JP6659704B2 - 風味分子としての糖ジペプチド結合体 - Google Patents
風味分子としての糖ジペプチド結合体 Download PDFInfo
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- JP6659704B2 JP6659704B2 JP2017536839A JP2017536839A JP6659704B2 JP 6659704 B2 JP6659704 B2 JP 6659704B2 JP 2017536839 A JP2017536839 A JP 2017536839A JP 2017536839 A JP2017536839 A JP 2017536839A JP 6659704 B2 JP6659704 B2 JP 6659704B2
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- 239000000796 flavoring agent Substances 0.000 title claims description 31
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- 235000000346 sugar Nutrition 0.000 title description 3
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- 239000004471 Glycine Substances 0.000 claims description 2
- 235000013372 meat Nutrition 0.000 claims description 2
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- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 11
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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- 239000008103 glucose Substances 0.000 description 3
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- 150000002431 hydrogen Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- 239000001096 (4-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol hydrochloride Substances 0.000 description 1
- NNKXWRRDHYTHFP-HZQSTTLBSA-N (r)-[(2s,4s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;hydron;dichloride Chemical compound Cl.Cl.C([C@H]([C@H](C1)C=C)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 NNKXWRRDHYTHFP-HZQSTTLBSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRSZFWQUAKGDAV-KQYNXXCUSA-N IMP Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H]1N1C(NC=NC2=O)=C2N=C1 GRSZFWQUAKGDAV-KQYNXXCUSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 229930195714 L-glutamate Natural products 0.000 description 1
- 239000005913 Maltodextrin Substances 0.000 description 1
- 229920002774 Maltodextrin Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000019606 astringent taste Nutrition 0.000 description 1
- 229940000635 beta-alanine Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 235000012206 bottled water Nutrition 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 150000002306 glutamic acid derivatives Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 108091005708 gustatory receptors Proteins 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- XKVWLLRDBHAWBL-UHFFFAOYSA-N imperatorin Natural products CC(=CCOc1c2OCCc2cc3C=CC(=O)Oc13)C XKVWLLRDBHAWBL-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229940035034 maltodextrin Drugs 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 235000019639 meaty taste Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
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- 235000019629 palatability Nutrition 0.000 description 1
- 210000003254 palate Anatomy 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 229960001811 quinine hydrochloride Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 235000019643 salty taste Nutrition 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 229910001415 sodium ion Inorganic materials 0.000 description 1
- GJBHGUUFMNITCI-QTNFYWBSSA-M sodium;(2s)-2-aminopentanedioate;hydron;hydrate Chemical compound O.[Na+].OC(=O)[C@@H](N)CCC([O-])=O GJBHGUUFMNITCI-QTNFYWBSSA-M 0.000 description 1
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- 210000001779 taste bud Anatomy 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- 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
- A23L23/00—Soups; Sauces; Preparation or treatment thereof
- A23L23/10—Soup concentrates, e.g. powders or cakes
-
- 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
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
-
- 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
- A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
