EP0838215A2 - Use of unsaturated aliphatic esters in perfumery - Google Patents

Use of unsaturated aliphatic esters in perfumery Download PDF

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Publication number
EP0838215A2
EP0838215A2 EP97116147A EP97116147A EP0838215A2 EP 0838215 A2 EP0838215 A2 EP 0838215A2 EP 97116147 A EP97116147 A EP 97116147A EP 97116147 A EP97116147 A EP 97116147A EP 0838215 A2 EP0838215 A2 EP 0838215A2
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Prior art keywords
perfume
dimethyl
pentenoate
ethyl
composition
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EP97116147A
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German (de)
French (fr)
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EP0838215A3 (en
EP0838215B1 (en
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Charles Fehr
José Galindo
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Firmenich SA
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Firmenich SA
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof

Definitions

  • the present invention relates to the field of perfumery. It relates more particularly to the use as a perfuming ingredient of a compound of formula having a double bond in one of the positions indicated by the dotted lines.
  • esters of formula (I) The structure of the esters of formula (I) is known.
  • ethyl 2,4-dimethyl-2-pentenoate and its cis and trans configuration isomers have been described in the literature, in particular in the context of organic syntheses (see, for example, VJ Lee, AR Branfman, TR Herrin, and KL Rinehart, JACS, vol. 100, 1978 , 4229-4234 or also O. Miyata, T. Shinada, I. Ninomiya, T. Naito, Synthesis, 1990 , 1123-1124).
  • the compounds of formula (I) according to the invention are capable of imparting to the perfume compositions or perfumes in which are integrated a pleasant and fresh scent.
  • the unsaturated aliphatic esters according to the invention have distinct olfactory properties, and in particular that the 2,4-dimethyl-2-pentenoate of ethyl exhales a flower note-chamomile well marked, having a slight tagete-like character, while 2,4-dimethyl-3-pentenoate ethyl has a slightly camomile, anise-fennel and fruity character a honey sub-note, and a nice top note reminiscent of the apple particularly refreshing.
  • ethyl 2,4-dimethyl-2-pentenoate and its isomers of configuration (E) and (Z) have distinct olfactory notes, the two isomers exhaling very powerful scents in which the top note of the chamomile type is very powerful and is accompanied by a very natural fruity character.
  • ethyl (Z) -2,4-dimethyl-2-pentenoate is also an ingredient useful fragrance developing a fruity, chamomile, pleasant and fresh scent, very natural, just as elegant as that of the (E) isomer.
  • mixtures of these isomers in all of their possible relative proportions, also turn out to be ingredients useful perfumers.
  • the mixtures in which the (E) isomer predominates are high-performance perfume ingredients according to the invention, having the characteristics typical fragrances of this compound.
  • ethyl (E) -2,4-dimethyl-2-pentenoate is ready for use in perfumery in compositions of various nature. This is how he can be very beneficial in a floral arrangement, for example, where it develops a significantly more powerful, fruity and more complex camomile smell than, for example, that of 1,3-dimethyl-3-butenyl-isobutyrate (see, for example, US 4,387,047), and thereby gives a new olfactory effect to the perfume.
  • an ester according to the invention constitutes a perfuming ingredient which can be very advantageous both in the isolated state and in mixture with others fragrant ingredients.
  • the perfumes or toilet waters, the soaps, the gels shower or bath, shampoos or other hair care products, cosmetic preparations, body or room air fresheners, detergents or fabric softeners, or cleaning products are examples of the perfumes or toilet waters, the soaps, the gels shower or bath, shampoos or other hair care products, cosmetic preparations, body or room air fresheners, detergents or fabric softeners, or cleaning products.
  • the proportions in which the compounds according to the invention can be incorporated in the aforementioned miscellaneous products vary in a range of values very extent. These values are dependent on the nature of the article or product that we want perfume and the desired olfactory effect, as well as the nature of the co-ingredients in a composition given when a compound of the invention is used in mixture with perfume co-ingredients, solvents or adjuvants commonly used in the art. Good understood, a compound according to the invention can also be added to the compositions and scented articles either alone or in solution in commonly used solvents.
  • perfuming composition is meant here a composition consisting of a mixture of perfuming ingredients which can be chosen from various chemical classes, comprising for example esters, aldehydes, alcohols, ethers, ketones, acetals, nitriles, terpene hydrocarbons, heterocyclic compounds nitrogen or sulfur, as well as essential oils of natural or synthetic origin.
  • a basic perfume composition was prepared by mixing the following ingredients: Ingredient Parts by weight Benzyl acetate 170 Cyclanol acetate 20 Verdyl acetate 20 Citronellol 40 Ethyl vanillin 10% 20 Exaltex ® 140 Heliotropin 40 Iralia ® 100 Lilial ® 100 Linalol 120 Phenethylol 40 Amyl salicylate 40 Benzyl salicylate 120 970
  • Ingredient Parts by weight Benzyl acetate 170 Cyclanol acetate 20 Verdyl acetate 20 Citronellol 40 Ethyl vanillin 10% 20 Exaltex ® 140 Heliotropin 40 Iralia ® 100 Lilial ® 100 Linalol 120 Phenethylol 40 Amyl salicylate 40 Benzyl salicylate 120 970
  • a basic perfume composition with a powdery-floral, woody connotation was prepared by mixing the following ingredients: Ingredient Parts by weight Cyclanol acetate 30 Verdyl acetate 80 Anisde aldehyde 30 Dihydromyrcenol 30 P-tert-butyl-cyclohexyl acetate 210 Exaltex ® 150 Isoraldeine ® 80 Jasmal ® 80 Amyl salicylate 60 Tonalid ® 60 Vertofix heart 80 Essence of violet 80 Total 970 The addition of 30 parts by weight of (E) -2,4-dimethyl-2-pentenoate to this floral base composition gives it a strong fruity connotation while imparting to it, in a more marked manner, a pleasant character. fresh.
  • a basic perfume composition with a fern-lavender-floral odor was prepared by mixing the following ingredients: Ingredient Parts by weight Benzyl acetate 45 Linalyl acetate 60 Styrallyl acetate 30 Verdyl acetate 80 Essence of Aspic 80 Benzophenone 60 Coumarin 30 Cyclomethylene citronellol 60 Eugenol 45 Exaltex ® 30 Lilial ® 45 Linalol 110 Iralia ® 80 Methylhexylketone 45 Methylnaphthylketone 80 Verdyl propionate 45 Amyl salicylate 45 ⁇ -Undecalactone 15 Total 985 The addition of 15 parts by weight of ethyl (E) -2,4-dimethyl-2-pentenoate to this very classic fern-type composition gives it an enriching chamomile note, giving it a particularly modern and camomile appearance .
  • E ethyl

