JP2023122248A - Composition for enhancing taste of foods and beverages or improving persistence of the taste in mouth - Google Patents

Composition for enhancing taste of foods and beverages or improving persistence of the taste in mouth Download PDF

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JP2023122248A
JP2023122248A JP2022025842A JP2022025842A JP2023122248A JP 2023122248 A JP2023122248 A JP 2023122248A JP 2022025842 A JP2022025842 A JP 2022025842A JP 2022025842 A JP2022025842 A JP 2022025842A JP 2023122248 A JP2023122248 A JP 2023122248A
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taste
food
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彩子 樋爪
Ayako Hizume
徹哉 八木
Tetsuya Yagi
守紘 青▲柳▼
Morihiro Aoyanagi
達也 生貝
Tatsuya Ikegai
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House Foods Corp
House Foods Group Inc
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House Foods Group Inc
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Abstract

To provide a composition containing a novel active ingredient, suitable for enhancing a salty taste.SOLUTION: Using the chemical compound represented by formula (1) not only enhances a salty taste but enhances the whole flavor of foods and beverages and improves the persistence of such a flavor in the mouth. (In the formula, R is shown as below and is substituted with 1-3 hydroxyl groups. The asterisk represents the bonding site with a carbon chain on the ester bond side. The solid line and the dashed double line represent a single bond and a double bond, respectively).SELECTED DRAWING: None

Description

本発明は、完熟サンショウに由来する化合物を含む、飲食品の味を増感するための又は当該味の口中での持続性を向上するための組成物、及び、当該組成物を含む飲食品に関する。 The present invention provides a composition for enhancing the taste of food or drink or improving the persistence of the taste in the mouth, which contains a compound derived from fully-ripened Japanese pepper, and food or drink containing the composition. Regarding.

健康志向の高まりを受けて、生活習慣病の一因となり得る食塩の摂取量を減らすことが望まれている。一方で、食塩相当量の低い食品は味が物足りなく感じられるため、その塩味を増強するために、種々の研究が行われている。例えば、特許文献1には、サンショウ破砕物と、当該破砕物の辛み成分を食前の数分程度口腔内に残すための基材とを含み、所定量のサンショオールを含む、食前に用いる塩味増強剤が記載されている。また、特許文献2には、サンショウ抽出物及びフタライド類を有効成分として含有する、所定の飲食品の塩味増強剤が記載されている。そして、特許文献3には、サンショウ抽出物とアルキル基を有するスルフィド化合物とを含有する塩味増感用組成物が記載されている。 In response to growing health consciousness, it is desired to reduce the intake of salt, which may contribute to lifestyle-related diseases. On the other hand, since foods with a low salt equivalent content are perceived as having an unsatisfactory taste, various studies have been conducted to enhance the salty taste. For example, Patent Document 1 discloses a salty taste used before eating, which contains crushed Japanese pepper and a base material for leaving the pungent component of the crushed product in the oral cavity for several minutes before eating, and contains a predetermined amount of sanshool. Enhancers are described. In addition, Patent Document 2 describes a salty taste enhancer for predetermined foods and drinks containing a Japanese pepper extract and phthalides as active ingredients. Patent Document 3 describes a salty taste sensitizing composition containing a Japanese pepper extract and a sulfide compound having an alkyl group.

特許第5625089号公報Japanese Patent No. 5625089 特許第5733737号公報Japanese Patent No. 5733737 特開2020-142号公報Japanese Unexamined Patent Application Publication No. 2020-142

従来は、サンショウ抽出物中に含まれるサンショオール類が塩味増強作用又は塩味増感作用の有効成分の1つであると考えられていたが、他の有効成分については十分には研究されていなかった。そこで、本発明は、新規有効成分を含む、塩味増感に適した組成物を提供することを目的としている。 In the past, sanshools contained in Japanese pepper extract were thought to be one of the active ingredients for enhancing or sensitizing salty taste, but other active ingredients have not been sufficiently studied. I didn't. Accordingly, an object of the present invention is to provide a composition containing a novel active ingredient and suitable for salty taste sensitization.

本発明者らは、上記課題を解決すべく鋭意検討した結果、食品原料として通常使用されている果皮の色が緑色のサンショウ(未熟サンショウ)ではなく、果皮の色が赤色の完熟サンショウの水性抽出物中には、サンショオール類以外の塩味増感作用を有する有効成分が含まれていること、及び、当該有効成分は、飲食品の塩味に限られない全体的な味を増感させたり、飲食品の味の口中での持続性を向上させたりする作用も有していることを見出し、本発明を完成させた。すなわち、本発明は、以下に示す飲食品の味の増感用組成物、飲食品の味の口中での持続性を向上するための組成物、及び飲食品を提供するものである。
〔1〕式(1):

