EP0380944A2 - Use of a cycloaliphatic oxo-ketone as a perfuming ingredient - Google Patents

Use of a cycloaliphatic oxo-ketone as a perfuming ingredient Download PDF

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Publication number
EP0380944A2
EP0380944A2 EP90100623A EP90100623A EP0380944A2 EP 0380944 A2 EP0380944 A2 EP 0380944A2 EP 90100623 A EP90100623 A EP 90100623A EP 90100623 A EP90100623 A EP 90100623A EP 0380944 A2 EP0380944 A2 EP 0380944A2
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Prior art keywords
oxo
ketone
perfuming
cycloaliphatic
perfuming ingredient
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EP90100623A
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German (de)
French (fr)
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EP0380944A3 (en
Inventor
Bruno Maurer
Ferdinand Naef
René DECORZANT
Ernest Wenkert
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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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms

Definitions

  • the present invention relates to the field of perfumery. It relates in particular to the use of a cycloaliphatic oxo-ketone of formula or 4- (2,5,6,6-tetramethyl-3-oxo-cyclohex-1-en-yl) -but-3-en-2-one, as a perfuming agent.
  • the subject of the invention is also a perfuming composition, characterized in that it contains, as an active perfuming ingredient, said ketone.
  • the oxo-ketone of the invention can serve as active principle for deodorizing or sanitizing devices for ambient air or closed chambers.
  • the proportions in which the compound of the invention can develop the desired odorous characteristics can of course vary within a very wide range of values. Those skilled in the art know from experience that such values depend on the particular effect sought as well as on the nature of the products which it is desired to flavor. It is also known that these values are a function of the nature of the other constituents in a given composition when the oxo-ketone (I) is used as an ingredient in a perfume base or in a concentrate, in mixture with other co-ingredients , common solvents or adjuvants.
  • proportions of the order of 5, 10 or even 20% by weight relative to the weight of the composition in which it is incorporated can be used without the smell of the resulting composition loses balance.
  • oxo-ketone (I) can be used in accordance with the invention either by direct addition to the products which it is desired to flavor in the isolated state, or more generally in admixture with other perfuming ingredients, additives or carriers, use is common in perfumery.
  • the perfume co-ingredients with which the compound of the invention can be combined in such use belong to various chemical classes, for example aldehydes, esters, ethers and alcohols; they can be natural or synthetic.
  • oxo-ketone (I) is a known compound which can be obtained using the method described by Kaiser and Lamparsky [op. cit.], from alpha-irone by epoxidation followed by the opening of the oxirane ring by means of a strong base and oxidation. The process followed can be illustrated by the following reaction scheme:
  • a basic perfume composition was prepared by mixing the following ingredients (parts by weight)

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)

Abstract

4-(2,5,6,6-Tetramethyl-3-oxo-1-cyclohexenyl)-3-buten-2-one is a compound which develops useful fragrant characteristics, and can as a result be used for the preparation of perfuming compositions and for the perfuming of miscellaneous products such as soaps, detergents or cosmetics.

Description

La présente invention a trait au domaine de la parfumerie. Elle concerne en particulier l'utilisation d'une oxo-cétone cycloaliphatique de formule

Figure imgb0001
ou 4-(2,5,6,6-tétraméthyl-3-oxo-cyclohex-1-én-yl)-but-3-én-2-one, à titre d'agent parfumant.The present invention relates to the field of perfumery. It relates in particular to the use of a cycloaliphatic oxo-ketone of formula
Figure imgb0001
 or 4- (2,5,6,6-tetramethyl-3-oxo-cyclohex-1-en-yl) -but-3-en-2-one, as a perfuming agent.

L'invention a également pour objet une composition parfumante caractérisée en ce qu'elle contient en tant qu'ingrédient parfumant actif ladite cétone.The subject of the invention is also a perfuming composition, characterized in that it contains, as an active perfuming ingredient, said ketone.

L'invention est définie comme indiqué aux revendications.The invention is defined as indicated in the claims.

La 4-(2,5,6,6-tétraméthyl-3-oxo-cyclohex-1-én-yl)-but-3-én-2-one est une entité chimique connue. Elle a été décrite par R. Kaiser et D. Lamparsky dans Helv. Chim. Acta 61, 2328 (1978) à titre de composé intermédiaire pour la préparation de dérivés de la mégastigmadiénone, sans que pour autant ses propriétés odorantes aient été reconnues.4- (2,5,6,6-tetramethyl-3-oxo-cyclohex-1-en-yl) -but-3-en-2-one is a known chemical entity. It has been described by R. Kaiser and D. Lamparsky in Helv. Chim. Acta 61 , 2328 (1978) as an intermediate compound for the preparation of megastigmadienone derivatives, although its odorous properties have not been recognized.