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A perfume composition or perfumed article (I) comprises a compound of formula (II) with a double bond in one of the two positions indicated:

Description

La présente invention a trait au domaine de la parfumerie. Elle concerne plus particulièrement l'utilisation à titre d'ingrédient parfumant d'un composé de formule

Figure 00010001
possédant une double liaison dans l'une des positions indiquées par les pointillés.The present invention relates to the field of perfumery. It relates more particularly to the use as a perfuming ingredient of a compound of formula
Figure 00010001
having a double bond in one of the positions indicated by the dotted lines.

La structure des esters de formule (I) est connue. Par exemple, le 2,4-diméthyl-2-penténoate d'éthyle et ses isomères de configuration cis et trans ont été décrits dans la littérature, notamment dans le cadre de synthèses organiques (voir, par exemple, V. J. Lee, A. R. Branfman, T. R. Herrin, et K. L. Rinehart, JACS, vol. 100, 1978, 4229-4234 ou encore O. Miyata, T. Shinada, I. Ninomiya, T. Naito, Synthesis, 1990, 1123-1124). Cependant, nous n'avons pu trouver aucune mention d'éventuelles propriétés olfactives utiles de ces composés.The structure of the esters of formula (I) is known. For example, ethyl 2,4-dimethyl-2-pentenoate and its cis and trans configuration isomers have been described in the literature, in particular in the context of organic syntheses (see, for example, VJ Lee, AR Branfman, TR Herrin, and KL Rinehart, JACS, vol. 100, 1978 , 4229-4234 or also O. Miyata, T. Shinada, I. Ninomiya, T. Naito, Synthesis, 1990 , 1123-1124). However, we could not find any mention of any useful odor properties of these compounds.

