EP0115278A2 - Use of 1-cyclopentenylacetic acid as perfuming ingredient, perfuming composition containing it and perfumed products - Google Patents
Use of 1-cyclopentenylacetic acid as perfuming ingredient, perfuming composition containing it and perfumed products Download PDFInfo
- Publication number
- EP0115278A2 EP0115278A2 EP84100217A EP84100217A EP0115278A2 EP 0115278 A2 EP0115278 A2 EP 0115278A2 EP 84100217 A EP84100217 A EP 84100217A EP 84100217 A EP84100217 A EP 84100217A EP 0115278 A2 EP0115278 A2 EP 0115278A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- perfuming
- acid
- cyclopentenylacetic
- ingredient
- composition containing
- 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.)
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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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
Definitions
- 1-cyclopentenylacetic acid of the formula could be used to impart or improve the honey-like fragrant note of perfumes and scented products without having the specific secondary characteristics of phenylacetic acid.
- the 1-cyclopentenylacetic acid of the invention finds a very wide use both in fine perfumery as in technical applications, for example in the perfuming of soaps, detergents, powder or liquids, maintenance articles or cosmetics, shampoos or beauty creams.
- the proportions in which the compound of the invention serves to develop the desired odorous effects can vary within a fairly wide range of values. Its power is such that quantities of the order of 1-10 o / oo by weight relative to the weight of the composition or of the scented article may already be sufficient to obtain a positive effect. Concentrations of 0.1-2% are preferably used in the manufacture of concentrated compositions or "hearts".
- 1-cyclopentenylacetic acid can be added either directly to the product which one wishes to perfume, or, more often, in the form of a solution mixed with other perfuming ingredients.
- the co-ingredients, the solvents or the usual supports, the use of which is well known to those skilled in the art, are perfectly suited for this purpose.
- the acid of the invention is a known chemical entity. Its preparation can be carried out in accordance with the methods described [see for this purpose US patent 1,965,792] or from cyclopentylidene-methyl acetate [see US patent 4,280,934] by hydrolysis thereof here following the diagram that here:
- reaction mixture was kept at 70 ° C overnight, then 2.5 lt of water was added thereto and the methanol was evaporated. After acidification with HCl, separation of the organic phase, followed by re-extraction with ether of the aqueous phase, the two combined organic phases were distilled under reduced pressure.
- the desired product was obtained with a yield of 82.3% at Eb. 96 ° C / approx. 6.65 Pa. Traces of the isomeric compound of formula were also present in the product obtained, but their presence does not have a practical influence on the quality of the main product.
- the 2-cyclopentenylacetic acid in solution at 25% in diethyl phthalate was added at a rate of 2% in a commercial soap paste with neutral odor and, according to the usual techniques, the resulting paste was used for the manufacture of bars of toilet soaps.
- the odor of the article thus obtained was judged by a group of experts who defined it as being characterized by a separate note of the "honey" type.
- a basic pink-type composition was prepared by mixing the following ingredients (parts by weight):
- a basic perfume composition intended to be incorporated into a shampoo was prepared by mixing the following ingredients (parts by weight):
- the olfactory stability was also confirmed by tests of prolonged ultraviolet irradiation of the products obtained.
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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)
- Detergent Compositions (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Abstract
On décrit l'utilisation de l'acide 1-cyclopenténylacétique de formule
L'acide en question sert en particulier à conférer ou améliorer la note de type miel de compositions parfumantes et produits parfumés.The acid in question is used in particular to impart or improve the honey-type note of perfume compositions and perfumed products.
Description
La présente invention a trait au domaine de la parfumerie et plus particulièrement elle concerne l'utilisation d'un acide cycloaliphatique insaturé à titre d'ingrédient parfumant pour la préparation de parfums et produits parfumé:The present invention relates to the field of perfumery and more particularly it relates to the use of an unsaturated cycloaliphatic acid as a perfuming ingredient for the preparation of perfumes and perfumed products:
Parmi la variété de composés d'emploi courant en parfumerie, bien peu nombreux sont ceux destinés à conférer le caractère olfactif de type "miel" aux compositions ou produits dans lesquels ils sont incorporés. Dans cette classe de composés, le représentant le plus marquant est certainement constitué par l'acide phénylacétique dont l'odeur est douce, tout à la fois animale et de type miel [voir à ce sujet S. Arctander, Perfume and Flavor Chemicals, Sec. 2492, Montclair, N.J., USA (1969)7. Sa note animale est considérée cependant comme étant trop prononcée et son emploi pose souvent des problèmes à l'utilisateur qui doit s'ingénier à trouver des accords appropriés afin de mieux l'harmoniser dans l'ensemble de la composition.Among the variety of compounds commonly used in perfumery, very few are those intended to confer the "honey" type olfactory character to the compositions or products in which they are incorporated. In this class of compounds, the most striking representative is certainly constituted by phenylacetic acid, the smell of which is sweet, both animal and honey-like [see on this subject S. Arctander, Perfume and Flavor Chemicals, Sec . 2492, Montclair, N.J., USA (1969) 7. Its animal note is however considered to be too pronounced and its use often poses problems for the user who must try to find suitable agreements in order to better harmonize it throughout the composition.
