JP4783421B2 - Sesame-like flavor enhancer - Google Patents
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Description
本発明は、ゴマ様の香味、特にゴマの煎りたて感、擂りたて感、油脂感等の香味を増強することができるゴマ様香味増強剤およびその使用に関する。 The present invention relates to a sesame-like flavor enhancer that can enhance a sesame-like flavor, particularly a sesame-like sensation, a savory, oily, and other flavor, and a use thereof.
ゴマは、多くの家庭料理に使用されるばかりでなく、様々に加工され加工食品や調味料などに利用されている。飲食品にゴマの香味を付与するには、ゴマそのものを使用するか、あるいはゴマ油を使用する場合が多い。ゴマそのものを使用する場合、固形であるためその使用範囲が制限され、また、ゴマ油を使用する場合は、ある程度大量に使用しなければゴマの香味を付与することができないため、飲食品の物性に悪影響を及ぼしたり、コスト高となるなどの問題がある。さらに、ゴマ油の場合は、搾油時にゴマの煎りたて、擂りたての香味が散逸してしまうなどの欠点がある。 Sesame is not only used in many home-cooked dishes, but also variously processed and used as processed foods and seasonings. In order to impart a sesame flavor to foods and drinks, sesame itself or sesame oil is often used. When using sesame itself, the range of use is limited because it is solid, and when using sesame oil, the flavor of sesame can not be imparted unless it is used in a certain amount. There are problems such as adverse effects and high costs. Furthermore, in the case of sesame oil, there is a drawback that the scent of sesame is roasted during oil extraction and the freshly savory flavor is lost.
飲食品にゴマ様香味を増強するための方法として、例えば、ゴマ種子を遠赤外線ヒーターにより加熱して採油する方法（特許文献１参照）、焙煎ゴマを水蒸気蒸留して得られる留出液を中鎖脂肪酸トリグリセライドで抽出する方法（特許文献２参照）などが提案されているが、ゴマの焙煎香を賦与する方法としては効果があるが、ゴマの煎りたて、擂りたての香味を増強する方法としては十分満足できるものではない。 As a method for enhancing the sesame-like flavor in foods and drinks, for example, a method of collecting oil by heating sesame seeds with a far infrared heater (see Patent Document 1), a distillate obtained by steam distillation of roasted sesame A method of extracting with medium-chain fatty acid triglyceride (see Patent Document 2) has been proposed, but it is effective as a method of adding roasted sesame sesame. It is not a satisfactory method for enhancing.
また、ゴマの香気成分の分析について様々な検討がなされ、例えば、非特許文献１には、２−メルカプト−３−ペンタノンが擂りたてゴマの特徴的な成分であることが報告されている。さらに、特許文献３には、２−プロピオニルチアゾールを含有するゴマ風味を有する液体調味料用のフレーバー組成物が開示され、特許文献４には、２−アセチルピリジンを含有するゴマ風味を有する液体調味料が開示されている。 Various studies have been made on the analysis of fragrance components of sesame. For example, Non-Patent Document 1 reports that 2-mercapto-3-pentanone is a characteristic component of fresh sesame. Further, Patent Document 3 discloses a flavor composition for a liquid seasoning having a sesame flavor containing 2-propionylthiazole, and Patent Document 4 discloses a liquid seasoning having a sesame flavor containing 2-acetylpyridine. Fees are disclosed.
近年、消費者の嗜好性の多様化により、飲食品等に使用する香料においても天然感、フレッシュ感あふれる素材が求められており、従来の香料物質を組み合わせることではその要求に十分対応しきれないのが現状である。したがって、本発明の目的は、ゴマの煎りたて感、擂りたて感、油脂感等の香味を増強することができるゴマ様香味増強剤および該増強剤を有効成分として含有する香料組成物、並びに該増強剤または該香料組成物を用いてゴマ様の香味が付与された飲食品を提供することにある。 In recent years, due to the diversification of consumer preferences, there is a demand for materials with a natural and fresh feel in fragrances used in foods and drinks, etc., and the combination of conventional fragrance substances cannot fully meet the demand. is the current situation. Accordingly, the object of the present invention is to provide a sesame-like flavor enhancer capable of enhancing the flavor of sesame, such as a freshly baked sensation, a fresh sensation, and a sense of oil and fat, and a fragrance composition containing the enhancer as an active ingredient, It is another object of the present invention to provide a food or drink provided with a sesame-like flavor using the enhancer or the fragrance composition.