Figure 2023122248000001
(1)
(式中、
Rは、
Figure 2023122248000002
であって、かつ1~3個のヒドロキシ基で置換されており、
アスタリスクは、エステル結合側の炭素鎖との結合部を示し、
実線及び破線の二重線は、単結合又は二重結合を示している)
で表される化合物を含む、飲食品の味の増感用組成物。
〔2〕前記飲食品の味が、塩味、旨味、甘味、酸味、及び苦味からなる群から選択される1種以上を含む、前記〔1〕に記載の組成物。
〔3〕式(1):
Figure 2023122248000003
(1)
(式中、
Rは、
Figure 2023122248000004
であって、かつ1~3個のヒドロキシ基で置換されており、
アスタリスクは、エステル結合側の炭素鎖との結合部を示し、
実線及び破線の二重線は、単結合又は二重結合を示している)
で表される化合物を含む、飲食品の味の口中での持続性を向上するための組成物。
〔4〕Rが、
Figure 2023122248000005
である、前記〔1〕~〔3〕のいずれか1項に記載の組成物。
〔5〕前記式(1)で表される化合物が、完熟サンショウの抽出物として配合されている、前記〔1〕~〔4〕のいずれか1項に記載の組成物。
〔6〕前記〔1〕~〔5〕のいずれか1項に記載の組成物を含む飲食品。
〔7〕減塩食品であり、前記〔6〕に記載の飲食品。 As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that, instead of green peppers (unripe peppers) that are usually used as food raw materials, mature peppers with red skins are used. contains an active ingredient other than sanshools that has a salty taste sensitizing effect, and that the active ingredient sensitizes the overall taste of food and drink, not limited to the salty taste The inventors have also found that it has an effect of improving the taste of food and drink in the mouth, and have completed the present invention. That is, the present invention provides a composition for enhancing the taste of food and drink, a composition for improving the persistence of the taste of food and drink in the mouth, and food and drink described below.
[1] Formula (1):
Figure 2023122248000001
(1)
(In the formula,
R is
Figure 2023122248000002
and substituted with 1 to 3 hydroxy groups,
The asterisk indicates the bond with the carbon chain on the side of the ester bond,
Solid and dashed double lines indicate single or double bonds)
A composition for enhancing the taste of food and drink containing a compound represented by
[2] The composition according to [1] above, wherein the taste of the food or drink includes one or more selected from the group consisting of saltiness, umami, sweetness, sourness, and bitterness.
[3] Formula (1):
Figure 2023122248000003
(1)
(In the formula,
R is
Figure 2023122248000004
and substituted with 1 to 3 hydroxy groups,
The asterisk indicates the bond with the carbon chain on the side of the ester bond,
Solid and dashed double lines indicate single or double bonds)
A composition for improving the sustainability of the taste of food and drink in the mouth, comprising a compound represented by.
[4] R is
Figure 2023122248000005
The composition according to any one of [1] to [3] above.
[5] The composition according to any one of [1] to [4] above, wherein the compound represented by formula (1) is blended as an extract of fully ripened Japanese pepper.
[6] A food or drink containing the composition according to any one of [1] to [5].
[7] The food and drink according to [6], which is a low-salt food.

本発明に従えば、上記式(1)で表される化合物を使用することにより、飲食品の塩味だけでなく全体的な味を増感させたり、飲食品の味の口中での持続性を向上させたりすることができる。したがって、例えば、減塩食品をより美味しく食することができる。 According to the present invention, by using the compound represented by the above formula (1), not only the salty taste of food and drink but also the overall taste can be enhanced, and the taste of food and drink can be maintained in the mouth. can be improved. Therefore, for example, low-salt foods can be eaten more deliciously.

ビジュアルアナログスケール法(VAS法)による評価結果を示す。Evaluation results by the visual analog scale method (VAS method) are shown. 時間強度測定法(TI法)による評価結果を示す。Evaluation results by the time intensity measurement method (TI method) are shown. 完熟サンショウの水性抽出物のクロマトグラム(逆相系カラム使用)を示す。Fig. 2 shows a chromatogram (using a reversed-phase column) of an aqueous extract of fully ripened Japanese pepper. 完熟サンショウの水性抽出物のクロマトグラム(順相系カラム使用)を示す。Fig. 2 shows a chromatogram (using a normal phase column) of an aqueous extract of fully ripened Japanese pepper. リサイクル分取HPLCのクロマトグラムを示す。FIG. 2 shows a chromatogram of recycle preparative HPLC.

以下、本発明をさらに詳細に説明する。
本発明は、飲食品の味の増感用組成物に関している。本明細書に記載の「飲食品の味の増感」とは、飲食品を口腔中に入れたときに感じる味が、当該飲食品における呈味成分の量が変わらないにもかかわらず、より強く感じられるようになることをいう。すなわち、本発明の組成物を、対象の飲食品を口腔内に入れる前に又はそれと同時に摂食すると、当該飲食品の味をより強く感じることができる。なお、本明細書に記載の「飲食品の味」とは、飲食品が呈する味全体のことをいうが、個別の味であってもよい。すなわち、前記飲食品の味は、塩味、旨味、甘味、酸味、及び苦味からなる群から選択される1種以上を含んでもよい。
The present invention will now be described in more detail.
The present invention relates to a composition for taste sensitization of food and drink. The term “taste sensitization of a food or drink” as used herein means that the taste felt when a food or drink is put into the oral cavity is enhanced even though the amount of the taste-exhibiting component in the food or drink does not change. It means to be able to feel strongly. That is, when the composition of the present invention is ingested before or at the same time as the target food or drink is put into the oral cavity, the taste of the food or drink can be felt more strongly. In addition, although the "taste of food and drink" described in this specification refers to the overall taste exhibited by food and drink, it may be an individual taste. That is, the taste of the food or drink may include one or more selected from the group consisting of saltiness, umami, sweetness, sourness, and bitterness.

また、本発明は、飲食品の味の口中での持続性を向上するための組成物にも関している。本発明の組成物により飲食品の味の濃さの強度が高まり、その味が口中で長く持続するようになる。例えば、飲食品を口に入れたときに最初に感じる味(先味)に続いて感じる味(中味)と、その後の口中に残る味(後味)の強度が高まり、全体として口中での持続時間が長くなると考えられる。本発明の組成物を、対象の飲食品を口腔内に入れる前に又はそれと同時に摂食すると、当該飲食品の味を長く堪能することができる。 The present invention also relates to compositions for improving the palatability of food and drink in the mouth. The composition of the present invention enhances the intensity of the flavor of food and drink, and the flavor lasts longer in the mouth. For example, when you put a food or drink in your mouth, the first taste (first taste) followed by the second taste (middle taste) and the subsequent taste that remains in your mouth (aftertaste) increase in intensity, and the duration of the taste in your mouth as a whole increases. is considered to be longer. By ingesting the composition of the present invention before or at the same time as placing the target food or drink in the oral cavity, the taste of the food or drink can be enjoyed for a long time.

