JP5072598B2 - 風味改良物質 - Google Patents
風味改良物質 Download PDFInfo
- Publication number
- JP5072598B2 JP5072598B2 JP2007538840A JP2007538840A JP5072598B2 JP 5072598 B2 JP5072598 B2 JP 5072598B2 JP 2007538840 A JP2007538840 A JP 2007538840A JP 2007538840 A JP2007538840 A JP 2007538840A JP 5072598 B2 JP5072598 B2 JP 5072598B2
- Authority
- JP
- Japan
- Prior art keywords
- lactoyl
- flavor
- tyramine
- substances
- dopamine
- 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
Links
- 239000000796 flavoring agent Substances 0.000 title claims description 83
- 235000019634 flavors Nutrition 0.000 title claims description 81
- 239000000126 substance Substances 0.000 title claims description 75
- 239000000203 mixture Substances 0.000 claims description 33
- 235000019640 taste Nutrition 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 22
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical group NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 claims description 19
- 235000013361 beverage Nutrition 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 14
- UCBDNGDXEQXYDK-UHFFFAOYSA-N 2-hydroxy-n-[2-(4-hydroxyphenyl)ethyl]propanamide Chemical compound CC(O)C(=O)NCCC1=CC=C(O)C=C1 UCBDNGDXEQXYDK-UHFFFAOYSA-N 0.000 claims description 11
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229960003732 tyramine Drugs 0.000 claims description 11
- -1 sulfonyl tyramine Chemical compound 0.000 claims description 9
- 229960003638 dopamine Drugs 0.000 claims description 6
- ZOGCTLJACHDYQJ-UHFFFAOYSA-N 2-hydroxy-n-[(4-hydroxyphenyl)methyl]propanamide Chemical compound CC(O)C(=O)NCC1=CC=C(O)C=C1 ZOGCTLJACHDYQJ-UHFFFAOYSA-N 0.000 claims description 5
- WRPWWVNUCXQDQV-UHFFFAOYSA-N vanillylamine Chemical compound COC1=CC(CN)=CC=C1O WRPWWVNUCXQDQV-UHFFFAOYSA-N 0.000 claims description 5
- 229940053939 vanillylamine Drugs 0.000 claims description 5
- RQJDUEKERVZLLU-UHFFFAOYSA-N p-hydroxy-benzylamine Natural products NCC1=CC=C(O)C=C1 RQJDUEKERVZLLU-UHFFFAOYSA-N 0.000 claims description 3
- 238000010348 incorporation Methods 0.000 claims description 2
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- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
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- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 3
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- 239000002253 acid Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 2
- 229940117916 cinnamic aldehyde Drugs 0.000 description 2
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- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 239000012138 yeast extract Substances 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
