dodecanal, benzaldehyde, vanillin, ethyl vanillin, furfural, heliotropin diethyl acetal and other aldehydes; ethyl formate, ethyl acetate, butyl acetate, isoamyl acetate, decyl acetate, acetic acid Dodecyl, phenethyl acetate, ethyl lactate, ethyl butyrate, ethyl 2-methylbutyrate, ethyl 3-ethylbutyrate, methyl valerate, methyl caproate, ethyl caproate, methyl heptanoate, ethyl heptanoate, ethyl caprylate, isoamyl caprylate , Heptyl caprylate, methyl nonanoate, ethyl nonanoate, methyl caprate, ethyl caprate, ethyl undecanoate, methyl laurate, ethyl laurate, ethyl myristate, ethyl palmitate, methyl salicylate, diethyl succinate, sebacic acid Diethyl, ethyl 5-hydroxyhexanoate, ethyl 5-hydroxydecanoate, ethyl 5-hydroxyundecanoate, propyl 5-hydroxydecanoate, isopropyl 5-hydroxydecanoate, 2-methylpropyl 5-hydroxyoctanoate Esters such as ethyl 5-hydroxy-9-methyldecanoate; alcohols such as ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, benzyl alcohol, phenylethyl alcohol, furfuryl alcohol; 2- Heptanone, 2-octanone, 3-octanone, 1-octen-3-one, 2-nonanone, 3-nonanone, 8-nonen-2-one, 2-undecanone, 2-tridecanone, acetoin, 5-hydroxy-4- Ketones such as octanone, diacetyl, 2,3-pentadione, 2,3-hexadione, 2,3-heptadione, acetylisovaleryl, p-methoxyacetophenone, benzophenone, maltol; phenylethylanthranilate Nitrogen-containing compounds such as trimethylamine, indole, skatole, pyridine, isoquinoline, pyrazine, methylpyrazine; methyl mercaptan, isobutyl mercaptan, 2,4-dithiapentane, dimethyl sulfide, dimethyl disulfide, 2,4-dithiapentane, dimethyl trisulfide, dimethyl Sulfoxide, dimethylsulfone, methanethiol, methylsulfonylmethane, methylisothiocyanate, ethylisothiocyanate, allylisothiocyanate, 2-methyl-3-butanethiol, methional, ethyl thioacetate, methyl thiobutyrate, 3-butenyliso Thiocyanate, 2-methylthiophene, benzothiazole, sulfuryl, acetyl lactate thiomethyl ester, propionyl lactate thiomethyl ester, Butyryl lactate thiomethyl ester, valeryl lactate thiomethyl ester, 2-methylbutyryl lactate thiomethyl ester, desilyl lactate thiomethyl ester, acetyl lactate thioethyl ester, propionyl lactate thioethyl ester, butyryl lactate thioethyl ester, valeryl lactate thioethyl ester, From known perfume compounds such as sulfur-containing compounds such as isocaproyl lactate propyl ester; lipase degradation product of milk fat; protease degradation product of milk protein; milk, concentrated milk, milk powder, milk whey, butter, cheese, yogurt or a mixture thereof And fractions of milk or processed milk products.
本発明の１２−メチルトリデカナールの配合量は、重要であり、その目的あるいは乳系香料組成物の種類によっても異なるが、例えば、乳系香料組成物の全体重量に対して１ｐｐｂ〜１０４ｐｐｍ、好ましくは、１０ｐｐｂ〜１０３ｐｐｍの範囲を例示することができる。これらの範囲内では、乳系香料組成物に対し乳脂肪感、ボディー感、コク味などを付与する優れた効果を有する。一方、乳系香料組成物に対する１２−メチルトリデカナールの配合量が１０４ｐｐｍを越える場合には、１２−メチルトリデカナール単独特有の獣脂様の異臭としての香気・香味特性が出てしまい好ましくない。また、乳系香料組成物に対する１２−メチルトリデカナールの配合量が１ｐｐｂを下回る場合は本発明特有の香気・香味付与効果が得られない。 The amount of 12-methyltridecanal of the present invention is important and varies depending on the purpose or the type of the milk-based fragrance composition. For example, 1 ppb to 10 4 ppm relative to the total weight of the milk-based fragrance composition. Preferably, a range of 10 ppb to 10 3 ppm can be exemplified. Within these ranges, the milk-based fragrance composition has an excellent effect of imparting milk fat feeling, body feeling, richness and the like. On the other hand, when the blending amount of 12-methyltridecanal with respect to the milk-based fragrance composition exceeds 10 4 ppm, aroma and flavor characteristics as tallow-like odor peculiar to 12-methyltridecanal alone appear, which is not preferable. . Moreover, when the compounding quantity of 12-methyl tridecanal with respect to a milk-type fragrance | flavor composition is less than 1 ppb, the fragrance and flavor imparting effect peculiar to this invention are not acquired.
