EP0178532B1 - Perfuming compositions and perfumed articles containing ethyl-2-acetyl-4-methyl-4-pentenoate - Google Patents
Perfuming compositions and perfumed articles containing ethyl-2-acetyl-4-methyl-4-pentenoate Download PDFInfo
- Publication number
- EP0178532B1 EP0178532B1 EP85112461A EP85112461A EP0178532B1 EP 0178532 B1 EP0178532 B1 EP 0178532B1 EP 85112461 A EP85112461 A EP 85112461A EP 85112461 A EP85112461 A EP 85112461A EP 0178532 B1 EP0178532 B1 EP 0178532B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- pentenoate
- acetyl
- methyl
- ethyl
- perfuming
- 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 - Lifetime
Links
- DVIFNSDZOSQUGX-UHFFFAOYSA-N ethyl 2-acetyl-4-methylpent-4-enoate Chemical compound CCOC(=O)C(C(C)=O)CC(C)=C DVIFNSDZOSQUGX-UHFFFAOYSA-N 0.000 title claims description 12
- 239000000203 mixture Substances 0.000 title claims description 11
- 239000004615 ingredient Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 2
- 239000013042 solid detergent Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000002453 shampoo Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000002386 air freshener Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal alkoxide Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000015092 herbal tea Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008096 xylene Substances 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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
Definitions
- the present invention relates to the field of perfumery. It relates more particularly to the use of an aliphatic keto-ester of formula or ethyl 2-acetyl-4-methyl-4-pentenoate.
- Ethyl 2-acetyl-4-methyl-4-pentenoate is used to develop a fruity-floral, aromatic and natural, slightly herbaceous odor; odor that evokes an aspect of the chamomile decoction as well as the fruity character of the pineapple.
- the keto-ester of the invention can lend itself to the scent of various articles such as soaps, cosmetics, shampoos, air fresheners, fabric softeners or liquid or cationic solid detergents , anionic, nonionic or zwitterionic. It has been found that ethyl 2-acetyl-4-methyl-4-pentenoate exhibits good stability even in relatively aggressive media as well as good substantivation on various fabrics, both natural and artificial.
- the proportions of which it can be used to produce the desired perfuming effects vary within a fairly wide range of values. Concentrations of the order of 1 or 2-5% by weight, based on the weight of the composition in which it is incorporated, can be used when the compound of the invention is used as a shade. Such concentrations, or even lower, are perfectly suitable when perfuming articles such as cosmetics, creams or shampoos, soaps or detergents. These values, of course, should not be interpreted restrictively; from experience, those skilled in the art can indeed determine the appropriate proportion according to the desired effect or the nature of the co-ingredients in a given composition.
- the compound of the invention can be used as a single ingredient, but preferably it is used in admixture with perfume coingredients and solvents customary in the art (for example, mention may be made for this purpose natural or synthetic compounds mentioned in the European patent application published under the number 0096243).
- the keto-ester of the invention is a chemical compound of known structure. It has in fact been described, as a synthesis intermediary, by TF Wood et al. [J. Org. Chem. 28, 2248 (1963)] in a study relating to the preparation of certain aromatic musks. Its odorous properties, however, have remained unknown to this day.
- ethyl 2-acetyl-4-methyl-4-pentenoate is obtained by an addition reaction, in basic medium, between ethyl acetoacetate and methallyl chloride according to the reaction scheme that here:
- the reaction is preferably carried out in a medium consisting of an aqueous, aqueous-alcoholic or alcoholic solvent, preferably in ethyl alcohol.
- aqueous, aqueous-alcoholic or alcoholic solvent preferably in ethyl alcohol.
- Other inert organic solvents such as acetone or an aromatic hydrocarbon, such as benzene, toluene or xylene, can also be used.
- an alkali metal alkoxide can be used, for example sodium ethylate, sodium carbonate, lithium or potassium carbonate or a hydroxide, such as potassium hydroxide.
- potassium carbonate is preferably used and the reaction is carried out in ethanol. Under these conditions, the operation is carried out at the boiling temperature of the reaction mixture, ie at approximately 75 ° C.
- the reaction temperature can be between approximately 50 and 110 ° C. It is at such temperatures that reaction times are relatively short, while the formation of side products is reduced.
- the process for the preparation of ethyl 2-acetyl-4-methyl-4-pentenoate will be illustrated in detail in the examples which follow; also illustrated will be its use. In the said examples, the temperatures are indicated in degrees centigrade and the abbreviations have the usual meaning in the art.
- the crude product (740 g) is distilled under nitrogen on a filled column packed with stainless steel propellers using a distillation head with total reflux. 555.8 g of the desired keto-ester having Eb are thus obtained. 115 ° / 2.66x10 3 Pa (yield by weight 107%, theoretic 75%).