本発明の組成物は、飲食品の味の増感のための又は飲食品の味の口中での持続性の向上のための有効成分として、式(1):

Figure 2023122248000006
(1)
(式中、
Rは、
Figure 2023122248000007
であって、かつ1~3個のヒドロキシ基で置換されており、
アスタリスクは、エステル結合側の炭素鎖との結合部を示し、
実線及び破線の二重線は、単結合又は二重結合を示している)
で表される化合物を含んでいる。前記式(1)で表される化合物は、サンショオール類の作用として知られている舌の痛みやしびれを引き起こしにくいため、飲食品の味を増感するため又は飲食品の味の口中での持続性を向上するために有利に使用できる。ある態様では、Rは、
Figure 2023122248000008
であってもよい。より具体的には、前記式(1)で表される化合物は、
Figure 2023122248000009
であってもよい。 The composition of the present invention comprises the formula (1) as an active ingredient for enhancing the taste of food or drink or improving the sustainability of the taste of food or drink in the mouth:
Figure 2023122248000006
(1)
(In the formula,
R is
Figure 2023122248000007
and substituted with 1 to 3 hydroxy groups,
The asterisk indicates the bond with the carbon chain on the side of the ester bond,
Solid and dashed double lines indicate single or double bonds)
Contains a compound represented by The compound represented by the above formula (1) is less likely to cause pain and numbness of the tongue known as the action of sanshools, so it is used to enhance the taste of food and drink or improve the taste of food and drink in the mouth. It can be used advantageously to improve sustainability. In one aspect, R is
Figure 2023122248000008
may be More specifically, the compound represented by the formula (1) is
Figure 2023122248000009
may be

前記式(1)で表される化合物の含有量は、味の増感作用又は味の持続性向上作用が奏される限り特に制限されないが、例えば、本発明の組成物の全質量に対して約0.01~約100質量ppm(以下、単に「ppm」という。)であってもよく、好ましくは約0.1~約1ppmである。このような量で前記式(1)で表される化合物が含まれていると、味の増感作用及び味の持続性向上作用がより良好に発揮され、かつ本発明の組成物と同時又はこれと連続して摂取される飲食品の風味への影響を最小限にすることができる。 The content of the compound represented by the formula (1) is not particularly limited as long as the taste sensitizing action or the taste persistence improving action is exhibited. It may be about 0.01 to about 100 mass ppm (hereinafter simply referred to as "ppm"), preferably about 0.1 to about 1 ppm. When the compound represented by the formula (1) is contained in such an amount, the taste sensitization action and the taste persistence improvement action are exhibited more satisfactorily, and at the same time or with the composition of the present invention. It is possible to minimize the influence on the flavor of the food and drink ingested continuously.

前記式(1)で表される化合物は、完熟サンショウの抽出物、特に完熟サンショウの水性抽出物に含まれているものであり、当該抽出物から単離することができる。すなわち、ある態様では、前記式(1)で表される化合物は、完熟サンショウの抽出物(特に水性抽出物)として本発明の組成物に配合されている。換言すれば、本発明は、完熟サンショウの抽出物(特に水性抽出物)を含む、飲食品の味の増感用組成物又は飲食品の味の口中での持続性の向上のための組成物に関しているとも言える。本明細書に記載の「完熟サンショウ」とは、ミカン科サンショウ属の植物の実であって、果皮の色に赤みがかかるまで樹上で熟した実のことをいい、赤ザンショウなどと呼ばれることもある。前記ミカン科サンショウ属の植物としては、当技術分野で通常使用されるものを特に制限されることなく採用することができ、例えば、サンショウ(Zanthoxylum piperitum DC)、アサクラザンショウ(Z.piperitum DC.forma inerme Makino)及びそれから派生したとされるブドウサンショウ、ヤマアサクラザンショウ(Z.piperitum DC.forma brevispinosum Makino)、イヌザンショウ(Z.schinifolium)、並びに花椒(Z.bungeanum)などが例示され得る。 The compound represented by the formula (1) is contained in an extract of fully-ripened Japanese pepper, particularly an aqueous extract of fully-ripened Japanese pepper, and can be isolated from the extract. That is, in one aspect, the compound represented by the formula (1) is blended into the composition of the present invention as an extract (particularly an aqueous extract) of ripe Japanese pepper. In other words, the present invention provides a composition for enhancing the taste of food and drink, or a composition for improving the sustainability of the taste of food and drink in the mouth, containing an extract (particularly an aqueous extract) of fully ripened Japanese pepper. You could say it's about things. The term "ripe Japanese pepper" as used herein refers to fruits of plants belonging to the genus Zanthoxylum of the Rutaceae family, which are ripened on the tree until the color of the pericarp becomes reddish, such as red Japanese pepper. It is sometimes called As the plant belonging to the genus Zanthoxylum of the Rutaceae family, those commonly used in the art can be employed without particular limitation. DC. forma inerme Makino) and the grape-sansho (Z.piperitum DC.forma brevispinosum Makino), which is said to be derived from it, Z.schinifolium and Z.bungeanum. obtain.

前記水性抽出物は、前記完熟サンショウを、そのまま又は破砕・粉砕処理及び乾燥処理などを行った後に水性溶媒で抽出することにより調製することができる。その抽出手段としては、前記式(1)で表される化合物が抽出される限り特に限定されないが、例えば、溶媒抽出法、水蒸気蒸留抽出法、及び超臨界又は亜臨界抽出法などを採用してもよい。前記水性溶媒としては、特に限定されないが、例えば、水や、エタノール及びメタノールなどのアルコール類などを使用してもよく、これらの2種以上を混合して使用してもよい。ある態様では、前記水性抽出物は、完熟サンショウの水抽出物(特に熱水抽出物)及び/又は完熟サンショウのアルコール抽出物(特にエタノール抽出物)を含む。 The aqueous extract can be prepared by extracting the fully-ripened Japanese pepper with an aqueous solvent as it is or after performing crushing/pulverizing treatment, drying treatment, and the like. The extraction means is not particularly limited as long as the compound represented by the formula (1) can be extracted. For example, solvent extraction, steam distillation extraction, and supercritical or subcritical extraction can be employed. good too. Although the aqueous solvent is not particularly limited, for example, water, alcohols such as ethanol and methanol may be used, and two or more of these may be mixed and used. In one aspect, the aqueous extract comprises an aqueous extract (especially a hot water extract) of ripe Japanese pepper and/or an alcoholic extract (especially an ethanolic extract) of ripe Japanese pepper.