C'est de façon surprenante que nous avons découvert que le composé en question pouvait développer des notes olfactives utiles et que, par conséquent, il pouvait être employé pour le parfumage d'articles divers et pour la préparation de bases parfumantes et de parfums. Son odeur peut être définie comme étant de type iris, dans la direction de l'iris concrète; elle est en outre balsamique et rappelle le caractère de l'opoponax. Il développe une note élégante et agréable de grande richesse et son emploi peut être envisagé dans bon nombre de compositions de nature variée.It was surprisingly that we discovered that the compound in question could develop useful olfactory notes and that, consequently, it could be used for the perfume of various articles and for the preparation of perfume bases and perfumes. Its odor can be defined as being of the iris type, in the direction of the concrete iris; it is also balsamic and recalls the opoponax character. It develops an elegant and pleasant note of great richness and its use can be envisaged in a good number of compositions of varied nature.

Parmi les articles qui peuvent être parfumés à l'aide de l'oxo-cétone de l'invention il convient de citer à titre d'exemple les savons, les détergents, solides et liquides, ioniques, anioniques ou zwitterioniques ou non-ioniques, les adoucissants textiles, les produits d'entretien ou encore les cosmétiques, les shampoings et les désodorisants corporels. Employé en tant qu'adjuvant actif dans des bases polymériques ou résines variées, l'oxo-cétone de l'invention peut servir comme principe actif pour des dispositifs désodorisants ou assainissants d'air ambiant ou d'enceintes fermées.Among the articles which can be perfumed using the oxo-ketone of the invention, it is appropriate to cite by way of example soaps, detergents, solid and liquid, ionic, anionic or zwitterionic or non-ionic, fabric softeners, cleaning products or cosmetics, shampoos and body deodorants. Used as an active adjuvant in various polymeric bases or resins, the oxo-ketone of the invention can serve as active principle for deodorizing or sanitizing devices for ambient air or closed chambers.

Les proportions dans lesquelles le composé de l'invention peut développer les caractères odorants désirés peuvent bien entendu varier dans une gamme de valeurs très étendue. L'homme de l'art sait par expérience que de telles valeurs dépendent de l'effet particulier recherché ainsi que de la nature des produits que l'on désire parfumer. On sait également que ces valeurs sont fonction de la nature des autres constituants dans une composition donnée lorsque l'oxo-cétone (I) est utilisée en tant qu'ingrédient dans une base parfumante ou dans un concentré, en mélange avec d'autres coingrédients, des solvants ou des adjuvants usuels.The proportions in which the compound of the invention can develop the desired odorous characteristics can of course vary within a very wide range of values. Those skilled in the art know from experience that such values depend on the particular effect sought as well as on the nature of the products which it is desired to flavor. It is also known that these values are a function of the nature of the other constituents in a given composition when the oxo-ketone (I) is used as an ingredient in a perfume base or in a concentrate, in mixture with other co-ingredients , common solvents or adjuvants.

A titre d'exemple, on peut mentionner que des proportions de l'ordre de 5, 10, voire 20% en poids par rapport au poids de la composition dans laquelle elle est incorporée peuvent être employées sans que l'odeur de la composition résultante perde de son équilibre.By way of example, it can be mentioned that proportions of the order of 5, 10 or even 20% by weight relative to the weight of the composition in which it is incorporated can be used without the smell of the resulting composition loses balance.

De telles valeurs peuvent être bien inférieures lors du parfumage d'articles tels les cosmétiques, les savons ou les détergents. L'oxo-cétone (I) peut être utilisée conformément à l'invention soit par adjonction directe aux produits que l'on désire parfumer à l'état isolé, soit plus généralement en mélange avec d'autres ingrédients parfumants, additifs ou supports dont l'utilisation est courante en parfumerie. Les coingrédients parfumants avec lesquels le composé de l'invention peut être combiné dans un tel emploi, appartiennent à des classes chimiques variées, par exemple aldéhydes, esters, éthers et alcools; ils peuvent être naturels ou synthétiques.Such values can be much lower when perfuming articles such as cosmetics, soaps or detergents. The oxo-ketone (I) can be used in accordance with the invention either by direct addition to the products which it is desired to flavor in the isolated state, or more generally in admixture with other perfuming ingredients, additives or carriers, use is common in perfumery. The perfume co-ingredients with which the compound of the invention can be combined in such use, belong to various chemical classes, for example aldehydes, esters, ethers and alcohols; they can be natural or synthetic.

