JP5805108B2 - 旨味フレーバー付与剤としてのオキサルアミド誘導体 - Google Patents
旨味フレーバー付与剤としてのオキサルアミド誘導体 Download PDFInfo
- Publication number
- JP5805108B2 JP5805108B2 JP2012551614A JP2012551614A JP5805108B2 JP 5805108 B2 JP5805108 B2 JP 5805108B2 JP 2012551614 A JP2012551614 A JP 2012551614A JP 2012551614 A JP2012551614 A JP 2012551614A JP 5805108 B2 JP5805108 B2 JP 5805108B2
- Authority
- JP
- Japan
- Prior art keywords
- umami
- products
- oxalamide
- pyridin
- flavor
- 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
- 235000019583 umami taste Nutrition 0.000 title claims description 32
- 239000000796 flavoring agent Substances 0.000 title claims description 20
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 title description 6
- 235000013355 food flavoring agent Nutrition 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 26
- 235000019634 flavors Nutrition 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 5
- RVFALLLOOYLSBC-MHWRWJLKSA-N n'-[(2e)-3,7-dimethylocta-2,6-dienyl]-n-(2-pyridin-2-ylethyl)oxamide Chemical compound CC(C)=CCC\C(C)=C\CNC(=O)C(=O)NCCC1=CC=CC=N1 RVFALLLOOYLSBC-MHWRWJLKSA-N 0.000 claims description 5
- 239000000047 product Substances 0.000 description 28
- 235000013923 monosodium glutamate Nutrition 0.000 description 15
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 14
- -1 2- (pyridin-2-yl) ethyl Chemical group 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 235000013361 beverage Nutrition 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- AFMZGMJNKXOLEM-JXMROGBWSA-N (2e)-3,7-dimethylocta-2,6-dien-1-amine Chemical compound CC(C)=CCC\C(C)=C\CN AFMZGMJNKXOLEM-JXMROGBWSA-N 0.000 description 2
- XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 108091028664 Ribonucleotide Proteins 0.000 description 2
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 2
- 235000014121 butter Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940112822 chewing gum Drugs 0.000 description 2
- 235000015218 chewing gum Nutrition 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 235000013622 meat product Nutrition 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 235000014571 nuts Nutrition 0.000 description 2
- 239000002336 ribonucleotide Substances 0.000 description 2
- 125000002652 ribonucleotide group Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000019640 taste Nutrition 0.000 description 2
- 235000019607 umami taste sensations Nutrition 0.000 description 2
- LRRQSQFTAUUTJO-UHFFFAOYSA-N 1-(2-hydroxy-4,5-dimethylphenyl)-3-pyridin-2-ylpropan-1-one Chemical compound C1=C(C)C(C)=CC(O)=C1C(=O)CCC1=CC=CC=N1 LRRQSQFTAUUTJO-UHFFFAOYSA-N 0.000 description 1
- ANKJXSOMEJINDX-UHFFFAOYSA-N 1-(2-hydroxy-4-isobutoxyphenyl)-3-(2-pyridyl)propan-1-one Chemical compound OC1=CC(OCC(C)C)=CC=C1C(=O)CCC1=CC=CC=N1 ANKJXSOMEJINDX-UHFFFAOYSA-N 0.000 description 1
- IPMVYTFFNWLSAN-UHFFFAOYSA-N 1-(2-hydroxy-4-methoxyphenyl)-3-(2-pyridyl)propan-1-one Chemical compound OC1=CC(OC)=CC=C1C(=O)CCC1=CC=CC=N1 IPMVYTFFNWLSAN-UHFFFAOYSA-N 0.000 description 1
- YSLJEHQBOCZVSN-UHFFFAOYSA-N 1-(2-hydroxy-4-methylphenyl)-3-pyridin-2-ylpropan-1-one Chemical compound OC1=CC(C)=CC=C1C(=O)CCC1=CC=CC=N1 YSLJEHQBOCZVSN-UHFFFAOYSA-N 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- UKNMSFRSBQONET-UHFFFAOYSA-N N-(3,7-dimethylocta-2,6-dien-1-yl)cyclopropanecarboxamide Chemical compound CC(C)=CCCC(C)=CCNC(=O)C1CC1 UKNMSFRSBQONET-UHFFFAOYSA-N 0.000 description 1
- YOBNUUGTIXQSPD-UHFFFAOYSA-N N-(Heptan-4-yl)benzo[d][1,3]dioxole-5-carboxamide Chemical compound CCCC(CCC)NC(=O)C1=CC=C2OCOC2=C1 YOBNUUGTIXQSPD-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 235000021557 concentrated beverage Nutrition 0.000 description 1
- 235000013409 condiments Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 235000021185 dessert Nutrition 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 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 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- OVLOBACKYAWDPD-FMIVXFBMSA-N ethyl 2-[[(2e)-3,7-dimethylocta-2,6-dienyl]amino]-2-oxoacetate Chemical compound CCOC(=O)C(=O)NC\C=C(/C)CCC=C(C)C OVLOBACKYAWDPD-FMIVXFBMSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
- 235000011868 grain product Nutrition 0.000 description 1
- 235000013882 gravy Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 235000013384 milk substitute Nutrition 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- MQNYSPJVIUCDEG-UHFFFAOYSA-N n-(5-methyl-2-propan-2-ylcyclohexyl)cyclopropanecarboxamide Chemical compound CC(C)C1CCC(C)CC1NC(=O)C1CC1 MQNYSPJVIUCDEG-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 235000019520 non-alcoholic beverage Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000014594 pastries Nutrition 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000021067 refined food Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 229940073490 sodium glutamate Drugs 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
