EP0045534B1 - Use of phenyl-n-hexyl ketone as a perfuming agent, and perfume compositions containing the same - Google Patents
Use of phenyl-n-hexyl ketone as a perfuming agent, and perfume compositions containing the same Download PDFInfo
- Publication number
- EP0045534B1 EP0045534B1 EP19810200744 EP81200744A EP0045534B1 EP 0045534 B1 EP0045534 B1 EP 0045534B1 EP 19810200744 EP19810200744 EP 19810200744 EP 81200744 A EP81200744 A EP 81200744A EP 0045534 B1 EP0045534 B1 EP 0045534B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- phenyl
- hexyl ketone
- same
- compositions containing
- perfume compositions
- 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
Links
Classifications
-
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
Definitions
- the invention relates to the field of perfumery. It more particularly relates to the use of phenyl-n-hexyl ketone as a perfuming ingredient for the preparation of perfumes and perfumed products. It also relates to a fragrance composition containing said phenyl-n-hexyl ketone as an odoriferous ingredient.
- Phenyl-n-hexyl ketone is a known chemical entity, described in particular in Beestein 7, 337; however, the state of the art is silent as to its organoleptic properties.
- this compound has very interesting olfactory properties and can therefore find wide use as an odoriferous ingredient in compositions of various kinds.
- phenyl-n-hexyl ketone can be used to give interesting olfactory effects vary relatively widely. Thus, concentrations of approximately 0.5 to 1%, by weight, relative to the total weight of the composition considered can already produce marked effects when perfuming products such as soaps, shampoos or cosmetic articles for example.
- a basic perfume composition of the "yellow narcissus" type was prepared by mixing the following ingredients (parts by weight): The addition to 85 g of the composition indicated above of 15 g of phenyl-n-hexyl ketone makes its odor more intense and more rounded by giving it a more natural and pleasant character.
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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)
Description
L'invention se rapporte au domaine de la parfumerie. Elle a plus particulièrement pour objet l'utilisation de phényl-n-hexyl cétone à titre d'ingrédient parfumant pour la préparation de parfums et produits parfumés. Elle a également pour objet une composition parfumante contenant ladite phényl-n-hexyl cétone en tant qu'ingrédient odoriférant.The invention relates to the field of perfumery. It more particularly relates to the use of phenyl-n-hexyl ketone as a perfuming ingredient for the preparation of perfumes and perfumed products. It also relates to a fragrance composition containing said phenyl-n-hexyl ketone as an odoriferous ingredient.
La phényl-n-hexyl cétone est une entité chimique connue, décrite notamment dans Beil- stein 7, 337; cependant l'état de la technique est muet quant à ses propriétés organo- leptiques.Phenyl-n-hexyl ketone is a known chemical entity, described in particular in Beestein 7, 337; however, the state of the art is silent as to its organoleptic properties.
Il a été découvert que ce composé possède des propriétés olfactives fort intéressantes et peut de ce fait trouver une utilisation étendue en tant qu'ingrédient odoriférant dans des compositions de nature variée.It has been discovered that this compound has very interesting olfactory properties and can therefore find wide use as an odoriferous ingredient in compositions of various kinds.
Son odeur, de bonne puissance, est de type fleuri et rappelle l'odeur développée par certaines fleurs appartenant à famille des amaryllidacées, la jonquille ou le narcisse en particulier.Its scent, of good power, is of the flowery type and recalls the smell developed by certain flowers belonging to the amaryllidaceae family, the daffodil or the narcissus in particular.
Ses propriétés odoriférantes sont cependant nettement distinctes de celles exhibées par des produits analogues, telle la phényl-n-amyl cétone par exemple qui ne trouve qu'une utilisation limitée en parfumerie, en tant que modifac- teur de l'effet exercé par la combinaison coumarine-salicylate d'amyle dans des compositions de type fourgère (voir S. ARCTANDER: "Perfume and flavor chemicals", 1969, Mont- clair, N. J. (US), no. 211).Its odoriferous properties are however clearly distinct from those exhibited by analogous products, such as phenyl-n-amyl ketone for example which finds only limited use in perfumery, as a modifier of the effect exerted by the combination amyl coumarin-salicylate in fourger-type compositions (see S. ARCTANDER: "Perfume and flavor chemicals", 1969, Mont-clair, NJ (US), no. 211).
