WO2012045608A1 - Alcools odorants - Google Patents

Alcools odorants Download PDF

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Publication number
WO2012045608A1
WO2012045608A1 PCT/EP2011/066713 EP2011066713W WO2012045608A1 WO 2012045608 A1 WO2012045608 A1 WO 2012045608A1 EP 2011066713 W EP2011066713 W EP 2011066713W WO 2012045608 A1 WO2012045608 A1 WO 2012045608A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
perfumery
perfuming
formula
product
Prior art date
Application number
PCT/EP2011/066713
Other languages
English (en)
Inventor
Robert Moretti
Original Assignee
Firmenich Sa
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Firmenich Sa filed Critical Firmenich Sa
Publication of WO2012045608A1 publication Critical patent/WO2012045608A1/fr

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
    • C11B9/0026—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered 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
    • C07C2601/14—The ring being saturated

Definitions

  • n 1
  • the compound of formula (I) is l-(3-methylbutan-2-yl)-cyclohexanol.
  • the invention's compounds distinguish themselves by a totally different note, for instance by not having a sap character but possessing a floral, indol character, the latter being absent in the prior art analogues. Said differences lend the invention's compounds and the prior art compounds to be each suitable for different uses, i.e. to impart different organoleptic impressions.
  • 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:
  • 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.
  • unpurified reaction mixtures are generally excluded from the present invention unless otherwise specified.
  • 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.
  • 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 30 % 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 10% 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 herein below in the Examples. Examples
  • 1,2-dibromoethane was added to a suspension of magnesium turnings (18.85 g, 768 mmol) in dry diethyl ether (350 ml). Once a visible reaction had started, 1,5-dibromopentane (105 g, 443 mmol) in dry diethyl ether (350 ml) was added at a rate such as to maintain a mild reflux (addition took 3 hours). The reaction was further refluxed for 2 hours, at which point a 2 phase mixture was observed. The reaction was cooled into an ice-water bath and methyl 3,3-dimethylpent-4-enoate (45.5 g, 307 mmol) was added over 30 minutes.
  • a perfuming composition for soap was prepared by admixing the following ingredients:
  • a perfuming composition for eau de toilette, of the fresh type was prepared by admixing the following ingredients:

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Abstract

Cette invention concerne l'utilisation d'un composé de formule (I) sous la forme de l'un quelconque de ses stéréoisomères ou d'un mélange de ceux-ci à titre de substance odorante pour conférer des notes florales et indolées. Dans la formule (I), n représente 0 ou 1, et au moins un des R représente un groupe méthyle et l'autre, un atome d'hydrogène ou un groupe méthyle.
PCT/EP2011/066713 2010-10-05 2011-09-27 Alcools odorants WO2012045608A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP10186582.2 2010-10-05
EP10186582 2010-10-05

Publications (1)

Publication Number Publication Date
WO2012045608A1 true WO2012045608A1 (fr) 2012-04-12

Family

ID=44675596

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/066713 WO2012045608A1 (fr) 2010-10-05 2011-09-27 Alcools odorants

Country Status (1)

Country Link
WO (1) WO2012045608A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0193008A2 (fr) * 1985-02-18 1986-09-03 Kao Corporation Dérivés de cycloalcan-1-ol et compositions de parfum les contenant
WO1999055811A1 (fr) * 1998-04-24 1999-11-04 Quest International B.V. Parfums comprenant des 4-isobutylcycloheyanols
WO2009093175A1 (fr) * 2008-01-22 2009-07-30 Firmenich Sa Composants parfumants conférant des notes de type sève et terre

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0193008A2 (fr) * 1985-02-18 1986-09-03 Kao Corporation Dérivés de cycloalcan-1-ol et compositions de parfum les contenant
WO1999055811A1 (fr) * 1998-04-24 1999-11-04 Quest International B.V. Parfums comprenant des 4-isobutylcycloheyanols
WO2009093175A1 (fr) * 2008-01-22 2009-07-30 Firmenich Sa Composants parfumants conférant des notes de type sève et terre
EP2234948A1 (fr) 2008-01-22 2010-10-06 Firmenich S.A. Composants parfumants conférant des notes de type sève et terre

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
M. SALAMONE ET AL., JOURNAL OF ORGANIC CHEMISTRY, vol. 69, 2004, pages 5281
M. STRATAKIS ET AL., IN SYNTHETIC COMMUNICATIONS, vol. 23, 1993, pages 425

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