本発明の組成物により味が増感される飲食品又は口中での味の持続性が向上される飲食品は、特に限定されないが、当該飲食品が減塩食品であると、前記組成物による味の増感作用又は味の持続性向上作用をより強く感じることができる。なお、本明細書に記載の「減塩食品」とは、通常流通している一般的な態様と比較して塩分濃度が低い食品のことをいう。前記減塩食品の塩分濃度は、特に限定されないが、例えば、通常流通している一般的な態様と比較して食塩相当量で約25~約70質量%低くてもよい。 The food and drink whose taste is sensitized by the composition of the present invention or the food and drink whose taste persistence in the mouth is improved is not particularly limited, but if the food or drink is a low-salt food, The taste sensitization action or the taste persistence improvement action can be sensed more strongly. The term "reduced-salt food" as used herein refers to a food with a lower salt concentration than that of a general food that is normally distributed. The salt concentration of the low-salt food is not particularly limited, but may be, for example, about 25 to about 70 mass% lower in terms of sodium chloride equivalent than that of a general form that is normally distributed.

本発明の組成物の形状は、摂食可能なものである限り特に限定されないが、例えば、液体状、ゼリー状、ペースト状、粉末状、顆粒状、及びブロック状などであってもよい。具体的には、前記組成物は、お茶などの飲料、ゼリー、飴、ふりかけ、味噌汁、及び調味料などの形態であってもよい。前記組成物は、そのまま摂食してもいいし、味を強く感じたい飲食品中に配合してもよい。また、味を強く感じたい飲食品と一緒に摂食する他の飲食品中に配合して、これらを交互に摂食してもよい。 The shape of the composition of the present invention is not particularly limited as long as it is edible, and may be, for example, liquid, jelly, paste, powder, granules, blocks, and the like. Specifically, the composition may be in the form of beverages such as tea, jellies, candies, sprinkles, miso soup, seasonings, and the like. The composition may be ingested as it is, or may be blended into food or drink that is desired to have a strong taste. In addition, it may be blended in other foods and beverages to be ingested together with the foods and beverages desired to have a strong taste, and these may be ingested alternately.

別の態様では、本発明は、上述した本発明の組成物を含む飲食品にも関している。本発明の飲食品は、前記式(1)で表される化合物を含んでいるため、味の増感作用又は味の持続性向上作用により、たとえ味が薄い(例えば塩分濃度が低い)食品であったとしても、その味の強度を高め、口中での持続性を向上し、おいしく摂食することが可能となる。 In another aspect, the present invention also relates to a food or drink product comprising the composition of the present invention as described above. Since the food and drink of the present invention contain the compound represented by the formula (1), the taste sensitization action or the taste persistence improvement action can be obtained even if it is a food with a light taste (for example, a low salt concentration). Even if there is, it increases the strength of the taste, improves the persistence in the mouth, and makes it possible to eat deliciously.

本発明の組成物及び飲食品は、本発明の目的を損なわない限り、当技術分野で通常使用される任意の食品原料又は任意の添加剤をさらに含んでもいいし、味の増感又は味の持続性向上のために有効な他の添加剤をさらに含んでもよい。 The composition and food or drink of the present invention may further contain any food raw material or any additive commonly used in the art, as long as it does not impair the purpose of the present invention. Other additives effective for improving durability may be further included.

以下、実施例により本発明を具体的に説明するが、本発明の範囲はこれら実施例に限定されるものではない。 EXAMPLES The present invention will be specifically described below with reference to Examples, but the scope of the present invention is not limited to these Examples.

〔試験例1〕
完熟ブドウサンショウ(赤色)及び未熟ブドウサンショウ(緑色)の生の実(冷凍)を10gずつ用意し、常法によりそれぞれの熱水抽出物を100gずつ調製した。各熱水抽出物中のヒドロキシαサンショールの濃度を高速液体クロマトグラフィー(HPLC)で測定すると、完熟ブドウサンショウの熱水抽出物では34ppm、未熟ブドウサンショウの熱水抽出物では18ppmだった。これらの熱水抽出物を、ヒドロキシαサンショールの最終濃度が1.5ppmになるようにウーロン茶に添加し、このウーロン茶による味の増強効果を、9名のパネラーが評価した。すなわち、各パネラーは、いずれかの熱水抽出物を含むウーロン茶又はいずれも含まないウーロン茶(対照群)を1口(約20mL)摂取した後、塩分0.4%のかつおだしを摂取して、官能評価ソフトウェア(FIZZ、ver.2.51 c 02、BIOSYSTEMS社)により、「先味」、「味の厚み」、「後味の伸び」、「味の濃さ」、「水っぽさのなさ」、「満足度」、及び「おいしさ」をビジュアルアナログスケール法(VAS法)で評価した。また、「味の濃さ」については、同じ官能評価ソフトウェアにより時間強度測定法(TI法)でも評価した。
[Test Example 1]
10 g each of fresh (frozen) ripened grape (red) and immature (green) grapes were prepared, and 100 g of each hot water extract was prepared by a conventional method. The concentration of hydroxy alpha sanshols in each hot water extract was measured by high performance liquid chromatography (HPLC) and was 34 ppm in the hot water extract of ripe grape sansho and 18 ppm in the hot water extract of immature grape sansho. . These hot water extracts were added to oolong tea at a final concentration of 1.5 ppm of hydroxy α-sanshool, and the taste enhancement effect of this oolong tea was evaluated by a panel of nine people. That is, each panelist ingested one mouthful (about 20 mL) of oolong tea containing either hot water extract or none (control group), then ingested bonito stock with a salt content of 0.4%, Sensory evaluation software (FIZZ, ver.2.51 c 02, BIOSSYSTEMS) was used to evaluate "starting taste", "thickness of taste", "longevity of aftertaste", "strength of taste", and "absence of wateriness". , "satisfaction", and "deliciousness" were evaluated by the visual analog scale method (VAS method). In addition, the "strength of taste" was also evaluated by the time intensity measurement method (TI method) using the same sensory evaluation software.