En effet, à notre connaissance, aucun document de l'art antérieur ne suggère l'utilisation d'esters aliphatiques insaturés de formule (I) en tant qu'ingrédients parfumants pour le parfumage de produits de consommation courants et pour la préparation de parfums et de bases parfumées.Indeed, to our knowledge, no document of the prior art suggests the use of unsaturated aliphatic esters of formula (I) as fragrance ingredients for perfuming everyday consumer products and for preparing perfumes and scented bases.

Or, nous avons maintenant découvert que les composés selon l'invention possèdent des propriétés odorantes très intéressantes et qu'ils peuvent, de ce fait, être utilisés pour la préparation de compositions parfumantes ou articles parfumés de nature variée. Now, we have now discovered that the compounds according to the invention have very interesting odorous properties and that they can, therefore, be used for the preparation of perfume compositions or perfumed articles of nature varied.

Nous avons également constaté que les composés de formule (I) selon l'invention sont à même de conférer aux compositions parfumantes ou parfums dans lesquels ils sont intégrés une senteur agréable et fraíche.We have also found that the compounds of formula (I) according to the invention are capable of imparting to the perfume compositions or perfumes in which are integrated a pleasant and fresh scent.

Par ailleurs, nous avons découvert que les esters aliphatiques insaturés selon l'invention possèdent des propriétés olfactives distinctes, et notamment que le 2,4-diméthyl-2-penténoate d'éthyle exhale une note fleurie-camomille bien marquée, possédant un léger caractère de type tagète, tandis que le 2,4-diméthyl-3-penténoate d'éthyle présente un caractère fruité légèrement camomillé, anisé-fenouil accompagné d'une sous-note miel, et une jolie note de tête rappelant la pomme particulièrement rafraíchissante.In addition, we discovered that the unsaturated aliphatic esters according to the invention have distinct olfactory properties, and in particular that the 2,4-dimethyl-2-pentenoate of ethyl exhales a flower note-chamomile well marked, having a slight tagete-like character, while 2,4-dimethyl-3-pentenoate ethyl has a slightly camomile, anise-fennel and fruity character a honey sub-note, and a nice top note reminiscent of the apple particularly refreshing.

Curieusement, le 2,4-diméthyl-2-penténoate d'éthyle et ses isomères de configuration (E) et (Z) possèdent des notes olfactives distinctes, les deux isomères exhalant des senteurs très performantes dans lesquelles la note de tête de type camomille est très puissante et est accompagnée d'un caractère fruité très naturel.Curiously, ethyl 2,4-dimethyl-2-pentenoate and its isomers of configuration (E) and (Z) have distinct olfactory notes, the two isomers exhaling very powerful scents in which the top note of the chamomile type is very powerful and is accompanied by a very natural fruity character.

C'est ainsi que le (E)-2,4-diméthyl-2-penténoate d'éthyle se révèle être un ingrédient parfumant de choix, son odeur possédant un caractère fruité, herbacé à forte connotation camomille romaine, ainsi qu'une sous-note miellée évoquant l'odeur caractéristique de l'acide phénylacétique. Il s'agit d'une jolie note olfactive camomillée à caractère fruité, très distincte et naturelle, rappelant l'odeur des esters de l'acide angélique, sans toutefois posséder le caractère butyrique gras de ces composés.Thus (E) -2,4-dimethyl-2-pentenoate turns out to be a fragrance ingredient of choice, its smell having a fruity, herbaceous to strong character Roman chamomile connotation, as well as a honeyed sub-note evoking the smell characteristic of phenylacetic acid. This is a nice, camomile olfactory note to fruity character, very distinct and natural, recalling the smell of the esters of angelic acid, without however possessing the fatty butyric character of these compounds.

