EP0056109B1 - Use of 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylic-acid methyl ester as a perfuming agent - Google Patents

Use of 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylic-acid methyl ester as a perfuming agent

Info

Publication number
EP0056109B1
EP0056109B1 EP19810109812 EP81109812A EP0056109B1 EP 0056109 B1 EP0056109 B1 EP 0056109B1 EP 19810109812 EP19810109812 EP 19810109812 EP 81109812 A EP81109812 A EP 81109812A EP 0056109 B1 EP0056109 B1 EP 0056109B1
Authority
EP
Grant status
Grant
Patent type
Prior art keywords
damascone
damascenone
trimethyl
cyclohex
yl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP19810109812
Other languages
German (de)
French (fr)
Other versions
EP0056109A2 (en )
EP0056109A3 (en )
Inventor
Karl-Heinrich Schulte-Elte
Dietrich Kastner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Firmenich SA
Original Assignee
Firmenich SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Grant date

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50Perfumes
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING (PRESSING, EXTRACTION), REFINING AND PRESERVING FATS, FATTY SUBSTANCES (e.g. LANOLIN), FATTY OILS AND WAXES, INCLUDING EXTRACTION FROM WASTE MATERIALS; ESSENTIAL OILS; PERFUMES
    • C11B9/00Essential oils; Perfumes
    • C11B9/0026Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms

Description

  • [0001]
    L'invention se rapporte à un nouvel ingrédient parfumant, dans le cas précis à un ester alicyclique de formule The invention relates to a new perfuming ingredient, in the specific case to an alicyclic ester of formula ou 2,6,6-triméthyl-cyclohex-2-ène-1-yl-carboxylate de méthyle, également dénommé a-cyclogéraniate de méthyle. or 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate, also known as a-methyl cyclogeranate.
  • [0002]
    L'invention a pour objet l'utilisation dudit composé (I) à titre d'ingrédient parfumant, notamment son utilisation à l'etat pur ou en mélange avec au moins un ingrédient parfumant ci-après: a-damascone, β-damascone, y-damascone, δ-damascone, s-damascone, a-damascenone, β-damascenone, y-damascenone et 8-damascenone The invention relates to the use of said compound (I) as perfuming ingredient, in particular its use in the pure state or in admixture with at least one perfuming ingredient below: a-damascone, β-damascone, y-damascone, δ-damascone, s-damascone, a-damascenone, β-damascenone, y-damascenone and 8-damascenone
  • [0003]
    L'invention a également pour objet une composition parfumante contenant ledit composé (1), notamment une composition parfumante contenant ledit composé (1) pur ou en melange avec aumoins un des ingrédients parfumants définis plus haut. The invention also relates to a fragrance composition containing said compound (1), in particular a perfuming composition comprising said compound (1) pure or in admixture with atleast one of the perfuming ingredients defined above.
  • [0004]
    Le 2,6,6-triméthyl-cyclohex-2-éne-1-yl-carboxylate de méthyle (1) est un composé connu [voir par exemple Helv. The 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylate (1) is a known compound [see, e.g., Helv. Chim. Chim. Acta 42, 2597 (1959)]; Acta 42, 2597 (1959)]; ses propriétés olfactives n'ont cependant pas été décrites jusqu'à maintenant. its olfactory properties however, have not been described until now.
  • [0005]
    Lorsque l'on considère les esters alicycliques analogues ou homologues du composé (I), on parvient à définir l'état présent de la technique au moyen du tableu ci-après: When considering similar alicyclic esters or homologues of compound (I) are able to define the present state of the art by means of the spreadsheet below:
  • [0006]
    De l'état de la technique précité, on peut aisément déduire que seuls présentent un intérêt pour la parfumerie les esters homologues supérieurs du 2,6,6-triméthyl-cyclohex-2-ène-1-yl-carboxylate de méthyle (I), notamment les esters éthyliques comportant un groupe éthyle en position 2 du cycle à 6 membres, voire un groupe méthyle additionnel en position 3, ainsi que des mélanges isomériques de composés polyinsaturés correspondants, a-, β-et y-safranates d'éthyle plus précisément. Of the abovementioned state of the art, one can easily deduce that only of interest for the perfumery higher homologs esters of 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate (I) including ethyl esters having an ethyl group at position 2 of the 6-membered ring, or an additional methyl group in position 3, and the corresponding isomeric mixtures of polyunsaturated compounds, a-, β-and y-ethyl safranates more precisely.
  • [0007]
    Les composés homologues inférieurs de la série définie ci-dessus, notamment le composé (I) et son isomère, le β-cyclogéraniate de méthyle, n'ont par contre jamais retenu l'attention des parfumeurs. The lower homologues of the series defined above, in particular the compound (I) and its isomer, methyl β-cyclogeranate, have never against by attention perfumers.
  • [0008]
    Dans un tel contexte, il était donc d'autant plus surprenant de découvrir que le 2,6,6-triméthyl-cyclohex-2-ène-1-yl-carboxylate de méthyle (I) pouvait présenter un grand intérêt pour la parfumerie. In such a context, so it was particularly surprising to discover that the 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylate (I) could be of great interest for perfumery.
  • [0009]
    Le composé (I) développe en effet une note olfactive originale que l'on peut qualifier de tout à la fois fruitée et florale, accompagnée d'une tonalité fraîche du genre hespéridé. Compound (I) indeed developing an original olfactory notes that can be called at once fruity and floral, with a fresh citrus tone of the genre. Ce fait est d'autant plus remarquable que ces caractères olfactifs ne se développent pleinement que lorsque le composé (I) est utilisé sous forme diluée, en particulier sous forme de solution à 10, 5 ou 1%, voire moins. This fact is even more remarkable that these olfactory characters do not develop fully as when compound (I) is used in diluted form, especially as a solution to 10, 5 or 1% or less.
  • [0010]
    De ce fait, le composé (I) peut être avantageusement utilisé pour le parfumage de produits tels que savons, détergents liquides ou solides, produits cosmétiques ou produits d'entretien par exemple. Therefore, the compound (I) can be advantageously used for perfuming of products such as soaps, liquid or solid detergents, cosmetics or care products for example. Il peut être en outre utilisé tout aussi avantageusement en parfumerie fine, notamment pour la préparation de compositions parfumantes de type fruité, fleuri, rosé, boisé, épicé, chypre ou hespéridé par exemple. It may further be used equally advantageously in fine perfumery, in particular for the preparation of perfuming compositions of fruity type floral, rose, woody, spicy, citrus chypre or eg.
  • [0011]