本発明者らは、前述の課題を解決するために鋭意検討した結果、今回、これまでゴマの香気分析からは見出されておらず、ましてやゴマの香料成分として利用されたことのない下記式（１） As a result of intensive studies to solve the above-mentioned problems, the present inventors have not found from the sesame aroma analysis so far, and have not been used as a fragrance component of sesame. (1)
（式中、Ｒはメチル基またはエチル基を示す。）
で表される化合物を極微量使用することによりゴマ様の香味、特に、ゴマの煎りたて感、擂りたて感、油脂感等の香味を増強することができることを見出し本発明を完成するに至った。
(In the formula, R represents a methyl group or an ethyl group.)
In order to complete the present invention, it has been found that the use of a very small amount of the compound represented by the formula can enhance the flavor of sesame-like flavors, in particular, the taste of freshly baked sesame, the sensation of sesame, the feeling of oil and fat. It came.
かくして本発明は、前記式（１）からなるゴマ様香味増強剤を提供するものである。 Thus, the present invention provides a sesame-like flavor enhancer comprising the above formula (1).
また本発明は、前記のゴマ様香味増強剤を１０−５〜１０３ｐｐｍの濃度範囲で含有することを特徴とするゴマ様香料組成物を提供することができる。 Moreover, this invention can provide the sesame-like fragrance | flavor composition characterized by including the said sesame-like flavor enhancer in the density | concentration range of 10 <-5 > -10 < 3 > ppm.
さらに本発明は、前記のゴマ様香味増強剤を１０−３〜１０５ｐｐｂの濃度範囲で含有することを特徴とするゴマ様香味を有する飲食品を提供するものである。 Furthermore, this invention provides the said sesame-like flavor enhancer in the density | concentration range of 10 < -3 > -10 < 5 > ppb, The food / beverage products which have the sesame-like flavor characterized by the above-mentioned.
本発明のゴマ様香味増強剤は、ゴマの香味、特にゴマの煎りたて感、擂りたて感、油脂感等の香味を増強することができ、該増強剤は、飲食品などに用いるゴマ様香味を増強する香料組成物の調合素材として有用である。 The sesame-like flavor enhancer of the present invention can enhance the flavor of sesame, in particular, the taste of sesame, such as freshly baked, savory, oily, etc. It is useful as a preparation material for a fragrance composition that enhances the flavor.
以下、本発明のゴマ様香味増強剤およびその使用について、さらに詳細に説明する。 Hereinafter, the sesame-like flavor enhancer and use thereof of the present invention will be described in more detail.
本発明のゴマ様香味増強剤は、前記式（１）で表される化合物、具体的には、３−メルカプト−２−ペンタノンと４−メルカプト−３−ヘキサノンを有効成分とする。３−メルカプト−２−ペンタノンは、加熱肉の香気成分として見出されており（Ｊ．Ａｇｒｉｃ．Ｆｏｏｄ Ｃｈｅｍ．１９９８，４６，１９５４−１９５８）、また、コーヒーフレーバーとしての使用（特表２００７−５０８８２８号公報）も知られているが、ゴマの香味、特に、ゴマの煎りたて感、擂りたて感、油脂感等の香味増強に有効であることは従来知られていなかった。 The sesame-like flavor enhancer of this invention uses the compound represented by the said Formula (1), specifically 3-mercapto-2-pentanone and 4-mercapto-3-hexanone as an active ingredient. 3-Mercapto-2-pentanone has been found as an aroma component of cooked meat (J. Agric. Food Chem. 1998, 46, 1954-1958), and also used as a coffee flavor (special table 2007-508828). However, it has not been known to be effective in enhancing the flavor of sesame, in particular, the flavor of sesame, such as freshly roasted, savory, and oily.