Par ailleurs, bien qu'évoquant par sa note camomille les esters de type camomille connus, le (E)-2,4-diméthyl-2-penténoate d'éthyle est doté, par rapport à ces derniers, d'une note plus naturelle, plus puissante. Nous avons en effet constaté que dans une essence de camomille synthétique, il s'est avéré nettement plus riche, plus complexe que la Méthylcamomille (2-méthyl-pentanoate de butyle ; origine : Givaudan-Roure, Vernier, Suisse), plus élégant dans le côté fruité naturel que l'ester d'acide angélique, plus fruité-camomille que le méthylbutyrate d'isopropyle.In addition, although evoking by its note chamomile esters of the type Chamomile known, ethyl (E) -2,4-dimethyl-2-pentenoate is endowed, compared to these last, with a more natural, more powerful note. We have indeed found that in a essence of synthetic chamomile, it turned out to be significantly richer, more complex that methylcamomile (butyl 2-methyl-pentanoate; origin: Givaudan-Roure, Vernier, Switzerland), more elegant in the natural fruity side than the ester of angelic acid, more fruity-chamomile as isopropyl methylbutyrate.

Pour sa part, le (Z)-2,4-diméthyl-2-penténoate d'éthyle est aussi un ingrédient parfumant utile développant une senteur fruitée, camomille, agréable et fraíche, très naturelle, tout aussi élégante que celle de l'isomère (E).For its part, ethyl (Z) -2,4-dimethyl-2-pentenoate is also an ingredient useful fragrance developing a fruity, chamomile, pleasant and fresh scent, very natural, just as elegant as that of the (E) isomer.

Par ailleurs, nous avons observé que les mélanges de ces isomères, dans toutes leurs proportions relatives possibles, se révèlent également être des ingrédients parfumants utiles. En particulier, les mélanges dans lesquels l'isomère (E) prédomine sont des ingrédients parfumants performants selon l'invention, possédant les caractères odorants typiques de ce composé.Furthermore, we observed that the mixtures of these isomers, in all of their possible relative proportions, also turn out to be ingredients useful perfumers. In particular, the mixtures in which the (E) isomer predominates are high-performance perfume ingredients according to the invention, having the characteristics typical fragrances of this compound.

De par ses qualités olfactives, le (E)-2,4-diméthyl-2-penténoate d'éthyle se prête à un usage en parfumerie dans des compositions de nature diverse. C'est ainsi qu'il peut se révéler fort avantageux dans une composition florale, par exemple, où il développe une odeur camomillée nettement plus puissante, plus fruitée et plus complexe que, par exemple, celle du 1,3-diméthyl-3-butényl-isobutyrate (voir, par exemple, US 4,387,047), et confère par la même un effet olfactif nouveau au parfum.Due to its olfactory qualities, ethyl (E) -2,4-dimethyl-2-pentenoate is ready for use in perfumery in compositions of various nature. This is how he can be very beneficial in a floral arrangement, for example, where it develops a significantly more powerful, fruity and more complex camomile smell than, for example, that of 1,3-dimethyl-3-butenyl-isobutyrate (see, for example, US 4,387,047), and thereby gives a new olfactory effect to the perfume.

