WO2007065755A1 - 2-methoxymethylphenol en tant que matiere olfactive et aromatique - Google Patents

2-methoxymethylphenol en tant que matiere olfactive et aromatique Download PDF

Info

Publication number
WO2007065755A1
WO2007065755A1 PCT/EP2006/067646 EP2006067646W WO2007065755A1 WO 2007065755 A1 WO2007065755 A1 WO 2007065755A1 EP 2006067646 W EP2006067646 W EP 2006067646W WO 2007065755 A1 WO2007065755 A1 WO 2007065755A1
Authority
WO
WIPO (PCT)
Prior art keywords
methoxymethylphenol
fragrance
ester
oil
methyl
Prior art date
Application number
PCT/EP2006/067646
Other languages
German (de)
English (en)
Inventor
Johannes Panten
Axel Schöning
Thomas Obrocki
Bernd Wiedwald
Original Assignee
Symrise Gmbh & Co. Kg
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 Symrise Gmbh & Co. Kg filed Critical Symrise Gmbh & Co. Kg
Publication of WO2007065755A1 publication Critical patent/WO2007065755A1/fr

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/204—Aromatic compounds
    • 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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • 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
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2068—Ethers

Definitions

  • the present invention relates primarily to the use of 2-methoxymethylphenol as a fragrance or aroma substance with a vanilla, carnation and / or leathery note.
  • the invention also relates to the use of 2-methoxymethylphenol as a booster (enhancer) for fragrance or flavoring substances, in particular for fragrance or flavoring substances with fresh, fruity and / or sweet notes.
  • the invention further relates to certain methods for imparting, modifying and / or enhancing (boosting) an odor or taste with one, several or all of the notes vanilla, clove-like and / or leathery, and methods for modifying and / or enhancing (boosting) a smell and / or taste with one, several or all of the notes fresh, fruity and / or sweet.
  • the invention also relates to certain fragrance or flavoring compositions which
  • 2-Methoxymethylphenol include and processes for the preparation of corresponding fragrance or flavoring compositions.
  • the invention also relates to a Product comprising a fragrance or flavoring composition according to the invention (for preferred product types see below).
  • the invention also relates to the use of 2-methoxymethylphenol or a mixture containing 2-methoxymethylphenol as an agent for providing (a) hair or (b) textile fibers with a vanilla, carnation and / or leathery fragrance and corresponding methods and (preferably surfactant-containing) Mixtures.
  • the invention also relates to the use of 2-methoxymethylphenol as an agent for increasing the substantivity and / or retention of an odorant mixture and / or as a fixator and the use of 2-methoxymethylphenol as an agent for increasing the odor of other odorants perceived via a surfactant-containing aqueous solution .
  • the invention also relates to methods for providing (a) hair or (b) textile fibers with a fruity, fresh and / or sweet smell.
  • the invention also relates to products containing 2-methoxymethylphenol and in addition, for. B. include other fragrances and / or surfactants.
  • fragrances which, in addition to their primary, namely odor properties, have additional positive secondary properties, such as, for example, greater stability under certain application conditions, higher yield, better quality Adhesion, a greater charisma or better dermatological and toxicological properties compared to comparable fragrances, such as good biodegradability.
  • additional positive secondary properties such as, for example, greater stability under certain application conditions, higher yield, better quality Adhesion, a greater charisma or better dermatological and toxicological properties compared to comparable fragrances, such as good biodegradability.
  • concerns about some of the commonly used fragrances have been raised regarding the latter properties. It is to be expected that their use will be limited in the future or that the use will have to be dispensed with entirely.
  • perfume industry for further fragrances which are suitable for producing fragrance compositions or perfumed articles.
  • odoriferous substances which, due to the technical properties mentioned above, such as strength or yield, lead to an increased use of perfume oils.
  • the present invention relates to the use of 2-methoxymethylphenol as a fragrance or aroma substance with a vanilla, carnation and / or leathery note.
  • Another aspect of the present invention relates to the use of 2-methoxymethylphenol as a booster for fragrance or flavoring substances, in particular for fragrance or flavoring substances with fresh, fruity and / or sweet notes.
  • 2-methoxymethylphenol enhances the smell or taste of odoriferous or aromatic substances, especially fresh, fruity and / or sweet notes.