本発明のゴマ様香味増強剤の有効成分である前記式（１）の化合物は、特に制限されないが、例えば、Ｊｕｓｔｕｓ Ｌｉｅｂｉｇｓ Ａｎｎ．Ｃｈｅｍ．１９６４，６７２，１５６−１７８に記載の方法により容易に得ることができる。 Although the compound of the said Formula (1) which is an active ingredient of the sesame-like flavor enhancer of this invention is not restrict | limited in particular, For example, Justus Liebigs Ann. Chem. 1964, 672, 156-178.
本発明のゴマ様香味増強剤は、そのまま飲食品などに極微量配合してゴマ様の香味を増強することができるが、他の成分と混合してゴマ様香料組成物を調製し、該香料組成物を用いて飲食品などにゴマ様の香味を増強することもできる。該香料組成物の前記式（１）の化合物と共に含有し得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。 The sesame-like flavor enhancer of the present invention can be added to foods and beverages and the like as it is to enhance the sesame-like flavor by mixing it with other ingredients to prepare a sesame-like flavor composition. The composition can also be used to enhance the sesame-like flavor of food and drink. Examples of other fragrance components that can be contained together with the compound of formula (1) of the fragrance composition include various synthetic fragrances, natural fragrances, natural essential oils, plant extracts, and the like.
本発明のゴマ様香料組成物における前記式（１）の化合物の含有量は、混合される他の香料成分により異なり一概にはいえないが、通常、該香料組成物の重量を基準として１０−５〜１０３ｐｐｍ、好ましくは１０−４〜１０２ｐｐｍの濃度範囲とすることができる。前記式（１）の化合物の含有量が１０−５ｐｐｍ未満であればゴマ様香味増強効果が得られず、１０３ｐｐｍを越える含有量であれば不快臭が強くなってしまい好ましくない。 The content of the compound of the formula (1) in the sesame-like fragrance composition of the present invention varies depending on other fragrance components to be mixed and cannot be generally specified, but is usually 10 − based on the weight of the fragrance composition. The concentration range may be 5 to 10 3 ppm, preferably 10 −4 to 10 2 ppm. If the content of the compound of the formula (1) is less than 10 −5 ppm, the sesame-like flavor enhancing effect cannot be obtained, and if the content exceeds 10 3 ppm, the unpleasant odor becomes unfavorable.
前記式（１）の化合物を含有する本発明のゴマ様香料組成物には、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、エタノール等の溶剤；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ライド等の香料保留剤を含有することができる。 The sesame-like fragrance composition of the present invention containing the compound of the formula (1) is usually used in a fragrance composition, if necessary, for example, a solvent such as water or ethanol; ethylene glycol, propylene glycol Fragrance 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.
本発明の前記式（１）の化合物からなるゴマ様香味増強剤は、上記したようにそれ自体単独で、または前記式（１）の化合物を含有するゴマ様香料組成物を調製して、各種の製品、例えば、飲食品などにゴマ様香味を付与することができる。 The sesame-like flavor enhancer comprising the compound of the formula (1) according to the present invention can be prepared by itself as described above or by preparing sesame-like fragrance compositions containing the compound of the formula (1). A sesame-like flavor can be imparted to other products such as food and drink.