    Dans un tel cas, le composé (I) peut s'utiliser pur ou en mélange avec un ou plusieurs ingrédients parfumants, un solvant ou un support usuel. In such a case, the compound (I) can be used pure or in admixture with one or more perfuming ingredients, solvent or a conventional support. Lors de la préparation de compositions parfumantes, le composé (I) s'utilise de préférence à raison de 0,1 à 5, voire 10% environ par rapport au poids de ladite composition. In the preparation of perfuming compositions, the compound (I) is preferably used at 0.1 to 5, or even about 10% by weight of said composition. Des proportions supérieures à 10% peuvent être également considérées, en particulier lors de la préparation de bases ou coeurs pour parfums. Some 10% higher proportions may also be considered, particularly when preparing bases for perfumes or hearts. Des proportions inférieures à 0,1 % peuvent être également envisagées, notamment lors du parfumage de produits tels que savons, détergents ou produits cosmétiques par exemple. Proportions less than 0.1% may also be envisaged, in particular during the perfuming of products such as soaps, detergents or cosmetics, for example.
  • [0012]
    Dans le cadre de la présente invention, il a été découvert en outre que le 2,6,6-triméthyl-cyclohex-2-ène-1-yl- carboxylate de méthyle (I) pouvait avoir une action particulièrement intéressante au niveau des effets olfactifs de certains ingrédients parfumants, notamment ceux de la série des damascones et damascénones. In the context of the present invention, it has been discovered further that the 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate (I) may have a particularly useful level action effects olfactory some fragrance ingredients, including those from the series of damascones and damascénones. Damascones et damascénones sont des ingrédients très appréciés tant en parfumerie fine que lors du parfumage de produits techniques: ils se caractérisent notamment par une note olfactive rosée et boisée remarquablement radiante, voire fruitée de type pomme, ou menthée selon les cas. Damascones and damascénones are popular ingredients in both fine fragrances that when perfuming of technical products: they are characterized by a particular olfactory note dew remarkably radiant and woody or fruity type of apple, or minty as appropriate.
  • [0013]
    Le tableau ci-après fait l'inventaire des représentants de cette importante série que l'on peut mettre à la disposition de l'industrie des parfums The table below takes stock of representatives of this important series that can be put at the disposal of the fragrance industry 3) DORICENONE® (Origine: FIRMENICH SA- Genève- Suisse) 3) DORICENONE® (Source: FIRMENICH SA- Geneva- Switzerland)
  • [0014]
    Du point de vue olfactif, le composé (I) a entre autres l'avantage de se combiner de façon très harmonieuse auxdites damascones et damascénones, contribuant à leur donner encore plus de richesse et de rondeur. Olfactory standpoint, the compound (I) including the advantage of combining in a very harmonious and said damascones damascénones, helping to give them even more richness and roundness. Le composé (I) a en outre la particularité d'abaisser sensiblement le niveau de perception olfactive des ingrédients sus-nommés: on peut parler à ce propos d'effet synergétique. Compound (I) has also the distinction of significantly lowering the level of olfactory perception of the above-named ingredients: we can talk about it with synergistic effect.
  • [0015]
    Lorsque le 2,6,6-triméthyl-cyclohex-2-ène-1-yl-carboxylate de méthyle (I) s'utilise en mélange avec une ou plusieurs desdites damascones ou damascénones, des effet olfactifs tels que ceux mentionnés ci-dessus peuvent être obtenus par l'emploi de mélanges composé (I)/damascone ou damascénone dans lesquels les proportions de chacun des constituants sont le plus généralement comprises entre 20:1 et 1:20. When the 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate (I) is used in admixture with one or more said damascones or damascénones, olfactory effect such as those mentioned above can be obtained by using mixtures of compound (I) / damascone or damascenone wherein the proportions of each component are most generally between 20: 1 and 1:20. Les proportions données ci-dessus ne sont cependant pas à considérer comme des limites absolues. The proportions given above, however, are not to be regarded as absolute limits.
  • [0016]
    Le 2,6,6-triméthyl-cyclohex-2-ène-1-yl-carboxalate de méthyle (I) peut être aisément obtenu selon les méthodes décrites dans la littérature, par exemple par estérification de l'acide cyclogéranique correspondant ou par cyclisation de géraniate de méthyle [voir par exemple Helv. The 2,6,6-trimethyl-cyclohex-2-en-1-yl-methyl carboxalate (I) can be easily obtained according to the methods described in the literature, for example by esterification of the corresponding acid or cyclogeranic by cyclization methyl géraniate [see, e.g., Helv. Chim. Chim. Acta 42, 2597 (1959) et Chem. Acta 42, 2597 (1959) and Chem. Abstr. Abstr. 57, 11239; 57, 11239; (1962)]. (1962)].
  • [0017]
    L'invention sera illustrée de façon plus détaillée à l'aide des exemples ci-après. The invention is illustrated in more detail using the examples below.
  • Exemple 1 example 1
  • [0018]
    Un détergent en poudre du commerce, olfactivement neutre, a été parfumé à raison de 0,05% à l'aide de 2,6,6-triméthyl-cyclohex-2-ène-1-yl-carboxylate de méthyle. A detergent commercially available powder, olfactory neutral, was flavored with 0.05% using 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate. Il acquiert ainsi une odeur agréable de type fruité, rappelant notamment celle de fruits mûrs. It thus acquires a pleasant aroma of fruity kind, recalling notably that of ripe fruit.
  • Exemple 2 example 2
  • [0019]
    On a préparé une composition parfumante de base comme suit: a perfuming composition base was prepared as follows:
  • [0020]
