JP6171125B1 - Perfume composition and milk, dairy product, food or drink containing milk or dairy product, or dairy product substitute containing the perfume composition - Google Patents
Perfume composition and milk, dairy product, food or drink containing milk or dairy product, or dairy product substitute containing the perfume composition Download PDFInfo
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Abstract
【課題】乳そのものを印象づけるインパクトのあるトップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味を付与し、また、乳関連製品の加熱による還元臭をマスキングする優れた効果を必要かつ十分なレベルで付与増強できる香料組成物、並びに当該香料組成物を配合してなる香料組成物、乳関連製品の提供。【解決手段】Ｔｒａｎｓ‐２‐メチル−２−ブテナール含有する、乳、乳製品、乳もしくは乳製品を含む飲食品、又は乳製品代用品用の香料組成物。【選択図】なし[PROBLEMS] To provide an effective top fragrance that impresses milk itself, a fresh feeling like raw milk, a sweet taste of milk, and an excellent effect of masking the reduced odor caused by heating milk-related products. A perfume composition that can be imparted and enhanced at a level, a perfume composition comprising the perfume composition, and a milk-related product. A perfume composition for milk, dairy products, foods and drinks containing milk or dairy products, or dairy substitutes, containing Trans-2-methyl-2-butenal. [Selection figure] None
Description
本発明は、乳、乳製品、乳もしくは乳製品を含む飲食品、又は乳製品代用品（これらをまとめて、以下「乳関連製品」という）に、乳そのものを印象づけるインパクトのあるトップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味を付与し、また、乳関連製品の加熱による還元臭をマスキングする香料組成物に関し、詳しくは、Ｔｒａｎｓ−２−メチル−２−ブテナールを有効成分として含有すること、又は３−メチル−２−ブテナール、チグリックアシッド、及び３−メチル−２−ブテノールからなる群より少なくとも１種以上の化合物と、前記のＴｒａｎｓ−２−メチル−２−ブテナールを有効成分として含有することにより、従来にない乳関連製品の香味を付与増強する香料組成物、当該香料組成物が含有された乳関連製品、ならびに乳関連製品の乳の香味増強法に関する。 The present invention relates to milk, dairy products, foods and drinks containing milk or dairy products, or dairy product substitutes (collectively these are hereinafter referred to as “milk-related products”), and has an impact on top fragrance that impresses milk itself, raw milk Concerning a fragrance composition that imparts a fresh feeling like the above, a sweet taste of milk and masks the reduced odor due to heating of milk-related products, it contains Trans-2-methyl-2-butenal as an active ingredient. Or at least one compound selected from the group consisting of 3-methyl-2-butenal, tiglic acid, and 3-methyl-2-butenol, and said trans-2-methyl-2-butenal as an active ingredient A perfume composition that enhances the flavor of an unprecedented milk-related product by containing it as a milk-related product containing the perfume composition, Flavor enhancement methods on the milk of dairy-related products.
国内の酪農状況は、減少する酪農家戸数と急激に高騰している飼料価格が経営を圧迫し飼養乳用牛等数が減っていることから、飲食用の生乳生産量は減少し続けている。また、世界規模での酪農市場は、経済成長が著しい中国やインドなどのアジア諸国、ロシアで乳製品の需要が急激に増加し、乳製品の需給が国際的に逼迫していることから、国際価格が急上昇している。今後も乳製品は世界的な需要増加で高価格に推移する中、日本の食品企業は原料となる生乳、乳製品の確保が困難になることも想定される。 The domestic dairy farming situation continues to decline, as the number of dairy farms and the rapidly increasing feed prices have put pressure on management and the number of cattle for feeding has decreased. . In addition, the global dairy market is growing rapidly in Asia, such as China and India, where economic growth is remarkable, and in Russia. Prices are soaring. As dairy products continue to increase in price due to increasing global demand, it is expected that Japanese food companies will find it difficult to secure raw milk and dairy products as raw materials.
そのため、食品企業の乳もしくは乳製品を含む飲食品、又は乳製品代用品の商品開発において、無くてはならない原料であるが、コストや配合の制約等で十分に使用できない場合もあり、また加工工程や殺菌工程で失われる風味を補うために、乳そのものを印象づけるインパクトのあるトップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味を直感させ、乳関連製品の加熱による還元臭のマスキング効果のある香料が強く要望されている。 Therefore, it is an indispensable ingredient in the development of foods and drinks including milk or dairy products of dairy companies, or dairy product substitutes, but it may not be able to be used sufficiently due to cost and formulation restrictions. In order to make up for the flavor lost in the process and sterilization process, the top scent with an impact that impresses milk itself, the freshness like raw milk, the sweetness of plump milk, and the masking effect of reduced odor by heating milk-related products There is a strong demand for fragrances with a high quality.
従来技術として、ジスルフィド化合物を乳関連製品に含有せしめることによりナチュラル感、フレッシュ感、ふくよかな乳感を乳関連製品に付与することが提案されている（特許文献１参照）。また、１２−メチルトリデカナールを飲食品に含有せしめることにより乳製品が有する香味またはコク味を付与または増強することが提案されている（特許文献２参照）。しかしながら、乳そのものを印象づけるインパクトのあるトップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味を付与する効果、更に、乳関連製品の加熱による還元臭のマスキング効果は十分ではなかった。 As a conventional technique, it has been proposed that a disulfide compound is included in a milk-related product to impart a natural feeling, a fresh feeling, and a full milk feeling to the milk-related product (see Patent Document 1). In addition, it has been proposed to add or enhance the flavor or richness of dairy products by adding 12-methyltridecanal to food and drink (see Patent Document 2). However, the top fragrance with an impact that impresses the milk itself, the fresh feeling like raw milk, the effect of imparting the sweetness of the milky milk, and the masking effect of the reduced odor by heating the milk-related products were not sufficient.
本発明は、Ｔｒａｎｓ−２−メチル−２−ブテナールを有効成分として含有することを、又は３−メチル−２−ブテナール、チグリックアシッド、及び３−メチル−２−ブテノールからなる群より少なくとも１種以上の化合物と、前記のＴｒａｎｓ−２−メチル−２−ブテナールを有効成分として含有することを特徴とする、乳関連製品に、乳そのものを印象づけるインパクトのあるトップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味を、乳関連製品の加熱による還元臭のマスキング効果を、必要かつ十分なレベルで付与増強できる香料組成物を提供することを目的とする。 The present invention contains Trans-2-methyl-2-butenal as an active ingredient, or at least one selected from the group consisting of 3-methyl-2-butenal, tiglic acid, and 3-methyl-2-butenol The above-mentioned compound and the above-mentioned Trans-2-methyl-2-butenal as an active ingredient, the milk-related product has an impact top flavor that impresses milk itself, a fresh feeling like raw milk, An object of the present invention is to provide a fragrance composition capable of imparting and enhancing a sweet taste of milk at a necessary and sufficient level with a masking effect of a reduced odor by heating a milk-related product.
本発明者らは、生まれたてのウサギの子が乳房に吸い付くようにするフェロモンの一種として発見同定された、２−メチル−２−ブテナール（ＣＡＳ ＮＯ．６０３８−０９−１英名：Ａｎｇｅｌａｌｄｅｈｙｄｅ）に着目した（非特許文献１）。２−メチル−２−ブテナールは香料としての登録が無く使用できないことが分かった。構造式がトランス型のＴｒａｎｓ−２−メチル−２−ブテナール（ＣＡＳ ＮＯ．４９７−０３−０）は食品用の香料とし登録され、わずかながら香気に関する報告が存在する。例えば、特許文献３、４では、発酵乳様香料組成物又はコーヒーフレーバー組成物を構成する香料成分の１つとしてＴｒａｎｓ−２−メチル−２−ブテナールが挙げられている。また、特許文献４では、乳又はコーヒーアロマに含まれることが既知の成分の１つとして２−メチル−２−ブテナールが挙げられている。しかしながら、Ｔｒａｎｓ−２−メチル−２−ブテナールそのものの乳の香味に関する報告はない。
本発明者らは、Ｔｒａｎｓ−２−メチル−２−ブテナールの香味特性を調べた結果、この成分単独の使用でもって、従来にない乳そのものを印象づけるインパクトのあるトップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味を付与し、乳関連製品の加熱による還元臭のマスキング効果を見出した。
The present inventors have focused on 2-methyl-2-butenal (CAS No. 6038-09-1 English name: Angeldehyde), which was discovered and identified as a kind of pheromone that allows a newborn rabbit pup to stick to the breast. (Non-Patent Document 1). It was found that 2-methyl-2-butenal cannot be used because it is not registered as a fragrance. Trans-2-methyl-2-butenal (CAS NO. 497-03-0) having a structural formula is registered as a fragrance for foods, and there are slight reports on aroma. For example, in Patent Documents 3 and 4, Trans-2-methyl-2-butenal is mentioned as one of the flavor components constituting the fermented milk-like flavor composition or the coffee flavor composition. Moreover, in patent document 4, 2-methyl-2-butenal is mentioned as one of the components known to be contained in milk or coffee aroma. However, there is no report regarding the flavor of milk of Trans-2-methyl-2-butenal itself.
As a result of examining the flavor characteristics of Trans-2-methyl-2-butenal, the present inventors have found that the use of this component alone has an impact top flavor that impresses unprecedented milk itself, a fresh feeling like raw milk The sweetness of plump milk was imparted, and the masking effect of reduced odor by heating milk-related products was found.
更に、Ｔｒａｎｓ−２−メチル−２−ブテナールと構造が似た、３−メチル−２−ブテナール、チグリックアシッド、及び３−メチル−２−ブテノールにも相乗効果があるものと考え、これらからなる群より少なくとも１種以上の化合物と、前記のＴｒａｎｓ−２−メチル−２−ブテナールとを有効成分として含有する香料組成物の香味特性を調べた結果、更に生乳のようなフレッシュ感、ふくよかな乳の甘味を増強し、乳関連製品の加熱による還元臭のマスキング効果が高くなることを見出し、本発明を完成するに至った。 Furthermore, 3-methyl-2-butenal, tiglic acid, and 3-methyl-2-butenol, which are similar in structure to Trans-2-methyl-2-butenal, are considered to have a synergistic effect, and consist of these. As a result of investigating the flavor characteristics of the fragrance composition containing at least one compound from the group and the above-mentioned Trans-2-methyl-2-butenal as an active ingredient, freshness such as raw milk, plump milk As a result, the present invention was completed.
本発明は下記の式（１）で表わされるＴｒａｎｓ−２−メチル−２−ブテナールを有効成分とする香料組成物、当該香料組成物を含有する乳性関連製品である。 The present invention is a fragrance composition containing Trans-2-methyl-2-butenal represented by the following formula (1) as an active ingredient, and a milk-related product containing the fragrance composition.