本発明の前記式（１）の化合物からなるゴマ様香味増強剤または前記式（１）の化合物を含有するゴマ様香料組成物によってゴマ様香味を付与することが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、炭酸飲料、清涼飲料、果汁飲料類、果実酒類、乳飲料類、乳酸菌飲料類、ドリンク剤類、豆乳、茶飲料などの飲料類；アイスクリーム、アイスミルク、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；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、チューインガム、饅頭、羊羹などの菓子類；和風スープ、洋風スープ、中華スープなどのスープ類；パン類；ジャム類；マヨネーズ、ドレッシングなどの調味料類；各種インスタント飲料類；各種インスタント食品類などを挙げることができる。 As a specific example of the food / beverage products which can provide sesame-like flavor with the sesame-like flavor enhancer which consists of a compound of said Formula (1) of this invention, or the sesame-like flavor composition containing the compound of said Formula (1). , But not limited to, beverages such as carbonated beverages, soft drinks, fruit juices, fruit liquors, milk beverages, lactic acid bacteria beverages, drinks, soy milk, tea beverages; ice cream, ice milk, lacto ice , Ice confectionery, yogurt, pudding, jelly, daily dessert, etc .; caramel, candy, tablet confectionery, crackers, biscuits, cookies, pie, chocolate, snacks, chewing gum, buns, mutton, etc .; Japanese-style soup, Western-style soup , Soups such as Chinese soup; breads; jams; seasonings such as mayonnaise and dressing; Tanto beverages; and various instant foods can be mentioned.
ゴマ様香味を付与する際の上記した各種の製品への前記式（１）の化合物の添加量は、製品の種類や形態に応じて異なり一概にはいえないが、通常、製品の重量を基準として１０−３〜１０５ｐｐｂ、好ましくは１０−２〜１０４ｐｐｂの濃度範囲とすることができる。前記式（１）の化合物の含有量が１０−３ｐｐｂ未満であればゴマ様香味増強効果が得られず、１０５ｐｐｂを越える含有量であれば不快臭が強くなってしまい好ましくない。 The amount of the compound of formula (1) added to the above-mentioned various products when imparting a sesame-like flavor differs depending on the type and form of the product and cannot be generally stated, but is usually based on the weight of the product. As a concentration range of 10 −3 to 10 5 ppb, preferably 10 −2 to 10 4 ppb. If the content of the compound of the formula (1) is less than 10 −3 ppb, the sesame-like flavor enhancing effect cannot be obtained, and if the content exceeds 10 5 ppb, the unpleasant odor becomes strong.
以下、実施例により本発明をさらに具体的に説明する。 Hereinafter, the present invention will be described more specifically with reference to examples.
実施例１：ゴマ油への式（１）の化合物の添加効果
ゴマ油（かどや製油社製）１００ｇに３−メルカプト−２−ペンタノン（本発明品１）、４−メルカプト−３−ヘキサノン（本発明品２）および２−メルカプト−３−ペンタノン（比較品１）をそれぞれ０．１ｍｇ（ゴマ油に対して１ｐｐｍ）添加して本発明品１、本発明品２および比較品１の香料組成物を調製した。それぞれの香料組成物の０．１％エタノール溶液をよく訓練されたパネラーにより香気評価を行った。香気評価は３０ｍＬサンプル瓶に前記０．１％エタノール溶液を用意し、瓶口の香気およびその溶液をにおい紙につけて行った。無添加品のゴマ油を対照品として、よく訓練された５名のパネラーの平均的な香気評価を表１に示す。
Example 1: Effect of addition of compound of formula (1) to sesame oil 3-mercapto-2-pentanone (product 1 of the present invention), 4-mercapto-3-hexanone (product of the present invention) to 100 g of sesame oil (manufactured by Kadoya Oil Co., Ltd.) 2) and 2-mercapto-3-pentanone (Comparative Product 1) were added in an amount of 0.1 mg (1 ppm relative to sesame oil), respectively, to prepare the perfume compositions of Invention Product 1, Invention Product 2 and Comparative Product 1. . Aroma evaluation was performed by a well-trained panel for 0.1% ethanol solution of each fragrance composition. The fragrance evaluation was performed by preparing the 0.1% ethanol solution in a 30 mL sample bottle and applying the fragrance of the bottle mouth and the solution to odor paper. Table 1 shows the average aroma evaluation of five well-trained panelists, with additive-free sesame oil as a control.
