EP0045534B1 - Use of phenyl-n-hexyl ketone as a perfuming agent, and perfume compositions containing the same - Google Patents

Description

The invention relates to the field of perfumery. It more particularly relates to the use of phenyl-n-hexyl ketone as a perfuming ingredient for the preparation of perfumes and perfumed products. It also relates to a fragrance composition containing said phenyl-n-hexyl ketone as an odoriferous ingredient.

Phenyl-n-hexyl ketone is a known chemical entity, described in particular in Beestein 7, 337; however, the state of the art is silent as to its organoleptic properties.

It has been discovered that this compound has very interesting olfactory properties and can therefore find wide use as an odoriferous ingredient in compositions of various kinds.

Its scent, of good power, is of the flowery type and recalls the smell developed by certain flowers belonging to the amaryllidaceae family, the daffodil or the narcissus in particular.

Its odoriferous properties are however clearly distinct from those exhibited by analogous products, such as phenyl-n-amyl ketone for example which finds only limited use in perfumery, as a modifier of the effect exerted by the combination amyl coumarin-salicylate in fourger-type compositions (see S. ARCTANDER: "Perfume and flavor chemicals", 1969, Mont-clair, NJ (US), no. 211).

The proportions in which phenyl-n-hexyl ketone can be used to give interesting olfactory effects vary relatively widely. Thus, concentrations of approximately 0.5 to 1%, by weight, relative to the total weight of the composition considered can already produce marked effects when perfuming products such as soaps, shampoos or cosmetic articles for example.

Higher proportions, up to 20% or more, can however be used for the preparation of perfume compositions or bases. Of course, such concentration limits should not be interpreted restrictively because they depend on the nature of the odorous co-ingredients of the given composition or on that of the articles which one wishes to perfume.

• SM: 190 (M⁺, 5); m/e:105(100), 120(76), 77(43), 51 (10), 43(9), 106(7), 133(6), 121(6);
• IR (liquide, film): 1675 cm ⁱ;
• RMN (60 MHz, CDCI₃): 0,89 (t, 3H); 1,0-2,0 (8H, bande large); 2,90 (2H, t, J=7 Hz); 7,2-7,5 (3H, m); 7,8-8,05 (2H, m) b ppm.

Phenyl-n-hexyl ketone can be prepared according to one of the current synthesis methods, for example by acylation of benzene by means of a Friedel-Crafts type reaction using heptanoyl chloride [see by example: Organikum, Org. Chem. Grund-praktikum, Berlin (1964), p. 290]. The product thus obtained possessed Eb. 85-90 ° / 1 Pa. Its analytical characteristics were as follows:

• MS: 190 (M ⁺ , 5); m / e: 105 (100), 120 (76), 77 (43), 51 (10), 43 (9), 106 (7), 133 (6), 121 (6);
• IR (liquid, film): 1675 cm ⁱ ;
• NMR (60 MHz, CDCI ₃ ): 0.89 (t, 3H); 1.0-2.0 (8H, broadband); 2.90 (2H, t, J = 7 Hz); 7.2-7.5 (3H, m); 7.8-8.05 (2H, m) b ppm.

The following example is intended to illustrate the invention in more detail, without however limiting it.

Example

L'adjonction à 85 g de la composition indiquée ci-dessus de 15 g de phényl-n-hexyl cétone rend son odeur plus intense et plus arrondie en lui conférant un caractère plus naturel et agréable.A basic perfume composition of the "yellow narcissus" type was prepared by mixing the following ingredients (parts by weight):

The addition to 85 g of the composition indicated above of 15 g of phenyl-n-hexyl ketone makes its odor more intense and more rounded by giving it a more natural and pleasant character.

Claims (2)

1. Utilization of phenyl-n-hexyl ketone as perfuming ingredient for the preparation of perfumes and perfumed products.

2. Perfume composition containing phenyl-n-hexyl ketone as odoriferous ingredient.