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- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
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- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000004716 alpha keto acids Chemical class 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- 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
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
-
- 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
- A23L27/204—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Seasonings (AREA)
- Fats And Perfumes (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
R1−CR2(OR3)−CO−NR4−Y−X (I)
R1−CR2(OR3)−CO−NR4−Y−X (I)
Xはフェニルであって、ヒドロキシル及びC1〜C3のアルコキシルから選択される1又は複数の置換基によって置換されており、及びC1〜C3のヒドロキシアルキルから選択される1又は複数の置換基によってさらに置換されていてもよい;
R2は水素;C1〜C8のアルキル、C2〜C8のアルケニル、C3〜C8のシクロアルキル、又はC3〜C8のシクロアルケニルであって、それぞれヒドロキシル、C1〜C3のアルキル、C2〜C3のアルケニル、及びC1〜C3のカルボキシルから選択される1〜8個の置換基によって置換されていてもよい;
R3は水素;又はC1〜C3のアシル又はC1〜C3のアルキルであって、それぞれ1〜3個のヒドロキシル基によって置換されていてもよい;及び
R4は水素;C1〜C6のアルキル、C2〜C6のアルケニル、C1〜C3のアシル、C3〜C6のシクロアルキル、C3〜C6のシクロアルケニル、又はC1〜C6のアシルであって、それぞれヒドロキシル、C1〜C3のアルキル、及びC2〜C3のアルケニルから選択される1〜6個の置換基によって置換されていてもよい。)
化学式(I)において、R4は好ましくは水素である。
特に好ましい実施形態において、本発明の風味改良物質は、N−ラクトイルチラミン、N−グルコニル−チラミン、N−ラクトイル4−ヒドロキシベンジルアミン、N−ラクトイルバニリルアミン、N−ラクトイル−ドーパミン、それらの食用塩、及びそれらの混合物からなる群から選択される。最も好ましくは、風味改良物質はN−ラクトイルチラミンである。
HNR4−Y−X (II)
R1−CR2(OR3)−COOR5 (III)
本発明を、以下の例を用いて、さらに説明する。
[実施例]
続いて、12gのマルトデクストリン(MD10)と6gの塩を加えて、そのスラリーを噴霧乾燥した。
40gの乳酸エチルと10gのチラミンを、120℃で4時間反応させた。反応生成物を冷却し、200gの水に溶解した。得られた溶液を、はじめに200mlの酢酸エチルで洗浄し、続いてさらに100mlの酢酸エチルで洗浄した。水相を真空下、70℃で蒸発乾固した。7.5gの、非常に粘着性のある液体が得られ、該液体に60%のN−ラクトイルチラミンが含まれることがLC−MS及びNMRにより示された。
1)実施例1で調製した組成物0.025%を水道水に添加した溶液;
2)実施例1で調製した組成物0.025%、及び0.3%の塩化ナトリウムを水道水に添加した溶液;
3)実施例1で調製した組成物0.025%、0.3%の塩化ナトリウム、及び0.03%のモノグルタミン酸ナトリウムを水道水に添加した溶液;
4)実施例2で調製した組成物0.005%を水道水に添加した溶液;
5)実施例2で調製した組成物0.005%及び0.3%の塩化ナトリウムを水道水に添加した溶液;及び
6)実施例2で調製した組成物0.005%、0.3%の塩化ナトリウム、及び0.03%のモノグルタミン酸ナトリウムを水道水に添加した溶液。
溶液1)及び4)は、すっきりした(clean)口あたりと、こくと深み(body and thickness)があると表現された。
溶液2)及び5)は、持続効果(long-lasting effect)と、すっきりした口あたりと、こくと深みがあり、ブイヨンのようであると表現された。
溶液3)及び6)は、持続効果と、非常にすっきりした口あたりと、こくと深みがあり、濃くて自然で複雑なブイヨンのようであると表現された。
1.魚のブイヨン;
2.魚のブイヨン+実施例1で調製した100ppmの組成物;
3.ナンプラー(Nam Pla)*(例えば、Unilever社製、タイ);
4.ナンプラー(例えば、Unilever社製、タイ)+実施例1で調製した100ppmの組成物;
5.魚のブイヨン+実施例2で調製した20ppmの組成物;及び
6.ナンプラー(例えば、Unilever社製、タイ)+実施例2で調製した20ppmの組成物。
* ナンプラーは、魚(アンチョビ)、塩、及び砂糖の混合物から製造されるタイの魚醤(fish sauce)であり、30〜35℃で6ヶ月より長く発酵させたものである。魚の微生物学的及び酵素による分解を経てタンパク質加水分解物及び脂質酸化生成物が生成される。
サンプル2をサンプル1と比較した場合、より深みがあり口あたりが良く、甘味の印象がより強く、持続効果がより長かった。
サンプル4をサンプル3と比較した場合、より深みがあり口あたりが良く、甘味の印象がより強く、持続効果がより長かった。
サンプル4をサンプル3と比較した場合、よりまろやかで、自然な発酵した魚の特徴も有し、より高品質のナンプラーであると感じられた。