なお、VAS法では、両端が短い縦線で閉じられている水平な直線をコンピューター画面上に表示し、その両端の基準を以下の表3のように設定して、パネラーの評価を直線上に縦線として記入した。そして、左端からパネラーが記入した縦線までの距離を計測し、それを線の全長で割った数値をスコアとして、ダネット検定を行った。

Figure 2023122248000010
In addition, in the VAS method, a horizontal straight line with both ends closed by short vertical lines is displayed on the computer screen, and the standards for both ends are set as shown in Table 3 below, and the panelists' evaluations are made on the straight line. Entered as a vertical line. Then, the distance from the left end to the vertical line drawn by the panelists was measured, and the numerical value obtained by dividing it by the total length of the line was used as a score, and Dunnett's test was performed.
Figure 2023122248000010

VAS法及びTI法による評価結果を図1及び図2にそれぞれ示す。図1に示されているように、塩分0.4%のかつおだしは、それだけでは塩分濃度が低いため、味は薄く感じられ、水っぽいものであったが、未熟サンショウの熱水抽出物を含むウーロン茶の事前摂取により、各評価項目のスコアはいずれも上昇した。そして、完熟サンショウの熱水抽出物を含むウーロン茶の事前摂取では、先味の項目を除いてさらに高いスコアを示した。特に「味の厚み」及び「後味の伸び」の向上は、塩分濃度が低い食品をおいしく摂取するために解決しなければいけない課題であり、それらが向上した結果として「味の濃さ」、「水っぽさのなさ」、「満足度」、及び「おいしさ」も向上したことから、完熟サンショウの熱水抽出物などの水性抽出物は、飲食品の味の増感に有用であり、特に減塩食品にける塩味増感のために適していることが分かった。 The evaluation results by the VAS method and the TI method are shown in FIGS. 1 and 2, respectively. As shown in FIG. 1, the bonito stock with a salt content of 0.4% by itself had a low salt concentration, so the taste was light and watery. Pre-ingestion of oolong tea containing oolong tea increased scores for each evaluation item. Pre-ingestion of oolong tea containing a hot water extract of fully ripened Japanese pepper showed even higher scores except for the item of taste. In particular, the improvement of "thickness of taste" and "strength of aftertaste" is a problem that must be solved in order to enjoy foods with a low salt concentration. Aqueous extracts such as hot-water extracts of fully-ripened Japanese pepper are useful for enhancing the taste of food and drink, since the lack of wateriness, satisfaction, and deliciousness were also improved. , was found to be particularly suitable for saltiness sensitization in low-salt foods.

また、図2に示されているように、サンショウの熱水抽出物を含まない対照のウーロン茶(実線)を事前摂取した場合と比較して、未熟サンショウの熱水抽出物を含むウーロン茶(破線)を事前摂取すると、味の濃さの強度が高くなり、かつ口中での味の持続時間が長くなったが、完熟サンショウの熱水抽出物を含むウーロン茶(一点破線)を事前摂取すると、口中での味の持続時間がさらに長くなった。すなわち、完熟サンショウの熱水抽出物などの水性抽出物は、味に対する感度を上げるだけでなく、口中での味の持続性も向上できることから、減塩食品の味の調整のために一層適していることが分かった。 In addition, as shown in FIG. 2, compared with the case of pre-ingestion of control oolong tea (solid line) without hot water extract of immature Japanese pepper, oolong tea containing hot water extract of immature Japanese pepper ( dashed line) increased the intensity of flavor and lengthened the duration of the taste in the mouth, whereas pre-dose of oolong tea containing hot water extract of ripe Japanese pepper (dashed line) , the duration of the taste in the mouth became longer. That is, aqueous extracts such as hot water extracts of fully ripened Japanese pepper not only increase taste sensitivity, but also improve the persistence of taste in the mouth, making them more suitable for adjusting the taste of low-salt foods. I found out that

〔試験例2〕
完熟ブドウサンショウの実(乾燥物)を用意し、5質量部の実から常法により100質量部の40%エタノール抽出物(ヒドロキシαサンショールの濃度は260ppm)を調製した。このエタノール抽出物を、以下の条件の官能評価用中圧分取クロマトグラフィーによってフラクション1~5(図3のFr.1~Fr.5)を分取した。
カラム:ODSカラム(ODS-SM-50C、山善社製)
移動相:水/メタノール(表4参照)
流速:30mL/分
温度:30℃
検出波長:270nm

Figure 2023122248000011
[Test Example 2]
Ripe grape sansho fruits (dry matter) were prepared, and 100 parts by weight of a 40% ethanol extract (hydroxy α-sanshool concentration: 260 ppm) was prepared from 5 parts by weight of the fruits by a conventional method. Fractions 1 to 5 (Fr.1 to Fr.5 in FIG. 3) were separated from this ethanol extract by medium pressure preparative chromatography for sensory evaluation under the following conditions.
Column: ODS column (ODS-SM-50C, manufactured by Yamazen Co., Ltd.)
Mobile phase: water/methanol (see Table 4)
Flow rate: 30 mL/min Temperature: 30°C
Detection wavelength: 270 nm
Figure 2023122248000011

標準物質を用いたHPLC分析により、フラクション3にはヒドロキシαサンショールが含まれており、フラクション4にはαサンショールが含まれていることが分かった。各フラクションの溶媒をエバポレーターで蒸発乾固し、回収した乾固物の量を測定した(表5)。そして、フラクション3の乾固物が全量ヒドロキシαサンショールであるとみなし、その1mgを1mLの60%エタノールに溶解(1000ppm)し、これを最終濃度が1.0ppmになるように水で希釈した。他のフラクションについても同様に操作し、最終的な希釈率がフラクション3と同じになるように、すなわち各乾固物の回収量の比が水溶液中の溶解量の比と一致するように、それぞれの水溶液を作製した。

