JP2021080326A - 香味付与剤としてのジエチル メルカプトサクシネート - Google Patents
香味付与剤としてのジエチル メルカプトサクシネート Download PDFInfo
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- JP2021080326A JP2021080326A JP2019206816A JP2019206816A JP2021080326A JP 2021080326 A JP2021080326 A JP 2021080326A JP 2019206816 A JP2019206816 A JP 2019206816A JP 2019206816 A JP2019206816 A JP 2019206816A JP 2021080326 A JP2021080326 A JP 2021080326A
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- flavor
- present
- fragrance
- control product
- diethyl mercaptosuccinate
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- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
[1] 下記式(1)で表されるジエチル メルカプトサクシネートからなる香味付与剤。
[3] [1]に記載の香味付与剤または[2]に記載の香料組成物を配合してなる消費財。
[4] [1]に記載の香味付与剤を香料組成物に配合することを含む、香料組成物の香味改善方法。
[5] [1]に記載の香味付与剤または[2]に記載の香料組成物を消費財に配合することを含む、消費財の香味改善方法。
本発明の香味付与剤は、下記式(1)で表されるジエチル メルカプトサクシネートからなることを特徴とする。
ジエチル メルカプトサクシネートは、当業者によってなし得る任意の方法で入手してよい。例えば、このジエチル メルカプトサクシネートは医薬品の合成中間体として知られており、例えば、殺虫剤として使用されるマラチオンの合成に関する文献を参照して合成することができる。文献の具体例としては、Chem.Res.Toxicol.,6,pp.718〜723(1993)に記載の方法によって合成することができる。
本発明の香料組成物は、ジエチル メルカプトサクシネートからなる香味付与剤を、有効成分として所定量含み、香味の付与を目的として、各種物品に配合することができるものである。具体例としては、飲食品用香料組成物(フレーバー組成物ともいう)、香粧品用香料組成物(フレグランス組成物ともいう)が挙げられる。配合対象となる物品の例としては、上述のように、飲食品、香粧品、医薬衛生品などの消費財が挙げられる。本発明の香料組成物の形態は特に限定されず、水溶性香料組成物、油溶性香料組成物、乳化香料組成物、粉末香料組成物が例示できる。
ジエチル メルカプトサクシネートからなる本発明の香味付与剤、およびそれを含む本発明の香料組成物は、各種物品またはそれに用いる香料組成物に配合して使用することができる。
300mL三口フラスコに対し、メルカプトこはく酸(15.0g、100mmol)および99%エタノール(100mL)を入れ、p−トルエンスルホン酸(0.19g、1mmol)を加えた後加熱還流下10時間撹拌した。反応液を加熱し溶媒を常圧回収後、そのまま減圧蒸留に付し(87−91℃/0.2kPa)、無色油状物質として目的物であるジエチル メルカプトサクシネートを得た(15.98g、77.2mmol、収率77%)。
1H−NMR(CDCl3,400MHz):δ4.19(q,2H,J=7.2Hz),4.13(q,2H,J=7.2Hz),3.71(dt,1H,J=6.0Hz,9.6Hz),2.97(dd,1H,J=16.8Hz,9.6Hz),2.73(dd,1H,J=16.8Hz,6.0Hz),2.17(d,1H,J=9.6Hz),1.27(t,3H,J=7.2Hz),1.23(t,3H,J=7.2Hz)
13C−NMR(CDCl3,100MHz):δ172.3,170.3,61.8,61.0,39.8,36.2,14.1,14.0.
MS(EI,70eV):m/z 206(8),161(37),160(85),133(58),132(100),104(28),87(36),86(14),61(15),29(24).
得られたジエチル メルカプトサクシネートの香りは、グレープフルーツ様、フルーティな香りであった。
下記表1の処方に従って、グレープフルーツエッセンス基本調合香料組成物を調製した。
(天然感に関する評価基準)
対照品に比べて大きく増加した 4
対照品に比べてある程度増加した 3
対照品に比べて若干増加した 2
対照品と同等である 1
グレープフルーツとは異質な香りがする 0
市販の果汁50%のマンゴージュースに、ジエチル メルカプトサクシネートを本発明の香味付与剤として下記表3の通り配合し、本発明のフルーツ飲料を調製した。そして、得られた本発明のフルーツ飲料について、15名のよく訓練されたパネラー(経験年数10年以上)による官能評価を行った。官能評価では、市販のマンゴージュースを対照品として、対照品と比べた本発明品の香味についてコメントさせるとともに、果肉感および熟成感について下記の基準に従って点数付けさせた。ここで果肉感とは、マンゴー果実そのものをまるごと食したような繊維感、甘さや果汁感を包含する感覚を意味し、熟成感とは、熟した果実のような甘くジューシーで濃厚な香味を意味するものとする。
(果肉感)
対照品に比べて大きく増加した 4
対照品に比べてある程度増加した 3
対照品に比べて若干増加した 2
対照品と同等である 1
マンゴーとは異質な香りがする 0
(熟成感)
対照品に比べて大きく増加した 4
対照品に比べてある程度増加した 3
