IL31964A - Tryptophane derivatives and their use as sweetening agents - Google Patents
Tryptophane derivatives and their use as sweetening agentsInfo
- Publication number
- IL31964A IL31964A IL31964A IL3196469A IL31964A IL 31964 A IL31964 A IL 31964A IL 31964 A IL31964 A IL 31964A IL 3196469 A IL3196469 A IL 3196469A IL 31964 A IL31964 A IL 31964A
- Authority
- IL
- Israel
- Prior art keywords
- sweetener
- tryptophane
- chlorotryptophane
- nutritive
- percent
- Prior art date
Links
- 235000003599 food sweetener Nutrition 0.000 title claims description 26
- 239000003765 sweetening agent Substances 0.000 title claims description 26
- 150000003653 tryptophane derivatives Chemical class 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 18
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 16
- 239000006035 Tryptophane Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 229960004799 tryptophan Drugs 0.000 claims description 16
- 239000000796 flavoring agent Substances 0.000 claims description 13
- -1 tryptophane compound Chemical class 0.000 claims description 13
- 235000013615 non-nutritive sweetener Nutrition 0.000 claims description 11
- 231100000252 nontoxic Toxicity 0.000 claims description 9
- 230000003000 nontoxic effect Effects 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 235000013355 food flavoring agent Nutrition 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- FICLVQOYKYBXFN-VIFPVBQESA-N 6-chloro-L-tryptophan Chemical compound ClC1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 FICLVQOYKYBXFN-VIFPVBQESA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- JXLKNMYKLNHNNN-VIFPVBQESA-N (2s)-2-amino-3-[6-(trifluoromethyl)-1h-indol-3-yl]propanoic acid Chemical compound FC(F)(F)C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 JXLKNMYKLNHNNN-VIFPVBQESA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000000430 tryptophan group Chemical class [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 31
- 239000013543 active substance Substances 0.000 description 25
- FICLVQOYKYBXFN-UHFFFAOYSA-N 6-chlorotryptophan Chemical compound ClC1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 FICLVQOYKYBXFN-UHFFFAOYSA-N 0.000 description 18
- 235000009508 confectionery Nutrition 0.000 description 16
- 235000017103 tryptophane Nutrition 0.000 description 14
- WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 235000001014 amino acid Nutrition 0.000 description 9
- 150000001413 amino acids Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 229930006000 Sucrose Natural products 0.000 description 8
- 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 8
- 239000000243 solution Substances 0.000 description 8
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- 150000003654 tryptophanes Chemical class 0.000 description 8
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 7
- 241000282472 Canis lupus familiaris Species 0.000 description 6
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- 239000002253 acid Substances 0.000 description 6
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- GDMRVYIFGPMUCG-UHFFFAOYSA-N 2-azaniumyl-3-(6-methyl-1h-indol-3-yl)propanoate Chemical compound CC1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 GDMRVYIFGPMUCG-UHFFFAOYSA-N 0.000 description 2
- YMEXGEAJNZRQEH-UHFFFAOYSA-N 6-Fluoro-DL-tryptophan Chemical compound FC1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 YMEXGEAJNZRQEH-UHFFFAOYSA-N 0.000 description 2
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- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 229940029982 garlic powder Drugs 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000011868 grain product Nutrition 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229940010454 licorice Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000013622 meat product 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
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 235000020166 milkshake Nutrition 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- RCGABEQHDDFFRR-UHFFFAOYSA-N n-ethyl-n-(1h-indol-3-ylmethyl)ethanamine Chemical class C1=CC=C2C(CN(CC)CC)=CNC2=C1 RCGABEQHDDFFRR-UHFFFAOYSA-N 0.000 description 1
- ITVGXXMINPYUHD-CUVHLRMHSA-N neohesperidin dihydrochalcone Chemical compound C1=C(O)C(OC)=CC=C1CCC(=O)C(C(=C1)O)=C(O)C=C1O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 ITVGXXMINPYUHD-CUVHLRMHSA-N 0.000 description 1
- 229940089953 neohesperidin dihydrochalcone Drugs 0.000 description 1
