EP0115278B1 - 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
- EP0115278B1 EP0115278B1 EP84100217A EP84100217A EP0115278B1 EP 0115278 B1 EP0115278 B1 EP 0115278B1 EP 84100217 A EP84100217 A EP 84100217A EP 84100217 A EP84100217 A EP 84100217A EP 0115278 B1 EP0115278 B1 EP 0115278B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- perfuming
- acid
- cyclopentenylacetic
- composition containing
- ingredient
- 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
- 239000000203 mixture Substances 0.000 title claims description 13
- 239000004615 ingredient Substances 0.000 title claims description 8
- 239000012437 perfumed product Substances 0.000 title claims description 3
- 239000002453 shampoo Substances 0.000 claims description 4
- 239000000344 soap Substances 0.000 claims description 4
- 230000003796 beauty Effects 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- -1 household articles Substances 0.000 claims 2
- 239000000454 talc Substances 0.000 claims 1
- 229910052623 talc Inorganic materials 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000012907 honey Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- QOGMZIQMZUXOKM-UHFFFAOYSA-N 2-(cyclopenten-1-yl)acetic acid Chemical compound OC(=O)CC1=CCCC1 QOGMZIQMZUXOKM-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- KQENDZXFFPZPFV-UHFFFAOYSA-N cyclopentylidenemethyl acetate Chemical compound CC(=O)OC=C1CCCC1 KQENDZXFFPZPFV-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- 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.
- 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 and in technical applications, for example in the perfume of soaps, detergents, powder or liquids, cleaning articles or cosmetics, shampoos or beauty creams.
- the proportions in which the compound of the invention is used 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 r 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 suitable for this purpose.
- the acid of the invention is a known chemical entity. Its preparation can be carried out according to the methods described [see for this purpose US Pat. No. 1,965,762] or from cyclopentylidene-methyl acetate [see US Pat. No. 4,280,934] by hydrolysis thereof according to the scheme that is here :
- reaction mixture was kept at 70 ° C overnight, then 2.5 l 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 has no practical influence on the quantity 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 perfuming 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.
Landscapes
- 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)
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 parfumés.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)]. 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)]. 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, shampooings 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 and in technical applications, for example in the perfume of soaps, detergents, powder or liquids, cleaning 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 roo 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 is used 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 r 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 connue 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 suitable 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 1 965 762] 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 It 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 l 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 It d'eau y ont été ajoutés et le méthanol a été évaporé. Après acidification avec de l'HCI, 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 l 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 shampooing 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 shampooing 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 mild 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 ultra-violette prolongée des produits obtenus.The olfactory stability was also confirmed by tests of prolonged ultraviolet irradiation of the products obtained.
Claims (3)
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 EP0115278A2 (en) | 1984-08-08 |
| EP0115278A3 EP0115278A3 (en) | 1986-03-19 |
| EP0115278B1 true 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) |
Families Citing this family (6)
| 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 |
| ES2047188T3 (en) * | 1989-04-27 | 1994-02-16 | Firmenich & Cie | PERFUMED PROCEDURE. |
| 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 |
| US10876067B2 (en) | 2016-02-15 | 2020-12-29 | Symrise Ag | Fragrant mixtures containing esters and ketones |
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
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59144714A (en) | 1984-08-18 |
| EP0115278A3 (en) | 1986-03-19 |
| EP0115278A2 (en) | 1984-08-08 |
| JPS6127368B2 (en) | 1986-06-25 |
| US4584127A (en) | 1986-04-22 |
| DE3469562D1 (en) | 1988-04-07 |
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