本発明の１２−メチルトリデカナールを含有する乳系香料組成物には、必要に応じて、香料組成物において通常使用されている、例えば、水、エタノール、当の溶剤；エチレングリコール、プロピレングリコール、ジプロピレングリコール、グリセリン、ヘキシルグリコール、ベンジルベンゾエート、トリエチルシトレート、ジエチルフタレート、ハーコリン、中鎖脂肪酸トリグリセライド、中鎖脂肪酸ジグリセリド等の香料保留剤を含有することができる。 The milk-based fragrance composition containing 12-methyltridecanal of the present invention, if necessary, is usually used in the fragrance composition, for example, water, ethanol, the solvent of interest; ethylene glycol, propylene glycol, Perfume retention agents such as dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, hercoline, medium chain fatty acid triglyceride, medium chain fatty acid diglyceride and the like can be contained.
本発明の１２−メチルトリデカナールからなる乳風味賦与乃至増強剤は、上記したようにそれ自身単独で、または、１２−メチルトリデカナールを含有させた乳系香料組成物を調製して、各種の製品、例えば、飲食品、香粧品、保健・衛生・医薬品に乳製品が有する風味またはコク味を付与又は増強することもできる。 The milk flavor imparting or enhancing agent comprising 12-methyltridecanal according to the present invention can be used alone or as described above, and various milk flavoring compositions containing 12-methyltridecanal can be prepared. The flavor or richness of dairy products can be imparted to or enhanced in products such as foods and drinks, cosmetics, health / hygiene / pharmaceuticals.
本発明の１２−メチルトリデカナールからなる乳風味賦与乃至増強剤又は１２−メチルトリデカナールを含有させた乳系香料組成物によって乳製品が有する風味またはコク味を付与することのできる飲食品の具体例としては何ら限定されるものではなく、例えば、コーラ飲料、果汁入炭酸飲料、乳類入炭酸飲料などの炭酸飲料類；果汁飲料、野菜飲料、スポーツドリンク、ハチミツ飲料、豆乳、ビタミン補給飲料、ミネラル補給飲料、栄養ドリンク、滋養ドリンク、乳酸菌飲料、乳飲料などの食系飲料類；緑茶、紅茶、ウーロン茶、ハーブティー、コーヒー飲料などの嗜好飲料類；チューハイ、カクテルドリンク、発泡酒、果実酒、薬味酒などのアルコール飲料類；バター、チーズ、ミルク、ヨーグルトなどの乳製品；アイスクリーム、ラクトアイス、氷菓、ヨーグルト、プリン、ゼリー、デイリーデザートなどのデザート類及びそれらを製造するためのミックス類；キャラメル、キャンディー、錠菓、クラッカー、ビスケット、クッキー、パイ、チョコレート、スナックなどの菓子類及びそれらを製造するためのケーキミックスなどのミックス類；パン、スープ、各種インスタント食品などの一般食品類；をあげることができる。 Specifics of foods and drinks that can impart the flavor or richness of dairy products with a milk flavor imparting or enhancing agent comprising 12-methyltridecanal or a milk-based fragrance composition containing 12-methyltridecanal of the present invention Examples include, but are not limited to, for example, carbonated drinks such as cola drinks, carbonated drinks with fruit juice, carbonated drinks with milk; fruit drinks, vegetable drinks, sports drinks, honey drinks, soy milk, vitamin supplement drinks, Mineral supplement drinks, nutrition drinks, nourishing drinks, lactic acid bacteria drinks, milk drinks and other food drinks; green teas, teas, oolong teas, herbal teas, coffee drinks and other favorite drinks; Chuhai, cocktail drinks, sparkling liquor, fruit liquor, Alcoholic beverages such as condiments; dairy products such as butter, cheese, milk, yogurt; ice cream, Desserts such as ice, ice confectionery, yogurt, pudding, jelly, daily dessert and mixes for producing them; caramel, candy, tablet confectionery, crackers, biscuits, cookies, pie, chocolate, snacks and other confectionery And a mix such as a cake mix for producing a food; a general food such as bread, soup and various instant foods.