さらに、前記のＴｒａｎｓ−２−メチル−２−ブテナールと、下記の式（２）で表わされる３−メチル−２−ブテナール、式（３）で表わされるチグリックアシッド及び式（４）で表わされる３−メチル−２−ブテノールからなる群より選ばれた１種以上の化合物とを有効成分として含有する香料組成物、当該香料組成物を含有する乳関連製品である。 Further, the above-described Trans-2-methyl-2-butenal, 3-methyl-2-butenal represented by the following formula (2), tiglic acid represented by the formula (3), and formula (4) A perfume composition containing as an active ingredient one or more compounds selected from the group consisting of 3-methyl-2-butenol, and a milk-related product containing the perfume composition.
すなわち、本発明は下記の通りである。
（１）Ｔｒａｎｓ−２−メチル‐２‐ブテナールを０．０１ｐｐｂ〜１０ｐｐｍ含有 することを特徴とする、乳、乳製品、乳もしくは乳製品を含む飲食品、又は乳製品代用品。
（２）乳、乳製品、乳もしくは乳製品を含む飲食品、又は乳製品代用品におけるＴｒａｎｓ−２−メチル‐２‐ブテナールの最終濃度が０．０１ｐｐｂ〜１０ｐｐｍとなるように添加することを特徴とする、乳、乳製品、乳もしくは乳製品を含む飲食品、又は乳製品代用品の香味増強方法。
（３）Ｔｒａｎｓ−２−メチル‐２‐ブテナールと、３−メチル−２−ブテナール、チグリックアシッド、及び３−メチル−２−ブテノールからなる群より選ばれる少なくとも１種又は２種以上の化合物とを合計で０．０１ｐｐｂ〜１０ｐｐｍ含有する、乳、乳製品、乳もしくは乳製品を含む飲食品、又は乳製品代用品。
（４）乳、乳製品、乳もしくは乳製品を含む飲食品、又は乳製品代用品における、Ｔｒａｎｓ−２−メチル‐２‐ブテナールと、３−メチル−２−ブテナール、チグリックアシッド、及び３−メチル−２−ブテノールからなる群より選ばれる少なくとも１種又は２種以上の化合物との最終濃度が合計で０．０１ｐｐｂ〜１０ｐｍとなるように添加する、乳、乳製品、乳もしくは乳製品を含む飲食品、又は乳製品代用品の香味増強方法。
（５）乳、乳製品、乳もしくは乳製品を含む飲食品、又は乳製品代用品における使用のための、Ｔｒａｎｓ−２−メチル‐２‐ブテナールを０．１ｐｐｂ〜１０００ｐｐｍ含有する香料組成物。
（６）前記香料組成物が、３−メチル−２−ブテナール、チグリックアシッド、及び３−メチル−２−ブテノールからなる群より選ばれた少なくとも１種又は２種以上の化合物を更に含有し、Ｔｒａｎｓ−２−メチル‐２‐ブテナールと、３−メチル−２−ブテナール、チグリックアシッド、及び３−メチル−２−ブテノールからなる群より選ばれる少なくとも１種又は２種以上の化合物との香料組成物中の合計含有量が０．１ｐｐｂ〜１５００ｐｐｍ である、（５）に記載の香料組成物。
That is, the present invention is as follows.
(1) A milk, a dairy product, a food or drink containing milk or a dairy product, or a dairy substitute, containing 0.01 ppb to 10 ppm of Trans-2-methyl-2-butenal.
(2) It is characterized by being added so that the final concentration of Trans-2-methyl-2-butenal in milk, dairy products, foods and drinks containing milk or dairy products, or dairy product substitutes is 0.01 ppb to 10 ppm. A method for enhancing flavor of milk, dairy products, foods and drinks containing milk or dairy products, or dairy substitutes.
(3) Trans-2-methyl-2-butenal and at least one compound selected from the group consisting of 3-methyl-2-butenal, tiglic acid, and 3-methyl-2-butenol, or two or more compounds Milk, dairy products, foods and drinks containing milk or dairy products, or dairy substitutes, containing 0.01 ppb to 10 ppm in total.
(4) Trans-2-methyl-2-butenal, 3-methyl-2-butenal, tiglic acid, and 3-in milk, dairy products, foods and drinks containing milk or dairy products, or dairy substitutes Including milk, dairy products, milk or dairy products added so that the final concentration with at least one or two or more compounds selected from the group consisting of methyl-2-butenol is 0.01 ppb to 10 pm in total A method for enhancing flavor of food and drink or dairy products.
(5) A perfume composition containing 0.1 ppb to 1000 ppm of Trans-2-methyl-2-butenal for use in milk, dairy products, food or drink containing milk or dairy products, or dairy substitutes.
(6) The perfume composition further contains at least one compound or two or more compounds selected from the group consisting of 3-methyl-2-butenal, tiglic acid, and 3-methyl-2-butenol, Fragrance composition of Trans-2-methyl-2-butenal and at least one or two or more compounds selected from the group consisting of 3-methyl-2-butenal, tiglic acid, and 3-methyl-2-butenol The fragrance composition according to (5), wherein the total content in the product is 0.1 ppb to 1500 ppm.
本発明によれば、ＴＲＡＮＳ−２−メチル−２−ブテナールを有効成分として、香料組成物中に０．１ｐｐｂ〜１０００ｐｐｍ、又は乳関連製品中に０．０１ｐｐｂ〜１０ｐｐｍ含有すると、乳そのものを印象づけるインパクトのあるトップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味を乳関連製品に付与し、また、乳関連製品の濃縮、乾燥、殺菌、粉体加工等の過程で、乳タンパクが変性して出てくる香りである還元臭をマスキングする優れた効果を有し、乳関連製品の品質を満足に向上させることができる。 According to the present invention, when TRANS-2-methyl-2-butenal is used as an active ingredient and 0.1 ppb to 1000 ppm in a fragrance composition or 0.01 ppb to 10 ppm in a milk-related product, the impact impresses milk itself. It gives milk-related products a fresh top-like fragrance, fresh milk-like sweetness, and a sweet milky sweetness, and milk proteins are denatured during the process of concentration, drying, sterilization, and powder processing of milk-related products. It has an excellent effect of masking the reduced odor, which is a scent that comes out, and can satisfactorily improve the quality of milk-related products.
本発明で使用されるＴＲＡＮＳ−２−メチル−２−ブテナール、３−メチル−２−ブテナール、チグリックアシッド及び３−メチル−２−ブテノールは公知の化合物であり、当該化合物は食品香料に使用することが認められている。（食品香料化合物データベース２０１５年版：日本香料工業協会参照） TRANS-2-methyl-2-butenal, 3-methyl-2-butenal, tiglic acid and 3-methyl-2-butenol used in the present invention are known compounds, and the compounds are used in food flavors. It is recognized that (Refer to Food Fragrance Compound Database 2015 Edition: Japan Fragrance Industry Association)
ＴＲＡＮＳ−２−メチル−２−ブテナールはラズベリー等のきいちご類、パッションフルーツ、マウンテン・パパイヤ、たまねぎ、マルメロ等の食品中に存在し、また、牛肉等の加熱調理により生成する成分であり、焼菓子、清涼飲料、乳製品類、プリン類、キャンディー類、チューインガム等様々な加工食品に、香りの再現、風味の向上等の目的で添加され、アーモンドフレーバー、チーズフレーバー、チェリーフレーバー、コーヒーフレーバー、グレープフレーバー、トマトフレーバー、バニラフレーバーなどに使用される、α，β‐不飽和アルデヒドの一つである。 TRANS-2-Methyl-2-butenal is present in foods such as raspberry and other strawberries, passion fruit, mountain papaya, onion, quince, etc., and is also produced by cooking beef etc. Added to various processed foods such as confectionery, soft drinks, dairy products, puddings, candy, and chewing gum for the purpose of reproducing fragrance and improving flavor, almond flavor, cheese flavor, cherry flavor, coffee flavor, grape It is one of α, β-unsaturated aldehydes used in flavors, tomato flavors, vanilla flavors and the like.
３−メチル−２−ブテナールは、ラズベリー、ホップ等の食品中に存在し、鶏肉等の加熱調理により生成する成分であり、チューインガム、キャンディー類、焼菓子、製菓材料、プリン類などの様々な加工食品において香りを再現、風味の向上等の目的で添加され、アーモンドフレーバー、アップルフレーバー、チェリーフレーバー、シナモンフレーバー、スパイス系フレーバーなどに使用される。 3-Methyl-2-butenal is an ingredient that is present in foods such as raspberries and hops, and is produced by cooking such as chicken. Various processing such as chewing gum, candy, baked confectionery, confectionery materials, and puddings It is added for the purpose of reproducing fragrance and improving flavor in foods and used for almond flavor, apple flavor, cherry flavor, cinnamon flavor, spice flavor and the like.
チグリックアシッドは、ストロベリー、セロリ、大豆、コーヒー等の食品中に存在している。食品用香料としては、バナナフレーバー、ブレッドフレーバー、キャラメルフレーバー、チーズフレーバー、パパイヤフレーバーなどに使用される。 Tigric acid is present in foods such as strawberry, celery, soy and coffee. As a fragrance for food, it is used for banana flavor, bread flavor, caramel flavor, cheese flavor, papaya flavor and the like.
３−メチル−２−ブテノールは、ホップ、コーヒー、ラズベリー等のきいちご類、アセロラ、ライチ、はちみつ等の食品中に存在する成分であり、チューインガム、ハードキャンディー類、ソフトキャンディー類、焼菓子、ゼラチン・プリン類、ジャム・ゼリーなどの様々な加工食品において香りを再現、風味の向上等の目的で添加され、アップルフレーバー、バナナフレーバー、コーヒーフレーバー、マンゴーフレーバーなどに使用される。 3-Methyl-2-butenol is an ingredient present in foods such as strawberry such as hop, coffee, raspberry, acerola, lychee, honey, chewing gum, hard candy, soft candy, baked confectionery, gelatin -It is added for the purpose of reproducing flavor and improving flavor in various processed foods such as puddings, jams, and jelly, and is used in apple flavors, banana flavors, coffee flavors, mango flavors and the like.
ＴＲＡＮＳ−２−メチル−２−ブテナールを単一の有効成分として、香料組成物中に０．１ｐｐｂ〜１０００ｐｐｍ、又は乳関連製品中に０．０１ｐｐｂ〜１０ｐｐｍ含有すると、乳そのものを印象づけるインパクトのあるトップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味を乳関連製品に付与し、また、乳関連製品の濃縮、乾燥、殺菌、粉体加工等の過程で、乳タンパクが変性して出てくる香りである還元臭をマスキングする優れた効果を有し、乳関連製品を含む飲食品の品質を満足に向上させることができる。好ましくは、香料組成物中に０．０１ｐｐｍ〜１００ｐｐｍ、乳関連製品中に０．０００１ｐｐｍ〜１ｐｐｍ、更に好ましくは香料組成物中に１ｐｐｍ〜１０ｐｐｍ、乳関連製品中に０．０１ｐｐｍ〜１ｐｐｍ含有する When TRANS-2-methyl-2-butenal is contained as a single active ingredient in an amount of 0.1 ppb to 1000 ppm in a fragrance composition, or 0.01 ppb to 10 ppm in a milk-related product, the top with an impact that impresses milk itself Gives milk-related products freshness such as incense, raw milk, and sweetness of milk, and milk proteins are denatured in the process of concentration, drying, sterilization, and powder processing of milk-related products. It has an excellent effect of masking the reduced odor, which is a coming scent, and can satisfactorily improve the quality of foods and drinks including milk-related products. Preferably, the fragrance composition contains 0.01 ppm to 100 ppm, the dairy product contains 0.0001 ppm to 1 ppm, more preferably the fragrance composition contains 1 ppm to 10 ppm, and the dairy product contains 0.01 ppm to 1 ppm.