  • the so-called “boost effect” is particularly pronounced in perfume oils, especially perfume oils with fruity, fresh and / or sweet notes.
  • 2-methoxymethylphenol is outstandingly suitable for enhancing (boosting) an odor or taste with fruity, fresh and / or sweet notes.
  • This property of 2-methoxymethylphenol is illustrated using a perfume oil with a fruity raspberry note in Example 2 (see below).
  • particularly good results were obtained when 2-methoxymethylphenol was combined with one or more of the compounds listed in Table 2.
  • 2-methoxymethylphenol is used as a fragrance or aroma substance with a vanilla, carnation and / or leathery note.
  • a corresponding method according to the invention for imparting, modifying and / or enhancing (boosting) an odor or taste with one, several or all of the notes vanilla, clove-like and / or leathery comprises a step in which a quantity of 2-methoxymethylphenol or a 2-methoxymethylphenol comprehensive fragrance or flavoring composition is brought into contact with a product or mixed.
  • the product can be, for example, a further fragrance or flavoring substance or a mixture of other fragrance or flavoring substances.
  • a corresponding method for modifying and / or enhancing (boosting) an odor and / or taste with one, several or all of the notes fresh, fruity and / or sweet comprises the following step:
  • the 2-methoxymethylphenol to be used according to the invention is able to intensify the intensity of the fragrance or aroma substance mixture even in small doses and to round off the overall appearance of the mixture and to give the mixture more radiance, gloss, harmony and naturalness to lend.
  • Fragrance or flavoring compositions which comprise 2-methoxymethylphenol and one or more further fragrance or flavoring substances (in particular fragrance or flavoring substances with a fruity, fresh and / or sweet note) have a surprising olfactory quality.
  • the invention also relates to corresponding fragrance or flavoring compositions which comprise 2-methoxymethylphenol and one or more further fragrance or flavoring substances.
  • At least three different types of fragrance or flavoring compositions according to the invention can be distinguished from one another, although the transitions from one type to the other are fluid.
  • type (i) of a fragrance or aroma composition according to the invention the amount of 2-methoxymethylphenol is sufficient to impart one, more or all of the notes vanilla, clove-like and / or leathery.
  • composition (i) exists in particular when none of the other fragrance or aroma substances itself conveys one, several or all of the notes vanilla, carnation and / or leathery, but the amount of 2-methoxymethylphenol is sufficient to convey one, several or all of these notes.
  • the further fragrance or flavoring agent (s) impart one, several or all of the notes vanilla, clove-like, leathery, fresh, fruity and / or sweet and the amount of 2-methoxymethylphenol is sufficient, modify and / or reinforce (to boost) one or more of these notes.
  • the amount of 2-methoxymethylphenol is sufficient to give the fragrance or flavoring composition (out) radiation, gloss, roundness, naturalness and / or harmony.
  • fragrance or flavoring compositions according to the invention which, in addition to the 2-methoxymethylphenol to be used according to the invention, contain one or more further fragrance or flavorings which are selected from the group consisting of:
  • compositions comprising 2-methoxymethylphenol and one or more further odoriferous or aromatic substances selected from the group consisting of 2-methyl-butyric acid ethyl ester, 4- (p-hydroxyphenyl) -2-butanone, ethyl-3-methyl-3- phenylglycidate, butyric acid isoamyl ester, acetic acid isoamyl ester, acetic acid n-butyl ester, butyric acid ethyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, ethyl 2-trans-4-cis-decadienoate, 1, 1-dimethoxy-2,2 5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al, gamma-undecalactone, and gamma-nonalactone, ie
  • fragrance or flavoring compositions according to the invention which contain an amount of 2-methoxymethylphenol in the range from 0.0001 to 90% by weight, preferably 0.01 to 70% by weight and particularly preferred 0.1 to 50 wt .-%, based on the total amount of the fragrance or flavoring composition.
  • 2-methoxymethylphenol is mainly used to give a fragrance or aroma composition more radiation, shine, roundness, naturalness and / or harmony and / or to modify or reinforce certain notes, especially notes of the fruity, fresh and / or sweet
  • the proportion of 2-methoxymethylphenol is preferably quite low and preferably in the range from 0.01 to 5% by weight, preferably in the range from 0.1 to 2% by weight, based on the total amount of odoriferous or Flavor composition. If a comparatively low concentration is selected within the preferred concentration ranges, depending on the other components of the respective composition, the intrinsic odor or taste notes given above are not conveyed in some cases.