Ainsi de par leurs propriétés odorantes, les composés de formule (I) se prêtent aussi bien pour des applications en parfumerie fine qu'en parfumerie fonctionnelle. Du fait de son emploi très varié, un ester selon l'invention constitue un ingrédient parfumant qui peut se révéler fort avantageux tant à l'état isolé qu'en mélange avec d'autres ingrédients odorants. Parmi les articles dans lesquels il peut être employé en tant qu'ingrédient parfumant, on peut citer les parfums ou eaux de toilette, les savons, les gels de douche ou de bain, les shampoings ou autres produits de soins capillaires, les préparations cosmétiques, les désodorisants corporels ou d'air ambiant, les détergents ou adoucissants textiles, ou les produits d'entretien.Thus by their odorous properties, the compounds of formula (I) lend themselves both for fine perfume and functional perfume applications. Of made of its very varied use, an ester according to the invention constitutes a perfuming ingredient which can be very advantageous both in the isolated state and in mixture with others fragrant ingredients. Among the articles in which it can be used as that perfuming ingredient, one can quote the perfumes or toilet waters, the soaps, the gels shower or bath, shampoos or other hair care products, cosmetic preparations, body or room air fresheners, detergents or fabric softeners, or cleaning products.

Les proportions dans lesquelles les composés selon l'invention peuvent être incorporés dans les produits divers susmentionnés varient dans une gamme de valeurs très étendue. Ces valeurs sont dépendantes de la nature de l'article ou produit que l'on veut parfumer et de l'effet olfactif recherché, ainsi que de la nature des coingrédients dans une composition donnée lorsqu'un composé de l'invention est utilisé en mélange avec des coingrédients parfumants, des solvants ou des adjuvants d'usage courant dans l'art. Bien entendu, un composé selon l'invention peut également être ajouté aux compositions et articles parfumés soit seul, soit en solution dans des solvants d'usage courants.The proportions in which the compounds according to the invention can be incorporated in the aforementioned miscellaneous products vary in a range of values very extent. These values are dependent on the nature of the article or product that we want perfume and the desired olfactory effect, as well as the nature of the co-ingredients in a composition given when a compound of the invention is used in mixture with perfume co-ingredients, solvents or adjuvants commonly used in the art. Good understood, a compound according to the invention can also be added to the compositions and scented articles either alone or in solution in commonly used solvents.

A titre d'exemple on peut citer des concentrations de l'ordre de 1 à 5%, voire 10% ou plus en poids de composé de formule (I), par rapport au poids de composition parfumante dans laquelle il est incorporé. Des concentrations bien inférieures à celles-ci peuvent être utilisées lorsque ce composé est appliqué dans le parfumage des produits de consommation divers cités auparavant. By way of example, mention may be made of concentrations of the order of 1 to 5%, or even 10% or more by weight of compound of formula (I), relative to the weight of composition fragrance in which it is incorporated. Concentrations much lower than these can be used when this compound is applied in the fragrance of various consumption mentioned above.

Par composition parfumante, on entend ici une composition constituée par un mélange d'ingrédients parfumants pouvant être choisis dans des classes chimiques variées, comprenant par exemple des esters, des aldéhydes, des alcools, des éthers, des cétones, des acétals, des nitriles, des hydrocarbures terpéniques, des composés hétérocycliques azotés ou soufrés, ainsi que des huiles essentielles d'origine naturelle ou synthétiques.By perfuming composition is meant here a composition consisting of a mixture of perfuming ingredients which can be chosen from various chemical classes, comprising for example esters, aldehydes, alcohols, ethers, ketones, acetals, nitriles, terpene hydrocarbons, heterocyclic compounds nitrogen or sulfur, as well as essential oils of natural or synthetic origin.

Les composés de la présente invention ayant une double liaison en position 2 ont été préparés comme mentionné plus haut selon les synthèses décrites dans les références citées.The compounds of the present invention having a double bond in position 2 were prepared as mentioned above according to the syntheses described in the references cited.