- a perfuming composition for shampoos was by mixing the following ingredients (parts by weight):
- Ethyl 2-acetyl-4-methyl-4-pentenoate has been used to flavor various products, the nature of which is given in the table below. In this table also appear the concentration values respective of the ester used in the finished product as well as the indication as to the stability of the odor 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)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
Description
La présente invention a trait au domaine de la parfumerie. Elle concerne plus particulièrement l'utilisation d'un céto-ester aliphatique de formule
Nous avons découvert que ledit composé possède des propriétés odorantes advantageuses et peut de ce fait trouver un emploi étendu tant en parfumerie alcoolique qupen parfumerie technique. Le 2-acétyl-4-méthyl-4-penténoate d'éthyle sert à développer une odeur fruitée-fleurie, aromatique et naturelle, légèrement herbacée; odeur qui évoque un aspect de la décoction de camomille ainsi que le caractère fruité de l'ananas.We have discovered that said compound has advantageous odorous properties and can therefore find widespread use in both alcoholic perfume and technical perfumery. Ethyl 2-acetyl-4-methyl-4-pentenoate is used to develop a fruity-floral, aromatic and natural, slightly herbaceous odor; odor that evokes an aspect of the chamomile decoction as well as the fruity character of the pineapple.
De par ses qualités olfactives, le céto-ester de l'invention peut se prêter au parfumage d'articles divers tels les savons, les cosmétiques, les shampoings, les désodorants d'air ambiant, les adoucissants textiles ou les détergents liquides ou solides cationiques, anioniques, non ioniques ou zwitterioniques. Il s'est avéré que le 2-acétyl-4-méthyl-4-penténoate d'éthyle présente une bonne stabilité même dans des milieux relativement agressifs ainsi qu'une bonne substantivé sur différents tissus tant à fibre naturelle qu'artificielle.Due to its olfactory qualities, the keto-ester of the invention can lend itself to the scent of various articles such as soaps, cosmetics, shampoos, air fresheners, fabric softeners or liquid or cationic solid detergents , anionic, nonionic or zwitterionic. It has been found that ethyl 2-acetyl-4-methyl-4-pentenoate exhibits good stability even in relatively aggressive media as well as good substantivation on various fabrics, both natural and artificial.
Les proportions des lesquelles il peut être utilisé par produire les effets parfumants désirés varient dans une gamme de valeurs assez étendue. Des concentrations de l'ordre de 1 ou 2-5% parties en poids, par rapport au poids de la composiion dans laquelle il est incorporé, peuvent être employées lorsque le composé de l'invention est utilisé en tant que nuanceur. De telles concentrations, voire même inférieures, conviennent parfaitement lors du parfumage d'articles tes les cosmétiques, crèmes ou shampoings, les savons ou les détergents. Ces valeurs, bien entendu, ne doivant pas être interprétées de façon restrictive; par expérience l'homme de l'art sait en effet déterminer la proportion appropriée en fonction de l'effet recherché ou de la nature des coingrédients dans une composition donnée.The proportions of which it can be used to produce the desired perfuming effects vary within a fairly wide range of values. Concentrations of the order of 1 or 2-5% by weight, based on the weight of the composition in which it is incorporated, can be used when the compound of the invention is used as a shade. Such concentrations, or even lower, are perfectly suitable when perfuming articles such as cosmetics, creams or shampoos, soaps or detergents. These values, of course, should not be interpreted restrictively; from experience, those skilled in the art can indeed determine the appropriate proportion according to the desired effect or the nature of the co-ingredients in a given composition.
Le composé de l'invention peut être utilisé en tant qu'ingrédient unique, mais de préférence, il est employé en mélange avec des coingrédients parfumants et des solvants usuels dans l'art (à titre d'exemple, on peut citre à cet effet les composés naturels ou synthétiques mentionnés dans la demande de brevet européen publiée sous le n° 0096243).The compound of the invention can be used as a single ingredient, but preferably it is used in admixture with perfume coingredients and solvents customary in the art (for example, mention may be made for this purpose natural or synthetic compounds mentioned in the European patent application published under the number 0096243).