表１の評価結果から明らかなように、３−メルカプト−２−ペンタノン、４−メルカプト−３−ヘキサノンを配合したゴマ油は、構造類似化合物である２−メルカプト−３−ペンタノンを配合したゴマ油に比べて格段にゴマの煎りたて感、擂りたて感、油脂感の香味が増強されていた。 As is apparent from the evaluation results in Table 1, sesame oil blended with 3-mercapto-2-pentanone and 4-mercapto-3-hexanone is compared with sesame oil blended with 2-mercapto-3-pentanone, which is a structurally similar compound. The flavor of freshly baked sesame, freshly baked sensation, and oily fat was enhanced.
実施例２：ゴマ油への式（１）の化合物の添加濃度の検討
ゴマ油（かどや製油社製）１００ｇに対して、３−メルカプト−２−ペンタノンを０．０００１μｇ（１０−６ｐｐｍ：比較品２）、０．０１μｇ（１０−４ｐｐｍ：本発明品３）、１０μｇ（１０−１ｐｐｍ：本発明品４）、１０ｍｇ（１０２ｐｐｍ：本発明品５）、１ｇ（１０４ｐｐｍ：比較品３）を添加して本発明品３〜５、比較品２および比較品３の香料組成物を調製した。それぞれの香料組成物の０．１％エタノール溶液をよく訓練されたパネラーにより香気評価を行った。香気評価は３０ｍＬサンプル瓶に前記０．１％エタノール溶液を用意し、瓶口の香気およびその溶液をにおい紙につけて行った。無添加品のゴマ油を対照品として、よく訓練された５名のパネラーの平均的な香気評価を表２に示す。
Example 2 Examination of Addition Concentration of Compound of Formula (1) to Sesame Oil 0.0001 μg (10 −6 ppm: Comparative Product 2) of 3-mercapto-2-pentanone with respect to 100 g of sesame oil (manufactured by Kadoya Oil Co., Ltd.) ), 0.01 μg (10 −4 ppm: product of the present invention 3), 10 μg (10 −1 ppm: product of the present invention 4), 10 mg (10 2 ppm: product of the present invention 5), 1 g (10 4 ppm: comparative product) 3) was added to prepare perfume compositions of Invention Products 3 to 5, Comparative Product 2 and Comparative Product 3. Aroma evaluation was performed by a well-trained panel for 0.1% ethanol solution of each fragrance composition. The fragrance evaluation was performed by preparing the 0.1% ethanol solution in a 30 mL sample bottle and applying the fragrance of the bottle mouth and the solution to odor paper. Table 2 shows the average aroma evaluation of five well-trained panelists, using additive-free sesame oil as a control.
また、４−メルカプト−３−ヘキサノンについても上記と同一の添加濃度にて本発明品６〜８、比較品４および比較品５の香料組成物を調製し、上記と同様に香気評価を行い、その結果を表３に示す。 Further, for 4-mercapto-3-hexanone, the fragrance compositions of the present invention products 6 to 8, comparative product 4 and comparative product 5 were prepared at the same addition concentration as described above, and the fragrance evaluation was performed in the same manner as described above. The results are shown in Table 3.
表２および表３の評価結果から明らかなように、比較品２および比較品４では３−メルカプト−２−ペンタノンまたは４−メルカプト−３−ヘキサノンの添加効果はみられず、本発明品３〜５および本発明品６〜８では、ゴマの煎りたて感、擂りたて感、油脂感の香気が増強されていた。一方、比較品３および比較品５ではゴマとは異なる異質な不快臭が感じられたとの評価であった。 As is apparent from the evaluation results in Tables 2 and 3, Comparative Product 2 and Comparative Product 4 did not show the effect of adding 3-mercapto-2-pentanone or 4-mercapto-3-hexanone, and the product of the present invention 3 No. 5 and products 6 to 8 of the present invention had enhanced sesame scent, freshness, and oily aroma. On the other hand, the comparative product 3 and the comparative product 5 were evaluated as having felt an unpleasant odor different from sesame.