Le 2,4-diméthyl-3-penténoate d'éthyle a été préparé comme suit. Sous azote dans un ballon de 25 ml équipé d'un réfrigérant, 1,0 g (6,4 mmole) de 2,4-diméthyl-2-penténoate d'éthyle et 0,975 g (6,4 mmole) de DBU (1,8-diazabicyclo[5.4.0]undéc-7-ène) sont chauffés à 160°C. Après 18 heures, une fois refroidi, le mélange réactionnel est versé sur de l'eau et extrait avec de l'éther. La phase organique est lavée successivement avec une solution aqueuse à 5% de HCl, de l'eau, une solution de NaHCO3 saturée, et de la saumure, puis séchée sur Na2SO4 et concentrée. On obtient après distillation au four à boules (80-100°C, 5,32 x 102 Pa) 0,734 g d'un mélange 55 : 45 de 2,4-diméthyl-2-penténoate d'éthyle et de 2,4-diméthyl-3-penténoate d'éthyle. Les deux composés ont été séparés par chromatographie flash [SiO2 (30 g), cyclohexane : acétate d'éthyle = 98 : 2]. 0,180 g de 2,4-diméthyl-3-penténoate d'éthyle ont été obtenus.

  • RMN(1H) : 1,19(d, J=7, 3H) ; 1,25(t, J=7, 3H) ; 1,66(d, J=1, 3H) ; 1,72(d, J=1, 3H) ; 3,30(d, J=9 ; q, J=7, 1H) ; 4,12(q, J=7, 2H) ; 5,15(d, J=9 ; t, J=1, 1H) δppm.
  • RMN(13C) : 175,6(s) ; 133,9(s) ; 124,0(d) ; 60,3(t) ; 39,1(d) ; 25,7(q) ; 18,1(q) ; 18,0(q) ; 14,2(q) δppm.
  • SM : 156(M+, 14), 141(4), 83(100), 67(10), 55(42).
    • Ethyl 2,4-dimethyl-3-pentenoate was prepared as follows. Under nitrogen in a 25 ml flask equipped with a condenser, 1.0 g (6.4 mmol) of ethyl 2,4-dimethyl-2-pentenoate and 0.975 g (6.4 mmol) of DBU (1 , 8-diazabicyclo [5.4.0] undéc-7-en) are heated to 160 ° C. After 18 hours, once cooled, the reaction mixture is poured onto water and extracted with ether. The organic phase is washed successively with a 5% aqueous solution of HCl, water, a saturated NaHCO 3 solution, and brine, then dried over Na 2 SO 4 and concentrated. After distillation in a ball oven (80-100 ° C., 5.32 x 10 2 Pa), 0.734 g of a 55:45 mixture of ethyl 2,4-dimethyl-2-pentenoate and 2.4 is obtained. -dimethyl-3-pentenoate. The two compounds were separated by flash chromatography [SiO 2 (30 g), cyclohexane: ethyl acetate = 98: 2]. 0.180 g of ethyl 2,4-dimethyl-3-pentenoate were obtained.
  • NMR (1 H): 1.19 (d, J = 7, 3H); 1.25 (t, J = 7.3H); 1.66 (d, J = 1.3H); 1.72 (d, J = 1.3H); 3.30 (d, J = 9; q, J = 7, 1H); 4.12 (q, J = 7.2H); 5.15 (d, J = 9; t, J = 1, 1H) δppm.
  • NMR ( 13 C): 175.6 (s); 133.9 (s); 124.0 (d); 60.3 (t); 39.1 (d); 25.7 (q); 18.1 (q); 18.0 (q); 14.2 (q) δppm.
  • MS: 156 (M + , 14), 141 (4), 83 (100), 67 (10), 55 (42).

    • La présente invention sera maintenant décrite de façon plus détaillée à l'aide des exemples suivants.The present invention will now be described in more detail using following examples.

    Exemple 1Example 1 Préparation d'une composition parfumantePreparation of a perfume composition

