BR9814091A - Processo para a separação e purificação de n- [ n- (3,3-dimetilbutil) -l-alfa-aspartil] -l-fenilalanina metil éster, processo para a produção de n- [n- (3,3-dimetilbutil) -l-alfa-aspartil] - l-fenilalanina metil éster ou a produção de n- [n- (3,3-dimetilbutil) -l-alfa-aspartil] -l-fenilalanina metil éster e n,n-di(3,3-dimetilbutil) -apm, derivado de apm, e, adoçante - Google Patents
Processo para a separação e purificação de n- [ n- (3,3-dimetilbutil) -l-alfa-aspartil] -l-fenilalanina metil éster, processo para a produção de n- [n- (3,3-dimetilbutil) -l-alfa-aspartil] - l-fenilalanina metil éster ou a produção de n- [n- (3,3-dimetilbutil) -l-alfa-aspartil] -l-fenilalanina metil éster e n,n-di(3,3-dimetilbutil) -apm, derivado de apm, e, adoçanteInfo
- Publication number
- BR9814091A BR9814091A BR9814091-4A BR9814091A BR9814091A BR 9814091 A BR9814091 A BR 9814091A BR 9814091 A BR9814091 A BR 9814091A BR 9814091 A BR9814091 A BR 9814091A
- Authority
- BR
- Brazil
- Prior art keywords
- dimethylbutyl
- methyl ester
- apm
- phenylalanine methyl
- alpha
- Prior art date
Links
- -1 3,3-dimethylbutyl Chemical group 0.000 title abstract 10
- 229960004717 insulin aspart Drugs 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 4
- 238000000746 purification Methods 0.000 title abstract 4
- 238000000926 separation method Methods 0.000 title abstract 4
- 235000003599 food sweetener Nutrition 0.000 title abstract 3
- 239000003765 sweetening agent Substances 0.000 title abstract 3
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 abstract 5
- 108010011485 Aspartame Proteins 0.000 abstract 4
- 239000000605 aspartame Substances 0.000 abstract 4
- 229960003438 aspartame Drugs 0.000 abstract 4
- 235000010357 aspartame Nutrition 0.000 abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 2
- 238000005932 reductive alkylation reaction Methods 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- HLIAVLHNDJUHFG-HOTGVXAUSA-N neotame Chemical compound CC(C)(C)CCN[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-HOTGVXAUSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 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 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
- A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
''PROCESSO PARA A SEPARAçãO E PURIFICAçãO DE N-[N-(3,3-DIMETILBUTIL)-L-ALFA-ASPARTIL]-L-FENILALANINA METIL éSTER, PROCESSO PARA A PRODUçãO DE N-[N-(3,3-DIMETILBUTIL)-L-ALFA-ASPARTIL]-L-FENILALANINA METIL éSTER OU A PRODUçãO DE N-[N-(3,3-DIMETILBUTIL)-L-ALFA-ASPARTIL]-L-FENILALANINA METIL éSTER E N,N-DI(3,3-DIMETILBUTIL)-APM, DERIVADO DE APM, E, ADOçANTE''. Na separação e purificação do N-[N-(3,3-dimetilbutil) -L-<244>-aspartil]-L-fenilalanina metil éster produzido na alquilação redutiva do aspartame (APM) com 3,3-dimetilbutilaldeído, sendo que o APM utilizado no material inicial para a alquilação, que é difícil de ser separado por meio de recristalização apenas dos cristais brutos do produto de reação, pode ser separado e removido por meio de extração ou solução do mesmo, com o solvente orgânico especificado, da solução de reação concentrada da alquilação redutiva e, adicionalmente, o N,N-di(3,3-dimetilbutil)-APM, como o subproduto, pode ser separado e removido por meio de separação e purificação, como a cristalização, cromatografia, extração, tratamento com carvão ativado, etc. Como um resultado, o N-[N-(3,3-dimetilbutil)-L-<244>-aspartil]-L-fenilalanina metil éster, que é um adoçante com um alto grau de edulcoramento, pode ser purificado eficientemente, e também o derivado de APM é possivelmente produzido industrialmente com um alto grau de pureza.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9290216A JPH11130794A (ja) | 1997-10-23 | 1997-10-23 | アスパルテーム誘導体の精製方法 |
| PCT/JP1998/004783 WO1999020648A1 (en) | 1997-10-23 | 1998-10-21 | Process for the purification of aspartame derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BR9814091A true BR9814091A (pt) | 2000-10-03 |
Family
ID=17753266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR9814091-4A BR9814091A (pt) | 1997-10-23 | 1998-10-21 | Processo para a separação e purificação de n- [ n- (3,3-dimetilbutil) -l-alfa-aspartil] -l-fenilalanina metil éster, processo para a produção de n- [n- (3,3-dimetilbutil) -l-alfa-aspartil] - l-fenilalanina metil éster ou a produção de n- [n- (3,3-dimetilbutil) -l-alfa-aspartil] -l-fenilalanina metil éster e n,n-di(3,3-dimetilbutil) -apm, derivado de apm, e, adoçante |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6335461B1 (pt) |