Le céto-ester de l'invention est un composé chimique de structure connue. Il a en effet été décrit, en qualité d'intermédiaire de synthèse, par T. F. Wood et al. [J. Org. Chem. 28, 2248 (1963)] dans une étude relative à la préparation de certains muscs aromatiques. Ses propriétés odorantes cependant sont restées inconnues jusqu'à ce jour. Suivant l'invention, le 2-acétyl-4-méthyl-4-pentenoate d'éthyle est obtenu par une réaction d'addition, en milieu basique, entre l'acétoacétate d'éthyle et le chlorure de méthallyle suivant le schéma réactionnel que voici:
La réaction est effectuée de préférence dans un milieu constitué par un solvant aqueux, aqueux- alcoolique ou alcoolique, de préférence dans l'alcooléthylique. D'autres solvants organiques inertes, tels l'acétone ou un hydrocarbure aromatique, telle benzène, le toluène ou le xylène, peuvent également être employés. A titre d'agent basique on peut utiliser un alcoolate d'un métal alcalin, par exemple l'éthylate de sodium, le carbonate de sodium, de lithium ou de potassium ou encore un hydroxyde, tel l'hydroxyde de potassium. Pour des raisons d'ordre pratique et économique, on utilise de préférence le carbonate de potassium et on effectue la réaction dans l'éthanol. Dans ces conditions, l'on opère à la température d'ébullition du mélange réacionnel, soit à environ 75°C. Suivant le solvant choisi, la température de réaction peut être comprise entre environ 50 et 110°C. C'est à de telles témperature que les temps de réaction sont relativement courts, tandis que la formation de produits secondaires est réduite. Le procédé de préparation du 2-acétyl-4-méthyl-4-penténoate d'éthyle sera illustré dans le détail dans les exemples qui suivent; également illustrée sera son utilisation. Dans lesdits exemples, les températures sont indiquées en degrés centigrades et les abréviations ont le sens usuel dans l'art.The reaction is preferably carried out in a medium consisting of an aqueous, aqueous-alcoholic or alcoholic solvent, preferably in ethyl alcohol. Other inert organic solvents, such as acetone or an aromatic hydrocarbon, such as benzene, toluene or xylene, can also be used. As a basic agent, an alkali metal alkoxide can be used, for example sodium ethylate, sodium carbonate, lithium or potassium carbonate or a hydroxide, such as potassium hydroxide. For practical and economic reasons, potassium carbonate is preferably used and the reaction is carried out in ethanol. Under these conditions, the operation is carried out at the boiling temperature of the reaction mixture, ie at approximately 75 ° C. Depending on the solvent chosen, the reaction temperature can be between approximately 50 and 110 ° C. It is at such temperatures that reaction times are relatively short, while the formation of side products is reduced. The process for the preparation of ethyl 2-acetyl-4-methyl-4-pentenoate will be illustrated in detail in the examples which follow; also illustrated will be its use. In the said examples, the temperatures are indicated in degrees centigrade and the abbreviations have the usual meaning in the art.
Dans un réacteur de 1,5 muni d'une agitation mécanique, d'un réfrigérant, d'un thermomètre et d'une entrée d'azote, on mélange 600 g (5,61 mol) d'acétoacétate d'éthyle, 375,9 g (4,15 mol) de chlorure de méthallyle, 500 ml d'éthanol et 636,9 g (4,61 mol) de carbonate de potassium. On chauffe la suspension à reflux pendant 2 h et le mélange jaunit légèrement tout en devenant plus dense. On distille l'éthanol et dissout le résidu obtenu avec 900 ml d'eau. Les deux phases formées sont séparées et le phase organique est lavée à l'eau (900 ml). Le produit brut (740 g) est distillé sous azote sur colonne remplie garnie d'hélices en acier inoxydable en utilisant une tête de distillation à reflux total. On obtient ainsi 555,8 g du céto-ester désiré ayant Eb. 115°/2,66x103 Pa (rend. en poids 107%, théor. 75%).600 g (5.61 mol) of ethyl acetoacetate are mixed in a 1.5 liter reactor with mechanical stirring, a condenser, a thermometer and a nitrogen inlet. , 9 g (4.15 mol) of methallyl chloride, 500 ml of ethanol and 636.9 g (4.61 mol) of potassium carbonate. The suspension is heated at reflux for 2 h and the mixture turns slightly yellow while becoming more dense. The ethanol is distilled and the residue obtained is dissolved with 900 ml of water. The two phases formed are separated and the organic phase is washed with water (900 ml). The crude product (740 g) is distilled under nitrogen on a filled column packed with stainless steel propellers using a distillation head with total reflux. 555.8 g of the desired keto-ester having Eb are thus obtained. 115 ° / 2.66x10 3 Pa (yield by weight 107%, theoretic 75%).
Une composition parfumante pour shampoings a été en mélangeant les ingrédients suivants (parties en poids):
En ajoutante à cette composition fleurie 140 g de 2-acétyl-4-méthyl-4-penténoate d'éthyle, on obtient une nouvelle composition à la senteur fleurie-fruitée aromatique et herbacée qui rappelle l'aspect naturel d'une tisane aux herbes. Un tel caractère odorant rend la composition parfaitement adaptée au parfumage de shampoings.By adding 140 g of ethyl 2-acetyl-4-methyl-4-pentenoate to this flowery composition, a new composition with a floral-fruity aromatic and herbaceous scent is obtained which recalls the natural appearance of an herbal tea. . Such an odorous character makes the composition perfectly suitable for perfuming shampoos.