Figure 2023122248000012
HPLC analysis using standards showed that fraction 3 contained hydroxy alpha sanshols and fraction 4 contained alpha sanshols. The solvent in each fraction was evaporated to dryness using an evaporator, and the amount of recovered dry matter was measured (Table 5). Then, the dry matter of fraction 3 was considered to be the total amount of hydroxy α-sanshool, and 1 mg thereof was dissolved in 1 mL of 60% ethanol (1000 ppm) and diluted with water to a final concentration of 1.0 ppm. . The other fractions were treated in the same manner so that the final dilution rate was the same as that of fraction 3, that is, the ratio of the recovered amount of each dry matter was the same as the ratio of the dissolved amount in the aqueous solution. was prepared.
Figure 2023122248000012

各フラクションの水溶液を一口(約20mL)摂取した後に、塩分0.7%の味噌汁を飲み、味噌汁の先味、中味、及び後味のどこを強く感じるかを4人のパネラーが評価した。結果を表4に示す。

Figure 2023122248000013
After taking a mouthful (about 20 mL) of the aqueous solution of each fraction, they drank miso soup with a salt content of 0.7%, and four panelists evaluated which of the initial taste, middle taste, and aftertaste of miso soup they felt strongly. Table 4 shows the results.
Figure 2023122248000013

フラクション3、フラクション4、又はフラクション5を摂取した後に味噌汁を飲むと、味噌汁の先味が強くなったと感じたパネラーが多かったが、フラクション2を摂取した後に味噌汁を飲むと、味噌汁の後味が強くなったと感じたパネラーが多かった。フラクション3に含まれているヒドロキシαサンショール及びフラクション4に含まれているαサンショールは、未熟サンショウの水性抽出物にも含まれ得るものであるが、フラクション2には含まれていない。したがって、味の濃さを高め口中での味の持続性を向上する完熟サンショウに特有の効果を奏する成分は、フラクション2に含まれている可能性がある。 Many panelists felt that the aftertaste of miso soup became stronger when they drank miso soup after ingesting fraction 3, fraction 4, or fraction 5, but the aftertaste of miso soup became stronger when they drank miso soup after ingesting fraction 2. There were many panelists who felt that it had become. The hydroxy alpha sanshols contained in fraction 3 and the alpha sanshols contained in fraction 4, which may also be present in the aqueous extract of immature sansho, are not present in fraction 2. Therefore, it is possible that fraction 2 contains components that have the unique effect of fully ripened Japanese pepper, which enhances the strength of the taste and improves the persistence of the taste in the mouth.

〔試験例3〕
完熟ブドウサンショウの実及び未熟ブドウサンショウの実(乾燥物)を用意し、5質量部の実から常法により100質量部の40%エタノール抽出物をそれぞれ調製した。試験例2と同様の方法で官能評価用中圧分取クロマトグラフィーのフラクション2の水溶液を調製し、その濃度をヒドロキシαサンショール相当量で1.0ppm(フラクション2の乾固物に基づくと0.2ppm)になるように調整した(表5)。

Figure 2023122248000014
[Test Example 3]
Ripe grape-sansho fruits and unripe grape-sansho fruits (dry matter) were prepared, and 100 parts by weight of a 40% ethanol extract was prepared from 5 parts by weight of the fruits by a conventional method. An aqueous solution of fraction 2 for medium pressure preparative chromatography for sensory evaluation was prepared in the same manner as in Test Example 2, and its concentration was adjusted to 1.0 ppm (0 based on the dry matter of fraction 2) in terms of hydroxy α-sanshool equivalent. .2 ppm) (Table 5).
Figure 2023122248000014

各溶液を一口(約20mL)摂取した後に、塩分0.7%の味噌汁を飲み、味噌汁の先味、中味、及び後味のどこを強く感じるかを3人のパネラーが評価した。その結果、3人のパネラー全員が、未熟サンショウのフラクション2は味噌汁の味に影響を与えなかったが、完熟サンショウのフラクション2を摂取すると味噌汁の塩味が増強され、後味が強く感じられたと回答した。したがって、塩味を増強し、口中の味を持続させる効果は、完熟サンショウに特有のものである。 After taking a mouthful (about 20 mL) of each solution, they drank miso soup with a salt content of 0.7%, and three panelists evaluated which of the initial taste, middle taste, and aftertaste of miso soup they felt strongly. As a result, all three panelists said that the immature pepper fraction 2 had no effect on the taste of the miso soup, but that the ingestion of the ripe pepper fraction 2 enhanced the saltiness of the miso soup and left a strong aftertaste. I answered. Therefore, the effect of enhancing the salty taste and sustaining the taste in the mouth is unique to fully ripened Japanese pepper.

〔試験例6〕
完熟サンショウの65%エタノール抽出物(「国産サンショウeエキス」、日本粉末薬品株式会社製)をロータリーエバポレーター(日本ビュッヒ社製)で乾固し、得られた乾固物に100%メタノールを添加した。この溶液を、順相系カラムを使用した以下の条件の中圧分取クロマトグラフィーによって分画し、試験例2(逆相系カラムを使用した試験系)のフラクション2に相当する保持時間22~25分のフラクション(図4の枠囲い部分)を分取して、これをロータリーエバポレーターで乾固した。完熟サンショウ5g(乾燥物換算)から64.6mgの最終乾固物を取得した。
使用装置:中圧分取液体クロマトグラフYFLC W-Prep 2XY(山善株式会社製)
カラム:Si-40D
カラムサイズ:50×300mm
移動相:クロロホルム/メタノール(表2参照)
流速:45mL/分
温度:25℃
検出波長:254nm
分画モード:タイム

Figure 2023122248000015
[Test Example 6]
A 65% ethanol extract of fully ripe Japanese pepper (“domestic Japanese pepper e extract”, manufactured by Nippon Powder Chemical Co., Ltd.) was dried with a rotary evaporator (manufactured by Nippon Buchi Co., Ltd.), and 100% methanol was added to the obtained dried product. added. This solution was fractionated by medium pressure preparative chromatography using a normal phase column under the following conditions, and the retention time corresponding to fraction 2 in Test Example 2 (test system using a reversed phase column) was 22 to A 25 minute fraction (boxed portion in FIG. 4) was taken and dried on a rotary evaporator. 64.6 mg of final dried matter was obtained from 5 g of fully-ripened Japanese pepper (converted to dry matter).
Apparatus used: Medium-pressure preparative liquid chromatograph YFLC W-Prep 2XY (manufactured by Yamazen Co., Ltd.)
Column: Si-40D
Column size: 50 x 300 mm
Mobile phase: chloroform/methanol (see Table 2)
Flow rate: 45 mL/min Temperature: 25°C
Detection wavelength: 254 nm
Fraction Mode: Time
Figure 2023122248000015