| EP (1) | EP1081158A1 (pt) |
| JP (1) | JPH11130794A (pt) |
| KR (1) | KR20010024551A (pt) |
| CN (1) | CN1276795A (pt) |
| BR (1) | BR9814091A (pt) |
| CA (1) | CA2301688A1 (pt) |
| HU (1) | HUP0004030A3 (pt) |
| SK (1) | SK5612000A3 (pt) |
| WO (1) | WO1999020648A1 (pt) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL1010063C2 (nl) * | 1998-09-10 | 2000-03-13 | Holland Sweetener Co | Werkwijze voor de bereiding van neotaam. |
| US6914151B1 (en) | 1998-10-30 | 2005-07-05 | Ajinomoto Co., Inc. | Crystallization processes for the formation of stable crystals of aspartame derivative |
| AU2158700A (en) * | 1998-11-25 | 2000-06-19 | Nutrasweet Company, The | Process for purification of N- (N-(3,3-dimethylbutyl) -l-alpha-aspartyl) -l-phenylalanine 1-methyl ester |
| WO2000052019A2 (en) * | 1999-03-03 | 2000-09-08 | The Nutrasweet Company | Crystallization products of neotame and methods for producing 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 |
| AU4884101A (en) * | 2000-05-10 | 2001-11-20 | Ajinomoto Co., Inc. | Process for producing aspartyl dipeptide ester derivatives |
| US6281380B1 (en) * | 2000-05-18 | 2001-08-28 | The Nutra Sweet Company | Synthesis of N-(N-(3,3-dimethylbutyl)-L-α-aspartyl)L-phenylalanine1-methyl ester by reductive alkylation and crystallization/ isolation in aqueous methanol |
| US8962698B2 (en) | 2011-01-28 | 2015-02-24 | Tate & Lyle Ingredients Americas Llc | Rebaudioside-mogroside V blends |
| PL3395184T3 (pl) | 2011-01-28 | 2025-11-17 | Tate & Lyle Solutions Usa Llc | Mieszanki stewii zawierające rebaudiozyd B |
| GB201217700D0 (en) | 2012-08-01 | 2012-11-14 | Tate & Lyle Ingredients | Sweetener compositions containing rebaudioside B |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4017472A (en) * | 1973-03-05 | 1977-04-12 | G. D. Searle & Co. | Process for isolation of aspartyl dipeptide esters |
| US3901871A (en) * | 1973-09-21 | 1975-08-26 | American Cyanamid Co | Process of preparing ' -l-aspartyl-l-phenylalanine methyl ester |
| US4440667A (en) * | 1982-07-02 | 1984-04-03 | Exxon Research And Engineering Co. | Catalyst regeneration in a catalytic reforming process |
| US5055588A (en) * | 1988-07-06 | 1991-10-08 | Daicel Chemical Industries Ltd. | Process for preparing N-substituted amino acid esters |
| 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. |
| US5286415A (en) | 1992-12-28 | 1994-02-15 | Advanced Products, Inc. | Water-based polymer thick film conductive ink |
| 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. |
| US5728862A (en) | 1997-01-29 | 1998-03-17 | The Nutrasweet Company | Method for preparing and purifying an N-alkylated aspartame derivative |
| JP3651162B2 (ja) | 1997-03-10 | 2005-05-25 | 味の素株式会社 | 甘味料組成物 |
| JP3651161B2 (ja) * | 1997-03-10 | 2005-05-25 | 味の素株式会社 | 改善された呈味を有する甘味料組成物 |
| 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 |
-
1997
- 1997-10-23 JP JP9290216A patent/JPH11130794A/ja active Pending
-
1998
- 1998-10-21 HU HU0004030A patent/HUP0004030A3/hu unknown
- 1998-10-21 KR KR1020007004369A patent/KR20010024551A/ko not_active Withdrawn
- 1998-10-21 SK SK561-2000A patent/SK5612000A3/sk unknown
- 1998-10-21 EP EP98967118A patent/EP1081158A1/en not_active Withdrawn
- 1998-10-21 CA CA002301688A patent/CA2301688A1/en not_active Abandoned
- 1998-10-21 BR BR9814091-4A patent/BR9814091A/pt not_active IP Right Cessation
- 1998-10-21 CN CN98810383A patent/CN1276795A/zh active Pending
- 1998-10-21 WO PCT/JP1998/004783 patent/WO1999020648A1/ja not_active Ceased
-
2000
- 2000-02-29 US US09/515,097 patent/US6335461B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11130794A (ja) | 1999-05-18 |
| WO1999020648A1 (en) | 1999-04-29 |
| CN1276795A (zh) | 2000-12-13 |
| US6335461B1 (en) | 2002-01-01 |
| HUP0004030A3 (en) | 2001-04-28 |
| CA2301688A1 (en) | 1999-04-29 |
| SK5612000A3 (en) | 2000-10-09 |
| HUP0004030A2 (en) | 2001-03-28 |
| KR20010024551A (ko) | 2001-03-26 |
| EP1081158A1 (en) | 2001-03-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B08F | Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette] |
Free format text: REFERENTE A 6A,7A,8A E 9A ANUIDADES. |
|
| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: REFERENTE AO DESPACHO 8.6 PUBLICADO NA RPI 1910 DE 14/08/2007. |
|
| B15K | Others concerning applications: alteration of classification |
Free format text: PROCEDIMENTO AUTOMATICO DE RECLASSIFICACAO. AS CLASSIFICACOES IPC ANTERIORES ERAM: C07K 5/075; C07K 1/14; C07K 1/16; A23L 1/236. Ipc: C07K 5/072 (2006.01), A23L 27/30 (2016.01) Ipc: C07K 5/072 (2006.01), A23L 27/30 (2016.01) |