Process for the preparation of naphthalen-2-yl-pyrazol-3-one intermediates useful in the synthesis of sigma receptor inhibitors
申请人:Laboratorios Del. Dr. Esteve, S.A.
公开号:EP2112139A1
公开(公告)日:2009-10-28
The invention relates to a process for preparing naphthalen-2-yl-pyrazol-3-one intermediates, tautomers, and salts thereof, to novel intermediates, and to the use of the intermediates in the preparation of sigma receptor inhibitors.
A process for preparing a savoury flavour, the process comprising reacting a compound of general formula X with hydrogen sulphide and/or cystein , wherein
X is:
in which R1 represents an alkyl group having 1 or 2 carbon atoms or hydrogen, R2 represents an alkyl group having from 1 to 4 carbon atoms or hydrogen, R3 represents an alkyl group having from 1 to 5 carbon atoms or hydrogen and R4 represents hydrogen or an organic radical consisting of from 1 to 6 carbon atoms, hydrogen and from 0 to 2 oxygen atoms.
X is preferably 4-hydroxy-2,5-dimethyl-2-(2-hydroxy-3-oxo-2-butyl)-3(2H)-furanone, and is formed from the reaction of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and diacetyl.
2,5-dimethyl-4-mercapto-3(2H)-furanone is a flavour compound obtainable by this process.
The present invention relates to flavour generation. In particular the invention relates to a process for the preparation of a flavour composition. The process comprises combining glycerol with a quaternary ammonium compound, adding at least one flavour precursor to form a reaction mixture and heating the reaction mixture to form aroma compounds, wherein the glycerol is combined with a quaternary ammonium compound at a molar ratio ranging between 5:1 and 0.8:1. The flavour precursor comprises preferably an amino compound such as an amino acid. A further aspect of the invention is a food product comprising the flavour composition obtainable by the process of the invention.
The invention relates to a process for the preparation of a savoury flavour which comprises reacting mono- and/or di-methyl-3(2H)-furanone or precursors thereof with cystein and/or hydrogen sulphide. Suitable precursors of mono- or di-methyl-3(2H)-furanone are oligomers of diacetyl, pyruvic aldehyde, pyruvic acid, acetoin, acetol, ethylene glycol aldehyde and glyceraldehyde, including mixed oligomers. The reaction is preferably carried out with cystein and hydrogen sulphide. The latter may be obtained before or during the reaction from a hydrogen sulphide donor.
The reaction is preferably carried out at pH below 7, at 60-160°C for 0.5-4 hours. A food grade acid such as acetic acid may be present.
The reaction mixtures obtained are rich in methyl substituted furanthiols or derivatives thereof.
The invention also relates to flavour precursor mixtures which generate a savoury flavour upon heating and comprises a mono- and/or di-methyl-3(2H)-furanone and/or precursor thereof, cystein and optionally a hydrogen sulphide donor.