Nous avons maintenant découvert que l'acide 1-cyclopenténylacétique de formule
Doté de très bonne puissance et d'excellente substantivité, l'acide 1-cyclopenténylacétique de l'invention trouve un emploi fort étendu tant en parfumerie fine que dans des applications techniques, par exemple dans le parfumage de savons, de détergents, en poudre ou liquides, d'articles d'entretien ou de cosmétiques, shampoings ou crèmes de beauté.Endowed with very good power and excellent substantivity, the 1-cyclopentenylacetic acid of the invention finds a very wide use both in fine perfumery as in technical applications, for example in the perfuming of soaps, detergents, powder or liquids, maintenance articles or cosmetics, shampoos or beauty creams.
Les proportions dans lesquelles le composé de l'invention sert à développer les effets odorants recherchés peuvent varier dans une gamme de valeurs assez étendue. Sa puissance est telle que des quantités de l'ordre de 1-10 o/oo en poids par rapport au poids de la composition ou de l'article parfumé peuvent déjà être suffisantes pour obtenir un effet positif. Des concentrations de 0,1-2 % sont utilisées de préférence dans la manufacture de compositions concentrées ou de "coeurs".The proportions in which the compound of the invention serves to develop the desired odorous effects can vary within a fairly wide range of values. Its power is such that quantities of the order of 1-10 o / oo by weight relative to the weight of the composition or of the scented article may already be sufficient to obtain a positive effect. Concentrations of 0.1-2% are preferably used in the manufacture of concentrated compositions or "hearts".
Les techniques de parfumage usuelles peuvent également être utilisées dans le cas de l'emploi de l'acide dont il est question ici. C'est ainsi que l'acide 1-cyclopenténylacétique peut être ajouté soit directement au produit que l'on désire parfumer, soit, plus souvent, sous forme de solution en mélange avec d'autres ingrédients parfumants. Les coingrédients, les solvants ou les supports usuels dont l'utilisation est bien connu par l'homme de l'art conviennent parfaitement à cet effet.The usual perfuming techniques can also be used in the case of the use of the acid which is discussed here. Thus 1-cyclopentenylacetic acid can be added either directly to the product which one wishes to perfume, or, more often, in the form of a solution mixed with other perfuming ingredients. The co-ingredients, the solvents or the usual supports, the use of which is well known to those skilled in the art, are perfectly suited for this purpose.
L'acide de l'invention est une entité chimique connue. Sa préparation peut s'effectuer conformément à des méthodes décrites [voir à cet effet le brevet US 1'965'792] ou à partir de cyclopentylidène-acétate de méthyle [voir le brevet US 4'280'934] par hydrolyse de celui-ci suivant le schéma que voici :
La méthode spécifique suivie a été la suivante :The specific method followed was as follows:
A une solution de l'ester méthylique (700 g) dans 2 lt de méthanol on a ajouté goutte à goutte à reflux (70°C) une solution aqueuse à 30 % de NaOH.To a solution of the methyl ester (700 g) in 2 lt of methanol was added dropwise at reflux (70 ° C) a 30% aqueous solution of NaOH.
Le mélange réactionnel a été maintenu à 70°C pendant 1 nuit, puis 2,5 lt d'eau y ont été ajoutés et le méthanol a été évaporé. Après acidification avec de l'HCl, séparation de la phase organique, suivie de réextraction à l'éther de la phase aqueuse, on a distillé sous pression réduite les deux phases organiques réunies.The reaction mixture was kept at 70 ° C overnight, then 2.5 lt of water was added thereto and the methanol was evaporated. After acidification with HCl, separation of the organic phase, followed by re-extraction with ether of the aqueous phase, the two combined organic phases were distilled under reduced pressure.
Le produit désiré a été obtenu avec un rendement de 82,3 % à Eb. 96°C/env. 6,65 Pa. Des traces du composé isomérique de formule
Il convient de mentionner que le brevet US 1'965'792 précité décrit l'utilisation de certains esters de l'acide en question en tant qu'agents parfumants. Les propriétés utiles de l'acide même avaient cependant échappé à l'inventeur.It should be mentioned that the aforementioned US Patent 1,965,792 describes the use of certain esters of the acid in question as perfuming agents. The useful properties of the acid itself, however, had eluded the inventor.
L'invention est illustrée de manière plus détaillée par les exemples suivants.The invention is illustrated in more detail by the following examples.
L'acide 1-cyclopenténylacétique en solution à 25 % dans le phtalate diéthylique a été ajouté à raison de 2 % dans une pâte de savon commercial à odeur neutre et, suivant les techniques usuelles, la pâte résultante a servi à la manufacture de barres de savons de toilette. L'odeur de l'article obtenu ainsi a été jugée par un groupe d'experts qui l'ont définie comme étant caractérisée par une note distincte de type "miel".The 2-cyclopentenylacetic acid in solution at 25% in diethyl phthalate was added at a rate of 2% in a commercial soap paste with neutral odor and, according to the usual techniques, the resulting paste was used for the manufacture of bars of toilet soaps. The odor of the article thus obtained was judged by a group of experts who defined it as being characterized by a separate note of the "honey" type.