また、本発明の１２−メチルトリデカナールからなる乳風味賦与乃至増強剤又は１２−メチルトリデカナールを含有させた乳系香料組成物によって乳風味を付与することのできる香粧品、保健・衛生・医薬品の具体例としては何ら限定されるものではなく、例えば、フレグランス製品、基礎化粧品、仕上げ化粧品、頭髪化粧品、日焼け化粧品、薬用化粧品、ヘアケア製品、石鹸、身体洗剤、浴用剤、洗剤、柔軟仕上げ剤、漂白剤、エアゾール剤、消臭・芳香剤、忌避剤、口腔用組成物、皮膚外溶剤などを挙げることができる。 Further, a cosmetic, health, hygiene and pharmaceutical product capable of imparting a milk flavor with a milk flavor imparting or enhancing agent comprising the 12-methyl tridecanal of the present invention or a milk-based fragrance composition containing 12-methyl tridecanal. Specific examples of are not limited at all, for example, fragrance products, basic cosmetics, finish cosmetics, hair cosmetics, tanning cosmetics, medicated cosmetics, hair care products, soaps, body detergents, bath preparations, detergents, softeners, A bleaching agent, an aerosol agent, a deodorizing / fragrance agent, a repellent, a composition for oral cavity, an external skin solvent, etc. can be mentioned.
また、本発明の１２−メチルトリデカナールの飲食品への配合量は、その目的あるいは飲食品の種類によっても異なるが、前記の乳風味賦与乃至増強剤または乳系香料組成物を有効量添加することにより乳の脂肪感、ボディー感、コク味などを付与することができる。その際の飲食品の１２−メチルトリデカナールの添加量は、製品の種類や形態に応じて異なり一概に言えないが、例えば、飲食品の全体重量に対して１ｐｐｔ〜１００ｐｐｍ、好ましくは、１０ｐｐｔ〜１０ｐｐｍの範囲を例示することができる。一方、飲食品の全体重量に対する１２−メチルトリデカナールの配合量が１００ｐｐｍを越える場合には、１２−メチルトリデカナール単独特有の獣脂様、ロウ様の異臭としての香気・香味特性が出てしまい好ましくない。また、飲食品の全体重量に対する１２−メチルトリデカナールの配合量が１ｐｐｔを下回る場合は本発明特有の香気・香味付与効果が得られない。 The amount of 12-methyltridecanal of the present invention added to food or drink varies depending on the purpose or the type of food or drink, but an effective amount of the above-described milk flavor imparting or enhancing agent or milk-based fragrance composition is added. As a result, milk fatness, body feeling, richness and the like can be imparted. The amount of 12-methyltridecanal added to the food or drink at that time varies depending on the type and form of the product and cannot be generally stated. For example, it is 1 ppt to 100 ppm, preferably 10 ppt to the total weight of the food and drink. A range of 10 ppm can be exemplified. On the other hand, when the blending amount of 12-methyltridecanal with respect to the total weight of the food and drink exceeds 100 ppm, the tallow-like and waxy off-flavor characteristics unique to 12-methyltridecanal alone are preferable. Absent. Moreover, when the compounding quantity of 12-methyl tridecanal with respect to the whole weight of food / beverage products is less than 1 ppt, the fragrance and flavor imparting effect peculiar to this invention are not acquired.
以下、本発明を実施例および比較例によりさらに具体的に説明する。 Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples.
［実施例１、比較例１］
バター様調合香料組成物への１２−メチルトリデカナールの添加効果
バター様の調合香料組成物として下記の各成分（質量％）を調合した。
[Example 1, Comparative Example 1]
Effect of adding 12-methyltridecanal to a butter-like blended fragrance composition The following components (mass%) were formulated as a butter-like blended fragrance composition.