-
- 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
- A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
- A23L27/215—Synthetic spices, flavouring agents or condiments containing amino acids heated in the presence of reducing sugars, e.g. Maillard's non-enzymatic browning
-
- 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
- A23L27/88—Taste or flavour enhancing agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Organic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Biophysics (AREA)
- Medicinal Chemistry (AREA)
- Seasonings (AREA)
- Seeds, Soups, And Other Foods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
Description
(式中、R1は、水素、C1アルキル基、C2アルキル基、又はC3アルキル基である。)の化合物、又は当該化合物の塩を提供する。
化合物:亜硫酸水素ナトリウム及びグリセロールはSigmaより、グルコースはSDfine Chemicalsより、β−アラニルグリシンはAksciより、メタノール及び酢酸はMerckより購入した。全ての市販の試薬は、それぞれの供給元から入手したまま使用した。
官能試験は、官能パネル室において、20〜25℃で実施した。喉から鼻に抜けるアロマ又は味覚による印象を除外するため、ノーズクリップを使用した。官能パネルは、8〜14人の訓練を受けた担当者で構成された。パネルは、3点試験法を使用して以下の標準的な味化合物水溶液(それぞれ1mL)の味を評価するよう訓練された:甘味に関しては、それぞれ、サッカロース(50mmol/L)及びL−アラニン(15mmol/L);酸味に関しては、乳酸(20mmol/L);塩味に関しては、NaCl(12mmol/L);苦味に関しては、それぞれ、カフェイン(1mmol/L)及びキニーネ塩酸塩(0.05mmol/L);うまみに関しては、グルタミン酸ナトリウム(8mmol/L、pH5.7);並びに渋味に関しては、タンニン(0.05%)。「白身肉のような」口腔の感覚は、ボトル入り飲料水(pH5.9)にグルタミン酸一ナトリウム一水和物(1.9g/L)、酵母抽出物(2.1g/L)、マルトデキストリン(6.375g/L)及び塩化ナトリウム(2.9g/L)を加え調製したモデルブロス溶液で評価した。
1−デオキシ−D−フルクトシル−N−β−アラニル−L−グリシンの味覚閾値濃度を、実施例2で説明したように、モデルブロス中で測定し、同一の実験モデル系(実施例2を参照)下で、濃厚な酸味の感覚及び白身肉のような口腔の印象に関しては、4,620μmol/L(1.4mg/g)であることが判明した。実際に、これは、味覚閾値モル濃度の、係数約4分の1の低下に相当する。
チキンベース粉末(詳細な配合を表1に示す)6g及びグルタミン酸一ナトリウム1gを温水500mLに溶かし、チキンスープを調製した。1−デオキシ−D−フルクトシル−N−β−アラニル−L−グリシンを2g/Lで加えた。
トマトベース粉末(詳細な配合を表2に示す)6gを温水500mLに溶かし、トマトスープを調製した。1−デオキシ−D−フルクトシル−N−β−アラニル−L−グリシンを2g/Lで加えた。
Claims (12)
- 1−デオキシ−D−フルクトシル−N−β−アラニル−L−グリシンである化合物又はその塩。
- 請求項1に記載の化合物又はその塩を少なくとも1mg/gの量で含む、組成物。
- 前記組成物が植物材料及び/又は肉材料からの抽出物である、請求項2に記載の組成物。
- 前記組成物が食品グレードである、請求項2又は3に記載の組成物。
- 前記組成物が、料理用の調味料、調理補助剤、ソースの濃縮物又はスープの濃縮物、乾燥ペットフード製品又は湿潤ペットフード製品からなる群から選択される、請求項2〜4のいずれか一項に記載の組成物。
- 請求項2〜5のいずれか一項に記載の組成物の製造方法であって、風味反応の結果として該組成物を得ることを含む、方法。
- 食品製品の風味を増強するための、請求項1に記載の化合物又はその塩の使用。
- 食品製品のうまみを増強するための、請求項1に記載の化合物又はその塩の使用。
- 食品製品の風味を増強するための、請求項2〜5のいずれか一項に記載の組成物の使用。
- 食品製品のうまみを増強するための、請求項2〜5のいずれか一項に記載の組成物の使用。
- 請求項1に記載の化合物若しくはその塩、又は請求項2〜5のいずれか一項に記載の組成物を食品製品に加えるステップを含む、料理用の食品製品の風味及び/又はうまみを増強するための方法。
- 請求項1に記載の化合物又はその塩の前記食品製品中の最終濃度が少なくとも1mg/gである、請求項11に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP15153278 | 2015-01-30 | ||
EP15153278.5 | 2015-01-30 | ||
PCT/EP2016/051530 WO2016120250A1 (en) | 2015-01-30 | 2016-01-26 | Sugar-dipeptide conjugates as flavor molecules |
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EP (1) | EP3250580B1 (ja) |
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EP1252825A1 (en) * | 2001-04-25 | 2002-10-30 | Société des Produits Nestlé S.A. | Flavouring compositions |
DE102008024206A1 (de) | 2008-05-14 | 2009-11-19 | Symrise Gmbh & Co. Kg | Aromakompositionen und Zubereitungen umfassend Nα-β-Alanyl-Dipeptide |
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US10787481B2 (en) | 2020-09-29 |
CN107108678A (zh) | 2017-08-29 |
PT3250580T (pt) | 2019-01-28 |
MX364718B (es) | 2019-05-06 |
ES2704746T3 (es) | 2019-03-19 |
BR112017013905A2 (pt) | 2018-01-02 |
SG11201704202WA (en) | 2017-08-30 |
AU2016212192A1 (en) | 2017-06-08 |
US20180009844A1 (en) | 2018-01-11 |
IL252359B (en) | 2020-03-31 |
IL252359A0 (en) | 2017-07-31 |
WO2016120250A1 (en) | 2016-08-04 |
PL3250580T3 (pl) | 2019-05-31 |
CN107108678B (zh) | 2020-07-17 |
AU2016212192B2 (en) | 2020-01-16 |
EP3250580A1 (en) | 2017-12-06 |
JP2018506522A (ja) | 2018-03-08 |
PH12017550033A1 (en) | 2018-01-15 |
MX2017009581A (es) | 2017-11-01 |
CL2017001743A1 (es) | 2018-03-23 |
CA2974857A1 (en) | 2016-08-04 |
EP3250580B1 (en) | 2018-10-24 |
TR201901055T4 (tr) | 2019-02-21 |
MY179679A (en) | 2020-11-11 |
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