３−メチル−２−ブテナール、チグリックアシッド及び３−メチル−２−ブテノールからなる群より少なくとも１種以上の化合物と、前記のＴｒａｎｓ−２−メチル−２−ブテナールとを併用して香料組成物に用いる場合、その含有量は、その目的あるいは香料組成物の種類によってことなるものの、一般的には、香料組成物中にＴｒａｎｓ−２−メチル−２−ブテナールと、３−メチル−２−ブテナール、チグリックアシッド及び３−メチル−２−ブテノールからなる群より少なくとも１種以上の化合物とを、好ましくは０．１ｐｐｂ〜１５００ｐｐｍ、より好ましくは１０ｐｐｍ〜１５０ｐｐｍ含有し、乳関連製品中に好ましくは０．０１ｐｐｂ〜１０ｐｐｍ、より好ましくは１０ｐｐｂ〜１ｐｐｍ含有する。これらの範囲内では、香料組成物に対して乳そのものを印象づけるインパクトのあるトップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味を付与し、また、乳関連製品を濃縮、乾燥、殺菌等の、粉体加工処理過程で、乳タンパクが変性して出てくる香りである還元臭をマスキングする優れた効果を有する。香料組成物中に１５００ｐｐｍ以下の含有量とすることで、当該化合物の特有の香味が出ることなく飲食品のバランスを崩すおそれもない。 A perfume composition comprising at least one compound selected from the group consisting of 3-methyl-2-butenal, tiglic acid, and 3-methyl-2-butenol and the aforementioned Trans-2-methyl-2-butenal In general, the content varies depending on the purpose or the type of the fragrance composition, but generally, trans-2-methyl-2-butenal and 3-methyl-2-butenal are contained in the fragrance composition. And at least one compound from the group consisting of tiglic acid and 3-methyl-2-butenol, preferably 0.1 ppb to 1500 ppm, more preferably 10 ppm to 150 ppm, and preferably 0 in milk-related products. 0.01 ppb to 10 ppm, more preferably 10 ppb to 1 ppm. Within these ranges, the top fragrance that has the impact of impressing the milk itself to the fragrance composition, the freshness like raw milk, and the sweetness of plump milk are added, and the milk-related products are concentrated, dried, sterilized, etc. It has an excellent effect of masking the reduced odor, which is a fragrance produced by denatured milk protein during the powder processing process. By setting it as 1500 ppm or less content in a fragrance | flavor composition, there is no possibility that the balance of food-drinks may be lost, without the characteristic flavor of the said compound appearing.
本発明の香料組成物に配合される他の香料成分としては、特に制限はないが、例えば「特許庁２０００．１周知・慣用技術集（香料）第２部食品用香料」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 other fragrance ingredients to be blended in the fragrance composition of the present invention are not particularly limited, and are described in, for example, “Patent Office 2000.1 Well-known / conventional technology collection (fragrance) Part 2 Food fragrance”. Listed are natural essential oils, natural fragrances, and synthetic fragrances.
例えば、オクタノール、ヘプタノール、フェニルエタノールなどのアルコール類；ヘキサナール、ヘプタナール、バニリンなどのアルデヒド類；アセトイン、ジアセチル、２−ペンタノン、３−ヘキサノン、２−ヘプタノン、２−オクタノン、２−ノナノン、２−ウンデカノン、２−トリデカノンなどのケトン類；酢酸、酪酸、５−デセン酸、カプロン酸、カプリル酸、ラウリン酸、ミリスチン酸などの酸類；エチルヘキサノエート、エチルブチレート、レブリン酸エチル、ブチルブチリルラクテート、フェニルエチルアセテート、エチルミリステートなどのエステル類；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−オクタラクトン、δ−デカラクトン、δ−ウンデカラクトン、δ−デカラクトン、δ−トリデカラクトン、γ−ノナラクトンなどのラクトン類；メチルメルカプタンなどのチオール類；ジメチルスルフィド、ジメチルジスルフィドなどのチオエーテル類やメチオナールなどの硫黄化合物など公知の合成香料化合物及び乳、濃縮乳、全脂粉乳、脱脂粉乳、ミルクホエイ、バター、チーズ、ヨーグルトなどの乳製品の溶剤抽出、水蒸気蒸留回収香、リパーゼ、プロテアーゼ、ラクターゼ等による酵素処理、加熱反応、分画物を利用した乳製品由来の香料組成物を挙げることができ、これらを任意に組合せ混合した香料組成物を挙げることができる。
また本発明の香料組成物は、既知の香料組成物であるミルク様香料組成物、乳製品由来の香料組成物、バター様香料組成物、又はチーズ様香料組成物を含むことができる。
For example, alcohols such as octanol, heptanol and phenylethanol; aldehydes such as hexanal, heptanal and vanillin; acetoin, diacetyl, 2-pentanone, 3-hexanone, 2-heptanone, 2-octanone, 2-nonanone and 2-undecanone Ketones such as 2-tridecanone; acids such as acetic acid, butyric acid, 5-decenoic acid, caproic acid, caprylic acid, lauric acid, myristic acid; ethyl hexanoate, ethyl butyrate, ethyl levulinate, butyl butyryl lactate , Esters such as phenylethyl acetate, ethyl myristate; γ-decalactone, γ-undecalactone, γ-dodecalactone, δ-octalactone, δ-decalactone, δ-undecalactone, δ-decalactone, δ-tri Decalactone Lactones such as γ-nonalactone; thiols such as methyl mercaptan; thioethers such as dimethyl sulfide and dimethyl disulfide; and known synthetic perfume compounds such as sulfur compounds such as methional; milk, concentrated milk, whole milk powder, skimmed milk powder, List dairy product-derived fragrance compositions using solvent extraction of milk products such as milk whey, butter, cheese, yogurt, enzymatic treatment with steam-distilled incense, lipase, protease, lactase, etc., heating reaction, fractions And a fragrance composition in which these are arbitrarily combined and mixed.
Moreover, the fragrance | flavor composition of this invention can contain the milk-like fragrance | flavor composition which is a known fragrance | flavor composition, the fragrance composition derived from a dairy product, a butter-like fragrance | flavor composition, or a cheese-like fragrance | flavor composition.
本発明の香料組成物は、必須成分であるＴｒａｎｓ−２−メチル−２−ブテナールを有効成分として含有し、又は３−メチル−２−ブテナール、チグリックアシッド、及び３−メチル−２−ブテノールからなる群より選ばれる少なくとも１種以上の化合物と、前記のＴｒａｎｓ−２−メチル−２−ブテナールとを有効成分として含有していれば、必要に応じて上記の付加的成分を適当な希釈剤もしくは担体との組成物の形態でも良い。このような希釈剤もしくは担体としては、例えばアラビアガム、デキストリン、シクロデキストリン、キサンタンガム、グアーガム、グルコース、シュークロースなどの固形希釈剤もしくは担体、または、水、エタノール、プロピレングリコール、グリセリン、ベンジルベンゾエート、トリエチルシトレート、中鎖脂肪酸トリグリセライドなどの液体もしくは担体を用いて任意の剤形、例えば、液状、乳液状、ペースト状、粉末状、顆粒状、その他適宜の剤形に調整することができる。 The fragrance composition of the present invention contains Trans-2-methyl-2-butenal, which is an essential component, as an active ingredient, or from 3-methyl-2-butenal, tiglic acid, and 3-methyl-2-butenol. As long as it contains at least one compound selected from the group consisting of the above-mentioned Trans-2-methyl-2-butenal as an active ingredient, the above-mentioned additional ingredients can be added to a suitable diluent or It may be in the form of a composition with a carrier. Examples of such diluents or carriers include solid diluents or carriers such as gum arabic, dextrin, cyclodextrin, xanthan gum, guar gum, glucose, sucrose, or water, ethanol, propylene glycol, glycerin, benzyl benzoate, triethyl. Using a liquid or carrier such as citrate or medium chain fatty acid triglyceride, it can be adjusted to any dosage form, for example, liquid, emulsion, paste, powder, granule, and other appropriate dosage forms.
本発明の香料組成物を添加する対象製品として、乳関連製品、すなわち（ａ）乳、（ｂ）乳製品、（ｃ）乳もしくは乳製品を含む飲食品、又は（ｄ）乳製品代用品として制限はなく、例としては以下のとおりである。
（ａ）乳としては、「乳及び乳製品の成分規格等に関する省令」（昭和２６年１２月２７日厚生省令第５２号）に規定された生乳、牛乳、特別牛乳、部分脱脂乳、加工乳などを挙げることができる。
（ｂ）乳製品としては、前記省令に規定されたクリーム、バター、バターオイル、ヨーグルトなどの発酵乳、乳酸菌飲料、乳飲料、チーズ、アイスクリーム類、濃縮乳、脱脂濃縮乳、練乳、全粉乳、脱脂粉乳、加糖練乳、濃縮ホエー、ホエーパウダーなどを挙げることができる。
As a target product to which the fragrance composition of the present invention is added, a milk-related product, that is, (a) milk, (b) dairy product, (c) food or drink containing milk or dairy product, or (d) dairy product substitute There is no restriction, and examples are as follows.
(A) As milk, raw milk, milk, special milk, partially skimmed milk, processed milk specified in “Ministerial Ordinance on Component Standards of Milk and Dairy Products” (December 27, 1951, Ministry of Health and Welfare Ordinance No. 52) And so on.
(B) As dairy products, fermented milk such as cream, butter, butter oil, yogurt, lactic acid bacteria drink, milk drink, cheese, ice cream, concentrated milk, skim concentrated milk, condensed milk, whole milk powder Non-fat dry milk, sweetened condensed milk, concentrated whey, whey powder and the like.
（ｃ）乳もしくは乳製品を含む飲食品としては、例えば、上記の牛乳、クリーム類、バター、チーズ、練乳、粉乳などを添加したコーヒー飲料、茶飲料、果汁飲料、炭酸飲料、冷菓類、キャンディーやクッキー・ビスケットなどの洋菓子類、和菓子類、パン類、カレーやクリームシチュー、クリームスープなどの各種インスタント飲食品、各種スナック食品、ドレッシングなどの調味料などを挙げることができる。
（ｄ）乳製品代用品としては、例えば、植物性油脂を乳化して製造されるチーズフードなどのチーズ代用品、マーガリン、ショートニングやファットスプレッドなどのバター代用品、コーヒーや紅茶などに添加するコーヒーホワイトナーなどのクリーム代用品を挙げることができる。
(C) Examples of foods and drinks containing milk or dairy products include coffee drinks, tea drinks, fruit juice drinks, carbonated drinks, frozen confectionery, candy, to which the above-mentioned milk, creams, butter, cheese, condensed milk, powdered milk, etc. are added. And confectionery such as confectionery, cookies and biscuits, Japanese confectionery, breads, curry, cream stew, cream soup, and other instant foods and drinks, and snacks and dressings.
