JPH10500403A - 甘味剤として有用なN−[N−(3,3−ジメチルブチル)−L−α−アスパルチル]−L−ヘキサヒドロフェニルアラニン1−メチルエステル、その製造方法 - Google Patents
甘味剤として有用なN−[N−(3,3−ジメチルブチル)−L−α−アスパルチル]−L−ヘキサヒドロフェニルアラニン1−メチルエステル、その製造方法Info
- Publication number
- JPH10500403A JPH10500403A JP7528725A JP52872595A JPH10500403A JP H10500403 A JPH10500403 A JP H10500403A JP 7528725 A JP7528725 A JP 7528725A JP 52872595 A JP52872595 A JP 52872595A JP H10500403 A JPH10500403 A JP H10500403A
- Authority
- JP
- Japan
- Prior art keywords
- aspartame
- hexahydrophenylalanine
- aspartyl
- dimethylbutyl
- methyl ester
- 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.)
- Granted
Links
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- VOMXSOIBEJBQNF-UTTRGDHVSA-N novorapid Chemical compound C([C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CS)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CS)NC(=O)[C@H](CS)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(O)=O)C1=CC=C(O)C=C1.C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CS)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 VOMXSOIBEJBQNF-UTTRGDHVSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000011548 physical evaluation Methods 0.000 description 1
- 239000001259 polydextrose Substances 0.000 description 1
- 235000013856 polydextrose Nutrition 0.000 description 1
- 229940035035 polydextrose Drugs 0.000 description 1
- 238000000247 postprecipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 235000019204 saccharin Nutrition 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
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 210000000697 sensory organ Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 150000003398 sorbic acids Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940013618 stevioside Drugs 0.000 description 1
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 description 1
- 235000019202 steviosides Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000000892 thaumatin Substances 0.000 description 1
- 235000010436 thaumatin Nutrition 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Seasonings (AREA)
- Peptides Or Proteins (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. 下記式: で表されるN−[N−(3,3−ジメチルブチル)−L−α−アスパルチル]− L−ヘキサヒドロフェニルアラニン1−メチルエステルであることを特徴とする 甘味化合物。 2. 室温におけるアスパルテーム及び3,3−ジメチルブチルアルデヒドから なる溶液を白金系触媒の存在下に、3バールの相対圧力下に水素で処理すること を特徴とする下記式: で表されるN−[N−(3,3−ジメチルブチル)−L−α−アスパルチル]− L−ヘキサヒドロフェニルアラニン1−メチルエステルの製造方法。 3. 触媒が、白金黒又は酸化白金である請求の範囲第2項記載の方法。 4. アスパルテーム及び3,3−ジメチルブチルアルデヒドからなる溶液が、 0.1M酢酸とメタノールの混合により得られるpH4.5〜5の水性/アルコ ール性溶液である請求の範囲第2項及び第3項記載の方法。 5. 水性/アルコール性溶液中におけるアスパルテームの濃度が、50〜60 g/lであり、3,3−ジメチルブチルアルデヒドの濃度が、20〜30g/l である請求の範囲第2〜4項記載の方法。 6. 生成物が、溶媒のアルコール部分の減圧蒸発の後に、沈殿及び濾過により 精製されるものである請求の範囲第2〜5項記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR94/05675 | 1994-05-09 | ||
FR9405675A FR2719591B1 (fr) | 1994-05-09 | 1994-05-09 | Nouveau composé utile comme agent édulcorant, son procédé de préparation. |
PCT/FR1995/000588 WO1995030688A1 (fr) | 1994-05-09 | 1995-05-05 | N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-HEXAHYDROPHENYLALANINE 1-METHYL ESTER UTILE COMME AGENT EDULCORANT, SON PROCEDE DE PREPARATION |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH10500403A true JPH10500403A (ja) | 1998-01-13 |
JP3627062B2 JP3627062B2 (ja) | 2005-03-09 |
Family
ID=9463025
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP52872595A Expired - Fee Related JP3627062B2 (ja) | 1994-05-09 | 1995-05-05 | 甘味剤として有用なN−[N−(3,3−ジメチルブチル)−L−α−アスパルチル]−L−ヘキサヒドロフェニルアラニン1−メチルエステル、その製造方法 |
