Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1988-12-27
1990-03-13
Hollrah, Glennon H.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514330, 546221, C07D21174
Patent
active
049083732
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to 1-[2-(4-hydroxybenzoyl)ethanoyl]-2-piperidone represented by structural formula (I): ##STR1## and a process for production as well as an alcohol fermentation promoter containing the same as effective ingredient.
BACKGROUND
Alcohol fermentation is known from old in fermentation of alcohols such as Japanese sake, beer, wine, etc. In recent years, the alcohol fermentation has also been applied to preparation of energy alcohol as biofuel, as a substitute for petroleum.
In alcohol fermentation as biofuel, fermentation should efficiently be performed using inexpensive starchy raw materials from a standpoint of preparation of alcohol fuel and, survey of cheap raw materials of development and investigations on excellent various yeasts have been extensively made.
On the other hand, development has also been made from fermentation engineering, in which yeast cells are immobilized to prepare alcohol continuously and efficiently.
However, these techniques are all insufficient for improving fermentation efficiency to such an extent that they could achieve any economical effect. Under the actual situation, alcohol fermentation as biofuel still remains at the stage of research.
The present inventors previously began to work on physiologically active substances for plant, synthesized a variety of compounds and found that N-acyl lactam compounds were excellent as active substances (Japanese Patent Application Laid Open No. 61-246105). As a result of further investigations, they have found that 1-[2-(4-hydroxybenzoyl)ethanoyl]-2-piperidone of the present invention, which is a novel N-acyl lactam compound, shows an excellent fermentation promotive capacity and have accomplished the present invention, based on such a finding.
DISCLOSURE OF THE INVENTION
That is, the present invention relates to 1-[2-(4-hydroxybenzoyl)ethanoyl]-2-piperidone represented by structural formula (I): ##STR2## and a process for production as well as an alcohol fermentation promoter containing the same as effective ingredient.
1-[2-(4-Hydroxybenzoyl)ethanoyl]-2-piperidone of the present invention is a novel compound and exhibits as an alcohol fermentation promoter an excellent fermentation promoting effect that is hitherto unknown.
Hereafter the present invention will be described in detail.
1-[2-(4-Hydroxybenzoyl)ethanoyl]-2-piperidone of the present invention is a novel compound, which structural formula (I) is represented by: ##STR3##
A process for producing the compound is described below. The compound can be prepared by converting a compound represented by structural formula (II): ##STR4## into the acid chloride, then coupling the acid chloride with 2-piperidone or an alkylate of 2-piperidone and then subjecting to debenzylation.
This compound (II) can be obtained, for example, by the following process. Firstly, using methyl 4-hydroxybenzoate, the hydroxyl group is benzylated with benzyl chloride to obtain methyl 4-benzyloxybenzoate. Next, the benzylated compound is hydrolyzed to obtain 4-benzyloxybenzoic acid. The acid is converted into the acid chloride to give 4-benzyloxybenzoyl chloride. 4-Benzyloxybenzoyl chloride is reacted with monoanion of bistrimethylsilyl malonate and water is added to the reaction product to effect hydrolysis and decarbonation, whereby the compound represented by structural formula (II) can be obtained. The reaction in this case may be carried out in a manner described in J. W. F. K. Barnick et al., Synthesis, No. 10, 787-788 (1979).
The compound (II) which can readily be obtained by such a well known process is then provided to the reaction of converting into the acid chloride.
For conversion into the acid chloride, thionyl chloride, phosphorus pentachloride, phosphorus trichloride, oxalyl chloride, etc. can be used, but in view of preventing formation of by-products, it is desired to use oxalyl chloride.
Further as a solvent used in this case, dry benzene and dry tetrahydrofuran (hereafter simply referred to as THF) are desired to prevent formation of by
Maekawa Yoshio
Mizuno Hironori
Okumura Minoru
Yagiyu Osamu
Hollrah Glennon H.
Taki Chemical Co. Ltd.
Trinh Ba K.
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