EP0688856A2 - Use of an alkyl substituted pyridine as perfuming ingredient - Google Patents

Abstract

Use of 3-(2,2-dimethylpropyl) pyridine (I) as a perfume component is new. Also claimed are: (i) a perfume compsn. contg. (I) as active agent; (ii) method for providing, improving or modifying perfuming properties in perfumes, toilet waters, cosmetics, body or air deodorants, shampoos, hair or scalp care products, soaps, detergents, textile softeners and household cleaning products, involving adding (I); and (iii) perfumes, cosmetics, body or air deodorants, shampoos, hair or scalp care products, textile softeners and household cleaning products, contg. (I) as perfuming ingredient.

Description

The present invention relates to the field of perfumery, it relates in particular to the use of an alkyl-substituted pyridine, 3- (2,2-dimethyl-propyl) -pyridine, as a perfuming ingredient.

Pyridine as well as some of its alkylated derivatives are known in the art of flavoring, in particular for the reconstitution of coffee-type, or even meaty, flavors. The situation is different in the perfume industry, where the use of pyridines is less documented.

The pyridine itself is described by S. Arctander [Perfume and Flavor Chemicals, Montclair, N.J. (USA), 1969, sec. 2776] as having an irritating, penetrating and diffuse odor, sometimes defined as disgusting, which can be revealed at high dilution as hot, burnt and of very weak tenacity.

Certain alkylated pyridines have been identified in products of natural origin. Thus, n-pentyl-pyridine has been identified in the jasmine absolute of Egyptian origin [see Mostafa A. Nofah et al., Perfumer & Flavorist 6 , 24 (1982)], while 2-, 3- and 4-butyl-pyridine represent constituents of the essence of crepe mint [T. Tsuneya et al., Bioactive volatile compounds from Plants, ACS Symposium Series 525 (1992)].

Finally, 3-ethyl- and 4-methyl-3-ethyl-pyridine have been identified in jasmine essential oil by T. Toyoda et al. [Proceedings VII th International Essential Oil Congress, Kyoto, p. 473-76 (1979)]. To our knowledge, no particular mention has been made to date of the use of 3- (2,2, -dimethyl-propyl) -pyridine in perfumery, nor moreover of its occurrence in a natural product.

We have been able to note that the compound in question possessed a very pleasant odorous character of the fruity type. It develops in particular a pleasant fresh-fruity note which in some ways recalls the smell of pear or ripe banana with a connotation reminiscent of chamomile or caraway. 3- (2,2-Dimethyl-propyl) -pyridine showed excellent toughness and very good substantivity on the laundry, associated with high power. In use, it appeared that this compound had a fresh and fruity fragrant note, which is in itself surprising given the characteristics shown by other known analogous compounds which are rather phenolic, pyrogenic and amino.

Due to its odorous properties, 3- (2,2-dimethyl-propyl) -pyridine finds wide use in various applications, both in alcoholic and functional perfumery. It can also be used for the total or partial reconstitution of concentrated perfume bases.

By direct addition to the products which it is desired to flavor or, more often, in mixture with other usual odorous ingredients, diluents or excipients of current use, 3- (2,2-dimethyl-propyl) -pyridine can serve to confer, improve or modify the inherent odor properties of consumer products as varied as perfumes, eau de toilette, cosmetics, body or air fresheners, shampoos or in general products for hair or scalp care, soaps, detergents, fabric softeners or even cleaning and household products.

Of course, it can also be used for the preparation of concentrated perfume bases.

The proportions in which the pyridine in question is used in the context of the use defined in the present invention can vary within a fairly wide range of values. They can indeed vary between 1 and 10% by weight relative to the weight of the product to which 3- (2,2-dimethyl-propyl) -pyridine is added. It goes without saying that such concentration values cannot represent absolute values, the person skilled in the art being able to adapt the proportion of the ingredient in question as a function of the desired odor effect, the nature of the products to be perfumed and that of any co-ingredients present.

When perfuming soaps or detergents, for example, lower proportions, of the order of 0.1 - 0.5% by weight, may be perfectly suitable, while concentrations above 10% may be necessary to the preparation of concentrated perfume bases.

3- (2,2-dimethyl-propyl) -pyridine is a known chemical compound, described in particular in the scientific literature as a synthetic intermediate or as a starting material for the preparation of compounds having use in industry polymers or drugs.

Several synthetic routes for its preparation have been described, in particular by O. Tsuge et al., Chemistry Letters Japan, 1984 , 1255-58; O. Tsuge et al., Bull. Chem. Soc. Japan 60 , 1497-1504 (1987) and E. Langhals et al., Chem. Ber. 117 , 1259-1261 (1984).

The present invention therefore relates to the use of 3- (2,2-dimethyl-propyl) -pyridine as a perfuming ingredient.

The subject of the invention is also a perfuming composition containing, as active ingredient, 3- (2,2-dimethyl-propyl) -pyridine.

Another object of the invention consists in a process for imparting, improving or modifying the perfuming properties of perfumes, eau de toilette, cosmetics, body or air fresheners, shampoos, products for hair or scalp care, soaps , detergents, fabric softeners, cleaning and household products, which process is characterized in that 3- (2,2-dimethyl-propyl) -pyridine is added to said products as an active perfuming ingredient.