上記バター様調合香料組成物（対照品１）１００ｇに、１２−メチルトリデカナールを０．０１μｇ（１０−４ｐｐｍ：比較品１）、０．１μｇ（１０−３ｐｐｍ：本発明品１）、１０μｇ（１０−１ｐｐｍ：本発明品２）、１ｍｇ（１０ｐｐｍ：本発明品３）、１００ｍｇ（１０３ｐｐｍ：本発明品４）、１ｇ（１０４ｐｐｍ：本発明品５）、１０ｇ（１０５ｐｐｍ：比較品２）混合して、比較品１および２、本発明品１〜３のバター調合香料組成物を調製した。それぞれの香料組成物の０．１％エタノール溶液を良く訓練されたパネラー１０人により風味評価を行った。該化合物を加えていない対照品１の０．１％エタノール溶液を対照とした、パネラーの平均的な香気評価を表２に示す。 To 100 g of the above butter-like blended fragrance composition (control product 1), 0.01 μg of 12-methyltridecanal (10 −4 ppm: comparative product 1), 0.1 μg (10 −3 ppm: product of the present invention 1), 10 μg (10 −1 ppm: Invention product 2), 1 mg (10 ppm: Invention product 3), 100 mg (10 3 ppm: Invention product 4), 1 g (10 4 ppm: Invention product 5), 10 g (10 5 ppm: Comparative product 2) A butter blended fragrance composition of Comparative products 1 and 2, and inventive products 1 to 3 was prepared by mixing. Taste evaluation was performed by 10 panelists who were well trained in a 0.1% ethanol solution of each fragrance composition. Table 2 shows the average odor evaluation of the panelists using the 0.1% ethanol solution of the control product 1 to which the compound was not added as a control.
表２の結果から明らかなように、該化合物を加えた本発明品１〜５は、乳脂肪独特のバター感が増強されていた。特に本発明品３および４は乳脂肪独特のリッチで良好なバター感が著しく増強されており、パネラー全員が好ましいとの評価を与えた。一方、比較品１は対照品１と大差なく、比較品２はバターとは異質な強い不快臭が感じられたとの評価であった。
［実施例２、比較例２］
チーズ様調合香料組成物への１２−メチルトリデカナールの添加効果
チーズ様の調合香料組成物として下記の各成分（質量％）を調合した。
As is clear from the results in Table 2, the products 1 to 5 of the present invention to which the compound was added had enhanced butteriness peculiar to milk fat. In particular, the products 3 and 4 of the present invention were remarkably enhanced in the rich and good butter feeling unique to milk fat, and all the panelists were evaluated as preferable. On the other hand, Comparative Product 1 was not much different from Control Product 1, and Comparative Product 2 was evaluated as having a strong unpleasant odor that was different from butter.
[Example 2, Comparative Example 2]
Effect of 12-methyltridecanal addition to cheese-like blended fragrance composition
The following components (mass%) were prepared as a cheese-like blended fragrance composition.
上記チーズ様調合香料組成物（対照品２）１００ｇに、１２−メチルトリデカナールを０．０１μｇ（１０−４ｐｐｍ：比較品３）、０．１μｇ（１０−３ｐｐｍ：本発明品６）、１０μｇ（１０−１ｐｐｍ：本発明品７）、１ｍｇ（１０ｐｐｍ：本発明品８）、１００ｍｇ（１０３ｐｐｍ：本発明品９）、１ｇ（１０４ｐｐｍ：本発明品１０）、１０ｇ（１０５ｐｐｍ：比較品４）混合して、比較品３および４、本発明品６〜１０のバター調合香料組成物を調製した。それぞれの香料組成物の０．１％エタノール溶液を良く訓練されたパネラー１０人により風味評価を行った。該化合物を加えていない対照品２の０．１％エタノール溶液を対照とした、パネラーの平均的な香気評価を表２に示す。 To 100 g of the cheese-like blended fragrance composition (control product 2), 0.01 μg (10 −4 ppm: comparative product 3), 0.1 μg (10 −3 ppm: invention product 6) of 12-methyltridecanal, 10 μg (10 −1 ppm: Invention product 7), 1 mg (10 ppm: Invention product 8), 100 mg (10 3 ppm: Invention product 9), 1 g (10 4 ppm: Invention product 10), 10 g (10 5 ppm: Comparative product 4) Mixed to prepare butter blended fragrance compositions of Comparative products 3 and 4 and Invention products 6 to 10. Taste evaluation was performed by 10 panelists who were well trained in a 0.1% ethanol solution of each fragrance composition. Table 2 shows the average odor evaluation of the panelists using the 0.1% ethanol solution of the control product 2 to which the compound was not added as a control.
