WO2012110281A1 - Perfuming ingredient of the galbanum family - Google Patents
Perfuming ingredient of the galbanum family Download PDFInfo
- Publication number
- WO2012110281A1 WO2012110281A1 PCT/EP2012/050936 EP2012050936W WO2012110281A1 WO 2012110281 A1 WO2012110281 A1 WO 2012110281A1 EP 2012050936 W EP2012050936 W EP 2012050936W WO 2012110281 A1 WO2012110281 A1 WO 2012110281A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- perfuming
- perfumery
- compound
- formula
- product
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/557—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings having unsaturation outside the rings
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Definitions
- the present invention relates to the field of perfumery. More particularly, it concerns l-(5-ethyl-5-methyl-l-cyclohexen-l-yl)-4-penten-l-one and its use as perfuming ingredient. Moreover, the present invention comprises the invention's compound as part of a perfuming composition or of a perfuming consumer product.
- Galbanum oil is a natural perfuming ingredient highly appreciated by perfumers for its green character. However, its use is limited by a high cost. The perfumery industry has been looking and still searches for synthetic replacers having an odor as close as possible and being as substantive as possible. By the term “substantive” it is meant the strength and the olfactive performance of an odor note over a defined period of time.
- Neobutenone® alpha (l-(5,5-dimethyl-l-cyclohexen-l-yl)-4-penten-l-one; sold by Firmenich SA) and is described as having a green-metallic, fruity (pineapple) and floral (hyacinth) odor pronounced of galbanum.
- perfuming ingredient for instance to impart odor notes of the galbanum type.
- any one of its enantiomers it is meant the normal meaning understood by a person skilled in the art, e.g. that the invention's compound can be a pure enantiomer or racemate.
- the particularly surprising aspect of the present invention is that the compound (I) possesses surprising organoleptic properties in the sense that it combines an improved odor profile with an improved substantivity despite having a structure clearly described as unfavorable for such properties.
- the odor of the invention's compound is described as being a complex green, metallic galbanum note with an elegant earthy, pyrazinic aspect reminding of the earthy aspect of fig.
- 1 -(5 -ethyl-5-methyl- 1 -cyclohexen- 1 -yl)-4-penten- 1 -one distinguishes itself from Neobutenone ® alpha by having a green note more complex, more earthy, heavy while the Neobutenone ® alpha possesses a green note significantly more herbal and fresh.
- l-(5-Ethyl-5-methyl-l-cyclohexen-l-yl)-4-penten-l-one distinguishes itself from Spirogalbanone" by lacking the typical glycolate, pineapple green sweet character of the latter, as well as by lacking the fatty aspect of Spirogalbanone ® .
- l-(5-ethyl-5-methyl-l-cyclohexen-l-yl)-4-penten-l-one is characterized by a very close galbanum character, of the earthy pyrazine type, while Neobutenone ® alpha deviates from said galbanum character by having a fresher and acidic note and Spirogalbanone ® deviates from said galbanum character by having a fruity, sweety note.
- l-(5-ethyl-5-methyl-l-cyclohexen-l-yl)-4- penten-l-one not only possesses a specific character which distinguishes itself from the prior art ones, but also possesses a significantly improved sustantivity, as shown in the examples. Indeed, a panel of ten perfumers, using standard procedures, scored the invention's compound as having a substantivity far above that of its closest analogue Neobutenone ® alpha and significantly higher than the one of Spirogalbanone ® .
- the present invention fulfills the above-mentioned need of the perfumery industry by providing a new compound showing an improved galbanum resemblance and an improved substantivity while having a structure clearly described in the prior art as unfavorable for such goal.
- the invention concerns the use of a compound of formula (I) as perfuming ingredient.
- it concerns a method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I).
- use of a compound of formula (I) it has to be understood here also the use of any composition containing a compound (I) and which can be advantageously employed in perfumery industry.
- compositions which in fact can be advantageously employed as perfuming ingredients, are also an object of the present invention.
- Another object of the present invention is a perfuming composition
- a perfuming composition comprising:
- perfumery adjuvant we mean here a material which is practically neutral from a perfumery point of view, i.e. that does not significantly alter the organoleptic properties of perfuming ingredients.
- Said carrier may be a liquid or a solid.
- liquid carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery.
- a solvent and a surfactant system i.e. a solvent and a surfactant system
- a detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive.
- solvents such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2- ethoxyethoxy)-l-ethanol or ethyl citrate, which are the most commonly used.
- compositions which comprise both a perfumery carrier and a perfumery base can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar ® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol ® (origin: Dow Chemical Company).