The invention finally relates to one of the perfumed products resulting from said process.

The invention is illustrated but not limited by the following examples.

Example 1

a) dipropylène glycol 1) acétate de (tricyclo[5.2.1.0^2,6]déc-4-yl)méthyle 2) origine : Firmenich SA, Genève, Suisse 3) 1-(5,5-diméthyl-cyclohex-1-ényl)-pent-4-én-1-one; origine : Firmenich SA, Genève, Suisse 4) origine : Givaudan-Roure (marque enregistrée) 5) 2,6-diméthyl-5-hepténal 6) 2,2,5-triméthyl-5-pentyl-cyclopentanone ; origine : Firmenich SA, Genève, Suisse A basic fragrance composition of fruity-pear character was prepared by mixing the following ingredients (parts by weight): Ingredients Parts by weight Hexyl acetate 10 Linalyl acetate 100 Terpenyl acetate 190 TCD acetate ¹⁾ 100 Methyl cinnamate 20 γ-Dodecalactone 25 Dorinone® β 50% ^{a) 2)} 220 Dynascone® 10% ^{a) 3)} 10 Lilial® ⁴⁾ 200 Melonal® 10% ^{a) 4) 5)} 5 Linalyl oxide 10 Veloutone ⁶⁾ 50 γ-Undecalactone 50 Total $\overline{\text{990}}$

a) dipropylene glycol 1) (tricyclo [5.2.1.0 ^2,6 ] dec-4-yl) methyl acetate 2) origin: Firmenich SA, Geneva, Switzerland 3) 1- (5,5-dimethyl-cyclohex-1-enyl) -pent-4-en-1-one; origin: Firmenich SA, Geneva, Switzerland 4) origin: Givaudan-Roure (registered trademark) 5) 2,6-dimethyl-5-heptenal 6) 2,2,5-trimethyl-5-pentyl-cyclopentanone; origin: Firmenich SA, Geneva, Switzerland

When a part of 3- (2,2-dimethyl-propyl) -pyridine is added to 99 parts by weight of the base thus prepared, a new composition is obtained whose fruity-pear character is reinforced; it appears more natural with a skin side. The whole results moreover as being less food juice.

Example 2

a) dipropylène glycol 1), 2) origine : Firmenich SA, Genève, Suisse 3) méthylionone ; origine : Firmenich SA, Genève, Suisse 4) origine : Polak's Frutal Works (marque enregistrée) A basic perfume composition of the tobacco-floral type, powdered, was prepared by mixing the following ingredients (parts by weight): Ingredients Parts by weight Benzyl acetate 60 Linalyl acetate 80 Phenylacetic acid 20 Bergamot essence 180 Birch essence 10% ^a) 20 Coumarin 80 Damascenone 10% ^{a) 1)} 20 Dimethylhydroquinone 80 Dorinone® β 10% ^{a) 2)} 20 Heliotropin 90 Iralia® ³⁾ 90 Irone α 10% ^a) 20 Linalol BJ 60 Myrrh essence 70 Methyl phenylacetate 20 Phenylethyl phenylacetate 20 Tonalide® ⁴⁾ 30 Total $\overline{\text{960}}$

a) dipropylene glycol 1), 2) origin: Firmenich SA, Geneva, Switzerland 3) methylionone; origin: Firmenich SA, Geneva, Switzerland 4) origin: Polak's Frutal Works (registered trademark)

When 96 parts by weight of the basic composition are added above 4 parts by weight of 3- (2,2-dimethyl-propyl) -pyridine, a new composition with an elegant character is obtained, the typical note of which is conferred by the presence of phenylacetic acid was significantly improved. The overall character also becomes more floral, more natural as well as less animal and more fruity-sweet.

The 3- (2,2-dimethyl-propyl) -pyridine used in the previous examples had the following analytical characteristics:
Eb. 80-83 ° / 1.33x10³ Pa
IR (CHCl₃): 2961, 1577, 1478, 1424, 1366, 1238 and 1192 cm⁻¹
NMR (¹H): 0.92 (s, 9H); 2.48 (s, 2H); 7.19 (m, 1H); 7.44 (m, 1H); 8.39 (m, 1H); 8.45 (m, 1H) δppm
SM: 149 (10, M⁺), 134 (10), 93 (100), 65 (8), 57 (21)

Claims (4)

Use of 3- (2,2-dimethyl-propyl) -pyridine as a perfuming ingredient. Perfuming composition containing as active ingredient 3- (2,2-dimethyl-propyl) -pyridine. Process for imparting, improving or modifying the perfuming properties of perfumes, eau de toilette, cosmetics, body or air fresheners, shampoos, products for hair or scalp care, soaps, detergents, fabric softeners, cleaning products and cleaning, characterized in that the said products are added 3- (2,2-dimethyl-propyl) -pyridine as active perfuming ingredient. Perfume, eau de toilette, cosmetic, body or air freshener, shampoo, product for hair or scalp care, soap, detergent, fabric softener, cleaning and household product containing as active perfuming ingredient 3- (2,2-dimethyl-propyl) -pyridine.