JP7026624B2 - アミド化合物の溶液及び分散液 - Google Patents
アミド化合物の溶液及び分散液 Download PDFInfo
- Publication number
- JP7026624B2 JP7026624B2 JP2018540379A JP2018540379A JP7026624B2 JP 7026624 B2 JP7026624 B2 JP 7026624B2 JP 2018540379 A JP2018540379 A JP 2018540379A JP 2018540379 A JP2018540379 A JP 2018540379A JP 7026624 B2 JP7026624 B2 JP 7026624B2
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- Prior art keywords
- compound
- water
- dimethoxyphenyl
- acrylamide
- soluble compound
- Prior art date
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- 239000006185 dispersion Substances 0.000 title claims description 14
- -1 Amide compound Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 23
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 21
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 16
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- 239000007962 solid dispersion Substances 0.000 claims description 11
- OPKGRQCLNIPVGV-YRNVUSSQSA-N (e)-3-(3,4-dimethoxyphenyl)-n-[2-(4-methoxyphenyl)ethyl]prop-2-enamide Chemical compound C1=CC(OC)=CC=C1CCNC(=O)\C=C\C1=CC=C(OC)C(OC)=C1 OPKGRQCLNIPVGV-YRNVUSSQSA-N 0.000 claims description 10
- 238000004090 dissolution Methods 0.000 claims description 10
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- 239000004471 Glycine Substances 0.000 claims description 8
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- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
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- 229920000642 polymer Polymers 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 4
- OMPIYDSYGYKWSG-UHFFFAOYSA-N Citronensaeure-alpha-aethylester Natural products CCOC(=O)CC(O)(C(O)=O)CC(O)=O OMPIYDSYGYKWSG-UHFFFAOYSA-N 0.000 claims description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
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- 239000001087 glyceryl triacetate Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
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- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
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Description
いくつかのフレーバー分子は、水に難溶性である。特に、特許出願番号PCT/EP2012/060641号(参照をもって本明細書に組み込まれたものとする)において記載されたアミドは、水に難溶性であり、可溶化し難い。したがって、これらの化合物の水中での溶解速度を高めるための手段を提供することが有利である。
本明細書では、難水溶性のフレーバー又は味覚修飾化合物の水中での溶解速度を高めるための方法であって、
a)前記化合物と易水溶性の第二の化合物とを水系溶液中で混合して、前記化合物の溶液又は分散液を形成すること、
b)前記溶液又は分散液を乾燥させて、前記化合物の固体分散液を形成すること、ここで、該化合物は、水のみで溶解又は分散させた場合の化合物と比較して、水中で高められた溶解速度を有する
を含む方法、が提供される。
要約書、明細書及び特許請求の範囲について、“又は”の使用は、特に明記されない限り“及び/又は”を意味する。同様に、“含む(comprise)”、“含む(comprises)”、“含んでいる(comprising)”、“含む(include)”、“含む(includes)”及び“含んでいる(including)”は、置き換えることができ、かつ制限することを意図しない。
- 出し汁
- 疎水性活性物質の取り込み、並びに水中での速い溶解及び高い活性濃度を要求する任意の食品及び飲料品用途
である。
- 調味料又は香辛料、例えば煮出し汁、風味付けキューブ(savory cube)、パウダーミックス、フレーバー付けしたオイル、ソース(例えば、レリッシュ、バーベキューソース、ドレッシング、グレービーソース又は甘い及び/又は酸味のあるソース)、サラダドレッシング又はマヨネーズ;
- 肉ベースの製品、例えば家禽、ビーフもしくはポークベースの製品、シーフード、すり身、又は魚肉ソーセージ;
- スープ、例えば澄ましスープ、クリームスープ、チキン又はビーフスープ、トマト又はアスパラガススープ;
- 炭水化物ベースの製品、例えばインスタント麺、米、パスタ、ポテトフレーク又はフライドポテト、麺、ピザ、トルティーヤ、ラップ;
- 乳製品または脂製品、例えばスプレッド、チーズ、普通のマーガリン、低脂肪マーガリン、バター/マーガリンブレンド、バター、ピーナッツバター、ショートニング、加工又は味付けチーズ;
- 風味付けした製品、例えばスナック、ビスケット(例えばチップスもしくはクリスプ)又は卵製品、ポテト/トルティーヤチップ、電子レンジ用ポップコーン、ナッツ、プレッツェル、餅、煎餅など;
- 模造品、例えば乳製品(例えば、油、脂肪及び増粘剤から製造された改良チーズ(reformed cheese))又はシーフード又は肉(例えば、ベジタリアンの肉の代用品、野菜バーガー)類似品;又は
- ペット又は動物の食品。
実施例1
本発明による(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミドとグリシンとの固体分散液の調製及び溶解動力学