Deux détergentes en poudre ont été préparées en mélangeant les ingrédients suivants (parties en poids):
Lorsqu'on additionne à un échantillon de l'une des poudres détergentes ci-dessus le 2-acétyl-4-méthyl-4-penténoate d'éthyle, à raison d'environ 1% en poids, on lui confère une odeur agréable, fraîche et herbacée.When ethyl 2-acetyl-4-methyl-4-pentenoate is added to a sample of one of the above detergent powders, in an amount of approximately 1% by weight, it is given a pleasant odor, fresh and herbaceous.
Le 2-acétyl-4-méthyl-4-penténoate d'éthyle a été utilisé pour parfumer divers produits dont la nature figure dans le tableau ci-dessous. Dans ledit tableau figurent également les valeurs de concentrations respectives de l'ester employé dans le produit terminé ainsi que l'indication quant à la stabilité de l'odeur obtenue.
Claims (3)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH4985/84 | 1984-10-18 | ||
| CH498584 | 1984-10-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0178532A2 EP0178532A2 (en) | 1986-04-23 |
| EP0178532A3 EP0178532A3 (en) | 1989-02-08 |
| EP0178532B1 true EP0178532B1 (en) | 1990-06-06 |
Family
ID=4285949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP85112461A Expired - Lifetime EP0178532B1 (en) | 1984-10-18 | 1985-10-02 | Perfuming compositions and perfumed articles containing ethyl-2-acetyl-4-methyl-4-pentenoate |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4647407A (en) |
| EP (1) | EP0178532B1 (en) |
| JP (1) | JPS6197214A (en) |
| DE (1) | DE3578082D1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG74666A1 (en) | 1997-10-21 | 2000-08-22 | Givaudan Roure Int | Beta-ketoester |
| EP0911315B1 (en) * | 1997-10-21 | 2003-06-11 | Givaudan SA | Beta-ketoester |
| ES2228355T3 (en) | 1999-07-14 | 2005-04-16 | Firmenich Sa | ALIFATIC ESTERS AND ITS USE BY PERFUMING INGREDIENTS. |
| FR2805991B1 (en) * | 2000-03-13 | 2003-03-21 | Rhodia Chimie Sa | PROCESS FOR OBTAINING PERFUMING COMPOSITIONS AND PERFUMED PRODUCTS AND PRODUCTS THUS OBTAINED |
| WO2018196988A1 (en) * | 2017-04-28 | 2018-11-01 | Symrise Ag | Ethyl-2-acetyl-2,4-dimethyl-pent-4-enoate as a fragrance |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4245122A (en) * | 1979-12-05 | 1981-01-13 | International Flavors & Fragrances Inc. | Process for the production of allyl acetone |
| US4348416A (en) * | 1980-08-07 | 1982-09-07 | International Flavors & Fragrances Inc. | Flavoring with 1-ethoxy-1-ethanol acetate - acetaldehyde mixtures |
| US4357316A (en) * | 1980-12-18 | 1982-11-02 | International Flavors & Fragrances Inc. | Use of 1-n-butoxy-1-ethanol acetate for augmenting or enhancing the taste of toothpaste |
| EP0096243B1 (en) * | 1982-06-03 | 1985-08-07 | L. GIVAUDAN & CIE Société Anonyme | Cyclohex(en)yl methanols and their esters, with perfuming properties |
| DE3306560A1 (en) * | 1983-02-25 | 1984-08-30 | Henkel KGaA, 4000 Düsseldorf | NEW 2-METHYLPENTANIC ACID ESTERS, THEIR PRODUCTION AND USE AS A FRAGRANCE, AND THESE COMPOSITIONS CONTAINING THEM |
-
1985
- 1985-10-02 EP EP85112461A patent/EP0178532B1/en not_active Expired - Lifetime
- 1985-10-02 DE DE8585112461T patent/DE3578082D1/en not_active Expired - Lifetime
- 1985-10-04 US US06/784,125 patent/US4647407A/en not_active Expired - Lifetime
- 1985-10-18 JP JP60231450A patent/JPS6197214A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4647407A (en) | 1987-03-03 |
| JPH0347678B2 (en) | 1991-07-22 |
| DE3578082D1 (en) | 1990-07-12 |
| JPS6197214A (en) | 1986-05-15 |
| EP0178532A2 (en) | 1986-04-23 |
| EP0178532A3 (en) | 1989-02-08 |
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