Nitrile

Details Nitrile Nitrile

1998-04-14

2000-05-30

Kelly, Cynthia Harris

Perfume compositions

Perfume compositions

Ring containing active ingredient

512 8, 558388, 424 761, 510102, A61K 746, C07C25500, A61L 900, C11D 350, C11D 944

Patent

active

060691255

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

Cyclohex-1-en-yl-phenylacetonitrile C.sub.6 H.sub.5 CH(CN)--C.sub.6 H.sub.9 is described by V. J. Harding and W. N. Haworth in J.Chem.Soc. (1910), 486-498, as the product of the alkaline condensation of phenylacetonitrile and cyclohexanone.
However, it later emerged that the reaction product is in fact and reality cyclohexylidene-phenylacetonitrile C.sub.6 H.sub.5 C(CN).dbd.C.sub.6 H.sub.10 (I), D. E. Whyte, A. Cope, JACS 65 (1943), 1999-2000 and S. F. Birch, G. A. R. Kon, J. Chem. Soc. 123 (1923), 2442-2446.
Harding and Haworth describe the product obtained by them simply as a colourless oil having a pleasant ethereal odour. The later authors do not provide any information concerning this.
It is surprising that an odorant having extremely valuable properties and--as enlarged upon below--diverse use potentials is hidden behind this cursory, moreover extremely imprecise, non-specific olfactory description.


SUMMARY OF THE INVENTION

The invention is accordingly concerned with the compound I as an odorant, odorant compositions containing I and the use of I as an odorant.
The odour of I can be characterized as flowery-rosy, green, metallic, reminiscent of geranium.
On the basis of olfactory investigations it has furthermore been shown that I, especially having regard to its rose and geranium notes, is surprisingly outstandingly suitable as a replacement for rosacetol.


DETAILED DESCRIPTION OF THE INVENTION

Rosacetol (trichloro-methyl-phenyl-carbinyl acetate) is a much esteemed odorant because of its rose and geranium notes, but recently its use has declined more and more for ecological reasons (chlorine content).
It has also emerged that (I) is extraordinarily stable to acid and alkali and that (I) is distinguished by excellent substantivity. I is even quite clearly superior to roseacetol with respect to substantivity. The same is true for long-lastingness.
Under substantivity there is to be understood the adhesion of an odorant, e.g. to textiles, skin and hair after a washing operation.
Therefore, I is outstandingly suitable for use in the washing agent industry, e.g. as an odorant in detergents, conditioners, etc., as well as also as an odorant in cosmetics, e.g. in shampoos, soaps etc., especially as a replacement for rosacetol.
Having regard to the aforementioned valuable olfactory properties, compound I is suitable as an odorant, especially in combination with the extensive range of natural and synthetic odorants currently available on the market, for the creation of perfume compositions which can be used in all conventional fields of application. Examples of the numerous known odorant ingredients of natural or synthetic origin, whereby the range of the natural raw materials can embrace not only readily-volatile but also moderately-volatile and difficultly-volatile components and that of the synthetics can embrace representatives from quite a few classes of substance, are: (such as bergamot oil, mandarine oil, etc.), mastix absolute, myrtle oil, palmarosa oil, patchouli oil, petitgrain oil, wormwood oil, lavender oil, rose oil, jasmin oil, ylang-ylang oil, sandalwood oil, rhodinol, cinnamic alcohol, cis-3-hexenol, menthol, .alpha.-terpineol, Sandela (3-isocamphyl-(5)-cyclohexanol), Lilial.RTM. (p-tert.butyl-.alpha.-methyl-dihydrocinnamaldehyde), methylnonylacetaldehyde, phenylacetaldehyde, anisaldehyde, vanillin, (isomethyl-.alpha.-ionone), verbenone, nootkaton, geranylacetone, propionate, citronellyl acetate, decyl acetate, dimethylbenzylcarbinyl acetate, ethyl acetoacetate, ethyl acetylacetate, cis-3-hexenyl isobutyrate, linalyl acetate, methyl dihydrojasmonate, styrallyl acetate, vetiveryl acetate, benzyl acetate, cis-3-hexenyl salicylate, geranyl acetate, etc. pentadecan-15-olide, p-methane-8-thiol-3-one, methyleugenol, eugenol, anethol, etc.
The odorant compositions manufactured using compounds I, especially those of flowery, flowery-spicy, flowery-fruity and flowery-oriental direction, captivate especially by their originality.
When used as an odorant, the compound I

REFERENCES:
patent: 3408396 (1968-10-01), Suh et al.
D.E. Whyte, et al. JACS., 65 (1943):1999-2000.
S.F. Birch, et al. J. Chem. Soc., 123 (1923):2442-2446.

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