(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミド1.8g及びグリシン1.8gを、エタノール及び水の混合物(50:50(w/w))116gと混合した。その分散液を、固体材料が完全に溶解するまで60℃まで加熱した。明澄透明な溶液を得た。その溶液を60℃で維持し、噴霧乾燥し、そして微細な白色の粉末を得た。固体分散液中で50%(w/w)の(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミドの配合量を、NMR分光法により確認した。
比較例
(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミド20mgを60℃で水1L中に分散させた。溶解プロセスは、78分後に標的濃度20ppmの50%(10ppm)をもたらした(実施例1と比較して50倍遅い)。標的濃度の95%(19ppm)は、6時間後でも達せられなかった。6時間後の溶解した(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミドの濃度は、15ppm(標的の75%)であった。
本発明による(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミドとベタインとの固体分散液の調製及び溶解動力学
(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミド1.8g及びベタイン1.8gを、エタノール及び水の混合物(50:50(w/w))116gと混合した。その分散液を、固体材料が完全に溶解するまで60℃まで加熱した。その溶液を60℃で維持し、噴霧乾燥し、そして微細な白色の粉末を得た。
熱水中での本発明による化合物の旨味効果の評価
(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミド20ppmを含む水溶液と、本発明による(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミドとグリシンとの固体分散液(50:50(w/w))40ppmを含む水溶液とを、それぞれ熱水中で製造した。その溶液を、5分後に盲検試験に基づいて4名の訓練されたパネリストに提示した。彼らは、旨味の味覚強度0~10でサンプルを評価するように求められた(0は旨味効果なしを示し、10は非常に強い旨味を示す)。本発明によるサンプルは、比較例サンプル(3.8)よりも高い旨味強度(5.0)で評価された。
冷水中での本発明による化合物の旨味効果の評価
(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミド20ppmを含む水溶液と、本発明による(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミドとグリシンとの固体分散液(50:50(w/w))40ppmを含む水溶液とを、それぞれ冷水(室温)中で製造した。その溶液を、5分後に盲検試験に基づいて4名の訓練されたパネリストに提示した。本発明によるサンプルは、比較例サンプル(2.5)よりも高い旨味強度(3.4)で評価された。
熱いチキンブイヨン中での本発明による化合物の旨味効果の評価
(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミド20ppmを含むチキンブイヨンと、本発明による(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミドとグリシンとの固体分散液(50:50(w/w))40ppmを含むチキンブイヨンとを、それぞれ製造した。そのブイヨンを、5分後に盲検試験に基づいて4名の訓練されたパネリストに提示した。本発明によるサンプルは、比較例サンプル(5.5)よりも高い旨味強度(6.5)で評価された。
Claims (13)
- フレーバー及び味覚修飾物質からなる群から選択される難水溶性化合物の水中での溶解速度を高めるための方法であって、
a. 前記難水溶性化合物と易水溶性の第二の化合物とを水系溶液中で混合して、前記難水溶性化合物の溶液又は分散液を形成すること、及び
b. 前記溶液又は分散液を噴霧乾燥させて、前記難水溶性化合物の固体分散液を形成すること、を含み、
ここで、
前記難水溶性化合物は、水のみで溶解させた場合の難水溶性化合物と比較して、水中で高められた溶解速度を有し、
前記難溶性化合物は、その立体異性体のいずれか1つ又はそれらの混合物の形での式(I):
前記第二の化合物が、グリシン、ベタイン又はそれらの混合物である、
前記方法。 - 実質的にポリマーの不在下で実施する、請求項1に記載の方法。
- 前記水系溶液が、プロピレングリコール、ベンジルアルコール、プロパノール、エタノール、トリアセチン及びクエン酸エチルからなる群から選択される揮発性水混和性溶媒を含む、請求項1または2に記載の方法。
- 前記水系溶液が、水エタノール混合物を含む、請求項1から3までのいずれか1項に記載の方法。
- 前記難溶性化合物と前記第二の化合物との割合が、質量で1:99~99:1である、請求項1から4までのいずれか1項に記載の方法。
- 前記難溶性化合物と前記第二の化合物との割合が、質量で1:19~約19:1である、請求項5に記載の方法。
- 前記難溶性化合物と前記第二の化合物との割合が、質量で1:10~約1:1である、請求項6に記載の方法。
- 前記難溶性化合物と前記第二の化合物との割合が、約1:1である、請求項7に記載の方法。
- 前記難溶性化合物が、(E)-3-(3,4-ジメトキシフェニル)-N-(4-メトキシフェネチル)アクリルアミド、(E)-3-(3,4-ジメトキシフェニル)-N-(3-メトキシフェネチル)アクリルアミド、(E)-3-(3,4-ジメトキシフェニル)-N-(3-エトキシフェネチル)アクリルアミド、(E)-3-(3,4-ジメトキシフェニル)-N-(3-プロポキシフェネチル)アクリルアミド、(E)-3-(3,4-ジメトキシフェニル)-N-(4-イソプロポキシフェネチル)アクリルアミド、(E)-3-(3,4-ジメトキシフェニル)-N-(4-エチルフェネチル)アクリルアミド、(E)-3-(3,4-ジメトキシフェニル)-N-(3,4-ジメチルフェネチル)アクリルアミド、(E)-3-(3,4-ジメトキシフェニル)-N-(4-イソプロピルフェネチル)アクリルアミド又は(E)-3-(3,4-ジメトキシフェニル)-N-(3-メチルフェネチル)アクリルアミドからなる群から選択される、請求項1から9までのいずれか1項に記載の方法。
- 前記溶液又は分散液を噴霧乾燥させて固体粒子を形成する、請求項1から10までのいずれか1項に記載の方法。
- 請求項1から11までのいずれか1項に記載の方法により製造されるか又は得られる粒子。
- 約60℃の温度で15ppm/分までの速度で溶解する、請求項12に記載の粒子。
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JP2005524635A (ja) | 2002-02-08 | 2005-08-18 | アボット ゲーエムベーハー ウント カンパニー カーゲー | 難溶性化合物から水分散性の乾燥粉末を生成するための製法 |
US20120308703A1 (en) | 2011-05-31 | 2012-12-06 | Symrise Ag | Cinnamamides as savory flavorings |
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