Country Status (15)
Country | Link |
---|---|
US (1) | US5773640A (ja) |
EP (1) | EP0759030B1 (ja) |
JP (1) | JP3627062B2 (ja) |
CN (1) | CN1147818A (ja) |
AT (1) | ATE170872T1 (ja) |
AU (1) | AU2528495A (ja) |
BR (1) | BR9507628A (ja) |
CA (1) | CA2189558A1 (ja) |
DE (1) | DE69504651T2 (ja) |
DK (1) | DK0759030T3 (ja) |
ES (1) | ES2123984T3 (ja) |
FR (1) | FR2719591B1 (ja) |
HK (1) | HK1012407A1 (ja) |
RU (1) | RU2138511C1 (ja) |
WO (1) | WO1995030688A1 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11169132A (ja) * | 1997-12-15 | 1999-06-29 | Ajinomoto Co Inc | アスパルテームとアスパルテーム誘導体の混晶及びその製造方法 |
US6692778B2 (en) * | 1998-06-05 | 2004-02-17 | Wm. Wrigley Jr. Company | Method of controlling release of N-substituted derivatives of aspartame in chewing gum |
HUP0103426A3 (en) * | 1998-06-26 | 2004-09-28 | Ajinomoto Kk | Novel aspartyl dipeptide ester derivatives and sweeteners |
BR9914838A (pt) * | 1998-10-30 | 2001-08-14 | Ajinomoto Kk | Processo para preparar cristais altamente estáveis (cristais do tipo a) de éster metìlico de n-[n-(3,3-dimetilbutil)-l-alfa-aspartil]-l-fenilalanina |
KR20010075419A (ko) * | 1998-10-30 | 2001-08-09 | 에가시라 구니오 | 안정성이 우수한 아스파르탐 유도체 결정의 결정 석출법 |
US6844465B2 (en) | 1998-10-30 | 2005-01-18 | Ajinomoto Co., Inc. | Method for preparing highly stable crystals of aspartame derivative |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1258248A (ja) * | 1968-07-17 | 1971-12-22 | ||
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. |
-
1994
- 1994-05-09 FR FR9405675A patent/FR2719591B1/fr not_active Expired - Lifetime
-
1995
- 1995-05-05 JP JP52872595A patent/JP3627062B2/ja not_active Expired - Fee Related
- 1995-05-05 US US08/737,138 patent/US5773640A/en not_active Expired - Fee Related
- 1995-05-05 DK DK95919483T patent/DK0759030T3/da active
- 1995-05-05 CN CN95192974A patent/CN1147818A/zh active Pending
- 1995-05-05 ES ES95919483T patent/ES2123984T3/es not_active Expired - Lifetime
- 1995-05-05 AT AT95919483T patent/ATE170872T1/de not_active IP Right Cessation
- 1995-05-05 CA CA002189558A patent/CA2189558A1/en not_active Abandoned
- 1995-05-05 DE DE69504651T patent/DE69504651T2/de not_active Expired - Fee Related
- 1995-05-05 RU RU96123232A patent/RU2138511C1/ru active
- 1995-05-05 BR BR9507628A patent/BR9507628A/pt not_active Application Discontinuation
- 1995-05-05 EP EP95919483A patent/EP0759030B1/fr not_active Expired - Lifetime
- 1995-05-05 WO PCT/FR1995/000588 patent/WO1995030688A1/fr active IP Right Grant
- 1995-05-05 AU AU25284/95A patent/AU2528495A/en not_active Abandoned
-
1998
- 1998-12-16 HK HK98113670A patent/HK1012407A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE69504651D1 (de) | 1998-10-15 |
JP3627062B2 (ja) | 2005-03-09 |
EP0759030B1 (fr) | 1998-09-09 |
ES2123984T3 (es) | 1999-01-16 |
AU2528495A (en) | 1995-11-29 |
DK0759030T3 (da) | 1999-06-07 |
ATE170872T1 (de) | 1998-09-15 |
HK1012407A1 (en) | 1999-07-30 |
RU2138511C1 (ru) | 1999-09-27 |
US5773640A (en) | 1998-06-30 |
EP0759030A1 (fr) | 1997-02-26 |
FR2719591A1 (fr) | 1995-11-10 |
BR9507628A (pt) | 1997-09-23 |
WO1995030688A1 (fr) | 1995-11-16 |
CN1147818A (zh) | 1997-04-16 |
FR2719591B1 (fr) | 1996-07-26 |
DE69504651T2 (de) | 1999-04-08 |
CA2189558A1 (en) | 1995-11-16 |
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