分取したフラクションの乾固物を3mLの100%メタノールに溶解し、この溶液を、以下の条件のリサイクル分取クロマトグラフィーにアプライした。そして、1回目の分離工程で保持時間23分~26分に検出された重なったピーク(図5の枠囲い部分)についてのみ、以降のリサイクル分離工程を繰り返した。合計7回目の分離工程で分離されたピーク(図5のピーク1~3)をそれぞれ分取し、ロータリーエバポレーターで乾固した。ピーク1~3の収量は、それぞれ3.2mg、2.0mg、及び1.1mgだった。
使用装置:LC-9110(日本分析工業社製)
カラム:Inertsil(R)ODS-3(ジーエルサイエンス社製)
カラムサイズ:20×250mm
粒子径:5μm
移動相:60%メタノール
流速:5mL/分
温度:25℃
検出波長:200nm
The fractionated dried product was dissolved in 3 mL of 100% methanol, and this solution was applied to recycle preparative chromatography under the following conditions. Then, the subsequent recycling separation step was repeated only for the overlapped peaks (the framed portion in FIG. 5) detected at the retention time of 23 minutes to 26 minutes in the first separation step. The peaks (peaks 1 to 3 in FIG. 5) separated in a total of 7 separation steps were fractionated and dried with a rotary evaporator. Yields for peaks 1-3 were 3.2 mg, 2.0 mg, and 1.1 mg, respectively.
Apparatus used: LC-9110 (manufactured by Nippon Analytical Industry Co., Ltd.)
Column: Inertsil (R) ODS-3 (manufactured by GL Sciences)
Column size: 20 x 250 mm
Particle size: 5 μm
Mobile phase: 60% methanol Flow rate: 5 mL/min Temperature: 25°C
Detection wavelength: 200 nm

〔試験例4〕
単離したピーク1~3の化合物を、終濃度が0.1ppmになるようにそれぞれ水に溶解した。化合物1~3のいずれかを含む水又は対照の単なる水を1口(約20mL)摂取した後、塩分0.4%のかつおだし汁を摂取して、対照に対する塩味の増強効果の有無を4名のパネラーが評価した。結果を表7に示す。
[Test Example 4]
The isolated compounds of peaks 1 to 3 were each dissolved in water to a final concentration of 0.1 ppm. After ingesting one mouthful (about 20 mL) of water containing any of compounds 1 to 3 or plain water as a control, 0.4% salt content of bonito broth was ingested, and the presence or absence of a salty taste enhancing effect on the control was evaluated by 4 people. of panelists evaluated. Table 7 shows the results.

Figure 2023122248000016
Figure 2023122248000016

どのパネラーも、化合物1の摂取後に塩味の増強を感じ、他の化合物の摂取後には塩味の増強は感じなかった。したがって、飲食品の味の増感作用を奏する完熟サンショウの水性抽出物中の有効成分は、化合物1であることが示された。 None of the panelists felt an enhancement of salty taste after ingestion of compound 1 and no enhancement of salty taste after ingestion of the other compounds. Therefore, it was shown that compound 1 was the active ingredient in the aqueous extract of fully ripened Japanese pepper that sensitized the taste of food and drink.

〔試験例5〕
3名のパネラーが、対照の単なる水を1口(約20mL)摂取した後、以下の評価対象品を摂取した。
塩味及び旨味評価用:塩分0.4%のかつおだし汁
甘味及び酸味評価用:オレンジジュース(ポンジュース、えひめ飲料社製)
苦味評価用:インスタントコーヒー(ネスカフェゴールドブレンド、ネスレ社製;製品の説明に従ってコーヒーを調製)
[Test Example 5]
Three panelists ingested one mouthful (approximately 20 mL) of plain water as a control, and then ingested the following items to be evaluated.
For evaluation of saltiness and umami: Bonito soup stock with a salt content of 0.4% For evaluation of sweetness and sourness: Orange juice (Pon juice, manufactured by Ehime Beverage Co., Ltd.)
For bitterness evaluation: Instant coffee (Nescafe Gold Blend, Nestle; prepare coffee according to product instructions)

水で口をゆすぎ、化合物1を1ppm含む水を1口(約20mL)摂取した後、同じ評価対象品を摂取し、塩味、旨味、甘味、酸味、及び苦味についての強度と持続性を、次の基準で評価した。結果を表8に示す。
(強度)
++:対照を摂取した後より非常に強く味を感じる
+:対照を摂取した後より強く味を感じる
-:対照を摂取した後と変わらない
(持続性)
++:対照を摂取した後より非常に長く味を感じる
+:対照を摂取した後より長く味を感じる
-:対照を摂取した後と変わらない
After rinsing the mouth with water and ingesting one mouthful (approximately 20 mL) of water containing 1 ppm of Compound 1, the same evaluation product was ingested, and the strength and persistence of salty, umami, sweet, sour, and bitter tastes were evaluated as follows. was evaluated according to the criteria of Table 8 shows the results.
(Strength)
++: The taste is felt much stronger after ingesting the control +: The taste is felt stronger after ingesting the control -: No change from after ingesting the control (persistence)
++: Tastes much longer after ingesting control +: Tastes longer than after ingesting control -: Same as after ingesting control

Figure 2023122248000017
Figure 2023122248000017

塩味、旨味、甘味、酸味、及び苦味のいずれについても、味の増感作用及び持続性向上作用が過半数のパネラーで確認された。特に、塩味及び旨味の増感作用、並びに、塩味、旨味、及び苦味の持続性向上作用は、他の味における作用よりも顕著だった。 A majority of the panelists confirmed the taste sensitization action and persistency improvement action for all of salty, umami, sweet, sour, and bitter tastes. In particular, the effect of sensitizing salty taste and umami taste and the effect of improving sustainability of salty taste, umami taste and bitterness were more remarkable than the effects of other tastes.