- A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Seasonings (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1001796.0A GB201001796D0 (en) | 2010-02-04 | 2010-02-04 | Compounds |
| GB1001796.0 | 2010-02-04 | ||
| PCT/EP2011/051528 WO2011095533A1 (en) | 2010-02-04 | 2011-02-03 | Oxalamide derivative as umami flavouring agent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013518850A JP2013518850A (ja) | 2013-05-23 |
| JP2013518850A5 JP2013518850A5 (https=) | 2014-03-13 |
| JP5805108B2 true JP5805108B2 (ja) | 2015-11-04 |
Family
ID=42082444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012551614A Expired - Fee Related JP5805108B2 (ja) | 2010-02-04 | 2011-02-03 | 旨味フレーバー付与剤としてのオキサルアミド誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8470384B2 (https=) |
| EP (1) | EP2531489B1 (https=) |
| JP (1) | JP5805108B2 (https=) |
| CN (1) | CN102741231B (https=) |
| BR (1) | BR112012019663B1 (https=) |
| GB (1) | GB201001796D0 (https=) |
| SG (1) | SG182515A1 (https=) |
| WO (1) | WO2011095533A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013041599A1 (en) * | 2011-09-21 | 2013-03-28 | Givaudan Sa | Pyridine derivates and their use as umami tastants |
| CN103156154A (zh) * | 2011-12-09 | 2013-06-19 | 味之素株式会社 | 甜味剂组合物以及饮料食品 |
| CN119462490A (zh) * | 2023-08-09 | 2025-02-18 | 上海交通大学医学院附属仁济医院 | 一种海绵来源的吡啶内盐及其制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB913804A (en) * | 1960-03-21 | 1962-12-28 | Tweedales & Smalley Ltd | Improvements in textile ring spinning and like machines |
| EP1291342A1 (en) | 2001-09-06 | 2003-03-12 | Societe Des Produits Nestle S.A. | Pyridinium-betain compounds as taste enhancer |
| EP1312268A1 (en) | 2001-11-19 | 2003-05-21 | Société des Produits Nestlé S.A. | Flavouring compositions |
| ES2300418T3 (es) | 2002-04-22 | 2008-06-16 | Societe Des Produits Nestle S.A. | Composicion de condimento que contiene n-acetilglicina. |
| US7632531B2 (en) * | 2003-04-11 | 2009-12-15 | International Flavors & Fragnances Inc. | Alkyldienamides exhibiting taste and sensory effect in flavor compositions |
| US7906627B2 (en) | 2003-08-06 | 2011-03-15 | Senomyx, Inc. | Chimeric human sweet-umami and umami-sweet taste receptors |
| AR046078A1 (es) | 2003-08-06 | 2005-11-23 | Senomyx Inc | Nuevos sabores, modificadores de sabores, sustancias gustativas, mejoradores de gusto, sustancias gustativas y/o mejoradoras del gusto umani o dulce y uso de los mismos. |
| DE102004031588A1 (de) | 2004-06-30 | 2006-02-09 | Symrise Gmbh & Co. Kg | Verwendung von Äpfelsäureglucosiden als Geschmacksstoffe |
| DE102004032878A1 (de) * | 2004-07-07 | 2006-02-16 | Symrise Gmbh & Co. Kg | Verwendung von Alkyloxyalkansäureamiden insbesondere als Aromastoffe sowie neue Alkyloxyalkansäureamide |
| US20060045953A1 (en) | 2004-08-06 | 2006-03-02 | Catherine Tachdjian | Aromatic amides and ureas and their uses as sweet and/or umami flavor modifiers, tastants and taste enhancers |
| US7541055B2 (en) | 2004-09-10 | 2009-06-02 | International Flavors & Fragrances Inc. | Saturated and unsaturated N-alkamides exhibiting taste and flavor enhancement effect in flavor compositions |
| ES2640453T3 (es) | 2006-04-21 | 2017-11-03 | Senomyx, Inc. | Procesos para preparar composiciones saborizantes sólidas |
| DE102008042421A1 (de) | 2008-09-26 | 2010-04-01 | Symrise Gmbh & Co. Kg | Geranylaminderivate der Oxalsäure |
| KR20130055595A (ko) * | 2010-04-15 | 2013-05-28 | 크로모셀 코포레이션 | 쓴맛을 감소시키거나 제거하기 위한 화합물, 조성물 및 방법 |
-
2010
- 2010-02-04 GB GBGB1001796.0A patent/GB201001796D0/en not_active Ceased
-
2011
- 2011-02-03 BR BR112012019663-4A patent/BR112012019663B1/pt not_active IP Right Cessation
- 2011-02-03 WO PCT/EP2011/051528 patent/WO2011095533A1/en not_active Ceased
- 2011-02-03 JP JP2012551614A patent/JP5805108B2/ja not_active Expired - Fee Related
- 2011-02-03 CN CN201180008196.3A patent/CN102741231B/zh not_active Expired - Fee Related
- 2011-02-03 EP EP11701682.4A patent/EP2531489B1/en not_active Not-in-force
- 2011-02-03 SG SG2012051876A patent/SG182515A1/en unknown
- 2011-02-03 US US13/576,572 patent/US8470384B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB201001796D0 (en) | 2010-03-24 |
| US20120301587A1 (en) | 2012-11-29 |
| CN102741231A (zh) | 2012-10-17 |
| BR112012019663A2 (pt) | 2016-08-02 |
| WO2011095533A1 (en) | 2011-08-11 |
| SG182515A1 (en) | 2012-08-30 |
| EP2531489A1 (en) | 2012-12-12 |
| JP2013518850A (ja) | 2013-05-23 |
| US8470384B2 (en) | 2013-06-25 |
| BR112012019663B1 (pt) | 2018-01-23 |
| EP2531489B1 (en) | 2014-11-19 |
| CN102741231B (zh) | 2014-08-06 |
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