- 235000010434 neohesperidine DC Nutrition 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000012434 pretzels Nutrition 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000019505 tobacco product Nutrition 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
-
- 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
-
- 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
- A23L27/30—Artificial sweetening agents
- A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Seasonings (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71966668A | 1968-04-08 | 1968-04-08 | |
| US71973068A | 1968-04-08 | 1968-04-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31964A0 IL31964A0 (en) | 1969-06-25 |
| IL31964A true IL31964A (en) | 1972-09-28 |
Family
ID=27110117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31964A IL31964A (en) | 1968-04-08 | 1969-04-07 | Tryptophane derivatives and their use as sweetening agents |
Country Status (13)
| Country | Link |
|---|---|
| JP (2) | JPS4816624B1 (cg-RX-API-DMAC7.html) |
| BE (1) | BE731141A (cg-RX-API-DMAC7.html) |
| CH (1) | CH532369A (cg-RX-API-DMAC7.html) |
| CY (2) | CY797A (cg-RX-API-DMAC7.html) |
| DK (1) | DK139292B (cg-RX-API-DMAC7.html) |
| FR (1) | FR2007414A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1269851A (cg-RX-API-DMAC7.html) |
| HK (2) | HK17476A (cg-RX-API-DMAC7.html) |
| IE (1) | IE33208B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL31964A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1050158B (cg-RX-API-DMAC7.html) |
| MY (2) | MY7500104A (cg-RX-API-DMAC7.html) |
| NL (1) | NL151365B (cg-RX-API-DMAC7.html) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4072691A (en) * | 1974-01-12 | 1978-02-07 | Tanabe Seiyaku Co., Ltd. | Process for the resolution of DL-6-chlorotryptophan |
| US4198501A (en) * | 1977-12-20 | 1980-04-15 | Hoffmann-La Roche Inc. | Synthesis of tryptophans |
| JPS5758676U (cg-RX-API-DMAC7.html) * | 1980-09-25 | 1982-04-06 | ||
| JPS57131981U (cg-RX-API-DMAC7.html) * | 1981-02-12 | 1982-08-17 | ||
| JPS585582U (ja) * | 1981-07-01 | 1983-01-13 | 株式会社長谷川工務店 | 窓用額縁 |
| JPS5845849U (ja) * | 1981-09-25 | 1983-03-28 | フクビ化学工業株式会社 | ドア−、窓等の開口枠に取着する額縁材 |
| US4694017A (en) * | 1983-05-19 | 1987-09-15 | Otsuka Pharmaceutical Co., Ltd. | 2-amido 3(oxindol-3-yl)propionic acids having antiulcer activity |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1179933A (fr) * | 1955-08-01 | 1959-05-29 | Nouveau dérivé benzimidazolique et son procédé de préparation |
-
1969
- 1969-04-02 DK DK187769AA patent/DK139292B/da unknown
- 1969-04-03 GB GB07639/69A patent/GB1269851A/en not_active Expired
- 1969-04-03 IE IE457/69A patent/IE33208B1/xx unknown
- 1969-04-03 NL NL696905328A patent/NL151365B/xx unknown
- 1969-04-03 CY CY797A patent/CY797A/xx unknown
- 1969-04-03 CY CY796A patent/CY796A/xx unknown
- 1969-04-07 IL IL31964A patent/IL31964A/en unknown
- 1969-04-08 FR FR6910675A patent/FR2007414A1/fr not_active Withdrawn
- 1969-04-08 BE BE731141D patent/BE731141A/xx unknown
- 1969-04-08 IT IT36245/69A patent/IT1050158B/it active
- 1969-04-08 CH CH529969A patent/CH532369A/de not_active IP Right Cessation
- 1969-04-08 JP JP44027187A patent/JPS4816624B1/ja active Pending
-
1972
- 1972-08-23 JP JP47084398A patent/JPS5111628B1/ja active Pending
-
1975
- 1975-12-30 MY MY104/75A patent/MY7500104A/xx unknown
- 1975-12-30 MY MY105/75A patent/MY7500105A/xx unknown
-
1976
- 1976-03-25 HK HK174/76*UA patent/HK17476A/xx unknown
- 1976-03-25 HK HK173/76*UA patent/HK17376A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4816624B1 (cg-RX-API-DMAC7.html) | 1973-05-23 |
| HK17476A (en) | 1976-04-02 |
| GB1269851A (en) | 1972-04-06 |
| MY7500104A (en) | 1975-12-31 |
| IL31964A0 (en) | 1969-06-25 |
| DK139292C (cg-RX-API-DMAC7.html) | 1979-07-02 |
| DE1917844A1 (de) | 1969-11-06 |
| BE731141A (cg-RX-API-DMAC7.html) | 1969-10-08 |
| IT1050158B (it) | 1981-03-10 |
| IE33208B1 (en) | 1974-04-17 |
| HK17376A (en) | 1976-04-02 |
| MY7500105A (en) | 1975-12-31 |
| NL151365B (nl) | 1976-11-15 |
| JPS5111628B1 (cg-RX-API-DMAC7.html) | 1976-04-13 |
| NL6905328A (cg-RX-API-DMAC7.html) | 1969-10-10 |
| IE33208L (en) | 1969-10-08 |
| DK139292B (da) | 1979-01-29 |
| CY797A (en) | 1976-12-01 |
| CY796A (en) | 1976-12-01 |
| FR2007414A1 (cg-RX-API-DMAC7.html) | 1970-01-09 |
| DE1917844B2 (de) | 1976-11-04 |
| CH532369A (de) | 1973-01-15 |
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