AU2001248859A1 - Process for producing cinnamylaldehyde derivatives, use thereof and the like - Google Patents
Process for producing cinnamylaldehyde derivatives, use thereof and the likeInfo
- Publication number
- AU2001248859A1 AU2001248859A1 AU2001248859A AU4885901A AU2001248859A1 AU 2001248859 A1 AU2001248859 A1 AU 2001248859A1 AU 2001248859 A AU2001248859 A AU 2001248859A AU 4885901 A AU4885901 A AU 4885901A AU 2001248859 A1 AU2001248859 A1 AU 2001248859A1
- Authority
- AU
- Australia
- Prior art keywords
- hydroxy
- cinnamaldehyde
- derivative
- phenyl
- substituted
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/73—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Biophysics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Seasonings (AREA)
Abstract
There is provided an industrial process for conveniently and efficiently producing a highly pure cinnamaldehyde derivative, for example, (2E)-(3-hydroxy-4-methoxy)cinnamaldehyde, which comprises reacting a benzaldehyde derivative, such as isovanillin and the like, with acetaldehyde in the presence of an alkali, in particular preferably, dropping acetaldehyde little by little thereto in an aqueous solution at a low temperature for the reaction thereof. The cinnamaldehyde derivative thus obtained is selectively reduced to produce 3-(3-hydroxy-4-substituted (with methoxy group or the like)phenyl) propionaldehyde. Further, through a reductive alkylation reaction of the compound thus produced with an aspartame, N-ÄN-Ä3-(3-hydroxy-4-substituted (with methoxy group or the like)phenyl) propylÜ-L- alpha -aspartylÜ-L-phenylalanine 1-methyl ester, which is useful as a sweetener having a high sweetening potency, can be industrially and efficiently produced. The processes therefor are also provided.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000-142811 | 2000-05-16 | ||
JP2000142811 | 2000-05-16 | ||
PCT/JP2001/003545 WO2001087813A1 (en) | 2000-05-16 | 2001-04-24 | Process for producing cinnamylaldehyde derivatives, use thereof and the like |
Publications (1)
Publication Number | Publication Date |
---|---|
AU2001248859A1 true AU2001248859A1 (en) | 2001-11-26 |
Family
ID=18649714
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2001248859A Abandoned AU2001248859A1 (en) | 2000-05-16 | 2001-04-24 | Process for producing cinnamylaldehyde derivatives, use thereof and the like |
Country Status (10)
Country | Link |
---|---|
US (2) | US6965055B2 (en) |
EP (1) | EP1283197B1 (en) |
JP (1) | JP4706161B2 (en) |
KR (1) | KR100776924B1 (en) |
CN (1) | CN1252020C (en) |
AT (1) | ATE446308T1 (en) |
AU (1) | AU2001248859A1 (en) |
DE (1) | DE60140250D1 (en) |
ES (1) | ES2335193T3 (en) |
WO (1) | WO2001087813A1 (en) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100574684B1 (en) * | 2003-06-10 | 2006-04-28 | 한국생명공학연구원 | Cinnamaldehyde derivatives inhibiting growth of tumor cell and regulating cell cycle, preparations and pharmaceutical compositions thereof |
US9101160B2 (en) | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
US8017168B2 (en) | 2006-11-02 | 2011-09-13 | The Coca-Cola Company | High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
EP2088389B1 (en) * | 2008-02-05 | 2017-05-10 | Evonik Degussa GmbH | Absorption cooling machine |
CN103073403A (en) * | 2012-12-26 | 2013-05-01 | 淮安万邦香料工业有限公司 | Production process of anisyl propionaldehyde |
KR101356454B1 (en) | 2013-01-30 | 2014-02-04 | 강원대학교산학협력단 | Method of preparing unsaturated aldehyde compound |