- Isopar ® oil/ethanol mixtures
- glycol ethers and glycol ether esters such as those known under the trademark Dowanol ® (origin: Dow Chemical Company).
- solid carrier one may cite, as non-limiting examples, absorbing gums or polymers, or yet encapsulating materials.
- examples of such materials may comprise wall- forming and plasticizing materials, such as mono, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as H. Scherz, Hydrokolloids : Stabilisatoren, Dickungs- und Geherstoff in Struktur, Band 2 der committee Strukturchemie, claritat, Behr's VerlagGmbH & Co., Hamburg, 1996.
- the encapsulation is a well known process to a person skilled in the art, and may be performed, for instance, using techniques such as spray-drying, agglomeration or yet extrusion ; or consists of a coating encapsulation, including coacervation and complex coacervation techniques.
- perfumery base we mean here a composition comprising at least one perfuming co-ingredient.
- perfuming co-ingredient is not of formula (I).
- perfuming co- ingredient it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect.
- co-ingredient to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.
- perfuming co-ingredients present in the base do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to intended use or application and the desired organoleptic effect.
- these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S.
- perfumery adjuvant we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc.
- additional added benefit such as a color, a particular light resistance, chemical stability, etc.
- An invention's composition consisting of at least one compound of formula (I) and at least one perfumery carrier represents a particular embodiment of the invention as well as a perfuming composition comprising at least one compound of formula (I), at least one perfumery carrier, at least one perfumery base, and optionally at least one perfumery adjuvant.
- any mixture resulting directly from a chemical synthesis e.g. a reaction medium without an adequate purification, in which the compound of the invention would be involved as a starting, intermediate or end-product could not be considered as a perfuming composition according to the invention as far as said mixture does not provide the inventive compound in a suitable form for perfumery.
- the invention's compound can also be advantageously used in all the fields of modern perfumery, i.e. fine or functional perfumery, to positively impart or modify the odor of a consumer product into which said compound (I) is added. Consequently, a perfuming consumer product which comprises:
- the invention's compound can be added as such or as part of an invention's perfuming composition.
- perfuming consumer product it is meant a consumer product which is expected to deliver at least a perfuming effect, in other words it is a perfumed consumer product.
- perfumery consumer base we mean here the functional formulation, as well as optionally additional benefit agents, corresponding to a consumer product which is compatible with perfuming ingredients and is expected to deliver a pleasant odor to the surface to which it is applied (e.g. skin, hair, textile, or home surface).
- a perfuming consumer product according to the invention comprises the functional formulation, as well as optionally additional benefit agents, corresponding to the desired consumer product, e.g. a detergent or an air freshener, and an olfactive effective amount of at least one invention' s compound.
- Non-limiting examples of suitable perfumery consumer base can be a perfume, such as a fine perfume, a cologne or an after-shave lotion; a fabric care product, such as a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, or a bleach; a body-care product, such as a hair care product (e.g. a shampoo, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream or a deodorant or antiperspirant), or a skin-care product (e.g.
- a hair care product e.g. a shampoo, a coloring preparation or a hair spray
- a cosmetic preparation e.g. a vanishing cream or a deodorant or antiperspirant
- a skin-care product e.g.
- a perfumed soap, shower or bath mousse, oil or gel, or a hygiene product a perfumed soap, shower or bath mousse, oil or gel, or a hygiene product
- an air care product such as an air freshener or a "ready to use” powdered air freshener
- a home care product such as a wipe, a dish detergent or hard- surface detergent.
- consumer product bases may represent an aggressive medium for the invention's compound, so that it may be necessary to protect the latter from premature decomposition, for example by encapsulation or by chemically bounding it to another chemical which is suitable to release the invention's ingredient upon a suitable external stimulus, such as an enzyme, light, heat or a change of pH.
- a suitable external stimulus such as an enzyme, light, heat or a change of pH.
- the proportions in which the compounds according to the invention can be incorporated into the various aforementioned articles or compositions vary within a wide range of values. These values are dependent on the nature of the article to be perfumed and on the desired organoleptic effect as well as the nature of the co-ingredients in a given base when the compounds according to the invention are mixed with perfuming co- ingredients, solvents or additives commonly used in the art.
- concentrations are in the order of 0.001 % to 10 % by weight, or even more, of the compounds of the invention based on the weight of the composition into which they are incorporated. Concentrations lower than these, such as in the order of 0.01% to 5% by weight, can be used when these compounds are incorporated into perfumed articles, percentage being relative to the weight of the article.
- the invention's compounds can be prepared according to a method as described in the Examples.
- pTSA (1.5 g, cat.) was added in one portion to a well stirred solution of the enol obtained in step 1 (75 g, 446 mmol), methanol (150 ml) and trimethyl orthoformate (66 g).
