JP6534740B2 - アセトアルデヒド前駆体 - Google Patents
アセトアルデヒド前駆体 Download PDFInfo
- Publication number
- JP6534740B2 JP6534740B2 JP2017528580A JP2017528580A JP6534740B2 JP 6534740 B2 JP6534740 B2 JP 6534740B2 JP 2017528580 A JP2017528580 A JP 2017528580A JP 2017528580 A JP2017528580 A JP 2017528580A JP 6534740 B2 JP6534740 B2 JP 6534740B2
- Authority
- JP
- Japan
- Prior art keywords
- flavor
- acetaldehyde
- vinyltetrahydrofuran
- ethoxyethoxy
- propan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
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- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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Description
アセトアルデヒドは重要であるが、フレーバー成分をカプセル化することが依然として困難である。アセトアルデヒドは幅広い種類のフレーバーに使用されているが、特に、フレッシュさ及びジューシーさという重要な側面をフレーバーに付与するフルーツフレーバーにおいてその価値が認められている。また、アセトアルデヒドが揮発性であることによって、フレーバーの嗅覚的刺激に対して大いに寄与するアロマの増加が提供される。したがって、アセトアルデヒドの使用は、飲料などこれらの効果が望まれるフレーバーを生じるために不可欠である。しかしながら、沸点が20〜21℃であることから、取り扱い中に蒸発することにより使用するのが難しい材料であり、このことはまた、作業員の過度の暴露及び火災のリスクにより、安全でない状況が起こり得る。液体フレーバー中にこれを組み込む場合、蒸発によるアセトアルデヒドの損失は依然として問題であり、かかるフレーバーの取り扱いをも困難にする。高揮発性であるだけでなく、アセトアルデヒドは非常に反応性のある化学物質である。アセトアルデヒドは、フレーバー配合物中でアルコール類と反応し、アセタールを形成し得る。アセトアルデヒドは、アルドール縮合反応に関与し得る。アセトアルデヒドは容易に酸化する。また、アセトアルデヒドは三量体化して、パラアルデヒドを形成し得る。これらの化学反応によってアセトアルデヒドを失うだけでなく、形成される生成物によって、フレーバーの特性が変化する恐れがあり、最悪の場合には望ましくない異臭がもたらされかねない。
i)5−(2−(1−エトキシエトキシ)プロパン−2−イル)−2−メチル−2−ビニルテトラヒドロフラン、
ii)フレーバーキャリヤー及びフレーバーベースから成る群より選択される少なくとも1種の成分、並びに
iii)任意で少なくとも1種のフレーバー補助剤
を含有する、フレーバー若しくはアロマを改質する組成物が提供される。
本明細書で「フレーバーキャリヤー」とは、フレーバリング成分の官能特性を著しく変更しない限り、フレーバーの観点から実質的に中立である材料を意味する。前記キャリヤーは、液体又は固体であってよい。
実施例1
5−(2−(1−エトキシエトキシ)プロパン−2−イル)−2−メチル−2−ビニルテトラヒドロフランの合成
リナリルオキシド(CAS#1365−19−1)(59mmol)、ジエチルエーテル(50mL)、及びp−トルエンスルホン酸(0.06mmol)の混合物を5℃に冷却した。ジエチルエーテル(50mL)中に溶解させたエチルビニルエーテル(88mmol)を30分にわたり滴加し、そしてその混合物を室温で12時間攪拌した。5グラムの炭酸ナトリウムを添加し、混合物を濾過した。ロータリーエバポレータを用いてその生成物を濃縮し、クーゲルロール蒸留(70〜80℃、40mTorr)により精製して、5.19g(収率37%)の生成物を無色の油状物(4種のジアステレオマーの等モル混合物)として得た。
1H NMR (CDCl3, 400 MHz): δ 1.15-1.31 (m, 15H), 1.63-1.76 (m, 1H), 1.79-1.97 (m, 3H), 3.43-3.61 (m, 2H), 3.82-3.94 (m, 1H), 4.94-5.07 (m, 2H), 5.14-5.22 (m, 1H), 5.81-6.00 (overlapping dd, 1H).
MS (EI): 242 (M+, 0), 169 (2), 153 (38), 111 (46), 93 (27), 85 (18), 81 (24), 73 (100), 71 (31), 45 (39), 43 (47).
比較用試料1の合成:1−エトキシエチルアセテート
ジエチルエーテル(50mL)、氷酢酸(10g、167mmol)、及びpTSA(0.01g)を一緒にし、その混合物を氷浴中で冷却した。ジエチルエーテル50mL中でのエチルビニルエーテル(18g、250mmol)を、15分にわたり滴加した。その混合物を冷浴から取り出し、室温で2時間攪拌した。炭酸ナトリウム(5g)を添加し、そして混合物を濾過した。ジエチルエーテルを大気圧で分留により除去した。残留物の分留によって、17.7g(34〜35℃、19mbar)の1−エトキシエチルアセテート(134mmol、収率80%)が得られた。
1H NMR (CDCl3, 400 MHz): δ 1.21 (t, J=7.1 Hz, 3H), 1.40 (d, J=5.2 Hz, 3H), 2.07 (s, 3H), 3.49-3.77 (m, 2H), 5.93 (q, J=5.2 Hz, 1H).