Une composition de base de type rose a été préparée en mélangeant les ingrédients suivants (parties en poids) :
En ajoutant à la composition ci-dessus 0,5 parties en poids d'acide 1-cyclopenténylacétique on obtient une nouvelle composition dont le caractère est plus doux, plus arrondi et surtout plus montant.By adding to the above composition 0.5 parts by weight of 1-cyclopentenylacetic acid, a new composition is obtained, the character of which is softer, more rounded and above all more prominent.
Une composition parfumante de base destinée à être incorporée dans un shampoing a été préparée en mélangeant les ingrédients suivants (parties en poids) :
En ajoutant à la composition de base ci-dessus 10 parties de l'acide 1-cyclopenténylacétique, on obtient une nouvelle composition dont le caractère miel est très prononcé. Son effet doux rend la composition obtenue apte au parfumage d'un shampoing pour enfants.By adding 10 parts of 1-cyclopentenylacetic acid to the above basic composition, a new composition is obtained, the honey character of which is very pronounced. Its soft effect makes the composition obtained suitable for perfuming a shampoo for children.
L'acide 1-cyclopenténylacétique en solution à 10% dans le phtalate diéthylique a été utilisé pour la préparation des divers produits parfumés énumérés ci-dessous. La stabilité de l'effet olfactif obtenu ainsi que la coloration du produit parfumé ont été examinées dans les conditions décrites dans le tableau suivant:
La stabilité olfactive a été également confirmée par des essais d'irradiation ultraviolette prolongée des produits obtenus.The olfactory stability was also confirmed by tests of prolonged ultraviolet irradiation of the products obtained.
Claims (4)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH419/83 | 1983-01-26 | ||
| CH41983 | 1983-01-26 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0115278A2 true EP0115278A2 (en) | 1984-08-08 |
| EP0115278A3 EP0115278A3 (en) | 1986-03-19 |
| EP0115278B1 EP0115278B1 (en) | 1988-03-02 |
Family
ID=4186596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP84100217A Expired EP0115278B1 (en) | 1983-01-26 | 1984-01-11 | Use of 1-cyclopentenylacetic acid as perfuming ingredient, perfuming composition containing it and perfumed products |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4584127A (en) |
| EP (1) | EP0115278B1 (en) |
| JP (1) | JPS59144714A (en) |
| DE (1) | DE3469562D1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017140336A1 (en) * | 2016-02-15 | 2017-08-24 | Symrise Ag | Fragrant mixtures containing esters and ketones |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5164364A (en) * | 1986-09-30 | 1992-11-17 | Givaudan Corporation | Ethyl campholenates and dihydro derivatives thereof as flavorants and odorants |
| DE69003857T2 (en) * | 1989-04-27 | 1994-02-24 | Firmenich & Cie | Perfuming process. |
| US6720295B2 (en) * | 2001-08-27 | 2004-04-13 | Firmenich Sa | Use of tertiary alcohols or esters as perfuming ingredients |
| JP4486549B2 (en) * | 2005-06-06 | 2010-06-23 | 三菱重工業株式会社 | Gas turbine combustor |
| EP2474301B1 (en) * | 2011-12-14 | 2014-04-16 | Symrise AG | Perfume mixtures containing Cyclopent-2-Enyl-ethyl acetate |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1965792A (en) * | 1931-03-06 | 1934-07-10 | Cie De Bethune | Esters of unsubstituted and alphasubstituted cyclopentenylacetic acid and their production |
| US4031132A (en) * | 1974-07-19 | 1977-06-21 | Givaudan Corporation | Isopropenyl cyclopentene carboxylic acids |
| CH616077A5 (en) * | 1976-06-30 | 1980-03-14 | Firmenich & Cie |
-
1984
- 1984-01-11 DE DE8484100217T patent/DE3469562D1/en not_active Expired
- 1984-01-11 EP EP84100217A patent/EP0115278B1/en not_active Expired
- 1984-01-12 US US06/570,177 patent/US4584127A/en not_active Expired - Fee Related
- 1984-01-24 JP JP59009629A patent/JPS59144714A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017140336A1 (en) * | 2016-02-15 | 2017-08-24 | Symrise Ag | Fragrant mixtures containing esters and ketones |
| US10876067B2 (en) | 2016-02-15 | 2020-12-29 | Symrise Ag | Fragrant mixtures containing esters and ketones |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3469562D1 (en) | 1988-04-07 |
| US4584127A (en) | 1986-04-22 |
| EP0115278B1 (en) | 1988-03-02 |
| EP0115278A3 (en) | 1986-03-19 |
| JPS6127368B2 (en) | 1986-06-25 |
| JPS59144714A (en) | 1984-08-18 |
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