サンプル5をサンプル1と比較した場合、より深みがあり口あたりが良く、甘味の印象がより強く、持続効果がより長かった。
サンプル6をサンプル3と比較した場合、より深みがあり口あたりが良く、甘味の印象がより強く、持続効果がより長かった。
サンプル4及び6をサンプル3と比較した場合、よりまろやかで、自然な発酵魚の特徴も有し、より高品質のナンプラーであると感じられた。
Claims (5)
- 少なくとも0.1質量%の1又は複数のフレーバー物質、及び0.001〜80質量%の風味改良物質及び/又はその食用塩を含む風味組成物であり、前記風味改良物質がN−ラクトイルチラミン、N−グルコニルチラミン、N−ラクトイルドーパミン、N−ラクトイル4−ヒドロキシベンジルアミン、及びN−ラクトイルバニリルアミンから選択されることを特徴とする、風味組成物。
- 食料品、飲料、及び医薬品からなる群から選択される製品であって、N−ラクトイルチラミン、N−グルコニルチラミン、N−ラクトイルドーパミン、N−ラクトイル4−ヒドロキシベンジルアミン、及びN−ラクトイルバニリルアミンから選択される1又は複数の風味改良物質及び/又はそれらの食用塩を、少なくとも0.1ppm包含する、製品。
- 食料品、飲料、又は医薬品の風味を改良する方法であって、N−ラクトイルチラミン、N−グルコニルチラミン、N−ラクトイルドーパミン、N−ラクトイル4−ヒドロキシベンジルアミン、及びN−ラクトイルバニリルアミンから選択される1又は複数の風味改良物質及び/又はそれらの食用塩を、少なくとも0.1ppmの量で前記製品に組み入れることを包含する、方法。
- N−ラクトイルチラミン、N−グルコニルチラミン、N−ラクトイルドーパミン、N−ラクトイル4−ヒドロキシベンジルアミン、若しくはN−ラクトイルバニリルアミン、又はその食用塩から選択される1又は複数の風味改良物質。
- N−ラクトイルチラミン、N−グルコニルチラミン、N−ラクトイルドーパミン、N−ラクトイル4−ヒドロキシベンジルアミン、及びN−ラクトイルバニリルアミンから選択される1又は複数の風味改良物質及び/又はその食用塩を、少なくとも0.01ppm含有する組成物。
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PCT/NL2005/000258 WO2005096844A1 (en) | 2004-04-06 | 2005-04-06 | Process for preparing maillard flavour preparations |
NLPCT/NL2005/000258 | 2005-04-06 | ||
PCT/NL2005/000719 WO2006046853A1 (en) | 2004-10-29 | 2005-10-06 | Flavour modulating substances |
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GB814570A (en) | 1956-03-22 | 1959-06-10 | Us Vitamin Corp | d-ª‡-methylphenethylamides and pharmaceutical preparations containing such amides |
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WO1997004667A1 (fr) | 1995-07-26 | 1997-02-13 | Firmenich S.A. | Produits aromatises et procede pour leur preparation |
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EP1029849A1 (de) * | 1999-02-19 | 2000-08-23 | Haarmann & Reimer Gmbh | Hydroxymandelsäureamide phenolischer Amine |
WO2001077292A2 (en) | 2000-04-07 | 2001-10-18 | Senomyx, Inc. | Novel signal transduction molecules |
US20030130205A1 (en) * | 2000-04-12 | 2003-07-10 | Christian Samuel T. | Novel pharmaceutical anti-infective agents containing carbohydrate moieties and methods of their preparation and use |
US20050113846A1 (en) * | 2001-02-27 | 2005-05-26 | Carson Christopher P. | Surgical navigation systems and processes for unicompartmental knee arthroplasty |
AU2002308481A1 (en) * | 2001-05-01 | 2002-11-11 | Senomyx, Inc. | High throughput cell-based assay for monitoring sodium channel activity and discovery of salty taste modulating compounds |
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CN101090641A (zh) | 2007-12-19 |
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BRPI0518075A (pt) | 2008-10-28 |
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