Les proportions dans lesquelles la phényl-n-hexyl cétone peut être utilisée pour donner des effets olfactifs intéressants varient de façon relativement étendue. C'est ainsi que des concentrations de 0,5 à 1% environ, en poids, par rapport au poids total de la composition considérée peuvent déjà produire des effets marqués lors du parfumage de produits tels que savons, shampoings ou articles cosmétiques par exemple.The proportions in which phenyl-n-hexyl ketone can be used to give interesting olfactory effects vary relatively widely. Thus, concentrations of approximately 0.5 to 1%, by weight, relative to the total weight of the composition considered can already produce marked effects when perfuming products such as soaps, shampoos or cosmetic articles for example.
Des proportions supérieures, allant jusqu'à 20% ou au-delà, peuvent par contre être utilisées pour la préparation de compositions ou bases parfumantes. Bien entendu, de telles limites de concentration ne sauraient être interprétées de façon restrictive car elles dépendent de la nature des coingrédients odorants de la compostion donnée ou de celle des articles que l'on désire parfumer.Higher proportions, up to 20% or more, can however be used for the preparation of perfume compositions or bases. Of course, such concentration limits should not be interpreted restrictively because they depend on the nature of the odorous co-ingredients of the given composition or on that of the articles which one wishes to perfume.
La phényl-n-hexyl cétone peut être préparée selon l'une des méthodes de synthèse courante, par exemple par acylation du benzène au moyen d'une réaction du type de Friedel-Crafts à l'aide de chlorure d'heptanoyle [voir par exemple: Organikum, Org. Chem. Grund-praktikum, Berlin (1964), p. 290]. Le produit ainsi obtenu possédait Eb. 85-90°/1 Pa. Ses'caractères analytiques étaient les suivants:
- SM: 190 (M+, 5); m/e:105(100), 120(76), 77(43), 51 (10), 43(9), 106(7), 133(6), 121(6);
- IR (liquide, film): 1675 cm i;
- RMN (60 MHz, CDCI3): 0,89 (t, 3H); 1,0-2,0 (8H, bande large); 2,90 (2H, t, J=7 Hz); 7,2-7,5 (3H, m); 7,8-8,05 (2H, m) b ppm.
- MS: 190 (M + , 5); m / e: 105 (100), 120 (76), 77 (43), 51 (10), 43 (9), 106 (7), 133 (6), 121 (6);
- IR (liquid, film): 1675 cm i ;
- NMR (60 MHz, CDCI 3 ): 0.89 (t, 3H); 1.0-2.0 (8H, broadband); 2.90 (2H, t, J = 7 Hz); 7.2-7.5 (3H, m); 7.8-8.05 (2H, m) b ppm.
L'exemple suivant est destiné à illustrer l'invention de façon plus détaillée, sans pour autant la limiter.The following example is intended to illustrate the invention in more detail, without however limiting it.
Une composition parfumante de base de type "narcisse jaune" a été préparée en mélangeant les ingrédients suivants (parties en poids):
Claims (2)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH5833/80 | 1980-07-31 | ||
CH583380 | 1980-07-31 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0045534A1 EP0045534A1 (en) | 1982-02-10 |
EP0045534B1 true EP0045534B1 (en) | 1983-12-21 |
Family
ID=4300055
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19810200744 Expired EP0045534B1 (en) | 1980-07-31 | 1981-07-01 | Use of phenyl-n-hexyl ketone as a perfuming agent, and perfume compositions containing the same |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0045534B1 (en) |
JP (1) | JPS5754113A (en) |
DE (1) | DE3161699D1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3703584A1 (en) * | 1987-02-06 | 1988-08-18 | Consortium Elektrochem Ind | ALDEHYDE AND ALCOHOLS WITH 3-METHYL OR 3,5-DIMETHYLPHENYL GROUPS, THE PRODUCTION AND USE THEREOF AS A PERFUME |
DE60136178D1 (en) * | 2000-06-15 | 2008-11-27 | Firmenich & Cie | USE OF KETONES AS PREVIEW OF ACTIVE COMPOUNDS |
EP3870563A4 (en) * | 2018-10-24 | 2022-08-10 | International Flavors & Fragrances Inc. | Novel organoleptic compounds |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH583083A5 (en) * | 1973-09-25 | 1976-12-31 | Firmenich & Cie |
-
1981
- 1981-07-01 EP EP19810200744 patent/EP0045534B1/en not_active Expired
- 1981-07-01 DE DE8181200744T patent/DE3161699D1/en not_active Expired
- 1981-07-30 JP JP11858881A patent/JPS5754113A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5754113A (en) | 1982-03-31 |
JPH0138160B2 (en) | 1989-08-11 |
DE3161699D1 (en) | 1984-01-26 |
EP0045534A1 (en) | 1982-02-10 |
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