La mention spécifique de tels coingrédients est ici superflue. L'état de la technique est en effet riche en exemples et l'homme de l'art pourra choisir ceux parmi les coingrédients connus qui se prêtent le mieux à satisfaire son but de création. Une référence particulière est faite à l'ouvrage de S. Arctander, Perfume and Flavor Chemicals, Montclair, N.J. (USA), 1969.The specific mention of such co-ingredients is superfluous here. The state of the art is indeed rich in examples and those skilled in the art will be able to choose those among the known co-ingredients which best lend themselves to satisfying their creative goal. Particular reference is made to the work of S. Arctander, Perfume and Flavor Chemicals, Montclair, NJ (USA), 1969.

Comme il a été indiqué plus haut, l'oxo-cétone (I) est un composé connu qui peut être obtenu à l'aide du procédé décrit par Kaiser et Lamparsky [op. cit.], à partir d'alpha-irone par époxydation suivie de l'ouverture du cycle oxiranique au moyen d'une base forte et d'oxydation. Le procédé suivi peut être illustré par le schéma réactionnel que voici:

Figure imgb0002
As indicated above, oxo-ketone (I) is a known compound which can be obtained using the method described by Kaiser and Lamparsky [op. cit.], from alpha-irone by epoxidation followed by the opening of the oxirane ring by means of a strong base and oxidation. The process followed can be illustrated by the following reaction scheme:
Figure imgb0002

L'invention est illustrée mais non limitée par l'exemple suivant.The invention is illustrated but not limited by the following example.

ExempleExample

Une composition parfumante de base a été préparée en mélangeant les ingrédients suivants (parties en poids)

Figure imgb0003
A basic perfume composition was prepared by mixing the following ingredients (parts by weight)
Figure imgb0003

Lorsqu'on ajoute à 95 parties en poids de cette composition 5 parties en poids de 4-(2,5,6,6-tétraméthyl-3-oxo-cyclohex-1-én-yl)-but-3-én-2-one, on obtient une nouvelle composition dont le côté irisé est fortement augmenté. Le mélange acquiert en outre plus de volume et son caractère floral-poudré se trouve renforcé de façon marquée.When 5 parts by weight of 4- (2,5,6,6-tetramethyl-3-oxo-cyclohex-1-en-yl) -but-3-en-2 are added to 95 parts by weight of this composition -one, we obtain a new composition whose iridescent side is greatly increased. The mixture also acquires more volume and its floral-powdery character is markedly enhanced.

Claims (4)

1. Utilisation de la 4-(2,5,6,6-tétraméthyl-3-oxo-cyclohex-1-én-yl)-but-3-­én-2-one en tant qu'ingrédient parfumant dans des compositions parfumantes et produits parfumes. 1. Use of 4- (2,5,6,6-tetramethyl-3-oxo-cyclohex-1-en-yl) -but-3-en-2-one as a perfuming ingredient in perfuming compositions and perfume products. 2. Composition parfumante résultant de l'utilisation selon la revendication 1. 2. Perfuming composition resulting from the use according to claim 1. 3. A titre de produit parfumé résultant de l'utilisation selon la revendication 1, un détergent ionique, anionique, non-ionique ou zwitterionique, ou un savon. 3. As a perfumed product resulting from the use according to claim 1, an ionic, anionic, non-ionic or zwitterionic detergent, or a soap. 4. A titre de produit parfumé résultant de l'utilisation selon la revendication 1, un désodorisant d'air ambiant. 4. As a perfumed product resulting from the use according to claim 1, an air freshener.
EP19900100623 1989-02-01 1990-01-12 Use of a cycloaliphatic oxo-ketone as a perfuming ingredient Withdrawn EP0380944A3 (en)

Applications Claiming Priority (2)

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CH33789 1989-02-01
CH337/89 1989-02-01

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EP0380944A2 true EP0380944A2 (en) 1990-08-08
EP0380944A3 EP0380944A3 (en) 1991-12-18

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0012246A1 (en) * 1978-11-24 1980-06-25 L. Givaudan & Cie Société Anonyme Aromatic and flavouring substances, their preparation by fermentation, their use and products containing them
EP0211954A1 (en) * 1984-04-03 1987-03-04 T. Hasegawa Company, Ltd. Use of (+/-)-cis-gamma-irone in perfumery and novel process for preparing same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0012246A1 (en) * 1978-11-24 1980-06-25 L. Givaudan & Cie Société Anonyme Aromatic and flavouring substances, their preparation by fermentation, their use and products containing them
EP0211954A1 (en) * 1984-04-03 1987-03-04 T. Hasegawa Company, Ltd. Use of (+/-)-cis-gamma-irone in perfumery and novel process for preparing same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HELVETICA CHIMICA ACTA, vol. 61, fasc. 7, 1978, pages 2328-2335; R. KAISER et al.: "Inhaltsstoffe des Osmanthus-Absolues" *

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