Title:
PROCESS FOR PRODUCING CINNAMYLALDEHYDE DERIVATIVES, USE THEREOF AND THE LIKE
Document Type and Number:
WIPO Patent Application WO/2001/087813
Kind Code:
A1
Abstract:
An industrial process for conveniently and efficiently producing highly pure cinnamylaldehyde derivatives such as (2E)-(3-hydroxy-4-methoxy)cinnamylaldehyde which comprises reacting a benzaldehyde derivative (for example, isovanillin) with acetaldehyde in the presence of an alkali, preferably dropping acetaldehyde in portions in an aqueous solution at a low temperature. The cinnamylaldehyde derivatives thus obtained are selectively reduced into 3-(3-hydroxy-4-substituted(methoxy, etc.)phenyl)propionaldehydes. These compounds are further subjected to reductive alkylation with aspartame. Thus N-[N-[3-(3-hydroxy-4-substituted(methoxy, etc.)phenyl)propyl]-L-$g(a)-aspartyl]-L-phenylalanine 1-methyl esters, which are useful as sweeteners with high sweetness, can be efficiently produced. These processes are also provided.
Inventors:
MORI KENICHI (JP)
FUJITA SHINJI (JP)
FUNAKOSHI NAO (JP)
TAKEMOTO TADASHI (JP)
FUJITA SHINJI (JP)
FUNAKOSHI NAO (JP)
TAKEMOTO TADASHI (JP)
Application Number:
PCT/JP2001/003545
Publication Date:
November 22, 2001
Filing Date:
April 24, 2001
Export Citation:
Assignee:
AJINOMOTO KK (JP)
MORI KENICHI (JP)
FUJITA SHINJI (JP)
FUNAKOSHI NAO (JP)
TAKEMOTO TADASHI (JP)
MORI KENICHI (JP)
FUJITA SHINJI (JP)
FUNAKOSHI NAO (JP)
TAKEMOTO TADASHI (JP)
International Classes:
C07C45/62; C07C45/73; C07C45/74; C07C47/277; C07K5/072; C07K5/075; A23L27/30; (IPC1-7): C07C45/74; C07C47/27; C07C47/277; C07C45/62; C07K5/075; C07K1/02
Domestic Patent References:
| WO1999052937A1 | 1999-10-21 | |||
| WO2001025260A1 | 2001-04-12 |
Other References:
BRUCE J. MALCOLM ET AL.: "Light-induced and related reactions of quinones", J. CHEM. SOC. C, vol. 5, 1970, pages 649 - 653, XP002943454
DURAN E. ET AL.: "Synthese des aldehydes para-hydroxycinnamiques substrats de l'alcool cinnamylique deshydrogenase", HOLZFORSCHUNG, vol. 46, 1992, pages 21 - 24, XP002943455
DURAN E. ET AL.: "Synthese des aldehydes para-hydroxycinnamiques substrats de l'alcool cinnamylique deshydrogenase", HOLZFORSCHUNG, vol. 46, 1992, pages 21 - 24, XP002943455
Attorney, Agent or Firm:
Ishida, Yasumasa (7th Floor 20-12 Shin-Yokohama 3-chome Kohoku-ku, Yokohama-shi Kanagawa-ken, JP)
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