実施例３：ゴマ様基本調合香料組成物への添加検討
ゴマ様の調合香料組成物として、下記表４に示す成分からなる基本調合香料組成物（対照品）を調製した。
Example 3: Examination of addition to sesame-like basic fragrance composition As a sesame-like fragrance composition, a basic fragrance composition (control product) comprising the components shown in Table 4 below was prepared.
上記対照品のゴマ様基本調合香料組成物１０００ｇに３−メルカプト−２−ペンタノン１ｍｇ（１ｐｐｍ）を混合して、新規なゴマ様の調合香料組成物（本発明品９）を調製した。本発明品９と対照品の香気について、専門パネラー１０人により比較した。その結果、専門パネラー１０人の全員が本発明品９は、対照品に比べて、ゴマの煎りたて感、擂りたて感、油脂感、特に擂りたて感が格段に増強され、かつ持続性の点でも優れていると評価した。 1-mg (1 ppm) of 3-mercapto-2-pentanone was mixed with 1000 g of the sesame-like basic blended fragrance composition as a control product to prepare a novel sesame-like blended fragrance composition (Product 9 of the present invention). The aroma of the product 9 of the present invention and the control product were compared by 10 expert panelists. As a result, all 10 professional panelists showed that the product 9 of the present invention was greatly enhanced and sustained in the sense of freshly roasted, roasted, oily and faty, particularly freshly roasted, compared to the control product. It was evaluated that it was excellent in terms of sex.
また、３−メルカプト−２−ペンタノンに代えて４−メルカプト−３−ヘキサノンを同量加えて新規なゴマ様の調合香料組成物（本発明品１０）を調製し、上記と同様に評価した結果、本発明品１０は、対照品に比べて、ゴマの煎りたて感、擂りたて感が格段に増強され、かつ持続性の点でも優れていると評価した。 In addition, the same amount of 4-mercapto-3-hexanone was added instead of 3-mercapto-2-pentanone to prepare a novel sesame-like blended fragrance composition (product 10 of the present invention), and the results were evaluated in the same manner as described above. The product 10 of the present invention was evaluated to be significantly enhanced in the freshness and sensation of sesame seeds and superior in sustainability as compared with the control product.
実施例４：ゴマ風味ドレッシングへの賦香例
食酢２０ｇ、コーンサラダ油３８ｇ、ゴマ油２ｇ、市販練りゴマ１０ｇおよび水３０ｇを混合した分離型ドレッシング１００ｇとした中に、実施例３で得られたゴマ様調合香料組成物（本発明品９および本発明品１０）、並びにゴマ様基本調合香料組成物（対照品）をそれぞれ０．５ｇ配合して、それぞれのゴマ風味ドレッシングを作製した。それぞれのドレッシングについて、よく訓練された専門パネラー１０名にて香味の評価を行った。その結果、専門パネラー１０名全員が本発明品９および本発明品１０のゴマ様調合香料組成物を使用したものの方が対照品を使用したものに比べ、ゴマの煎りたて感、擂りたて感が格段に優れ、かつ香味の持続性もあると評価した。
Example 4: Perfume to sesame-flavored dressing Sesame-like obtained in Example 3 in a separate dressing of 100 g mixed with 20 g of vinegar, 38 g of corn salad oil, 2 g of sesame oil, 10 g of commercial kneaded sesame and 30 g of water. Each sesame-flavored dressing was prepared by blending 0.5 g each of the blended fragrance composition (present product 9 and present product 10) and the sesame-like basic blended fragrance composition (control product). Each dressing was evaluated for flavor by 10 well-trained professional panelists. As a result, all 10 professional panelists used the inventive product 9 and the inventive sesame-like fragrance composition of the inventive product 10 in comparison with the control product, making the sesame freshly roasted and roasted. It was evaluated that the feeling was remarkably excellent and the flavor was persistent.
Claims (3)
で表される化合物からなるゴマ様香味増強剤。 Following formula (1)
A sesame-like flavor enhancer comprising a compound represented by:
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