ZA200006876B - Novel aspartyl dipeptide ester derivatives and sweeteners. - Google Patents
Novel aspartyl dipeptide ester derivatives and sweeteners. Download PDFInfo
- Publication number
- ZA200006876B ZA200006876B ZA200006876A ZA200006876A ZA200006876B ZA 200006876 B ZA200006876 B ZA 200006876B ZA 200006876 A ZA200006876 A ZA 200006876A ZA 200006876 A ZA200006876 A ZA 200006876A ZA 200006876 B ZA200006876 B ZA 200006876B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- derivatives
- methyl
- hydrogen atoms
- hydroxyl
- Prior art date
Links
- -1 aspartyl Chemical group 0.000 title claims description 18
- 108010016626 Dipeptides Proteins 0.000 title claims description 7
- 150000002148 esters Chemical class 0.000 title claims description 7
- 235000003599 food sweetener Nutrition 0.000 title description 8
- 239000003765 sweetening agent Substances 0.000 title description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 2
- 239000004067 bulking agent Substances 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 12
- 235000010357 aspartame Nutrition 0.000 description 7
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical group OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 6
- 229960005190 phenylalanine Drugs 0.000 description 4
- FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 description 3
- 108010011485 Aspartame Proteins 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 239000000605 aspartame Substances 0.000 description 3
- 229960003438 aspartame Drugs 0.000 description 3
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 2
- HLIAVLHNDJUHFG-UHFFFAOYSA-N neotame Chemical compound CC(C)(C)CCNC(CC(O)=O)C(=O)NC(C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-UHFFFAOYSA-N 0.000 description 2
- 229960004441 tyrosine Drugs 0.000 description 2
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N 3-phenylprop-2-enal Chemical class O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 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
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
-
- 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
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
-
- 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
- A23L27/30—Artificial sweetening agents
- A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
- A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
-
- 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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
- A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Peptides Or Proteins (AREA)
- Seasonings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18020498 | 1998-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200006876B true ZA200006876B (en) | 2001-05-17 |
Family
ID=16079227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200006876A ZA200006876B (en) | 1998-06-26 | 2000-11-23 | Novel aspartyl dipeptide ester derivatives and sweeteners. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6630191B1 (sk) |
| EP (1) | EP1088829A4 (sk) |
| KR (1) | KR100631306B1 (sk) |
| CN (1) | CN1192036C (sk) |
| AR (1) | AR020095A1 (sk) |
| AU (1) | AU752473B2 (sk) |
| BR (1) | BR9911551B1 (sk) |
| CA (1) | CA2336133A1 (sk) |
| HU (1) | HUP0103426A3 (sk) |
| IL (1) | IL139657A0 (sk) |
| NO (1) | NO20006627L (sk) |
| NZ (1) | NZ508579A (sk) |
| OA (1) | OA11695A (sk) |
| PL (1) | PL345019A1 (sk) |
| RU (1) | RU2192430C2 (sk) |
| SK (1) | SK19792000A3 (sk) |
| TR (1) | TR200003750T2 (sk) |
| TW (1) | TWI221155B (sk) |
| UA (1) | UA64803C2 (sk) |
| WO (1) | WO2000000508A1 (sk) |
| ZA (1) | ZA200006876B (sk) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2383137A1 (en) | 1999-09-07 | 2001-03-15 | Ajinomoto Co., Inc. | Method for producing aspartame derivative, method for purifying the same, crystals thereof and uses of the same |
| JP2001097998A (ja) * | 1999-10-01 | 2001-04-10 | Ajinomoto Co Inc | アスパルチルジペプチドエステル誘導体及び甘味剤 |
| EP1221448A4 (en) | 1999-10-04 | 2003-01-15 | Ajinomoto Kk | HIGH-SWEETENESS SWEETENER COMPOSITIONS WITH INCREASED SWEETENESS POWER, TASTE CORRECTORS AND THEIR USE |
| WO2001025260A1 (fr) * | 1999-10-07 | 2001-04-12 | Ajinomoto Co., Inc. | Procede de production de derives esters aspartyldipeptidiques, nouveaux intermediaires correspondants et procede de production de ces intermediaires |
| CN1378558A (zh) | 1999-10-07 | 2002-11-06 | 味之素株式会社 | 天冬甜素衍生物的制造及精制方法以及中间体的生产制造方法 |
| EP1219633A4 (en) * | 1999-10-08 | 2004-10-20 | Ajinomoto Kk | PROCESS FOR PRODUCING ASPARTAME DERIVATIVE, CRYSTALS THEREOF, PRODUCTION OF NEW ASSOCIATED INTERMEDIATES AND PROCESS FOR PRODUCING INTERMEDIATE |