- the reaction mixture was then stirred for a further 30 minutes at ambient temperature, then poured into saturated NaHC0 3 , extracted with ether, washed organic phase with brine (3 x), dried over Na 2 S0 4 , filtered and the solvents removed in vacuo.
- the residue was further purified by Vigreux column distillation 0.24 mbar at 84-94°C to give the enol ether 43.7 g, 54% that was used directly in the next step without further purification.
- a perfuming composition for encapsulation and introduction into a detergent, of the fruity/green type was prepared by admixing the following ingredients:
- Neobutenone ® alpha When to the above-described composition were added 100 parts by weight of Neobutenone ® alpha, it was still imparted a note in the galbanum direction but fresher, and more herbal, citrusy, clearly less galbanum oil than the one imparted by the invention's compound.
- Three different perfumed detergents were obtained by adding into 100 g of a standard unperformed detergent power 0.2% w/w of A) the invention compound, B) Neobutenone ® alpha, C) Spirogalbanone ® .
- a perfuming composition for powder detergent was prepared by admixing the following ingredients:
- Nirvanol ® 12 20 10%* Cis-2-methyl-4-propyl-l,3-oxathiane 3)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR112013019102A BR112013019102B1 (en) | 2011-02-17 | 2012-01-23 | fragrant ingredient of the galbanum family |
ES12700506.4T ES2525923T3 (en) | 2011-02-17 | 2012-01-23 | Perfume ingredient of the Galbanum family |
CN201280008786.0A CN103370296B (en) | 2011-02-17 | 2012-01-23 | The perfuming component of galbanum race |
MX2013008819A MX354501B (en) | 2011-02-17 | 2012-01-23 | Perfuming ingredient of the galbanum family. |
US13/981,916 US8907134B2 (en) | 2011-02-17 | 2012-01-23 | Perfuming ingredient of the galbanum family |
JP2013553857A JP5907996B2 (en) | 2011-02-17 | 2012-01-23 | Aroma components of the galvanum line |
EP12700506.4A EP2675781B1 (en) | 2011-02-17 | 2012-01-23 | Perfuming ingredient of the galbanum family |
IL227810A IL227810A (en) | 2011-02-17 | 2013-08-05 | Perfuming ingredient of the galbanum family |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11154754 | 2011-02-17 | ||
EP11154754.3 | 2011-02-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012110281A1 true WO2012110281A1 (en) | 2012-08-23 |
Family
ID=44269549
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2012/050936 WO2012110281A1 (en) | 2011-02-17 | 2012-01-23 | Perfuming ingredient of the galbanum family |
Country Status (9)
Country | Link |
---|---|
US (1) | US8907134B2 (en) |
EP (1) | EP2675781B1 (en) |
JP (1) | JP5907996B2 (en) |
CN (1) | CN103370296B (en) |
BR (1) | BR112013019102B1 (en) |
ES (1) | ES2525923T3 (en) |
IL (1) | IL227810A (en) |
MX (1) | MX354501B (en) |
WO (1) | WO2012110281A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017140607A1 (en) * | 2016-02-15 | 2017-08-24 | Givaudan Sa | Process for preparing spirogalbanone |
WO2024047093A1 (en) | 2022-09-01 | 2024-03-07 | Givaudan Sa | Dimethylbicycloheptenyl and dimethylbicycloheptanyl derivatives and their use as odorants |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4147672A (en) | 1974-01-29 | 1979-04-03 | Firmenich Sa | Cyclic C6 ketones in perfumes |
EP0913383A1 (en) | 1997-10-29 | 1999-05-06 | Givaudan Roure (International) S.A. | New spirocyclic compounds |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4360032A (en) * | 1978-12-15 | 1982-11-23 | International Flavors & Fragrances Inc. | Use of hydrogenated derivatives of 2,6,6-trimethyl-cyclohexene derivatives in augmenting or enhancing the aroma or taste of smoking tobacco and smoking tobacco articles |
US4260527A (en) * | 1980-06-05 | 1981-04-07 | International Flavors & Fragrances Inc. | Use of 1-acetyl-22,6-trimethyl cyclohexene-1 in augmenting or enhancing the aroma of perfumes and cologne |
SG70655A1 (en) * | 1997-10-29 | 2000-02-22 | Givaudan Roure Int | New spirocyclic compounds |
ATE409512T1 (en) * | 2001-12-13 | 2008-10-15 | Firmenich & Cie | COMPOUNDS FOR THE CONTROLLED RELEASE OF ACTIVE MOLECULES |