  • Fragrance or flavoring compositions according to the invention are preferably used for the production of perfumed or flavored products (articles); for preferred perfumed or flavored products see below.
  • the sensory properties, material properties (such as solubility in common solvents and compatibility with other common constituents of such products) and the toxicological harmlessness of the compound to be used according to the invention underline their particular suitability for the purposes mentioned.
  • Fragrance or flavoring compositions according to the invention are particularly preferred in which the effects of types (i), (ii) and (iii) occur side by side and overlapping one another.
  • An example of such a preferred fragrance composition (perfume composition) is given in Example 2 below.
  • a fragrance or flavoring composition according to the invention is produced according to the invention by mixing 2-methoxymethylphenol with customary further constituents of a fragrance or flavoring composition, the 2-methoxymethylphenol being used in an amount sufficient to provide an odor in the fragrance or flavoring composition. or to convey, modify and / or reinforce taste.
  • the example of a "fruity-vanilla raspberry" fragrance composition given below clearly demonstrates the olfactory effect of 2-methoxymethylphenol.
  • the usual components are included the olfactory or aroma substance composition olfactory or aroma substances, which are selected from the group already mentioned above, which consists of: 2-methyl-butyric acid ethyl ester, 4- (p-hydroxyphenyl) -2-butanone, ethyl-3-methyl-3- phenylglycidate, butyric acid isoamyl ester, acetic acid isoamyl ester, acetic acid n-butyl ester, butyric acid ethyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, ethyl 2-trans-4-cis-decadienoate, 1, 1-dimethoxy-2,2-dimethoxy 5-trimethyl-4-hexane,
  • the compounds 2-methyl-butyric acid ethyl ester, 4- (p-hydroxyphenyl) -2-butanone, ethyl 3-methyl-3-phenylglycidate, butyric acid isoamyl ester, acetic acid isoamyl ester, acetic acid n-butyl ester, butyric acid ethyl ester, 3-methyl are particularly preferred -butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, ethyl 2-trans-4-cis-decadienoate, 1, 1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-heptene -1-al, gamma undecalactone, gamma-nonalactone and mixtures thereof.
  • the invention also relates to the use of 2-methoxymethylphenol as an agent for increasing the substantivity and / or retention of a fragrance mixture (fragrance composition) and / or as a fixator.
  • Fragrance mixtures containing 2-methoxymethylphenol or 2-methoxymethylphenol are characterized by a high absorbency (self-adhesion on a substrate) and a high substantivity (ability to absorb from a, usually aqueous, phase onto a substrate or also after a washing or rinsing process to remain on a substrate). This effect is particularly evident on substrates such as skin, hair and textile fibers (e.g. wool, cotton, linen, synthetic fibers).
  • perfumed products according to the invention are therefore detergents, hygiene or care products, in particular in the field of body and hair care, cosmetics and the household.
  • fragrances and fragrance mixtures are their substantivity towards or retention on the substrate, in particular hair or textile fibers.
  • substantially and retention are e.g. detailed in EP 1 201 738 A1, cf. there the sections [0004] - [0005]. Fragrance substances with high substantivity and / or retention are therefore also generally sought.
  • a fruity, fresh and / or sweet-scented for example, a fruity, fresh and / or sweet-scented, but due to insufficient substantivity of the fragrances contained, not suitable for passing on a fruity, fresh and / or sweet smell to laundry (textile fibers) or hair, an aqueous washing solution (or a Corresponding detergent or shampoo or the like) by adding 2-methoxymethylphenol into a solution that excellently transmits a fruity, fresh and / or sweet smell - and the fruity, fresh and / adheres to the treated substrates (hair or textile fibers) or sweet smell for a long time.
