EP0694604B1 - Use of 1,3-undecadien-5-yne as a perfuming ingredient - Google Patents

Description

The present invention relates to the field of perfumery. She relates more particularly to the use of 1,3-undecadien-5-yne as perfuming ingredient.

This compound is well known in the prior art. It has in fact been cited several times as a useful intermediary in the synthesis of 1,3,5-undecatriene and its isomers [see, for example, BP Andreini et al., Tetrahedron 43 , 4591 (1987); F. Näf et al., Helv. Chim. Acta, 58 , 1016 (1975)]. However, we did not find in these references any mention or even suggestion of the possible usefulness of this compound, or of one of its stereoisomers, for perfumery.

However, we have indeed discovered that 1,3-undecadien-5-yne and its configuration isomers (E) and (Z) have very powerful odors and that they serve to create olfactory effects that are both floral, green and galbanum. This is how (E) -1,3-undécadién-5-yne turns out to be a perfume ingredient of choice, its odor being remarkably powerful and presenting a character of galbanum type and fruity, recalling the smell of tangerine skin, with a very marked note of the type that is characteristic of methyl octynecarbonate and heptynecarbonate methyl. It is a very pretty fragrant note, evoking the smell of leaves violet, but also with a green and fruity character reminiscent of the smell of Dynascone® [1- (5,5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one; origin: Firmenich SA, Geneva, Switzerland], while being less allylic and endowed a more pronounced galbanum character, as well as a sub-note very clean citrus-mandarin. The use of this compound in perfumery thus constitutes a preferred embodiment of the present invention.

For its part, (Z) -1,3-undecadien-5-yne is also an ingredient useful fragrance, its smell being greener, with a character more pronounced putty-ocimene.

Due to their olfactory qualities, these two compounds thus find a very varied use in perfumery, in particular for the preparation of bases and perfume concentrates, perfumes, toilet waters and colognes, as well as in perfuming of various consumer articles such as soaps, shower gels or bath, shampoos and other hair hygiene products, preparations cosmetics, body or room air fresheners, or detergents or fabric softeners and cleaning products.

In these applications, they can be used either alone or, as is more common in perfumery, mixed with others fragrance ingredients, solvents or adjuvants commonly used in perfumery and that the skilled person is able to choose according to the desired effect and the nature of the product to be scented. A detailed description such ingredients are superfluous here and we can cite by way of example ingredients like those described in reference books like this de S. Arctander, Perfume & Flavor Chemicals, Montclair, N.J., USA (1969).

In particular, they can also be used in the form of their isomeric mixtures, in which the relative proportions (E) / (Z) can vary within a range of values between 1: 0 and 0: 1, taking all intermediate values. According to the invention, when these mixtures of (E) -1,3-undecadien-5-yne and (Z) -1,3-undecadien-5-yne, it is preferred those having 50% by weight or more of the first compound mentioned.

The concentrations in which these compounds and their mixtures above can be used to achieve the scent effects desired vary in a very wide range of values, being well known that these values depend on the nature of the item to be scented and the effect fragrance sought, as well as the nature of the other co-ingredients in a given composition. This is how concentrations of the order of 0.5 to 5%, or even 10% or more by weight of said compound, relative to the weight of the composition, are entirely suitable when the compounds mentioned are added to various perfume compositions. Concentrations significantly lower than these values can be used when they are used for perfuming various articles such as those mentioned above.

As mentioned above, the synthesis of these compounds has been described, in particular by F. Näf et al. in the reference cited above.

The invention therefore relates to their use in perfumery as well as perfume compositions and perfumed articles containing them. She will now described in more detail using the following examples.

Example 1 Perfuming composition

A basic perfume composition was prepared by mixing the following ingredients: ingredients Parts by weight 10% geranyl acetate 10 Linalyl acetate 15 Bergamot essence 120 Cedroxide ® 95 California lemon essence 20 coumarin 10 dihydromyrcenol 40 Exaltolide ® 55 Galaxolide ® 50 95 Hedione ® 40 Indol at 10% 5 Isobutylquinoléïne at 1% 20 Lyral ® 45 Mandarin essence 55 10% crystal foam 30 Nutmeg essence 10 trans-1- [2,2,6-Trimethyl-1-cyclohexyl] -3-hexanol at 10% 15 Essence of patchouli 15 Polysantol ® 5 Polywood ® 190 Amyl salicylate 15 Triplal® VS 5 γ-Undecalactone 1% 10 β-Ionone 10% 10 Total 930

The addition to this basic composition of woody-musky, floral, 70 parts by weight of a 10% solution in the DIPG of (E) -1,3-undécadién-5-yne gives it an effect both green and very marked violet leaves and enhances the fresh citrus note and in particular the mandarin character of composition.

Example 2 Perfume composition for fabric softener

A basic perfume composition intended for perfuming a fabric softener was prepared, by mixing the following ingredients: ingredients Parts by weight Benzyl acetate 55 Carbinol acetate 25 1% cis-3-hexenyl acetate 30 Lemonellyl acetate 5 P-tert-butyl-cyclohexyl acetate 45 Anisde aldehyde 5 Hexylcinnamic aldehyde 60 citronellol 55 γ-Decalactone 10% 15 β-Damascone 50% in ethyl citrate 10 Ethylvanillin 10% 5 Exaltex® 30 geraniol 75 Galaxolide ® 50 40 α-Ionone at 10% 20 Isobutylquinoléïne at 1% 25 Phenylethyl isobutyrate 5 Iralia ® 25 Lilial ® 35 linalool 35 Lyral ® 15 Methylnaphthyl ketone crist. 10 10% crystal foam 10 Phénéthylol 170 Polysantol ® 5 Verdyl propionate 20 Rosalva ® at 10% 5 Rosinol crist. 25 Amyl salicylate 60 Hexyl salicylate 50 Ylang synth. 20 Total 990

To this basic composition of floral, rosé, powdery, violet type, we added 10 parts by weight of a 10% solution in the DIPG of (E) -1,3-undécadién-5-yne, to obtain a new composition with a floral-violet type note, outsourced in particular by Iralia® and α-ionone, was clearly accentuated. Furthermore, the smell of the composition had then become more green-fruity, with a slight sweet connotation, whose effect was particularly pleasant on damp linen having been treated with a fabric softener containing, at 0.1% by weight, this composition news.

Claims (5)

1. Use of 1,3-undecadien-5-yne as perfuming ingredient, for the preparation of a perfuming composition or a perfumed article.
2. Use according to claim 1, characterized in that 1,3-undecadien-5-yne is present in the form of one of its (E) or (Z) configuration isomers, or of any mixture of these two isomers.
3. Use according to claim 2, characterized in that said mixture contains at least 50% by weight of (E)-1,3-undecadien-5-yne, relative to the weight of the mixture.
4. A perfuming composition or a perfumed article resulting from the use according to any one of claims 1 to 3.
5. As a perfumed article according to claim 4, a perfume or cologne, a soap, a bath or shower gel, a cosmetic preparation, a shampoo or other hair-care product, a body deodorant, an air-freshener, a detergent or a fabric softener, or a household product.