(D) Examples of dairy product substitutes include cheese substitutes such as cheese food manufactured by emulsifying vegetable oils, butter substitutes such as margarine, shortening and fat spread, coffee added to coffee and tea, etc. Mention cream substitutes such as whiteners.
本発明を下記の実施例により説明するが、これらは本発明の範囲を限定するものではない。
尚、下記の例１〜例９において、Ｔｒａｎｓ−２−メチル−２−ブテナールは、Ｓｉｇｍａ Ａｌｄｒｉｃｈ社の製品名「Ｗ３４０７０７ Ｔｒａｎｓ−２−ｍｅｔｈｙｌ−２ｂｕｔｅｎａｌ」を、３−メチル−２−ブテナールは、Ｓｉｇｍａ Ａｌｄｒｉｃｈ社の製品名「Ｗ３６４６２０ ３−Ｍｅｔｈｙｌ−２−ｂｕｔｅｎａｌ」を、チグリックアシッドは井上香料製造所の製品名「チグリックアシド」を、３−メチル−２−ブテノールは、（Ｓｉｇｍａ Ａｌｄｒｉｃｈ社製 製品名「Ｗ３６４７０３ ３−Ｍｅｔｈｙｌ−２−ｂｕｔｅｎ−１−ｏｌ」を使用した。
The present invention is illustrated by the following examples, which do not limit the scope of the invention.
In Examples 1 to 9 below, Trans-2-methyl-2-butenal is Sigma Aldrich's product name “W340707 Trans-2-methyl-2butenal”, and 3-methyl-2-butenal is Sigma. Aldrich's product name “W364620 3-Methyl-2-butenal”, Tigric Acid is the product name of Inoue Fragrance Factory, “Tiglic Acid”, 3-Methyl-2-butenol is the product name of “Sigma Aldrich” W364703 3-Methyl-2-buten-1-ol ”was used.
（例１）（Ｔｒａｎｓ−２−メチル−２−ブテナールの乳の香味付与増強効果）
Ｔｒａｎｓ−２−メチル−２−ブテナールは、Ｓｉｇｍａ Ａｌｄｒｉｃｈ社の製品名「Ｗ３４０７０７ Ｔｒａｎｓ−２−ｍｅｔｈｙｌ−２ｂｕｔｅｎａｌ」を使用し、該化合物の乳の香味感増強効果を評価した。
(Example 1) (Transformation enhancement effect of trans-2-methyl-2-butenal in milk flavor)
For Trans-2-methyl-2-butenal, the product name “W340707 Trans-2-methyl-2butenal” of Sigma Aldrich was used, and the flavor enhancing effect of the milk of the compound was evaluated.
実験方法
市販の超高温瞬間殺菌乳（商品名：明治おいしい牛乳、株式会社 明治社製。「以下、ＵＨＴ殺菌乳」という）、マーガリン(商品名： ラーマ バター風味、Ｊ−オイルミルズ社製)、チーズフード(下記の表１７の組成に従い調製)それぞれに対し、Ｔｒａｎｓ―２―メチル−２−ブテナールの乳関連製品における最終濃度がそれぞれ０．０００００１〜１００ｐｐｍ（表１〜３）となるように、Ｔｒａｎｓ−２−メチル−２−ブテナールをエチルアルコールにて９段階に希釈調製した香料組成物（０．００１〜１０００００ｐｐｍの９段階）を調製し、この得られた９種類の濃度の香料組成物をＵＨＴ殺菌乳全量に対し０．１質量％添加した。対照品１として、希釈溶剤エチルアルコールをＵＨＴ殺菌乳全量に対し同量の０．１質量％添加した。
Experimental method Commercially available ultra-high temperature instant pasteurized milk (trade name: Meiji delicious milk, manufactured by Meiji Co., Ltd., hereinafter referred to as “UHT pasteurized milk”), margarine (trade name: Rama butter flavor, manufactured by J-Oil Mills), For each cheese food (prepared according to the composition in Table 17 below), the final concentration of Trans-2-methyl-2-butenal in milk-related products is 0.000001-100 ppm (Tables 1-3), respectively. A fragrance composition (9 stages of 0.001 to 100000 ppm) prepared by diluting Trans-2-methyl-2-butenal with ethyl alcohol in 9 stages was prepared, and the obtained 9 kinds of fragrance compositions with different concentrations were prepared. 0.1 mass% was added with respect to UHT pasteurized milk whole quantity. As a control product 1, 0.1% by mass of the same amount of diluted solvent ethyl alcohol was added to the total amount of UHT pasteurized milk.
評価方法（官能評価）
年齢や性別の異なるよく訓練された１０名のパネラーが、ブラインドで本発明の香料組成物を添加した飲食品を試食して評価を行い、下記に示す６段階で点数を付けた。
乳とは異なる香味(違和感)を強く感じた場合には、コメントのみとし、点数は不要とした。
乳の香味に関する官能評価の項目は、匂った時に感じる乳そのものを印象づける乳のトップ香（乳のトップ香）、口に含んだ時に感じる劣化していない生乳のようなフレッシュ感（生乳のようなフレッシュ感）、生乳や乳から想起されるふくよかな乳の甘味（ふくよかな乳の甘味）の３項目の観点から判断してもらい、これらの各項目について、本発明の香料組成物を添加しない場合（対照品）に比べ、
乳の香味として非常に強く感じる場合：５点
乳の香味として強く感じる場合：４点
乳の香味としてやや強く感じる場合：３点
乳の香味として感じる場合：２点
乳の香味としてわずかながら感じる場合：１点
乳の香味に全く変化がないもの：０点
として、上記１０名のパネラーに点数を付けてもらい、１０名の点数の平均値を採用した
。例１においては、対照品１と比較して生乳のような香味が増強していると感じたものを全て選んでもらい、人数の合計を集計した。
また、飲食時の印象を自由にコメントしてもらい、そのうち多かった意見を表に抽出した。
Evaluation method (sensory evaluation)
Ten well-trained panelists of different ages and genders sampled and evaluated foods and drinks to which the fragrance composition of the present invention had been added blindly, and scored in the following 6 levels.
When a flavor (uncomfortable feeling) different from milk was felt strongly, only comments were made, and points were not required.
The sensory evaluation items related to the flavor of milk are the top scent of milk that impresses the milk itself that is felt when it smells (the top scent of milk), the freshness of raw milk that does not deteriorate when it is contained in the mouth (like fresh milk) (Fresh feeling), sweetness of plump milk recalled from raw milk and milk (sweetness of plump milk), and when the perfume composition of the present invention is not added to each of these items Compared to (control product)
When it feels very strongly as a flavor of milk: 5 points When it feels strongly as a flavor of milk: 4 points When it feels slightly strong as a flavor of milk: 3 points When it feels as a flavor of milk: 2 points When it feels slightly as a flavor of milk 1 point: No change in flavor of milk: 0 points were given to the above 10 panelists, and the average value of 10 points was adopted. In Example 1, all the items that felt that the flavor like raw milk was enhanced compared to Control 1 were selected, and the total number of people was counted.
In addition, they freely commented on their impressions when eating and drinking, and the opinions that were often found were extracted from the table.
表１〜３より明らかなように、飲食品の美味しさを決める要因の一つである香気の放散（フレーバーリリース）が比較的分りやすい液状の飲食品であるＵＨＴ殺菌乳や、フレーバーリリースの悪い固形又は粘性の高い乳製品代用品であるマーガリン、チーズフードに対し、Ｔｒａｎｓ−２−メチル−２−ブテナールの最終濃度が０．００００１〜１ｐｐｍ（ＵＨＴ殺菌乳）、０．００００１〜１０ｐｐｍ（マーガリン、チーズフード）となるように添加することで、乳の香味（トップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味）を付与増強することが分かった。ＵＨＴ殺菌乳では１ｐｐｍを超えると、またマーガリン、チーズフードでは１０ｐｐｍを超えると、フルーティー、アーモンド様といった牛乳の香りではないような違和感となり、Ｔｒａｎｓ−２−メチル−２−ブテナールは、ＵＨＴ殺菌乳における最終濃度０．０００１〜０．１ｐｐｍの範囲で、またマーガリン、チーズフードにおける最終濃度０．０００１〜１ｐｐｍの範囲で、有意に乳の香味を付与増強できていた。いずれの飲食品においても最終濃度が０．００１〜０．１ｐｐｍの範囲ではパネラー全員が乳の香味を付与増強できていると感じた。 As is clear from Tables 1 to 3, UHT pasteurized milk, which is a liquid food and drink that is relatively easy to understand the release of flavor (flavor release), which is one of the factors that determine the taste of food and drink, and poor flavor release The final concentration of Trans-2-methyl-2-butenal is 0.00001-1 ppm (UHT pasteurized milk), 0.00001-10 ppm (margarine, margarine, cheese food, which is a solid or highly viscous dairy substitute It was found that by adding so as to be a cheese food, the flavor of milk (top fragrance, fresh feeling like raw milk, sweetness of plump milk) was imparted and enhanced. If it exceeds 1 ppm for UHT pasteurized milk, and if it exceeds 10 ppm for margarine and cheese foods, it will be uncomfortable as if it is not the scent of milk such as fruity and almond-like. Trans-2-methyl-2-butenal In the final concentration range of 0.0001 to 0.1 ppm, and in the final concentration range of 0.0001 to 1 ppm in margarine and cheese food, the flavor of milk could be significantly increased. In any food or drink, all panelists felt that the flavor of milk could be imparted and enhanced within the final concentration range of 0.001 to 0.1 ppm.
（例２）Ｔｒａｎｓ−２−メチル−２−ブテナールのみを含む香料組成物、又は３−メチル−２−ブテナール若しくはチグリックアシッドの１種以上の化合物とＴｒａｎｓ−２−メチル−２−ブテナールとを組み合わせて含む香料組成物による乳の香味付与増強効果
３−メチル−２−ブテナールは、Ｓｉｇｍａ Ａｌｄｒｉｃｈ社の製品名「Ｗ３６４６２０ ３−Ｍｅｔｈｙｌ−２−ｂｕｔｅｎａｌ」を使用した。チグリックアシッドは井上香料製造所の製品名「チグリックアシド」を使用した。
(Example 2) A perfume composition containing only Trans-2-methyl-2-butenal, or one or more compounds of 3-methyl-2-butenal or tiglic acid and Trans-2-methyl-2-butenal Effect of imparting flavor to milk by a fragrance composition contained in combination As a 3-methyl-2-butenal, a product name “W364620 3-Methyl-2-butenal” of Sigma Aldrich was used. For tiglic acid, the product name “Chiglic Acid” manufactured by Inoue Fragrance Factory was used.
