CA2788717A1 - Compounds and methods for enhancing salty taste - Google Patents
Compounds and methods for enhancing salty taste Download PDFInfo
- Publication number
- CA2788717A1 CA2788717A1 CA2788717A CA2788717A CA2788717A1 CA 2788717 A1 CA2788717 A1 CA 2788717A1 CA 2788717 A CA2788717 A CA 2788717A CA 2788717 A CA2788717 A CA 2788717A CA 2788717 A1 CA2788717 A1 CA 2788717A1
- Authority
- CA
- Canada
- Prior art keywords
- sodium
- formula
- foodstuff
- compound
- sodium chloride
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims description 26
- 235000019643 salty taste Nutrition 0.000 title description 14
- 230000002708 enhancing effect Effects 0.000 title description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 54
- 239000011780 sodium chloride Substances 0.000 claims abstract description 27
- 235000019600 saltiness Nutrition 0.000 claims abstract description 23
- 235000013305 food Nutrition 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 9
- 230000001965 increasing effect Effects 0.000 claims description 7
- 150000003839 salts Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 235000021023 sodium intake Nutrition 0.000 claims description 3
- 235000019640 taste Nutrition 0.000 abstract description 5
- 229910052708 sodium Inorganic materials 0.000 description 42
- 239000011734 sodium Substances 0.000 description 42
- 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 40
- BVRYRDZJWMVPFS-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-methylpentanamide Chemical compound CC(C)CCC(=O)NCCO BVRYRDZJWMVPFS-UHFFFAOYSA-N 0.000 description 10
- 210000000287 oocyte Anatomy 0.000 description 10
- 235000005911 diet Nutrition 0.000 description 8
- 230000000378 dietary effect Effects 0.000 description 7
- 108091006146 Channels Proteins 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 235000009508 confectionery Nutrition 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 239000000232 Lipid Bilayer Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000019583 umami taste Nutrition 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 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
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 102000003837 Epithelial Sodium Channels Human genes 0.000 description 1
- 108090000140 Epithelial Sodium Channels Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OFQRUTMGVBMTFQ-UHFFFAOYSA-N Ethyl 4-methylpentanoate Chemical compound CCOC(=O)CCC(C)C OFQRUTMGVBMTFQ-UHFFFAOYSA-N 0.000 description 1
- 208000002682 Hyperkalemia Diseases 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 241000269370 Xenopus <genus> Species 0.000 description 1
- 241000269368 Xenopus laevis Species 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241000482268 Zea mays subsp. mays Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000018823 dietary intake Nutrition 0.000 description 1
- 235000021158 dinner Nutrition 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 108091005708 gustatory receptors Proteins 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- -1 ion salt Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000008960 ketchup Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000019449 other food additives Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000013550 pizza Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 235000013606 potato chips Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000012434 pretzels Nutrition 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000008371 tortilla/corn chips Nutrition 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A23L27/88—Taste or flavour enhancing agents
-
- 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
-
- 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
- A23L27/40—Table salts; Dietetic salt substitutes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30141910P | 2010-02-04 | 2010-02-04 | |
| US61/301,419 | 2010-02-04 | ||
| PCT/US2011/023546 WO2011097344A1 (en) | 2010-02-04 | 2011-02-03 | Compounds and methods for enhancing salty taste |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2788717A1 true CA2788717A1 (en) | 2011-08-11 |
Family
ID=44355762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2788717A Abandoned CA2788717A1 (en) | 2010-02-04 | 2011-02-03 | Compounds and methods for enhancing salty taste |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20130078351A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2531048A4 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2013518592A (cg-RX-API-DMAC7.html) |
| CN (1) | CN102811628A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2011212938B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2788717A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011097344A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6210669B2 (ja) * | 2012-10-18 | 2017-10-11 | 日清食品ホールディングス株式会社 | 塩味増強ペプチド |
| EP2910130B1 (en) * | 2012-10-18 | 2018-08-15 | Nissin Foods Holdings Co., Ltd. | Salty taste-enhancing agent and manufacturing method therefor, and salty taste-enhancing method |
| ES2831028T3 (es) * | 2013-02-08 | 2021-06-07 | Gen Mills Inc | Productos alimenticios reducidos en sodio |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2411655A (en) * | 1939-01-19 | 1946-11-26 | Chem Ind Basel | Process for condensation products of thiourea compounds |
| DE3218027A1 (de) * | 1982-05-13 | 1983-11-17 | A. Nattermann & Cie GmbH, 5000 Köln | Phospholipidloesungen |
| US5260091A (en) * | 1992-10-21 | 1993-11-09 | Interneuron Pharmaceuticals Inc. | Salt taste enhancers |
| EP1411781B1 (de) * | 2001-07-31 | 2006-01-25 | Berg & Schmidt GmbH & Co. | Zusatzstoff für futtermittel oder für trinkwasser |
| WO2004014135A2 (en) * | 2002-08-09 | 2004-02-19 | Nutra-Park, Inc. | Use of certain n-acylethanolamines to achieve ethylene- and cytokinin-like effects in plants and fungi |
| WO2005006881A2 (en) * | 2003-07-09 | 2005-01-27 | Virginia Commonwealth University | Salt taste modification |
| 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 |
| US7427421B2 (en) * | 2004-09-10 | 2008-09-23 | International Flavors & Fragrances Inc. | Saturated and unsaturated N-alkamides exhibiting taste and flavor enhancement effect in flavor compositions |
| CA2666962C (en) * | 2006-10-19 | 2015-12-08 | Monell Chemical Senses Center | Human salty taste receptor and methods of modulating salty taste perception |
| NZ552238A (en) * | 2006-12-20 | 2009-07-31 | Seperex Nutritionals Ltd | An extract |
-
2011
- 2011-02-03 US US13/576,855 patent/US20130078351A1/en not_active Abandoned
- 2011-02-03 AU AU2011212938A patent/AU2011212938B2/en not_active Ceased
- 2011-02-03 JP JP2012552074A patent/JP2013518592A/ja active Pending
- 2011-02-03 WO PCT/US2011/023546 patent/WO2011097344A1/en not_active Ceased
- 2011-02-03 CA CA2788717A patent/CA2788717A1/en not_active Abandoned
- 2011-02-03 EP EP11740331.1A patent/EP2531048A4/en not_active Withdrawn
- 2011-02-03 CN CN201180013716XA patent/CN102811628A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU2011212938B2 (en) | 2015-07-30 |
| EP2531048A4 (en) | 2015-10-28 |
| EP2531048A1 (en) | 2012-12-12 |
| JP2013518592A (ja) | 2013-05-23 |
| CN102811628A (zh) | 2012-12-05 |
| AU2011212938A1 (en) | 2012-09-13 |
| US20130078351A1 (en) | 2013-03-28 |
| WO2011097344A1 (en) | 2011-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20150910 |
|
| FZDE | Discontinued |
Effective date: 20180205 |