    On a préparé une composition parfumante de base par mélange des ingrédients suivants : Ingrédient Parties en poids Acétate de benzyle 170 Acétate de cyclanol 20 Acétate de verdyle 20 Citronellol 40 Ethyl vanilline à 10% 20 Exaltex ® 140 Héliotropine 40 Iralia ® 100 Lilial ® 100 Linalol 120 Phénéthylol 40 Salicylate d'amyle 40 Salicylate de benzyle 120 970 En ajoutant à la composition de base de type herbacé indiquée ci-dessus 30 parties en poids de (E)-2,4-diméthyl-2-penténoate d'éthyle on obtient une nouvelle composition dont la note de tête particulièrement fruitée rappelle la senteur de la Camomille romaine, ce qui confère à l'ensemble un aspect plus vivant, plus puissant et nettement plus élégant.A basic perfume composition was prepared by mixing the following ingredients: Ingredient Parts by weight Benzyl acetate 170 Cyclanol acetate 20 Verdyl acetate 20 Citronellol 40 Ethyl vanillin 10% 20 Exaltex ® 140 Heliotropin 40 Iralia ® 100 Lilial ® 100 Linalol 120 Phenethylol 40 Amyl salicylate 40 Benzyl salicylate 120 970 By adding to the basic composition of the herbaceous type indicated above 30 parts by weight of (E) -2,4-dimethyl-2-pentenoate, a new composition is obtained, the particularly fruity top note recalling the scent of Roman Chamomile, which gives the whole a more lively, more powerful and clearly more elegant appearance.

    Exemple 2Example 2 Préparation d'une composition parfumantePreparation of a perfume composition

    On a préparé une composition parfumante de base à connotation poudrée-fleurie, boisée par mélange des ingrédients suivants : Ingrédient Parties en poids Acétate de cyclanol 30 Acétate de verdyle 80 Aldéhyde anisique 30 Dihydromyrcénol 30 Acétate de p-tert-butyl-cyclohexyle 210 Exaltex ® 150 Isoraldeine ® 80 Jasmal ® 80 Salicylate d'amyle 60 Tonalid ® 60 Vertofix coeur 80 Essence de violette 80 Total 970 L'addition de 30 parties en poids de (E)-2,4-diméthyl-2-penténoate d'éthyle à cette composition de base florale lui confère une forte connotation fruitée tout en lui impartissant, de façon plus marquée, un agréable caractère frais.A basic perfume composition with a powdery-floral, woody connotation was prepared by mixing the following ingredients: Ingredient Parts by weight Cyclanol acetate 30 Verdyl acetate 80 Anisde aldehyde 30 Dihydromyrcenol 30 P-tert-butyl-cyclohexyl acetate 210 Exaltex ® 150 Isoraldeine ® 80 Jasmal ® 80 Amyl salicylate 60 Tonalid ® 60 Vertofix heart 80 Essence of violet 80 Total 970 The addition of 30 parts by weight of (E) -2,4-dimethyl-2-pentenoate to this floral base composition gives it a strong fruity connotation while imparting to it, in a more marked manner, a pleasant character. fresh.

    Exemple 3Example 3 Préparation d'une composition parfumantePreparation of a perfume composition

    On a préparé une composition parfumante de base à odeur fougère-lavande-florale par mélange des ingrédients suivants : Ingrédient Parties en poids Acétate de benzyle 45 Acétate de linalyle 60 Acétate de styrallyle 30 Acétate de verdyle 80 Essence d'aspic 80 Benzophénone 60 Coumarine 30 Cyclométhylène citronellol 60 Eugénol 45 Exaltex ® 30 Lilial ® 45 Linalol 110 Iralia ® 80 Méthylhexylcétone 45 Méthylnaphtylcétone 80 Propionate de verdyle 45 Salicylate d'amyle 45 γ-Undécalactone 15 Total 985 L'addition de 15 parties en poids de (E)-2,4-diméthyl-2-penténoate d'éthyle à cette composition de type fougère très classique lui confère une note camomille enrichissante, en lui donnant un aspect frais et camomillé particulièrement moderne.A basic perfume composition with a fern-lavender-floral odor was prepared by mixing the following ingredients: Ingredient Parts by weight Benzyl acetate 45 Linalyl acetate 60 Styrallyl acetate 30 Verdyl acetate 80 Essence of Aspic 80 Benzophenone 60 Coumarin 30 Cyclomethylene citronellol 60 Eugenol 45 Exaltex ® 30 Lilial ® 45 Linalol 110 Iralia ® 80 Methylhexylketone 45 Methylnaphthylketone 80 Verdyl propionate 45 Amyl salicylate 45 γ-Undecalactone 15 Total 985 The addition of 15 parts by weight of ethyl (E) -2,4-dimethyl-2-pentenoate to this very classic fern-type composition gives it an enriching chamomile note, giving it a particularly modern and camomile appearance .