IN2015CH02019A (en) | 2015-04-20 | 2015-06-05 | Divis Lab Ltd | |
CN109160875A (en) * | 2018-08-07 | 2019-01-08 | 华南理工大学 | A kind of sweetener intermediate 3- hydroxyl -4- methoxyl group-cinnamaldehyde and preparation method thereof |
CN108863745A (en) * | 2018-08-27 | 2018-11-23 | 上海华堇生物技术有限责任公司 | The preparation method of 3- hydroxycinnamaldehyde |
CN109020795A (en) * | 2018-08-27 | 2018-12-18 | 上海华堇生物技术有限责任公司 | The preparation method of 4- methoxycinnamic aldehyde |
CN109020794A (en) * | 2018-08-27 | 2018-12-18 | 上海华堇生物技术有限责任公司 | The preparation method of 3- methoxycinnamic aldehyde |
CN111875666B (en) * | 2020-07-07 | 2022-08-12 | 辽宁启康生物科技有限公司 | Method for synthesizing Edwarden sweet |
CN113620792A (en) * | 2021-08-09 | 2021-11-09 | 绵阳三香汇生物科技有限公司 | Preparation method of 3-hydroxy-4-methoxy phenylpropylaldehyde |
CN115403456B (en) * | 2022-09-22 | 2023-11-17 | 成都大学 | Method for synthesizing Edwan sweet intermediate 3-hydroxy-4-methoxy phenylpropionaldehyde |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2529186A (en) * | 1947-04-05 | 1950-11-07 | Us Rubber Co | Preparation of cinnamaldehyde |
FR2697844B1 (en) * | 1992-11-12 | 1995-01-27 | Claude Nofre | New compounds derived from dipeptides or dipeptide analogues useful as sweetening agents, process for their preparation. |
NL9401708A (en) * | 1994-10-17 | 1996-06-03 | Dsm Nv | Process for the preparation of 3-phenylpropanal. |
OA11537A (en) * | 1998-04-09 | 2004-05-24 | Ajinomoto Kk | Aspartyl dipeptide ester derivatives and sweeteners. |
CN1253423C (en) * | 1999-10-07 | 2006-04-26 | 味之素株式会社 | Process for production of aspartyl dipeptide ester derivative, novel production intermediate therefor, and process for production thereof |
AU1305201A (en) | 1999-11-18 | 2001-06-04 | Ajinomoto Co., Inc. | Novel intermediate for sweetener with high sweetness and process for producing the same |
KR20030045672A (en) * | 2000-05-10 | 2003-06-11 | 아지노모토 가부시키가이샤 | Process for producing aspartyl dipeptide ester derivatives |
-
2001
- 2001-04-24 AT AT01922073T patent/ATE446308T1/en not_active IP Right Cessation
- 2001-04-24 ES ES01922073T patent/ES2335193T3/en not_active Expired - Lifetime
- 2001-04-24 AU AU2001248859A patent/AU2001248859A1/en not_active Abandoned
- 2001-04-24 CN CNB018095348A patent/CN1252020C/en not_active Expired - Lifetime
- 2001-04-24 EP EP01922073A patent/EP1283197B1/en not_active Expired - Lifetime
- 2001-04-24 WO PCT/JP2001/003545 patent/WO2001087813A1/en active Application Filing
- 2001-04-24 JP JP2001584211A patent/JP4706161B2/en not_active Expired - Lifetime
- 2001-04-24 DE DE60140250T patent/DE60140250D1/en not_active Expired - Lifetime
- 2001-04-24 KR KR1020027015378A patent/KR100776924B1/en active IP Right Grant
-
2002
- 2002-11-18 US US10/295,997 patent/US6965055B2/en not_active Expired - Lifetime
-
2005
- 2005-06-17 US US11/154,658 patent/US7141263B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
ATE446308T1 (en) | 2009-11-15 |
ES2335193T3 (en) | 2010-03-23 |
US20030163004A1 (en) | 2003-08-28 |
DE60140250D1 (en) | 2009-12-03 |
US7141263B2 (en) | 2006-11-28 |
CN1252020C (en) | 2006-04-19 |
KR100776924B1 (en) | 2007-11-20 |
JP4706161B2 (en) | 2011-06-22 |
KR20020094954A (en) | 2002-12-18 |
CN1429193A (en) | 2003-07-09 |
EP1283197A4 (en) | 2004-05-26 |
EP1283197A1 (en) | 2003-02-12 |
US20050245759A1 (en) | 2005-11-03 |
WO2001087813A1 (en) | 2001-11-22 |
EP1283197B1 (en) | 2009-10-21 |
US6965055B2 (en) | 2005-11-15 |
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