ATE466925T1 (en) * | 2005-09-06 | 2010-05-15 | Procter & Gamble | FRAGRANCE PROCESS AND PRODUCT |
MX2009003539A (en) * | 2006-10-10 | 2009-04-15 | Firmenich & Cie | Polymer conjugates for a controlled release of active molecules. |
BRPI0915228B1 (en) * | 2008-06-16 | 2018-07-10 | Firmenich Sa | PREPARATION PROCESS OF POLYUREA MICROCapsules |
-
2012
- 2012-01-23 WO PCT/EP2012/050936 patent/WO2012110281A1/en active Application Filing
- 2012-01-23 JP JP2013553857A patent/JP5907996B2/en active Active
- 2012-01-23 US US13/981,916 patent/US8907134B2/en active Active
- 2012-01-23 EP EP12700506.4A patent/EP2675781B1/en active Active
- 2012-01-23 ES ES12700506.4T patent/ES2525923T3/en active Active
- 2012-01-23 MX MX2013008819A patent/MX354501B/en active IP Right Grant
- 2012-01-23 BR BR112013019102A patent/BR112013019102B1/en active IP Right Grant
- 2012-01-23 CN CN201280008786.0A patent/CN103370296B/en active Active
-
2013
- 2013-08-05 IL IL227810A patent/IL227810A/en active IP Right Grant
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4147672A (en) | 1974-01-29 | 1979-04-03 | Firmenich Sa | Cyclic C6 ketones in perfumes |
EP0913383A1 (en) | 1997-10-29 | 1999-05-06 | Givaudan Roure (International) S.A. | New spirocyclic compounds |
Non-Patent Citations (3)
Title |
---|
H. SCHERZ: "Hydrokolloids : Stabilisatoren, Dickungs- und Gehermittel in Lebensmittel, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualit5t", vol. 2, 1996, BEHR'S VERLAGGMBH & CO. |
J.ORG. CHEM., vol. 66, 2001, pages 733 |
S. ARCTANDER: "Perfume and Flavor Chemicals", 1969, MONTCLAIR |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017140607A1 (en) * | 2016-02-15 | 2017-08-24 | Givaudan Sa | Process for preparing spirogalbanone |
US10227280B1 (en) | 2016-02-15 | 2019-03-12 | Givaudan, S.A. | Process for preparing spirogalbanone |
WO2024047093A1 (en) | 2022-09-01 | 2024-03-07 | Givaudan Sa | Dimethylbicycloheptenyl and dimethylbicycloheptanyl derivatives and their use as odorants |
Also Published As
Publication number | Publication date |
---|---|
CN103370296A (en) | 2013-10-23 |
BR112013019102A2 (en) | 2019-01-08 |
EP2675781B1 (en) | 2014-10-29 |
EP2675781A1 (en) | 2013-12-25 |
IL227810A0 (en) | 2013-09-30 |
ES2525923T3 (en) | 2015-01-02 |
BR112013019102B1 (en) | 2019-08-13 |
MX354501B (en) | 2018-03-08 |
JP5907996B2 (en) | 2016-04-26 |
JP2014511379A (en) | 2014-05-15 |
US20130310293A1 (en) | 2013-11-21 |
IL227810A (en) | 2015-10-29 |
US8907134B2 (en) | 2014-12-09 |
MX2013008819A (en) | 2013-09-13 |
CN103370296B (en) | 2015-08-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8648033B2 (en) | Organic carbonates with vanilla odor | |
US10047319B2 (en) | 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient | |
EP2723842B2 (en) | Cyclododecadienone derivatives as perfuming ingredients | |
US8907134B2 (en) | Perfuming ingredient of the galbanum family | |
US8911716B2 (en) | Saffron odorants | |
US9752096B2 (en) | Bi-cyclo aldehyde as perfuming ingredient | |
US8841488B2 (en) | Ketones as perfuming ingredients | |
US9068140B2 (en) | Perfuming acetal | |
US7985403B2 (en) | 4-dodecene derivatives as perfuming ingredients | |
US9243210B2 (en) | Violet leaves odorants | |
WO2007129236A1 (en) | 1-oxaspiro (4, 5 ) dec-3-ene derivatives as perfuming ingredients | |
EP2417095B1 (en) | Carboxylic derivatives as violet and/or woody odorant | |
EP3068751A1 (en) | Compound with a woody odour | |
WO2011033410A1 (en) | Nitrile compounds as perfuming ingredients | |
WO2012045697A1 (en) | Esters as perfuming ingredients |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 12700506 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2012700506 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13981916 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: MX/A/2013/008819 Country of ref document: MX |
|
ENP | Entry into the national phase |
Ref document number: 2013553857 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112013019102 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 112013019102 Country of ref document: BR Kind code of ref document: A2 Effective date: 20130725 |