実験方法
有効成分としてＴｒａｎｓ−２−メチル−２ブテナールを０．２％含有するエチルアルコール希釈溶液を本発明に係る香料組成物Ａとし、有効成分としてＴｒａｎｓ−２−メチル−２−ブテナール、３−メチル−２−ブテナール、チグリックアシッドをそれぞれ０．２％、０．１％、１％混合含有するエチルアルコール希釈溶液を本発明に係る香料組成物Ｂとした。また、希釈溶剤として用いたエチルアルコールを対照品として調製した。ＵＨＴ殺菌乳全量に対して、本発明香料組成物Ａ、Ｂ及び対照品０．０１％をそれぞれ添加し本発明品Ａ、本発明品Ｂ及び対照品２を作成した。
Experimental Method Ethyl alcohol diluted solution containing 0.2% of Trans-2-methyl-2-butenal as an active ingredient is used as the perfume composition A according to the present invention, and Trans-2-methyl-2-butenal, 3- A diluted solution of ethyl alcohol containing 0.2%, 0.1%, and 1% of methyl-2-butenal and tiglic acid was used as the perfume composition B according to the present invention. In addition, ethyl alcohol used as a dilution solvent was prepared as a control. The present invention perfume compositions A and B and the control product 0.01% were added to the total amount of UHT pasteurized milk to prepare the present product A, the present product B and the control product 2.
評価方法（官能評価）
年齢や性別の異なるよく訓練された１０名のパネラーが、ブラインドで本発明の香料組成物を添加した飲食品を試食して評価を行い、下記に示す６段階で点数を付けた。
乳の香味に関する官能評価の項目は、匂った時に感じる乳そのものを印象づける乳のトップ香（乳のトップ香）、口に含んだ時に感じる劣化していない生乳のようなフレッシュ感（生乳のようなフレッシュ感）、生乳や乳から想起されるふくよかな乳の甘味（ふくよかな乳の甘味）の３項目の観点から判断してもらい、これらの各項目について、本発明の香料組成物を添加しない場合（対照品）に比べ、
乳の香味として非常に強く感じる場合：５点
乳の香味として強く感じる場合：４点
乳の香味としてやや強く感じる場合：３点
乳の香味として感じる程度の場合：２点
乳の香味としてわずかながら感じる場合：１点
乳の香味に全く変化がないもの：０点
として、上記１０名のパネラーに点数を付けてもらい、１０名の点数の平均値を採用した。
また上記１０名のパネラーに試食した飲食品のうち（但し対照品を除く）、牛乳の乳感が最も増強していると感じた飲食品、又は最も美味しいと感じた飲食品を１つだけ選んでもらい、その人数をカウントした。
さらに評価時に各飲食品の印象を上記１０名のパネラーに自由にコメントしてもらい、
そのうち多かった意見を表に抽出した。
Evaluation method (sensory evaluation)
Ten well-trained panelists of different ages and genders sampled and evaluated foods and drinks to which the fragrance composition of the present invention had been added blindly, and scored in the following 6 levels.
The sensory evaluation items related to the flavor of milk are the top scent of milk that impresses the milk itself that is felt when it smells (the top scent of milk), the freshness of raw milk that does not deteriorate when it is contained in the mouth (like fresh milk) (Fresh feeling), sweetness of plump milk recalled from raw milk and milk (sweetness of plump milk), and when the perfume composition of the present invention is not added to each of these items Compared to (control product)
When it feels very strong as a flavor of milk: 5 points When it feels strong as a flavor of milk: 4 points When it feels slightly strong as a flavor of milk: 3 points When it feels as a flavor of milk: 2 points Slightly as a flavor of milk When feeling: 1 point No change in milk flavor: 0 points were given to the above 10 panelists, and the average value of 10 points was adopted.
Also, out of the foods and beverages that were sampled by the above 10 panelists (except for the control product), select only one food or beverage that felt that the milk feels the most enhanced, or that felt the most delicious And counted the number of people.
Furthermore, at the time of evaluation, the above 10 panelists freely commented on the impression of each food and drink,
Many opinions were extracted from the table.
表２より明らかなように、Ｔｒａｎｓ−２−メチル−２−ブテナールは単独で０．２ｐｐｍの対ＵＨＴ殺菌乳添加濃度でも、ＵＨＴ殺菌乳に対し、乳の香味（トップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味）を強く付与増強することが分かった。単独では生乳のようなフレッシュ感を一番強く増強した。また、Ｔｒａｎｓ−２−メチル−２−ブテナール（添加濃度０．２ｐｐｍ）に、チグリックアシッド１ｐｐｍ、３−メチル−２−ブテナール０．１ｐｐｍを組み合わせて添加すると、ふくよかな乳の甘味を更に増強した。１０名のうち全員が牛乳の乳感を強く感じるものは本発明香料組成物Ａ、Ｂを含有するＵＨＴ殺菌乳（試験品Ａ，Ｂ）のものであった。 As is apparent from Table 2, Trans-2-methyl-2-butenal alone has a flavor of milk (top incense, fresh like fresh milk) with respect to UHT pasteurized milk even at a concentration of 0.2 ppm to UHT pasteurized milk. It was found that the feeling and the sweetness of plump milk are strongly enhanced. Alone, the freshness like raw milk was most strongly enhanced. Moreover, the addition of tiglic acid 1 ppm and 3-methyl-2-butenal 0.1 ppm in combination with Trans-2-methyl-2-butenal (addition concentration 0.2 ppm) further enhanced the sweetness of plump milk. . Of the 10 persons, all of them felt strongly the milk feeling of UHT pasteurized milk (test products A and B) containing the perfume compositions A and B of the present invention.
（例３）（本発明香料組成物の乳の香味付与増強効果）
＜ミルク様香料組成物内のＴｒａｎｓ−２−メチル−２−ブテナールの含有量と最終濃度の乳感の効果確認試験＞
下記配合処方に従い混合し、ミルク様香料組成物を調製した。
(Example 3) (Enhanced effect of imparting flavor to milk of the perfume composition of the present invention)
<Confirmation test of effect of milk feeling of trans-2-methyl-2-butenal content and final concentration in milk-like fragrance composition>
A milk-like fragrance composition was prepared by mixing according to the following formulation.
上記表５の配合処方に従い調製したミルク様香料組成物９５．５質量部に対してプロピレングリコール９０４．５質量部配合して１０００質量部とし、対照品の香料組成物とした。
上記ミルク様香料組成物９５．５質量部に、Ｔｒａｎｓ−２−メチル−２−ブテナール（Ｓｉｇｍａ Ａｌｄｒｉｃｈ社の製品名「Ｗ３４０７０７ Ｔｒａｎｓ−２−ｍｅｔｈｙｌ−２ｂｕｔｅｎａｌ」）１００質量部、プロピレングリコール８０４．５質量部配合し、Ｔｒａｎｓ−２−メチル−２−ブテナールの最終濃度１０００００ｐｐｍの本発明香料組成物を調製した（表６の最下行）。次に、上記ミルク様香料組成物９５．５質量部に、Ｔｒａｎｓ−２−メチル−２−ブテナール１０質量部、プロピレングリコール８９４．５質量部配合し、Ｔｒａｎｓ−２−メチル−２−ブテナールの最終濃度が１００００ｐｐｍの本発明香料組成物を調製した（表６の下から２行目）。このように、Ｔｒａｎｓ−２−メチル−２−ブテナールの配合量を１／１０ずつ減らし、一方プロピレングリコールの配合量で調整して全体で１０００質量部となる本発明香料組成物を調製することで、下記表６に示す本発明香料組成物内のＴｒａｎｓ−２−メチル−２−ブテナールの最終濃度が０．００００１〜１０００００ｐｐｍ（表６）となる１１段階の濃度の本発明に係る香料組成物を調製した。
上記得られた本発明香料組成物をミルクコーヒー（商品名：雪印コーヒー、雪印メグミルク社製)に０．１％質量添加した。また、上記対照品の香料組成物を前述のミルクコーヒーに０．１質量％添加したものを対照品とした。
官能評価は例１に記載の方法と同様である。
904.5 parts by mass of propylene glycol was mixed with 95.5 parts by mass of the milk-like fragrance composition prepared according to the formulation of Table 5 to obtain 1000 parts by mass as a control fragrance composition.
95.5 parts by mass of the milk-like fragrance composition, 100 parts by mass of Trans-2-methyl-2-butenal (product name “W340707 Trans-2-methyl-2butenal” by Sigma Aldrich), 804.5 parts by mass of propylene glycol Partly blended to prepare a perfume composition of the present invention having a final concentration of Trans-2-methyl-2-butenal of 100000 ppm (bottom line in Table 6). Next, 95.5 parts by mass of the milk-like fragrance composition is blended with 10 parts by mass of Trans-2-methyl-2-butenal and 894.5 parts by mass of propylene glycol, and the final of Trans-2-methyl-2-butenal. A fragrance composition of the present invention having a concentration of 10,000 ppm was prepared (second row from the bottom of Table 6). Thus, by reducing the blending amount of Trans-2-methyl-2-butenal by 1/10, while adjusting the blending amount of propylene glycol, the total amount of the fragrance composition of the present invention becomes 1000 parts by mass. The fragrance composition according to the present invention having 11 levels of concentration in which the final concentration of Trans-2-methyl-2-butenal in the fragrance composition of the present invention shown in Table 6 below is 0.00001 to 100,000 ppm (Table 6). Prepared.
0.1% by mass of the above-obtained fragrance composition of the present invention was added to milk coffee (trade name: Snow Brand Coffee, Snow Brand Megmilk Co., Ltd.). The control product was prepared by adding 0.1% by mass of the fragrance composition of the control product to the aforementioned milk coffee.
The sensory evaluation is the same as the method described in Example 1.
Ｔｒａｎｓ−２−メチル−２−ブテナールは、香料組成物内濃度０．０００１ｐｐｍ〜１０００ppmの範囲で乳の香味（トップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味）付与増強効果があり、好ましくは０．０１ppm〜１００ppmの範囲で更に増強した効果が認められた。 Trans-2-methyl-2-butenal has an effect of enhancing the flavor of milk (top fragrance, fresh feeling like raw milk, sweetness of plump milk) in the range of the concentration in the fragrance composition from 0.0001 ppm to 1000 ppm, A further enhanced effect was observed preferably in the range of 0.01 ppm to 100 ppm.