    La composition de base ainsi obtenue possède une odeur de type fleuri-vert relativement peu définie. The base composition thus obtained has a relatively defined floral green-like odor. En ajoutant à 92 parties de ladite base 8 parties de 2,6,6- trimethyl-cyclohex-2-ène-1-yl-carboxylate de méthyle, on confère à celle-ci une note de type "pomme verte" très caractéristique. By adding to 92 parts of said base 8 parts of 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate, is imparted thereto a note type "apple green" characteristic.
  • [0021]
    La nouvelle composition parfumante ainsi obtenue convient particulièrement bien au parfumage de produits tels que savons ou shampoings The new fragrance composition thus obtained is particularly suitable for perfuming products such as soaps or shampoos
  • Exemple 3 example 3
  • [0022]
    On a préparé une composition parfumante de base de type "rose" comme suit: We prepared a base perfuming composition of "pink" as follows:
  • [0023]
    La base ainsi préparée possède une odeur de type "rose rouge". The prepared base has a kind of smell "red rose." En ajoutant à 98 parties de ladite base 2 parties de 2,6,6-triméthyl-cyclohex-2-ène-1-yt-carboxylate de méthyle, on obtient une nouvelle composition parfumante dont l'odeur est devenue plus fraîche, plus montante et plus élégante que celle de ladite base; By adding to 98 parts of said base 2 parts of 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate, a new perfuming composition whose odor became cooler is obtained more uplink and more elegant than that of said base; elle peut être maintenant définie de type "rose thé". it can be now defined type "tea rose".
  • Exemple 4 example 4
  • [0024]
    On a préparé une composition parfumante de base de type "rose" comme suit: We prepared a base perfuming composition of "pink" as follows:
  • [0025]
    Ainsi constituée, la base présente une odeur de type 'rose'. Thus constituted, the base has a type of odor pink. Cette odeur devient nettement plus caractéristique après addition à ladite base de 15 parties d'une solution à 0,01% de β-damascénone dans l'alcool éthylique. This odor becomes considerably more characteristic after adding to said base 15 parts of a 0.01% solution of β-damascenone in ethyl alcohol.
  • [0026]
    L'addition de 30 parties d'une solution de 2,6,6-triméthyl-cyclohex-2-ène-1-yl-carboxylate de méthyle à 0,1% dans l'alcool éthylique à la nouvelle composition ci-dessus confère à cette dernière une note de tête rosée et fruitée encore plus riche et plus montante. The addition of 30 parts of a solution of 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate in 0.1% methyl ethyl alcohol to the new composition above gives the latter a dew note and fruity head still richer and rising.
  • Exemple 5 example 5
  • [0027]
    A 688 parties de la base parfumante préparée selon l'Exemple 4 on a ajouté 15 parties d'une solution à 0,01% de β-damascone dans l'alcool éthylique, pour obtenir une composition de type "rose" très caractéristique, à l'odeur fraîche et montante A 688 parts of the perfume base prepared according to Example 4 was added 15 parts of a 0.01% solution of β-damascone in ethyl alcohol, to obtain a composition of the type "rose" characteristic, in fresh and odor rising
  • [0028]
    L'addition de 30 parties d'une solution de 2,6,6-triméthyl-cyclohex-2-ène-1-yl-carboxylate de méthyle à 0,1% dans l'alcool éthylique à la composition ci-dessus renforce encore le côté frais, fruité et montant typique de la β-damascone The addition of 30 parts of a solution of 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate in 0.1% methyl ethyl alcohol to the above composition further strengthens the cool side, fruity and typical amount of β damascone
  • Exemple 6 example 6
  • [0029]
    100 g de talc ont été parfumés à raison de 0,15% au moyen d'un mélange 50:50 de p-damascone et 2,6,6-trimé- thyl-cyclohex-2-ène-1-yl-carboxylate de méthyle. 100 g of talc were perfumed in an amount of 0.15% by means of a 50:50 mixture of p-damascone and 2,6,6-trimethyl thyl-cyclohex-2-en-1-yl-carboxylate methyl. On obtien ainsi une poudre dégageant une odeur de type rosé, fruité et frais particulièrement plaisante. Thus obtien powder off a rose-like odor, fruity and particularly pleasant costs.
  • [0030]
    Des effets olfactifs comparables, et tout aussi plaisants, ont été obtenus par l'emploi de mélange 50:50 d'a-damascone et 2,6,6-triméthyl-cyclohex-2-ène-1-yl-carboxylate de méthyle, respectivement de β-damascénone et 2,6,6-triméthyl-cyclohex-2-éne-1-yl-carboxylate de méthyle Similar olfactory effects, and equally pleasing, were obtained by the use of 50:50 mixture of a-damascone and 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate, respectively β-damascenone and 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylate
  • Exemple 7 example 7
  • [0031]
    Un détergent liquide concentré a été parfumé à raison de 0,15% au moyen d'un mélange 1:10 de β-damascénone et 2,6,6-triméthyl-cyclohex-2-ène-1-yl-carboxylate de méthyle. A concentrated liquid detergent was perfumed in an amount of 0.15% using a 1:10 mixture of β-damascenone and 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate. Il développe désormais une odeur de type rosé fruité et frais particulièrement plaisante. It now develops a fruity and particularly pleasant chilled rose-like odor.
  • [0032]
    Des effets olfactifs comparables, et tout aussi plaisants, ont été obtenuspar l'emploi de mélanges 1:10 d'adamascone et 2,6,6-triméthyl-cyclohex-2-ène-1-yl-carboxylate de méthyle, respectivement de β-damascone et 2,6,6 triméthyl-cyclohex-2-ène-1-yl-carboxylate de méthyle. Similar olfactory effects, and equally pleasing were obtenuspar the use of mixtures 1:10 adamascone and 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate, respectively of β -damascone and 2,6,6-trimethyl-cyclohex-2-en-1-yl-carboxylate.