  • an aqueous washing solution or a Corresponding detergent or shampoo or the like
  • a corresponding method according to the invention for providing (a) hair or (b) textile fibers with a vanilla, carnation and / or leathery fragrance comprises the following steps:
  • a corresponding method according to the invention for providing (a) hair or (b) textile fibers with a fruity, fresh and / or sweet smell comprises the following steps:
  • fragrance mixture comprising 2-methoxymethylphenol and one or more further fragrances, which convey one, several or all of the (olfactory) notes fresh, fruity and / or sweet, the amount at
  • 2-methoxymethylphenol is sufficient to modify and / or enhance (to boost) one or more of these notes
  • a surfactant-containing mixture in particular a solution which comprises: (a) water, (b) 2-methoxymethylphenol (for example, for example), is particularly suitable for the uses according to the invention or the corresponding processes which relate to the treatment of hair or textile fibers. in the form of a fragrance combination according to the invention) and (c) one or more surfactants, the concentration of 2-methoxymethylphenol in the solution being in the range from 10 ⁇ 7-10 ⁇ 1 % by weight.
  • Other fragrances (as part of a fragrance composition according to the invention, in particular one with a vanilla, carnation, leathery, fresh, fruity and / or sweet note) and / or other conventional additives may be present.
  • Preferred products according to the invention are (a) perfume oil mixtures (as an example for fragrance compositions according to the invention) for formulations containing surfactants, such as e.g. Cleaning agents, detergents, fabric softeners and personal care products and (b) the corresponding surfactant-containing formulations themselves.
  • surfactants such as e.g. Cleaning agents, detergents, fabric softeners and personal care products
  • the preferred surfactant-containing formulations which can be used in the context of the present invention generally comprise, in addition to the fragrance compositions according to the invention, substances from the class of anionic surfactants, such as carboxylates , Sulfates, sulfonates and phosphates, the cationic surfactants such as quaternary ammonium salts, the amphoteric surfactants such as betaines, and the nonionic surfactants such as ethoxylates and propoxylates.
  • anionic surfactants such as carboxylates , Sulfates, sulfonates and phosphates
  • the cationic surfactants such as quaternary ammonium salts
  • amphoteric surfactants such as betaines
  • nonionic surfactants such as ethoxylates and propoxylates.
  • the sulfates and sulfonates are preferred among the anionic surfactants.
  • the sulfates those having 12 to 18 carbon atoms and a degree of ethoxylation of 1 to a maximum of 5 are preferred.
  • Sodium lauryl ether sulfate is particularly preferred, preferably with an average degree of ethoxylation of 2 to 4.
  • the linear sodium alkylbenzenesulfonates with an average of about 12 carbon atoms in the alkyl chain are particularly preferred, these consisting of homologous residues with 10 to 14 carbon atoms (“dodecylbenzenesulfonate”).
  • the ethoxylated fatty alcohols which are obtained by ethoxylating alcohols with 12 to 18 carbon atoms (fatty alcohol ethoxylates with 12 to 18 C atoms) are preferred.
  • the degree of ethoxylation can vary within wide limits, but products with an average degree of ethoxylation of 5 to 10, in particular 7 moles of added ethylene oxide per mole of fatty alcohol are particularly preferred.
  • betaines those of the acid amide type with the structure listed are particularly preferred.
  • a corresponding surfactant formulation according to the invention (as an example of an article according to the invention) comprises 2-methoxymethylphenol and one or more surfactants which are selected from the group consisting of:
  • Linear alkylbenzenesulfonates (especially those mentioned above, such as the linear sodium alkylbenzenesulfonates),
  • Fatty alcohol ethoxylates with 12-18 C atoms (in particular those mentioned above, i.e. for example those with the degree of ethoxylation designated above as preferred),
  • Lauryl ether sulfates in particular those mentioned above, for example the sodium lauryl ether sulfate mentioned above
  • Betaines in particular those mentioned above, for example betaines of the acid amide type with the structure listed above.
  • Linear alkylbenzenesulfonates and fatty alcohol ethoxylates with 12-18 C atoms are preferably used next to one another, in particular in detergent powders.
  • lauryl ether sulfates in particular the above-mentioned sodium lauryl ether sulfate
  • betaines in particular betaines of the acid amide type with the structure listed above
  • concentration of the surface-active substances in the surfactant formulations according to the invention is generally not critical. Preferred concentrations depend on the type of surfactant and the particular application. For example, they can be less than 1% by weight in special bleaching products, but more than 99% by weight in soaps or washing powder. For certain fields of application, certain combinations and concentrations are preferred in surfactant formulations according to the invention.