| JP3747737B2 (ja) * | 2000-05-10 | 2006-02-22 | 日本電気株式会社 | 広域精細画像生成方法及びシステム並びにコンピュータ可読記録媒体 |
| KR20030045672A (ko) * | 2000-05-10 | 2003-06-11 | 아지노모토 가부시키가이샤 | 아스파르틸 디펩타이드 에스테르 유도체의 제조방법 |
| JPWO2002062746A1 (ja) * | 2001-02-08 | 2004-06-03 | 味の素株式会社 | 新規ｎ−アルキルアスパルチルアミド誘導体及び甘味剤 |
| US7288527B2 (en) * | 2004-04-27 | 2007-10-30 | Oklahoma Medical Research Foundation | Inhibition of allergic contact dermatitis by N-L-alpha-aspartyl-L-phenylalanine 1-methyl ester |
| CN101430687B (zh) | 2007-11-09 | 2015-11-25 | 阿里巴巴集团控股有限公司 | 基于oltp环境的统计表应用方法及系统 |
| CN102206245A (zh) * | 2011-01-17 | 2011-10-05 | 汪志强 | 一种甜味剂艾克·本甜的制备方法及其在饲料领域的用途 |
| WO2016009686A1 (ja) * | 2014-07-16 | 2016-01-21 | 味の素株式会社 | 風味の向上した食肉及び食肉加工品並びにその製造方法 |
| CN109535225A (zh) * | 2018-11-22 | 2019-03-29 | 暨南大学 | 一种化合物及其合成方法与应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2653303B1 (fr) * | 1989-10-24 | 1992-09-18 | Noffre Claude | Agents edulcorants de grande stabilite derivant des acides l-aspartique et l-glutamique n-hydrocarbones 1-oxo-2-ramifies. |
| FR2697844B1 (fr) | 1992-11-12 | 1995-01-27 | Claude Nofre | Nouveaux composés dérivés de dipeptides ou d'analogues dipeptidiques utiles comme agents édulcorants, leur procédé de préparation. |
| FR2719590B1 (fr) * | 1994-05-09 | 1996-07-26 | Claude Nofre | Procédé perfectionné de préparation d'un composé dérivé de l'aspartame utile comme agent édulcorant. |
| FR2719591B1 (fr) | 1994-05-09 | 1996-07-26 | Claude Nofre | Nouveau composé utile comme agent édulcorant, son procédé de préparation. |
| JPH10259194A (ja) | 1997-03-18 | 1998-09-29 | Ajinomoto Co Inc | 新規ジペプチド誘導体及び甘味剤 |
| US6129942A (en) * | 1997-09-11 | 2000-10-10 | The Nutrasweet Company | Sweetener salts of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester |
| RU2179979C1 (ru) * | 1998-04-09 | 2002-02-27 | Адзиномото Ко., Инк. | Сложноэфирные производные аспартилдипептидов и подслащивающие вещества |
-
1999
- 1999-06-07 AU AU40602/99A patent/AU752473B2/en not_active Ceased
- 1999-06-07 RU RU2001102399/04A patent/RU2192430C2/ru not_active IP Right Cessation
- 1999-06-07 KR KR1020007014661A patent/KR100631306B1/ko not_active IP Right Cessation
- 1999-06-07 NZ NZ508579A patent/NZ508579A/xx unknown
- 1999-06-07 IL IL13965799A patent/IL139657A0/xx not_active IP Right Cessation
- 1999-06-07 CA CA002336133A patent/CA2336133A1/en not_active Abandoned
- 1999-06-07 OA OA1200000358A patent/OA11695A/en unknown
- 1999-06-07 BR BRPI9911551-4A patent/BR9911551B1/pt not_active IP Right Cessation
- 1999-06-07 WO PCT/JP1999/003050 patent/WO2000000508A1/ja not_active Application Discontinuation
- 1999-06-07 PL PL99345019A patent/PL345019A1/xx not_active Application Discontinuation
- 1999-06-07 CN CNB998079022A patent/CN1192036C/zh not_active Expired - Fee Related
- 1999-06-07 HU HU0103426A patent/HUP0103426A3/hu unknown
- 1999-06-07 TR TR2000/03750T patent/TR200003750T2/xx unknown
- 1999-06-07 EP EP99923954A patent/EP1088829A4/en not_active Withdrawn
- 1999-06-07 SK SK1979-2000A patent/SK19792000A3/sk unknown
- 1999-06-10 TW TW088109715A patent/TWI221155B/zh not_active IP Right Cessation
- 1999-06-24 AR ARP990103036A patent/AR020095A1/es unknown
- 1999-07-06 UA UA2001010584A patent/UA64803C2/uk unknown
-
2000
- 2000-11-23 ZA ZA200006876A patent/ZA200006876B/en unknown
- 2000-12-15 US US09/736,149 patent/US6630191B1/en not_active Expired - Lifetime
- 2000-12-22 NO NO20006627A patent/NO20006627L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000000508A1 (fr) | 2000-01-06 |
| SK19792000A3 (sk) | 2001-07-10 |
| US6630191B1 (en) | 2003-10-07 |
| TR200003750T2 (tr) | 2001-06-21 |
| IL139657A0 (en) | 2002-02-10 |
| EP1088829A1 (en) | 2001-04-04 |
| KR20010034924A (ko) | 2001-04-25 |
| BR9911551B1 (pt) | 2010-09-21 |
| NO20006627D0 (no) | 2000-12-22 |
| UA64803C2 (uk) | 2004-03-15 |
| NO20006627L (no) | 2001-02-12 |
| CN1307585A (zh) | 2001-08-08 |
| TWI221155B (en) | 2004-09-21 |
| PL345019A1 (en) | 2001-11-19 |
| HUP0103426A2 (hu) | 2002-01-28 |
| KR100631306B1 (ko) | 2006-10-09 |
| HUP0103426A3 (en) | 2004-09-28 |
| OA11695A (en) | 2005-01-13 |
| CA2336133A1 (en) | 2000-01-06 |
| CN1192036C (zh) | 2005-03-09 |
| RU2192430C2 (ru) | 2002-11-10 |
| AU4060299A (en) | 2000-01-17 |
| EP1088829A4 (en) | 2005-02-02 |
| RU2001102399A (ru) | 2004-03-20 |
| AR020095A1 (es) | 2002-04-10 |
| BR9911551A (pt) | 2001-10-09 |
| NZ508579A (en) | 2002-10-25 |
| AU752473B2 (en) | 2002-09-19 |
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