MS (EI): 132 (M+, 0), 131 (<1), 117 (3), 89 (5), 87 (12), 73 (55), 45 (61), 43 (100).
pH3.0での加水分解速度の評価
インスタント飲料の適用は、迅速にアセトアルデヒドを放出するために、前駆体分子の迅速な加水分解を要求する。かかる飲料は調製直後に消費され得るため、放出は可能な限り迅速であることが望ましい。
噴霧乾燥のフィード条件下での加水分解速度の評価
乾燥した粉末への付与に適したアセトアルデヒド前駆体は、様々なプロセスの段階中に著しい程度のアセトアルデヒドの放出を回避する必要がある。特に、アセトアルデヒド前駆体は、噴霧乾燥するフィードエマルションの調製の間に加水分解に対して抵抗性がなければならず、この噴霧乾燥するフィードエマルションは塩基性のpHに対して中立であってよく、また著しい体積分率の油相を含有してよい。
噴霧乾燥した粉末の製造
表3に従って、噴霧乾燥するフィードエマルションを調製した。前駆体分子の量は、化学量論に基づいてアセトアルデヒドが0.25g製造されるように選択した。実施例1の液体をオレンジフレーバー中に溶解させた。この混合物を、塩、マルトデキストリン、水、及びサポニンの溶液に添加し、ホモジナイザー(T25 UltraTurrax、IKA Works社、アメリカ合衆国在)を用いて2分間混合した。その後、入口空気温度を138℃、出口空気温度を95℃に設定して調製物を噴霧乾燥させた(model 190 Mini−Spray Drier、Buchi Corporation、アメリカ合衆国、ニューキャッスル(デラウェア州)在)。
インスタント飲料の調製及び評価
0.1gの前記調製物をクエン酸0.07g、スクロース7gと一緒にし、この混合物を100mLの蒸留水に溶解させることによって、噴霧乾燥調製物A及びBを再構成した。これらの飲料を迅速に調製し、5人のパネリストに試飲させた。噴霧乾燥物Aの試料は、噴霧乾燥物Bから調製された飲料よりもフレッシュで熟していると感じられた。
Claims (4)
- 5−(2−(1−エトキシエトキシ)プロパン−2−イル)−2−メチル−2−ビニルテトラヒドロフラン。
- アセトアルデヒドを水溶液に放出する方法であって、5−(2−(1−エトキシエトキシ)プロパン−2−イル)−2−メチル−2−ビニルテトラヒドロフランを水溶液に送達することを含む、前記方法。
- 以下のi)〜iii):
i)5−(2−(1−エトキシエトキシ)プロパン−2−イル)−2−メチル−2−ビニルテトラヒドロフラン、
ii)フレーバーキャリヤー及びフレーバーベースから成る群より選択される少なくとも1種の成分、並びに
iii)任意で少なくとも1種のフレーバー補助剤
を含有する、フレーバーを改質する組成物。 - 以下のi)及びii):
i)5−(2−(1−エトキシエトキシ)プロパン−2−イル)−2−メチル−2−ビニルテトラヒドロフラン、及び
ii)食材ベース
を含有する、フレーバー付けされた物品。
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PCT/EP2015/080718 WO2016102425A1 (en) | 2014-12-24 | 2015-12-21 | Acetaldehyde precursors |
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JP2018506265A (ja) * | 2014-12-24 | 2018-03-08 | フイルメニツヒ ソシエテ アノニムFirmenich Sa | プロフレーバー送達粉末 |
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JP6697429B2 (ja) | 2017-11-06 | 2020-05-20 | 長谷川香料株式会社 | 新規アルカンチオ酸誘導体および該化合物を含有する香料組成物 |
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CA947310A (en) | 1970-08-29 | 1974-05-14 | Seiji Wakayama | 2-(1'-hydroxymethyl-ethyl)-5-methyl-5-vinyl-tetrahydrofuran |
CH589426A5 (ja) | 1973-11-02 | 1977-07-15 | Firmenich & Cie | |
US5079023A (en) | 1977-01-21 | 1992-01-07 | Hercules Incorporated | Foodstuffs containing aldehyde generators |
US4419280A (en) * | 1980-08-07 | 1983-12-06 | International Flavors & Fragrances Inc. | 1-Ethoxy-1-ethanol acetate and uses thereof for augmenting or enhancing aroma or taste of consumable materials |
JPS59130879A (ja) | 1983-01-18 | 1984-07-27 | T Hasegawa Co Ltd | テトラヒドロフランエステル類 |
GB2332671B (en) * | 1997-12-22 | 2002-08-14 | Inst Francais Du Petrole | Acetals, their preparation and their use |
PL371375A1 (en) | 2002-03-28 | 2005-06-13 | Firmenich Sa | Compounds for the controlled release of active aldehydes |
EP3236774A1 (en) * | 2014-12-24 | 2017-11-01 | Firmenich SA | Proflavor delivery powders |
MX2017005855A (es) * | 2014-12-24 | 2017-09-26 | Firmenich & Cie | Particulas de liberacion de prosabor. |
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