表４の結果から明らかなように、該化合物を加えた本発明品６〜１０は、チーズ様のボディー感が増強されていた。特に本発明品８および９は乳脂肪独特のチーズ様のボディー感が、著しく増強されており、パネラー全員が好ましいとの評価を与えた。一方、比較品３は対照品２と大差なく、比較品４はチーズとは異質な不快臭が感じられたとの評価であった。
［実施例３、比較例３］
ミルク様調合香料組成物への１２−メチルトリデカナールの添加効果
ミルク様の調合香料組成物として下記の各成分（質量％）を調合した。
As is apparent from the results in Table 4, the products 6 to 10 of the present invention to which the compound was added had an enhanced cheese-like body feeling. In particular, the products 8 and 9 of the present invention were remarkably enhanced in the cheese-like body feeling peculiar to milk fat, and all panelists were evaluated as preferable. On the other hand, the comparative product 3 was not much different from the control product 2, and the comparative product 4 was evaluated as having an unpleasant odor different from cheese.
[Example 3, Comparative Example 3]
Effect of adding 12-methyltridecanal to milk-like fragrance composition
The following components (mass%) were prepared as milk-like blended fragrance compositions.
上記ミルク様調合香料組成物（対照品３）１００ｇに、１２−メチルトリデカナールを０．０１μｇ（１０−４ｐｐｍ：比較品５）、０．１μｇ（１０−３ｐｐｍ：本発明品１１）、１０μｇ（１０−１ｐｐｍ：本発明品１２）、１ｍｇ（１０ｐｐｍ：本発明品１３）、１００ｍｇ（１０３ｐｐｍ：本発明品１４）、１ｇ（１０４ｐｐｍ：本発明品１５）、１０ｇ（１０５ｐｐｍ：比較品６）混合して、比較品５および６、本発明品１１〜１５のバター調合香料組成物を調製した。それぞれの香料組成物の０．１％エタノール溶液を良く訓練されたパネラー１０人により風味評価を行った。該化合物を加えていない対照品３の０．１％エタノール溶液を対照とした、パネラーの平均的な香気評価を表６に示す。 To 100 g of the above milk-like blended fragrance composition (control product 3), 0.01 μg of 12-methyltridecanal (10 −4 ppm: comparative product 5), 0.1 μg (10 −3 ppm: product of the present invention 11), 10 μg (10 −1 ppm: Invention product 12), 1 mg (10 ppm: Invention product 13), 100 mg (10 3 ppm: Invention product 14), 1 g (10 4 ppm: Invention product 15), 10 g (10 5 ppm: Comparative product 6) Mixed to prepare butter blended fragrance compositions of Comparative products 5 and 6, and inventive products 11-15. Taste evaluation was performed by 10 panelists who were well trained in a 0.1% ethanol solution of each fragrance composition. Table 6 shows the average odor evaluation of the panelists using the 0.1% ethanol solution of Control 3 to which the compound was not added as a control.
表６の結果から明らかなように、該化合物を加えた本発明品１１〜１５は、乳脂肪独特のボディー感が賦与され、ミルク様香気が増強されていた。特に本発明品１３および１４は乳脂肪独特のリッチでコクのあるクリーミーなボディー感が賦与され、良好なミルク様香気が著しく強調されており、パネラー全員が好ましいとの評価を与えた。一方、比較品５は対照品３と大差なく、比較品６はミルクとは異質な不快臭が感じられたとの評価であった。
［実施例４、比較例４］
バター様調合香料組成物のクッキーへの添加効果
実施例１で得られたバター様調合香料組成物（本発明品４及び対照品１）を下記処方のクッキー生地に添加し、２２０℃で７分間焼き上げクッキーを調製した。本発明品４及び対照品１を添加したクッキーをそれぞれ本発明品１６及び比較品７とした。これらのクッキーを、専門パネラー２０人により官能評価を行った。
As is clear from the results in Table 6, the products 11 to 15 of the present invention to which the compound was added had a body feeling peculiar to milk fat and enhanced milk-like aroma. In particular, the products 13 and 14 of the present invention were given a rich and rich creamy body feeling peculiar to milk fat, and a good milk-like aroma was remarkably emphasized. On the other hand, Comparative Product 5 was not much different from Control Product 3, and Comparative Product 6 was evaluated as having an unpleasant odor that was different from milk.
[Example 4, Comparative Example 4]
Effect of adding butter-like fragrance composition to cookies
The butter-like blended fragrance composition obtained in Example 1 (the product 4 of the present invention and the control product 1) was added to a cookie dough having the following formulation to prepare a baked cookie at 220 ° C. for 7 minutes. Cookies added with the inventive product 4 and the control product 1 were designated as the inventive product 16 and the comparative product 7, respectively. These cookies were subjected to sensory evaluation by 20 professional panelists.