対照品に比べて若干増加した 2
対照品と同等である 1
マンゴーとは異質な香りがする 0
市販の容器詰めブラックコーヒー、無糖紅茶、麦茶、ココアに、本発明の香味付与剤としてのジエチル メルカプトサクシネートを、それぞれ1ppm、0.01ppm、0.01ppm、0.1ppmの濃度となるように配合して、本発明の嗜好飲料を調製した。各市販品を対照品として、15名のよく訓練されたパネラー(経験年数10年以上)による官能評価を行った。官能評価では、対照品である各市販品と比べた本発明品の熟成感および嗜好度について下記の基準に従って点数付けさせた。ここでは、ボリューム感とは、香味の全体的な厚みや濃厚感が豊富で、好ましい感覚を意味する。嗜好度とは、対照品と比べた、その飲料を好ましいと感じられる度合いを意味する。
(評価基準)
対照品に比べて大きく増加した 4
対照品に比べてある程度増加した 3
対照品に比べて若干増加した 2
対照品と同等である 1
市販のビール風味飲料(ノンアルコール)を用意し、本発明の香味付与剤としてのジエチル メルカプトサクシネートを1ppmの濃度となるように配合して、本発明のビール風味飲料を調製した。市販のビール風味飲料を対照品として、対照品と比べた本発明のビール風味飲料の風味について、5名のよく訓練されたパネラー(経験年数10年以上)による官能評価を行った。その結果、5名のパネラー全員が、ビールの原料であるホップのようなさわやかな苦い香味がトップから増強され、麦汁感も増強して飲みごたえが増強されたと回答した。
市販のアーモンドバターに、本発明の香味付与剤としてのジエチル メルカプトサクシネートを、0.1ppmの濃度となるように配合して、本発明のナッツ風味調味料を調製した。また、比較対象として、香料化合物として知られているジイソペンチル チオマレート(FEMA4096)を市販のアーモンドバターに0.1ppmの濃度となるように配合し、比較品のナッツ風味調味料を調製した。市販品を対照品として、15名のよく訓練されたパネラー(経験年数10年以上)による官能評価を行った。官能評価では、対照品である市販品と比べた本発明品の香味についてコメントさせるとともに、市販品と比べた嗜好度について下記の基準に従って点数付けさせた。嗜好度とは、対照品と比べた、その飲料を好ましいと感じられる度合いを意味する。
(評価基準)
対照品に比べて大きく増加した 4
対照品に比べてある程度増加した 3
対照品に比べて若干増加した 2
対照品と同等である 1
市販のガーリック風味、オニオン風味、コショウ風味、バジル風味の各ドレッシングを用意し、そこに、本発明の香味付与剤としてのジエチル メルカプトサクシネートを、それぞれ0.01ppmの濃度となるように配合して、本発明の香味ドレッシングを調製した。市販品を対照品として、5名のよく訓練されたパネラー(経験年数10年以上)に、対照品である市販品と比べた本発明品の香味についてコメントさせた。その結果、ガーリック風味、オニオン風味、コショウ風味の各ドレッシングについては、5名のパネラー全員が、本発明の香味ドレッシングは対照品と比べてトップからガーリックの刺激感、オニオンの刺激感、コショウの刺激感が増すとともにコクが増強された回答し、バジル風味ドレッシングについては、バジル生葉独特の苦さとスパイシー感がトップから強く感じられコクが増強されたと回答した。
市販の赤ワインおよびウイスキーを用意し、本発明の香味付与剤としてのジエチル メルカプトサクシネートをそれぞれ0.1ppmの濃度となるようによく混合して配合し、本発明の赤ワイン飲料およびウイスキー飲料を調製した。各市販品を対照品として、対照品と比べた本発明の酒飲料の香味について、7名のよく訓練されたパネラー(経験年数10年以上)による官能評価を行った。その結果、7名のパネラー全員が、本発明の赤ワイン飲料については、対照品と比べ長年熟成を重ねたようなコクとフルーティさが増強されていたと回答し、本発明のウイスキー飲料については、樽で熟成したようなナッツ様のコクが増強されていたと回答した。
市販のレトルトのオニオンコンソメスープに、本発明の香味付与剤としてのジエチル メルカプトサクシネートを当該スープ全量に対し0.01ppm配合して、本発明のスープを調製した。そして、市販品のスープを対照品として、対照品と比べた香味について、よく訓練された経験年数10年以上の調香師5名に評価させた。その結果、5名のパネラー全員が、本発明のスープは対照品と比べて、コンソメ様の香ばしさやコクが増してコンソメが濃くなったように感じられ、加熱されたタマネギ様の甘さも増強されて食べ応えが増強されたと回答した。
市販のオレンジ調、ローズ調、ピーチ調の香りの各台所用洗剤に、本発明の香味付与剤としてのジエチル メルカプトサクシネートをそれぞれ当該洗剤全量に対し0.1ppm配合して、本発明の台所用洗剤を調製した。そして、市販の各精油を対照品として、対照品と比べた香気について、よく訓練された経験年数10年以上の調香師15名に評価させた。評価基準は、香りの天然感が増加したかどうかについて、以下の基準で点数付け、さらに香気についてコメントさせた。天然感とは、対照品の各香調に対応する天然素材そのもの(例えば、オレンジ果実、ローズ生花、ピーチ果実)を感じさせるような感覚を包含するものとする。調香師15名の平均的な結果を下記表6に示す。
(評価基準)
対照品に比べて大きく増加した 4
対照品に比べてある程度増加した 3
対照品に比べて若干増加した 2
対照品と同等である 1
対照品とは異質な香りがする、または対照品より好ましくない 0
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JPH05112523A (ja) * | 1991-02-25 | 1993-05-07 | Ciba Geigy Ag | ヘテロ原子含有パーフルオロアルキル末端ネオペンチルマーカプト−アルコールおよびそれから得られた組成物 |
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