＜比較香料組成物の調製＞
表５の配合処方により調製したミルク様香料組成物の１０００質量部にＲ．Ｃ，Ｔｒｅａｔｔ社製のビス（２−メチル−３−フリル）ジスルフィド（特許文献１に開示）の０．０１％エチルアルコール希釈溶液１質量部を混合して香料組成物Ｃを調製した。
同様にミルク様香料組成物の１０００質量部にＲ．Ｃ，Ｔｒｅａｔｔ社製の１２−メチルトリデカナール（特許文献２に開示）を１０％含有するミグリオール（中鎖脂肪酸トリグリセリド）の１％エチルアルコール希釈溶液１質量部を混合して香料組成物Ｄを調製した。
<Preparation of comparative fragrance composition>
In 1000 parts by mass of the milk-like fragrance composition prepared by the formulation shown in Table 5, R.I. C, A perfume composition C was prepared by mixing 1 part by weight of a 0.01% ethyl alcohol diluted solution of bis (2-methyl-3-furyl) disulfide (disclosed in Patent Document 1) manufactured by Treatt.
Similarly, R.I. C, 1% by weight of 1% ethyl alcohol diluted solution of miglyol (medium chain fatty acid triglyceride) containing 10% 12-methyltridecanal (disclosed in Patent Document 2) manufactured by Treatt Co. is prepared. did.
＜本発明香料組成物Ｅ、Ｆ、Ｇの調製＞
表５の配合処方により調製したミルク様香料組成物の１０００質量部にＴｒａｎｓ−２−メチル−２ブテナールの１％エチルアルコール希釈溶液１質量部を混合して本発明香料組成物Ｅを調製した。
ミルク様香料組成物の１０００質量部にＴｒａｎｓ−２−メチル−２−ブテナール１％エチルアルコール希釈溶液１質量部、３−メチル−２−ブテナール１％エチルアルコール希釈溶液１質量部、及びチグリックアシッド１０％エチルアルコール希釈溶液１質量部を混合して本発明香料組成物Ｆを調製した。
ミルク様香料組成物の１０００質量部にＴｒａｎｓ−２−メチル−２−ブテナール１％エチルアルコール希釈溶液１．５質量部、３−メチル−２−ブテナール１％エチルアルコール希釈溶液０．５質量部、及びチグリックアシッド１０％エチルアルコール希釈溶液１質量部を混合して本発明香料組成物Ｇを調製した。
<Preparation of the present perfume composition E, F, G>
Perfume composition E of the present invention was prepared by mixing 1 part by mass of 1% ethyl alcohol diluted solution of Trans-2-methyl-2butenal with 1000 parts by mass of the milk-like perfume composition prepared according to the formulation of Table 5.
1000 parts by mass of a milk-like fragrance composition, 1 part by mass of Trans-2-methyl-2-butenal 1% ethyl alcohol diluted solution, 1 part by mass of 3-methyl-2-butenal 1% ethyl alcohol diluted, and tiglic acid The perfume composition F of the present invention was prepared by mixing 1 part by weight of a 10% ethyl alcohol diluted solution.
To 1000 parts by mass of the milk-like fragrance composition, 1.5 parts by mass of Trans-2-methyl-2-butenal 1% ethyl alcohol diluted solution, 0.5 parts by mass of 3-methyl-2-butenal 1% ethyl alcohol diluted solution, And 1 part by weight of a 10% ethyl alcohol diluted solution of tiglic acid 10% was mixed to prepare the perfume composition G of the present invention.
ＵＨＴ殺菌乳に対して、表５の配合処方により調製したミルク様香料組成物、比較香料組成物Ｃ、Ｄ、本発明香料組成物Ｅ、Ｆ、Ｇをそれぞれ０．０２質量％添加し、対照品３、比較品Ｃ、Ｄ、本発明品Ｅ、Ｆ、Ｇを作成し、本発明品、比較品について、例２に記載の評価基準に従い対照品と比較して官能評価を実施した。 To UHT pasteurized milk, 0.02% by mass of each of the milk-like fragrance composition prepared by the formulation shown in Table 5, comparative fragrance compositions C and D, and the present invention fragrance compositions E, F, and G was added, and the control Product 3, Comparative products C and D, Invention products E, F, and G were prepared, and Sensory evaluation was performed for the products of the present invention and comparison products in comparison with the control product according to the evaluation criteria described in Example 2.
表７より明らかなように、本発明香料組成物を含有した本発明品Ｅ、Ｆ、Ｇは、対照品３及び比較品Ｃ、Ｄより乳の香味（トップ香、生乳のようなフレッシュ感、ふくよかな乳の甘さ）を強く付与増強することが分かった。また、本発明品Ｅ、Ｆ、Ｇを含有するＵＨＴ殺菌乳を美味しいと感じたパネラーの人数が９名であったのに対し、有効成分として、ビス（２−メチル−３−フリル）ジスルフィド、１２−メチルトリデカナール含有する比較香料組成物を添加したＵＨＴ殺菌乳（比較品Ｃ、Ｄ）を美味しいと評価したのは１名のみであった。従って、本発明香料組成物は、従来のミルク様香料組成物よりも乳の香味付与増強効果において優れていることが確認された。 As is apparent from Table 7, the products E, F and G of the present invention containing the fragrance composition of the present invention are more flavorful of milk than the control product 3 and comparative products C and D. It was found that the sweetness of plump milk was strongly enhanced. Moreover, while the number of panelists who felt that the UHT pasteurized milk containing the products E, F and G of the present invention was delicious was nine, bis (2-methyl-3-furyl) disulfide, Only one person evaluated the UHT pasteurized milk (comparative products C and D) to which the comparative fragrance composition containing 12-methyltridecanal was added as delicious. Therefore, it was confirmed that this invention fragrance | flavor composition is excellent in the flavor imparting enhancement effect of milk rather than the conventional milk-like fragrance | flavor composition.
（例４）（本発明香料組成物の乳の香味付与増強効果）
ミルクコーヒー（商品名：雪印コーヒー、雪印メグミルク社製)に、例３で調製したミルク様香料組成物、比較香料組成物Ｃ、Ｄ、本発明香料組成物Ｅ、Ｆ、Ｇをそれぞれ０．０２質量％添加し、対照品４、比較品ＣＣ、ＤＤ、本発明品ＥＥ、ＦＦ及びＧＧを作成し、本発明品、比較品について、例２に記載の評価基準に従い対照品と比較して官能評価を実施した。
(Example 4) (Enhanced effect of imparting flavor to milk of the perfume composition of the present invention)
The milk-like fragrance composition prepared in Example 3 and the comparative fragrance compositions C and D and the present fragrance compositions E, F, and G were added to milk coffee (trade names: Snow Brand Coffee, Snow Brand Megmilk Co., Ltd.) by 0.02 The control product 4, comparative product CC, DD, the inventive product EE, FF and GG are prepared by adding mass%, and the inventive product and the comparative product are functionally compared with the control product according to the evaluation criteria described in Example 2. Evaluation was performed.
表８より明らかなように、本発明品ＥＥ、ＦＦ、ＧＧは、対照品４及び比較品ＣＣ、ＥＥより乳の香味（トップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味）を強く付与増強することが分かった。また、本発明品を含有するミルクコーヒーを美味しいと感じたパネラーの人数が９名であったのに対し、有効成分として、ビス（２−メチル−３−フリル）ジスルフィド、１２−メチルトリデカナール含有する比較香料組成物を添加したミルクコーヒー（比較品ＣＣ、はＤＤ）を美味しいと評価したのは１名のみであった。従って、本発明香料組成物は、従来のミルク様香料組成物よりも乳の香味付与増強効果において優れていることが確認された。 As is clear from Table 8, the products EE, FF, and GG of the present invention have stronger milk flavor (top fragrance, fresh feeling like raw milk, sweetness of plump milk) than the control product 4 and comparative products CC and EE. It was found to increase the grant. Moreover, while the number of panelists who felt that the milk coffee containing the product of the present invention was delicious was nine, bis (2-methyl-3-furyl) disulfide and 12-methyltridecanal contained as active ingredients Only one person evaluated the milk coffee (comparative product CC, DD) to which the comparative fragrance composition was added as delicious. Therefore, it was confirmed that this invention fragrance | flavor composition is excellent in the flavor imparting enhancement effect of milk rather than the conventional milk-like fragrance | flavor composition.
（例５）（乳製品由来の香料組成物に対する、本発明香料組成物の乳の香味付与増強効果）
下記配合処方に従い、混合撹拌後濾過精製し、乳製品由来の香料組成物を調製した。
According to the following formulation, the mixture was stirred and purified by filtration to prepare a perfume composition derived from dairy products.
上記乳製品由来の香料組成物の１０００質量部にＴｒａｎｓ−２−メチル−２ブテナールの10％エチルアルコール希釈溶液２質量部を混合撹拌後濾過精製し本発明に係る香料組成物Ｈを調製した。
Ｔｒａｎｓ−２−メチル−２−ブテナール10％エチルアルコール希釈液２質量部、３−メチル−２−ブテナール10％エチルアルコール希釈溶液１質量部、及びチグリックアシッド１質量部を、上記乳製品由来の香料組成物の１０００質量部に混合し、撹拌後濾過精製して本発明に係る香料組成物Ｉを調製した。
A fragrance composition H according to the present invention was prepared by mixing and stirring 2 parts by mass of a 10% ethyl alcohol diluted solution of Trans-2-methyl-2butenal with 1000 parts by mass of the fragrance composition derived from the dairy product, followed by filtration and purification.
2 parts by mass of Trans-2-methyl-2-butenal 10% ethyl alcohol diluted solution, 1 part by mass of 3-methyl-2-butenal 10% ethyl alcohol diluted solution, and 1 part by mass of tiglic acid were derived from the dairy product. It mixed with 1000 mass parts of the fragrance | flavor composition, it filtered and refine | purified after stirring, and the fragrance | flavor composition I based on this invention was prepared.
練乳（商品名：ツクバ コンデンスミルク、筑波乳業社製）１０質量部をイオン交換水９０重量部で調製した清涼飲料（１０％練乳溶液）に対して、乳製品由来の香料組成物、本発明香料組成物Ｈ、Ｉをそれぞれ０．０２質量％添加し、比較品、本発明品Ｈ、Ｉを作成した。また、無添加の清涼飲料（１０％練乳溶液）を対照品５とした。
本発明品、比較品について、例２に記載の評価基準に従い対照品と比較して官能評価を実施した。
A fragrance composition derived from a dairy product and a fragrance of the present invention with respect to a soft drink (10% condensed milk solution) prepared by mixing 10 parts by weight of condensed milk (trade name: Tsukuba condensed milk, manufactured by Tsukuba Milk Industry Co., Ltd.) with 90 parts by weight of ion-exchanged water Compositions H and I were added in an amount of 0.02% by mass to prepare comparative products and products H and I of the present invention. An additive-free soft drink (10% condensed milk solution) was used as the control product 5.
The inventive product and the comparative product were subjected to sensory evaluation in comparison with the control product according to the evaluation criteria described in Example 2.
