Perfume compositions – Perfume compositions – Cyano containing active ingredient
Patent
1995-09-26
1997-04-08
Richter, Johann
Perfume compositions
Perfume compositions
Cyano containing active ingredient
558447, A61K 746, C07C25517
Patent
active
056187840
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP93/03417 filed Dec. 2, 1993 and published as WO94/13626 Jun. 23, 1994.
The present invention relates to certain methylbutoxypropionitriles, to the use of these compounds as fragrance materials and to perfumes and perfumed products containing these compounds.
Many synthetic fragrance materials have been developed, especially in the last decades to substitute known perfume materials of natural origin. Nevertheless there is a constant need for new synthetic fragrance materials which are more stable than those previously developed and/or have additional or more delicate odour notes to further complete the fragrance palette from which the perfumer can chose in composing perfumes which are suitable also for various aggressive environments.
Various aliphatic and aromatic nitriles are known in the art of perfumery. They were developed because of their good stability in aggressive media and their general odour similarity with the corresponding aldehydes, many of which were already used in perfumery before the development of the nitriles. Various examples are described in S. Arctander, Perfume and Flavor Chemicals (Montclair, N.J., 1969). Certain ether-nitriles have been described in the art. They were prepared by addition of aliphatic alcohols to acrylonitrile, methacrylonitrile or crotonnitrile. The ether-nitriles are reported to have odours reminiscent of the alcohols from which they were prepared. Thus, J. Kulesza et al, Riechstoffe, Aromen, Korperpflegemittel. Nr. 2/75, pages 34, 37 describe a series of addition products of alcohols to acrylonitrile. From the odour decriptions it is clear that the odours of most ether-nitriles are similar to those of the corresponding alcohols. Similarly, in DE-A-2601825 the addition products of various saturated and unsaturated aliphatic alcohols to acrylonitrile have been described as possibly of interest in perfumery and as polar solvents.
Although this reference gives very little information on the actual odours of the compounds, it does say that the odour is determined, at least in part, by the corresponding alcohol. The odour of 3-methylbut-3-en-1-oxy-propionitrile is decribed as mainly fruity, green. No further particulars or examples of any use of the compounds in perfumery are given. Finally, in EP-A-0 491 127 various hexenyloxy-propionitriles and hexenyloxy-methylpropio-nitriles are described as having predominantly green odour notes.
It has now been found that 3-(2-methylbut-1-oxy)- and 3-(3-methylbut-1-oxy)-2-methylpropionitrile, of which the formulae are presented below, are valuable fragrance materials with jasmine-type odours with lactonic notes. ##STR1##
The olfactive properties of the compounds of the invention are thus surprisingly different from what might have been expected from the prior art in that they are not reminiscent of the corresponding alcohols, which both have a pungent and from a perfumery point of view useless odour. Also, the olfactive properties of the compounds of the invention are very different from those of the ether-nitriles of the prior art.
The ether-nitriles according to the invention are not only novel as perfume components, they are also novel as such. They may be prepared according to methods known in the art for similar compounds, such as described by J. H. MacGregor and C. Pugh, J. Chem Soc., 535 [1945], or as decribed in DE-A-2 121 325, DE-A-2 217 494 or EP-A-0 491 127.
The ether-nitriles according to the invention are powerful fragrance materials which may be used as such to impart, strengthen or improve a jasmine odour note in products, or they may be used as a component of a perfume to impart, strengthen or improve a jasmine note therein. For the purposes of this invention a perfume is intended to mean a mixture of fragrance materials, if desired mixed with or dissolved in a suitable solvent or mixed with a solid substrate, which is used to impart a desired odour to the skin and/or all types of products. Examples Of such products are: fabric washing powders and liquids and other fabric care p
REFERENCES:
patent: 5294602 (1994-03-01), Brunke et al.
Quest International B.V.
Richter Johann
Sackey Ebenezer
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