その結果、専門パネラー２０人全員が、本発明品１６は比較品７に較べて、独特のクリーミーな乳脂肪感が賦与され、バターリッチなイメージの風味が強調されているとの評価であった。
［実施例５、比較例５］
チーズ様調合香料組成物のクラッカーへの添加効果
実施例２で得られたチーズ様調合香料組成物（本発明品９及び対照品２）を下記処方のクラッカー生地に添加し、常法によりクラッカーを調製した。本発明品９及び対照品２を添加したクラッカーをそれぞれ本発明品１７及び比較品８とした。これらのクラッカーを、専門パネラー２０人により官能評価を行った。
As a result, all 20 professional panelists evaluated that the product 16 of the present invention was given a unique creamy milk fat feeling and the flavor of butter-rich image was emphasized compared to the comparative product 7. .
[Example 5, Comparative Example 5]
Effect of adding cheese-like fragrance composition to crackers
The cheese-like blended fragrance composition (invention product 9 and control product 2) obtained in Example 2 was added to a cracker dough having the following formulation, and a cracker was prepared by a conventional method. The crackers added with the inventive product 9 and the control product 2 were designated as the inventive product 17 and the comparative product 8, respectively. These crackers were subjected to sensory evaluation by 20 professional panelists.
その結果、専門パネラー２０人全員が、本発明品１７は比較品８に較べて、チーズ様のボディー感が著しく強調されていると評価した。
［実施例６、比較例６］
ミルク様調合香料組成物のアイスクリームへの添加効果
実施例３で得られたミルク様調合香料組成物（本発明品１４及び対照品３）を下記処方のアイスクリームに添加し、常法によりアイスクリームを調製した。本発明品１４及び対照品３を添加したアイスクリームをそれぞれ本発明品１８及び比較品９とした。これらのクッキーを、専門パネラー２０人により官能評価を行った。
As a result, all 20 professional panelists evaluated that the inventive product 17 was markedly emphasized in the cheese-like body feeling compared to the comparative product 8.
[Example 6, Comparative Example 6]
Effect of adding milk-like fragrance composition to ice cream The milk-like fragrance composition obtained in Example 3 (present invention product 14 and control product 3) was added to ice cream having the following formulation, and ice cream was prepared in a conventional manner. A cream was prepared. The ice creams added with the inventive product 14 and the control product 3 were designated as the inventive product 18 and the comparative product 9, respectively. These cookies were subjected to sensory evaluation by 20 professional panelists.
その結果、専門パネラー２０人全員が、本発明品１８は比較品９に較べて、良好な乳脂感が著しく強調され、クリーミーであると評価した。
［実施例７、比較例７］
ミルク様調合香料組成物のミルクコーヒーへの添加効果
実施例３で得られたミルク様調合香料組成物（本発明品１４及び対照品３）を下記処方のミルクコーヒーに添加し、常法によりミルクコーヒー飲料を調製した。本発明品１４及び対照品３を添加したミルクコーヒーをそれぞれ本発明品１９及び比較品１０とした。これらのミルクコーヒーを、専門パネラー２０人により官能評価を行った。
As a result, all 20 professional panelists evaluated the product 18 of the present invention as being creamy, with a good feeling of milk fat markedly emphasized compared to the comparative product 9.
[Example 7, Comparative Example 7]
Effect of adding milk-like blended fragrance composition to milk coffee The milk-like blended fragrance composition obtained in Example 3 (present invention product 14 and control product 3) was added to milk coffee having the following formulation, and milk was prepared in a conventional manner. A coffee drink was prepared. The milk coffee added with the inventive product 14 and the control product 3 was designated as the inventive product 19 and the comparative product 10, respectively. These milk coffees were subjected to sensory evaluation by 20 professional panelists.
その結果、専門パネラー２０人全員が、本発明品１９は比較品１０に較べて、すっきりした乳脂肪感、ボディー感があり、良好であると評価した。 As a result, all 20 professional panelists evaluated the product 19 of the present invention as having a clean milk fat feeling and body feeling as compared with the comparative product 10, and being good.
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| JP2019068756A (en) * | 2017-10-06 | 2019-05-09 | 長谷川香料株式会社 | Flavor improver |
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