〔試験例6〕
化合物1をメタノールに溶解し、液体クロマトグラフィー質量分析機(LC/MS)で分析したところ、1種の化合物が単離されていること、及び、当該化合物の分子式がC12224であり、分子量が230.30であることが分かった。なお、この化合物は、試験例2のフラクション2においても検出された。
[Test Example 6]
When compound 1 was dissolved in methanol and analyzed by liquid chromatography mass spectrometry (LC/MS), one compound was isolated and the molecular formula of the compound was C12H22O4 . and the molecular weight was found to be 230.30. This compound was also detected in Fraction 2 of Test Example 2.

また、3mgの化合物1をD4-メタノール500μLに溶解し、NMRにて1H-NMR、13C-NMR、COSY、HMQC、及びHMBCの測定を行った。その結果、化合物1は以下の構造を有することが分かった。

Figure 2023122248000018
1H NMR (500MHz, METHANOL-D3) Shift = 5.41 - 5.37 (m, 1H), 4.59 (d, J=7.4 Hz, 2H), 3.23 (dd, J=1.7, 10.9 Hz, 1H), 2.36 - 2.28 (m, 1H), 2.11 - 2.05 (m, 1H), 2.01 (s, 3H), 1.77 - 1.73 (m, 1H), 1.73 (s, 3H) 1.42 - 1.34 (m, 1H), 1.17 (s, 3H), 1.12 (s, 3H)
13C NMR (500MHz, METHANOL-D3) Shift = 171.6, 142.1, 118.5, 77.5, 72.4, 61.0, 36.4, 29.0, 24.5, 23.4, 19.5, 15.1 Also, 3 mg of compound 1 was dissolved in 500 μL of D4-methanol, and 1H-NMR, 13C-NMR, COZY, HMQC, and HMBC measurements were performed by NMR. As a result, compound 1 was found to have the following structure.
Figure 2023122248000018
1H NMR (500MHz, METHANOL-D3) Shift = 5.41 - 5.37 (m, 1H), 4.59 (d, J=7.4 Hz, 2H), 3.23 (dd, J=1.7, 10.9 Hz, 1H), 2.36 - 2.28 ( m, 1H), 2.11 - 2.05 (m, 1H), 2.01 (s, 3H), 1.77 - 1.73 (m, 1H), 1.73 (s, 3H) 1.42 - 1.34 (m, 1H), 1.17 (s, 3H) ), 1.12 (s, 3H)
13C NMR (500MHz, METHANOL-D3) Shift = 171.6, 142.1, 118.5, 77.5, 72.4, 61.0, 36.4, 29.0, 24.5, 23.4, 19.5, 15.1

以上より、上記式(1)で表される化合物を使用することにより、飲食品の塩味だけでなく全体的な味を増感させたり、飲食品の味の口中での持続性を向上させたりできることが分かった。したがって、例えば、減塩食品をより美味しく食することができる。 As described above, by using the compound represented by the above formula (1), not only the salty taste of food and drink but also the overall taste can be sensitized, and the sustainability of the taste of food and drink in the mouth can be improved. I found it possible. Therefore, for example, low-salt foods can be eaten more deliciously.

Claims (7)

式(1):
Figure 2023122248000019
(1)
(式中、
Rは、
Figure 2023122248000020
であって、かつ1~3個のヒドロキシ基で置換されており、
アスタリスクは、エステル結合側の炭素鎖との結合部を示し、
実線及び破線の二重線は、単結合又は二重結合を示している)
で表される化合物を含む、飲食品の味の増感用組成物。
Formula (1):
Figure 2023122248000019
(1)
(In the formula,
R is
Figure 2023122248000020
and substituted with 1 to 3 hydroxy groups,
The asterisk indicates the bond with the carbon chain on the side of the ester bond,
Solid and dashed double lines indicate single or double bonds)
A composition for enhancing the taste of food and drink containing a compound represented by
前記飲食品の味が、塩味、旨味、甘味、酸味、及び苦味からなる群から選択される1種以上を含む、請求項1に記載の組成物。 2. The composition according to claim 1, wherein the taste of said food or drink includes one or more selected from the group consisting of saltiness, umami, sweetness, sourness and bitterness. 式(1):
Figure 2023122248000021
(1)
(式中、
Rは、
Figure 2023122248000022
であって、かつ1~3個のヒドロキシ基で置換されており、
アスタリスクは、エステル結合側の炭素鎖との結合部を示し、
実線及び破線の二重線は、単結合又は二重結合を示している)
で表される化合物を含む、飲食品の味の口中での持続性を向上するための組成物。
Formula (1):
Figure 2023122248000021
(1)
(In the formula,
R is
Figure 2023122248000022
and substituted with 1 to 3 hydroxy groups,
The asterisk indicates the bond with the carbon chain on the side of the ester bond,
Solid and dashed double lines indicate single or double bonds)
A composition for improving the sustainability of the taste of food and drink in the mouth, comprising a compound represented by.
Rが、
Figure 2023122248000023
である、請求項1~3のいずれか1項に記載の組成物。
R is
Figure 2023122248000023
The composition according to any one of claims 1 to 3, which is
前記式(1)で表される化合物が、完熟サンショウの抽出物として配合されている、請求項1~4のいずれか1項に記載の組成物。 The composition according to any one of claims 1 to 4, wherein the compound represented by formula (1) is formulated as an extract of fully ripened Japanese pepper. 請求項1~5のいずれか1項に記載の組成物を含む飲食品。 Food and drink containing the composition according to any one of claims 1 to 5. 減塩食品であり、請求項6に記載の飲食品。 The food or drink according to claim 6, which is a low-salt food.
JP2022025842A 2022-02-22 2022-02-22 Composition for enhancing taste of foods and beverages or improving persistence of the taste in mouth Pending JP2023122248A (en)

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