    Claims (7)

    Utilisation à titre d'ingrédient parfumant d'un composé de formule
    Figure 00080001
    possédant une double liaison dans l'une des positions indiquées par les pointillés.    Use as a perfuming ingredient of a compound of formula
    Figure 00080001
    having a double bond in one of the positions indicated by the dotted lines.         Utilisation selon la revendication 1 du 2,4-diméthyl-2-penténoate d'éthyle.Use according to claim 1 of ethyl 2,4-dimethyl-2-pentenoate. Utilisation selon la revendication 2, caractérisée en ce que le 2,4-diméthyl-2-penténoate d'éthyle se trouve sous la forme de l'un de ses isomères de configuration (Z) ou (E).Use according to claim 2, characterized in that the Ethyl 2,4-dimethyl-2-pentenoate is in the form of one of its isomers of configuration (Z) or (E). Composition parfumante ou article parfumé, contenant en tant qu'ingrédient parfumant un composé de formule
    Figure 00080002
    possédant une double liaison dans l'une des positions indiquées par les pointillés.    Perfume composition or perfume article, containing as a perfume ingredient a compound of formula
    Figure 00080002
    having a double bond in one of the positions indicated by the dotted lines.         Composition parfumante ou article parfumé selon la revendication 4, contenant du 2,4-diméthyl-2-penténoate d'éthyle.Perfume composition or perfume article according to claim 4, containing ethyl 2,4-dimethyl-2-pentenoate. Composition perfumante ou article parfumé selon la revendication 5, caractérisée en ce que le 2,4-diméthyl-2-penténoate d'éthyle est present sous la forme de l'un de ses isomères de configuration (E) ou (Z).Perfuming composition or perfumed article according to claim 5, characterized in that ethyl 2,4-dimethyl-2-pentenoate is present in the form of one of its configuration isomers (E) or (Z). Article parfumé selon l'une des revendications 4 à 6, sous forme d'un parfum ou d'une eau de toilette, d'un savon, d'un gel de douche ou de bain, d'un shampoing ou autre produit de soins capillaires, d'une préparation cosmétique, d'un désodorisant corporel ou d'air ambiant, d'un détergent ou adoucissant textile, ou d'un produit d'entretien.Perfumed article according to one of claims 4 to 6, in the form of a perfume or eau de toilette, soap, shower or bath gel, shampoo or other hair care product, cosmetic preparation, body or room air freshener, fabric detergent or fabric softener, or cleaning product.
    EP97116147A 1996-10-23 1997-09-17 Use of unsaturated aliphatic esters in perfumery Expired - Lifetime EP0838215B1 (en)

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    CH258996 1996-10-23

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    FR2805991A1 (en) * 2000-03-13 2001-09-14 Rhodia Chimie Sa Perfumed composition for use in bath and shower products, deodorants, antiperspirants, shampoos, talc and air deodorizers comprises a hydroxy-3-butenoic acid ester

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    WO2018196988A1 (en) * 2017-04-28 2018-11-01 Symrise Ag Ethyl-2-acetyl-2,4-dimethyl-pent-4-enoate as a fragrance

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    EP0921186A3 (en) * 1997-12-08 2000-04-26 Firmenich Sa Use of ethyl 3-methyl-2-oxopentanoate as a perfuming ingredient
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    DE69728837T2 (en) 2005-02-03
    EP0838215A3 (en) 2000-05-10
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    US5814598A (en) 1998-09-29
    EP0838215B1 (en) 2004-04-28
    DE69728837D1 (en) 2004-06-03
    JPH10130688A (en) 1998-05-19

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