表７より明らかなように、本発明品Ｈ、Ｉは、乳製品由来の香料組成物のみを添加した清涼飲料（比較品）より乳の香味（乳のトップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味）を強く付与増強することが分かった。また、本発明香料組成物を含有する清涼飲料水（本発明品Ｈ、Ｉ）を美味しいと感じたパネラーの人数が１０名であったのに対し、比較品を美味しいと評価した者はいなかった。 As is apparent from Table 7, the products H and I of the present invention have a milk flavor (milk top fragrance, fresh feeling like raw milk) than a soft drink (comparative product) to which only a fragrance composition derived from dairy products is added. It was found that the sweetness of plump milk was strongly enhanced. Moreover, while the number of panelists who felt that the soft drinks (invention products H and I) containing the fragrance composition of the present invention were delicious was 10, no one evaluated the comparative product as delicious. .
（例６）（乳製品由来の香料組成物に対する、本発明香料組成物の乳の香味付与増強効果及び乳飲料の還元臭に対するマスキング効果）
脱脂粉乳（商品名：よつ葉北海道脱脂粉乳、よつ葉乳業社製）１０質量部をイオン交換水９０質量部で溶解した乳飲料に対して、例４で調製した乳製品由来の香料組成物、本発明香料組成物Ｈ、Ｉをそれぞれ０．０２質量％添加し、比較品、本発明品ＨＨ、ＩＩを作成した。また、無添加の乳飲料を対照品６とした。
本発明品、比較品について、例２に記載の評価基準に従い対照品と比較して官能評価を実施した。
(Example 6) (Milk flavor imparting enhancing effect of the fragrance composition of the present invention and masking effect on the reduced odor of the milk beverage)
Scented milk powder (trade name: Yotsuba Hokkaido skim milk powder, manufactured by Yotsuba Milk Industry Co., Ltd.) 10 parts by mass of ion-exchanged water dissolved in 90 parts by mass of ion-exchanged water, the fragrance composition derived from the dairy product prepared in Example 4, the present invention Perfume compositions H and I were added in an amount of 0.02% by mass to prepare comparative products and inventive products HH and II. Moreover, the additive-free milk drink was made into the control product 6.
The inventive product and the comparative product were subjected to sensory evaluation in comparison with the control product according to the evaluation criteria described in Example 2.
また、乳飲料の還元臭に対するマスキング効果については以下の官能評価を実施した。
乳飲料の還元臭に対するマスキング効果に関する評価方法（官能評価）
年齢や性別の異なるよく訓練された１０名のパネラーが、ブラインドで本発明の香料組成物を添加した飲食品を試食して評価を行い、下記に示す６段階で点数を付けた。
匂った時、および口に含んだ時感じる還元臭をマスキングできているか否かの、観点から判断してもらい、本発明の香料組成物を添加しない場合（対照品）に比べ、
還元臭のマスキング効果を非常に強く感じる場合：５点
還元臭のマスキング効果を強く感じる場合：４点
還元臭のマスキング効果をやや強く感じる場合：３点
還元臭のマスキング効果を感じる程度の場合：２点
還元臭のマスキング効果をわずかながら感じる場合：１点
還元臭のマスキング効果を感じられないもの：０点
として、上記１０名のパネラーに点数を付けてもらい、１０名の点数の平均値を採用した。
Moreover, the following sensory evaluation was implemented about the masking effect with respect to the reduced odor of a milk drink.
Evaluation method for masking effect on reduced odor of milk drink (sensory evaluation)
Ten well-trained panelists of different ages and genders sampled and evaluated foods and drinks to which the fragrance composition of the present invention had been added blindly, and scored in the following 6 levels.
Have you judge from the point of view whether you can mask the reduced odor when you smell and when you put it in your mouth, compared to the case where the fragrance composition of the present invention is not added (control product),
If you feel the reduced odor masking effect very strongly: 5 points If you feel the reduced odor masking effect strongly: 4 points If you feel the reduced odor masking effect slightly stronger: 3 points If you feel the reduced odor masking effect: 2 points If you feel the masking effect of the reduced odor a little: 1 point If you do not feel the masking effect of the reduced odor: 0 points, the above 10 panelists are given a score, the average value of the 10 people score Adopted.
表１１〜１２より明らかなように、本発明香料組成物を含む乳飲料（本発明品ＨＨ，ＩＩ）は、比較品の乳飲料より乳の香味（乳のトップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味）を強く付与増強することが分かった。また、本発明香料組成物を含有する乳飲料（本発明品ＨＨ，ＩＩ）を美味しいと感じたパネラーの人数が１０名であったのに対し、比較品の乳飲料を美味しいと評価したパネラーはいなかった。更に還元臭のマスキングに関しては本発明香料組成物Ｈ、Ｉによる効果が高く、本発明香料組成物Ｉの使用により更にマスキング効果が増強されることが分かった。 As is clear from Tables 11 to 12, the milk beverage containing the fragrance composition of the present invention (the product of the present invention HH, II) has a milk flavor (milk top fragrance, fresh feeling like raw milk) than the comparative milk drink. It was found that the sweetness of plump milk was strongly enhanced. In addition, while the number of panelists who felt that the milk beverage (the present invention product HH, II) containing the perfume composition of the present invention was delicious was 10 persons, the panelist evaluated the comparative milk drink as delicious Yes There wasn't. Furthermore, regarding the masking of reduced odor, the effect of the perfume compositions H and I of the present invention is high, and it was found that the use of the perfume composition I of the present invention further enhances the masking effect.
（例７）（乳製品由来の香料組成物に対する、本発明香料組成物の乳の香味付与増強効果
市販の低脂肪ヨーグルト（商品名：毎日酪農 ヨーグルト（低脂肪）日本酪農協同社製）対して、乳製品由来の香料組成物、本発明香料組成物Ｈ、Ｉをそれぞれ０．０３質量％添加し、比較品、本発明品ＨＨＨ、ＩＩＩを作成し。また、無添加の乳飲料を対照品７とした。
本発明品、比較品について、例２に記載の評価基準に従い対照品と比較して官能評価を実施した。
(Example 7) (For fragrance composition derived from dairy products, the effect of imparting the flavor of milk of the fragrance composition of the present invention to commercially available low-fat yogurt (trade name: Mainichi Dairy Yogurt (low-fat) manufactured by Nippon Dairy Co., Ltd.)) A dairy product-derived fragrance composition and the present invention fragrance compositions H and I are each added in an amount of 0.03% by mass to prepare comparative products and the present invention products HHH and III. It was set to 7.
The inventive product and the comparative product were subjected to sensory evaluation in comparison with the control product according to the evaluation criteria described in Example 2.
表１３から明らかなように、本発明香料組成物を含む低脂肪ヨーグルト（本発明品ＨＨＨ、ＩＩＩ）は、比較品の低脂肪ヨーグルトより乳の香味（乳のトップ香の強さ、生乳のようなフレッシュ感、ふくよかな乳の甘味）を強く付与増強することが分かった。また、本発明品を含有する低脂肪ヨーグルトを美味しいと感じたパネラーの人数が１０名であったのに対し、比較品の低脂肪ヨーグルトを美味しいと評価したのはいなかった。更に酸味がまろやかに軽減され、味が濃厚に感じる効果に関しては、本発明香料組成物Ｉの方が高いことが分かった。 As apparent from Table 13, the low-fat yogurt containing the flavor composition of the present invention (the product of the present invention HHH, III) has a milk flavor (the strength of the top scent of milk, like raw milk) than the low-fat yogurt of the comparative product. Freshness and sweetness of plump milk). Moreover, while the number of panelists who felt that the low-fat yogurt containing the product of the present invention was delicious was 10, no comparative low-fat yogurt was evaluated as delicious. Furthermore, it was found that the perfume composition I of the present invention is higher in terms of the effect that the acidity is mildly reduced and the taste feels rich.
（例８）（乳製品代替品マーガリンにおける、本発明香料組成物の乳の香味付与増強効果）
下記配合処方に従い混合し、バター様香料組成物を調製した。
The butter-like fragrance composition was prepared by mixing according to the following formulation.
バター様香料組成物１０００質量部に、Ｔｒａｎｓ−２−メチル−２ブテナールの１％エチルアルコール希釈溶液1質量部を混合して本発明香料組成物Ｌを調製した。
また、バター様香料組成物の１０００質量部に、Ｔｒａｎｓ−２−メチル−２ブテナールの１％エチルアルコール希釈溶液1質量部、３−メチル−２−ブテナール１％エチルアルコール希釈溶液1質量部、チグリックアシッド１０％エチルアルコール希釈溶液1質量部及び３−メチル−２−ブテノール（Ｓｉｇｍａ Ａｌｄｒｉｃｈ社製 製品名「Ｗ３６４７０３ ３−Ｍｅｔｈｙｌ−２−ｂｕｔｅｎ−１−ｏｌ」）１％エチルアルコール希釈溶液2質量部を混合し、本発明香料組成物Ｍを調製した。
バター様香料組成物１０００質量部に、Ｔｒａｎｓ−２−メチル−２ブテナール１％エチルアルコール希釈溶液1質量部、３−メチル−２−ブテナール１％エチルアルコール希釈溶液２質量部、チグリックアシッド１０％エチルアルコール希釈溶液０．５質量部及び３−メチル−２−ブテノール１％エチルアルコール希釈溶液２質量部を混合し、本発明香料組成物Ｎを調製した。
Fragrance composition L of the present invention was prepared by mixing 1 part by mass of 1% ethyl alcohol diluted solution of Trans-2-methyl-2butenal with 1000 parts by mass of a butter-like fragrance composition.
In addition, 1000 parts by weight of the butter-like fragrance composition was added 1 part by weight of 1% ethyl alcohol diluted solution of Trans-2-methyl-2-butenal, 1 part by weight of 1% ethyl alcohol diluted solution of 3-methyl-2-butenal, 1 part by weight of dilute solution of 10% ethyl alcohol with grick acid and 3-methyl-2-butenol (product name “W364703 3-Methyl-2-buten-1-ol” manufactured by Sigma Aldrich) 2 parts by weight of dilute solution with 1% ethyl alcohol Were mixed to prepare the perfume composition M of the present invention.
1000 parts by weight of a butter-like fragrance composition, 1 part by weight of Trans-2-methyl-2butenal 1% ethyl alcohol diluted solution, 2 parts by weight of 3-methyl-2-butenal 1% ethyl alcohol diluted solution, 10% tiglic acid Perfume composition N of the present invention was prepared by mixing 0.5 part by weight of an ethyl alcohol diluted solution and 2 parts by weight of a 1% ethyl alcohol diluted solution of 3-methyl-2-butenol.
比較香料組成物としてバター様香料組成物の１０００質量部にＲ．Ｃ，Ｔｒｅａｔｔ社製の１２−メチルトリデカナールを１０％含有するミグリオール（中鎖脂肪酸トリグリセリド）の１％エチルアルコール希釈溶液１質量部を混合して香料組成物Ｏを調製した。同様に上記バター様香料組成物の１０００質量部にＲ．Ｃ．Ｔｒｅａｔｔ社製のビス（２−メチル−３−フリル）ジスルフィドの０．０１％エチルアルコール希釈溶液１質量部を混合して香料組成物Ｐを調製した。 As a comparative fragrance composition, R.B. A fragrance composition O was prepared by mixing 1 part by weight of a 1% ethyl alcohol diluted solution of miglyol (medium chain fatty acid triglyceride) containing 10% of C-Treatt 12-methyltridecanal. Similarly, 1000 parts by weight of the butter-like fragrance composition was added to R.I. C. A fragrance composition P was prepared by mixing 1 part by mass of a 0.01% ethyl alcohol diluted solution of bis (2-methyl-3-furyl) disulfide manufactured by Treatt.