Claims (4)

1. Utilisation of methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate as perfuming ingredient.
2. Utilisation according to claim 1 of methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate in its pure form or in admixture with one or several perfum ingredients, a solvent or a support.
3. Utilisation according to claim 1 of methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate in admixture with at least one of the following Perfume ingredients: a-damascone, β-damascone, y-damascone, 8-damascone, ε-damascone, a-damascenone, β-damascenone, y-damascenone and 8-damascenone.
4. Perfume composition characterized in that it contains methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate in admixture with at least one of the following perfume ingredients: a-damascone, β-damascone, y-damascone, 8-damascone, e-damascone, a-damascenone, β-damascenone, y-damascenone and 8-damascenone.
EP19810109812 1981-01-13 1981-11-21 Use of 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylic-acid methyl ester as a perfuming agent Expired EP0056109B1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CH17781 1981-01-13
CH177/81 1981-01-13

Publications (3)

Publication Number Publication Date
EP0056109A2 true EP0056109A2 (en) 1982-07-21
EP0056109A3 true EP0056109A3 (en) 1983-08-31
EP0056109B1 true EP0056109B1 (en) 1986-01-15

Family

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Country Status (4)

Country Link
US (1) US4411829A (en)
EP (1) EP0056109B1 (en)
JP (1) JPS57139010A (en)
DE (1) DE3173535D1 (en)

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