市販の乳製品代用品マーガリン（商品名：-ラーマ バター風味、オイルミルズ社製)に対して、バター様香料組成物、本発明香料組成物Ｌ、Ｍ、Ｎ、比較香料組成物Ｏ、Ｐをそれぞれ０．１質量％添加して対照品８、本発明品Ｌ、Ｍ、Ｎと比較品Ｏ、Ｐを作成し、本発明品、比較品について、例２に記載の評価基準に従い対照品と比較して官能評価を実施した。 For a commercial dairy substitute margarine (trade name: -Rama butter flavor, manufactured by Oil Mills), butter-like fragrance composition, present fragrance composition L, M, N, comparative fragrance composition O, P Control product 8, invention products L, M, and N and comparative products O and P were prepared by adding 0.1% by mass, respectively. The product of the present invention and the comparison product were compared with the control product according to the evaluation criteria described in Example 2. Sensory evaluation was carried out in comparison.
表１５より明らかなように、本発明香料組成物を含有する本発明品Ｌ、Ｍ、Ｎは、対照品８及び比較品Ｏ、Ｐより乳の香味（乳のトップ香の強さ、生乳のようなフレッシュ感、ふくよかな乳のコク味）を強く付与増強することが分かった。また、本発明香料組成物を含有するマーガリンを美味しいと感じたパネラーの人数が１０名であったのに対し、有効成分として、ビス（２−メチル−３−フリル）ジスルフィド、１２−メチルトリデカナールを含有するマーガリン（比較品Ｏ、Ｐ）を美味しいと評価したのは０名であった。 As apparent from Table 15, the products L, M and N of the present invention containing the fragrance composition of the present invention are more flavorful of milk than the control product 8 and comparative products O and P (strength of top scent of milk, raw milk It was found that the freshness and the rich taste of milk were strongly imparted and enhanced. Moreover, while the number of panelists who felt that the margarine containing the fragrance composition of the present invention was delicious was 10 people, as active ingredients, bis (2-methyl-3-furyl) disulfide, 12-methyltridecanal No margarine (comparative products O and P) containing sucrose was evaluated as delicious.
（例９）（乳製品の代替品チーズフードにおける、本発明香料組成物の乳の香味付与増強効果）
下記配合処方に従い、混合し、チーズ様香料組成物を調製した。
(Example 9) (Enhanced effect of imparting flavor to milk of the fragrance composition of the present invention in cheese food substitutes for dairy products)
According to the following formulation, they were mixed to prepare a cheese-like fragrance composition.
上記チーズ様香料組成物の１０００質量部に、Ｔｒａｎｓ−２−メチル−２ブテナールの１％エチルアルコール希釈溶液1質量部を混合して本発明香料組成物Ｒを調製した。
また、チーズ様香料組成物の１０００質量部に、Ｔｒａｎｓ−２−メチル−２ブテナールの１％エチルアルコール希釈溶液1質量部、３−メチル−２−ブテナール１％エチルアルコール希釈溶液1質量部、チグリックアシッド１０％エチルアルコール希釈溶液1質量部及び３−メチル−２−ブテノール１％エチルアルコール希釈溶液2質量部を混合し、本発明香料組成物Ｓを調製した。
チーズ様香料組成物１０００質量部に、Ｔｒａｎｓ−２−メチル−２ブテナール１％エチルアルコール希釈溶液１質量部、３−メチル−２−ブテナール１％エチルアルコール希釈溶液２質量部、チグリックアシッド１0％エチルアルコール希釈溶液０．５質量部及び３−メチル−２−ブテノール１％エチルアルコール希釈溶液２質量部を混合し、本発明香料組成物Ｔを調製した。
比較香料組成物として、チーズ様香料組成物の１０００質量部にＲ．Ｃ，Ｔｒｅａｔｔ社製の１２−メチルトリデカナールを１０％含有するミグリオール（中鎖脂肪酸トリグリセリド）の１％エチルアルコール希釈溶液１質量部を混合して比較香料組成物Ｕを調製した。
同様に上記チーズ様香料組成物の１０００質量部にＲ．Ｃ，Ｔｒｅａｔｔ社製のビス（２−メチル−３−フリル）ジスルフィドの０．０１％エチルアルコール希釈溶液１質量部を混合して比較香料組成物Ｖを調製した。
Fragrance composition R of the present invention was prepared by mixing 1 part by mass of 1% ethyl alcohol diluted solution of Trans-2-methyl-2butenal with 1000 parts by mass of the cheese-like fragrance composition.
Further, 1000 parts by mass of the cheese-like fragrance composition, 1 part by mass of 1% ethyl alcohol diluted solution of Trans-2-methyl-2butenal, 1 part by mass of 1% ethyl alcohol diluted solution of 3-methyl-2-butenal, The perfume composition S of the present invention was prepared by mixing 1 part by mass of a 10% ethyl alcohol diluted solution of grick acid and 2 parts by weight of a 1% ethyl alcohol diluted solution of 3-methyl-2-butenol.
1000 parts by weight of cheese-like fragrance composition, 1 part by weight of Trans-2-methyl-2-butenal 1% ethyl alcohol diluted solution, 2 parts by weight of 3-methyl-2-butenal 1% ethyl alcohol diluted solution, 10% tiglic acid Perfume composition T of the present invention was prepared by mixing 0.5 parts by weight of an ethyl alcohol diluted solution and 2 parts by weight of a 1% ethyl alcohol diluted solution of 3-methyl-2-butenol.
As a comparative fragrance composition, R.I. C, A comparative fragrance composition U was prepared by mixing 1 part by weight of a 1% ethyl alcohol diluted solution of miglycol (medium chain fatty acid triglyceride) containing 10% of 12-methyltridecanal manufactured by Treatt.
Similarly, 1000 parts by mass of the cheese-like fragrance composition was added to R.I. Comparative perfume composition V was prepared by mixing 1 part by mass of a 0.01% ethyl alcohol diluted solution of bis (2-methyl-3-furyl) disulfide manufactured by C, Treatt.
上記に示した表１７の配合処方に従い作成したチーズフードに対して、チーズ様香料組成物、本発明香料組成物Ｒ、Ｓ、Ｔ、比較香料組成物Ｕ、Ｖをそれぞれ０．２質量％添加し、対照品９、本発明香料組成物を含有する本発明品Ｒ、Ｓ、Ｔと比較品Ｕ、Ｖを作成し、本発明品、比較品について、例２に記載の評価基準に従い対照品と比較して官能評価を実施した。 0.2% by mass of the cheese-like fragrance composition, the present invention fragrance composition R, S, T, and the comparative fragrance compositions U and V are added to the cheese food prepared according to the formulation of Table 17 shown above. The control product 9, the present product R, S, T containing the perfume composition of the present invention and the comparative products U, V were prepared. The control product according to the evaluation criteria described in Example 2 was used for the present product and the comparative product. Sensory evaluation was carried out in comparison with
表１８より明らかなように、本発明香料組成物を含有したチーズフード（本発明品Ｒ、Ｓ、Ｔ）は、対照品９及び比較品Ｕ、Ｖより乳の香味（乳のトップ香の強さ、生乳のフレッシュ感、ふくよかな乳のコク）を強く付与増強することが分かった。また、本発明香料組成物を含有するチーズフード（本発明品Ｒ、Ｓ，Ｔ）を美味しいと感じたパネラーの人数が７名であったのに対し、有効成分として、ビス（２−メチル−３−フリル）ジスルフィド、又は１２−メチルトリデカナール含有するチーズフード（比較品Ｕ，Ｖ）を美味しいと評価したのは３名であった。 As is clear from Table 18, the cheese food containing the fragrance composition of the present invention (the products of the present invention R, S, T) has a milk flavor (the strength of the top scent of milk) from the control product 9 and the comparative products U, V. It was found that the freshness of raw milk and the richness of full milk were strongly imparted and enhanced. Moreover, while the number of panelists who felt that the cheese food containing the fragrance composition of the present invention (the products of the present invention R, S, T) was delicious was seven, bis (2-methyl- Three people evaluated the cheese food (comparative products U and V) containing 3-furyl) disulfide or 12-methyltridecanal as delicious.
本発明により乳そのものを印象づけるインパクトのあるトップ香、生乳のようなフレッシュ感、ふくよかな乳の甘味を付与し、また、乳関連製品の加熱による還元臭をマスキングする優れた効果を有する香料組成物が提供される。よって、本発明により得られたＴＲＡＮＳ−２−メチル−２−ブテナールを有効成分として含有する香料組成物、又は３−メチル−２−ブテナール、チグリックアシッド及び３−メチル−２−ブテノールからなる群より少なくとも１種以上の化合物と、前記のＴｒａｎｓ−２−メチル−２−ブテナールを有効成分として含有する香料組成物は食品工業分野において有用である。 According to the present invention, a perfume composition having an excellent effect of masking the reduced odor due to heating of milk-related products, imparting a top fragrance that gives an impression of the milk itself, a fresh feeling like raw milk, a sweet taste of milk. Is provided. Therefore, the fragrance composition containing TRANS-2-methyl-2-butenal obtained by the present invention as an active ingredient, or the group consisting of 3-methyl-2-butenal, tiglic acid and 3-methyl-2-butenol A perfume composition containing at least one or more compounds and the aforementioned Trans-2-methyl-2-butenal as active ingredients is useful in the food industry.
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| JP2006020526A (en) * | 2004-07-06 | 2006-01-26 | Kiyomitsu Kawasaki | Coffee flavor composition, and food and drink containing the same |
| JP2006124490A (en) * | 2004-10-28 | 2006-05-18 | Kiyomitsu Kawasaki | Fermented-milk-like perfume composition |
| JP2014077067A (en) * | 2012-10-11 | 2014-05-01 | Ogawa & Co Ltd | Production method of dairy flavor |
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| JP2006020526A (en) * | 2004-07-06 | 2006-01-26 | Kiyomitsu Kawasaki | Coffee flavor composition, and food and drink containing the same |
| JP2006124490A (en) * | 2004-10-28 | 2006-05-18 | Kiyomitsu Kawasaki | Fermented-milk-like perfume composition |
| JP2014077067A (en) * | 2012-10-11 | 2014-05-01 | Ogawa & Co Ltd | Production method of dairy flavor |
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| "TRANS-2-メチル-ブテナール", [ONLINE], 2016.4.23, [2017.1.6 検索], インターネット<URL: HTTPS://WEB, JPN6017000413 * |
| FOOD RES. INT., vol. Vol.62, JPN6017000414, 2014, pages 846 - 859 * |
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