  • Mixtures according to the invention are preferred in which the proportion of linear alkylbenzenesulfonates in the range from 7 to 10% by weight and / or the proportion of fatty alcohol ethoxylates with 12-18 C atoms in the range from 3 to 6% by weight is based on the total mass of the mixture.
  • Mixtures according to the invention (formulations for mild detergents, shampoos and shower gels) are also preferred in which the proportion of sodium lauryl ether sulfate is in the range from 7 to 13% by weight and / or the proportion of betaine (in particular betaine of the acid amide type with the structure listed above) Range of 1 - 3 wt .-%, based in each case on the total mass of the mixture.
  • 2-methoxymethylphenol is characterized by its fixing properties.
  • a fixator increases the adhesive strength of other fragrances, whether by lowering their vapor pressure or enhancing their odor (e.g. lowering the threshold value).
  • the invention therefore also relates, as already mentioned, to the use of 2-methoxymethylphenol or a fragrance mixture comprising 2-methoxymethylphenol (as characterized above) as a fixator.
  • 2-Methoxymethylphenol is preferably prepared using one of the etherification methods described above, starting from salicyl alcohol.
  • 2-methoxymethylphenol was produced, for example, from salicylaldehyde by reduction with sodium borohydride and subsequent etherification of the salicyl alcohol formed with methanol in the presence of sulfuric acid (see Example 1, below):
  • 2-methoxymethylphenol is particularly suitable for use in fragrance and flavoring compositions.
  • the compound can be used in numerous products in combination with a large number of other fragrance or aroma substances.
  • the compound can be combined particularly advantageously with other odoriferous or aromatic substances in different, different proportions to form novel odoriferous or aromatic substance compositions.
  • Extracts from natural raw materials such as essential oils, concretes, absolute, resins, resinoids, balms, tinctures such as B. Ambratincture; Amyris oil; Angelica seed oil; Angelica root oil; Anise oil; Valerian oil; Basil oil; Baummoos -Absolue; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Beeswax absolute; Birch tar oil; Bitter almond oil; Savory oil; Bucco leaf oil; Cabreuva oil; Cade oil; Calmus oil; Camphor oil; Cananga oil; Cardamom oil; Cascarilla oil; Cassia oil; Cassie absolute; Castoreum-absolue; Cedar leaf oil; Cedarwood oil; Cistus oil; Citronell oil; Lemon oil; Copaiva balm; Copaivabalsam oil; Coriander oil; Costus root oil; Cumin oil; Cypress oil; Davana oil; Dill herb oil; Dill seed oil; Eau de brouts absolute; Oakmoss absolute; Ele
  • fragrances from the group of hydrocarbons such as 3-carene; alpha-pinene; beta-pinene; alpha terpinene; gamma terpinene; p-cymene; Bisabolene; Camphene; Caryophyllene; Cedren; Farnese; Lime; Longifolene; Myrcene; Ocimen; Valencene; (E 1 Z) -1, 3, 5-undecatriene; Styrene; Diphenylmethane; aliphatic alcohols such as hexanol; Octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; (E) - and (Z) -3-hexenol; 1-octen-3-ol; Mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-o
  • Methyl 2-noninate Allyl-2-isoamyloxyacetate; Methyl 3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate; the acyclic terpene alcohols such as B.
  • Trimethylcyclohexylmethanol 1- (4-isopropylcyclohexyl) ethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 2-ethyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) pentan-2-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3,3-dimethyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1 - (2,2,6-trimethylcyclohexyl) pentan-3-ol; 1 - (2,2,6-trimethylcyclohexy
  • Trimethylcyclohexyl) hexan-3-ol Trimethylcyclohexyl) hexan-3-ol; cyclic and cycloaliphatic ethers such as e.g. Cineol; Cedryl methyl ether; Cyclododecyl methyl ether; 1, 1-dimethoxycyclododecane; (Ethoxymethoxy) cyclododecane; alpha-cedrenepoxide; 3a, 6, 6,9a-
  • Pentylcyclopentanone 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; S-methyl- ⁇ -cyclopentadecenone; 3-
  • Methylcyclopentadecanone 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1,1,3,3-pentamethyl-4 (5H) -indanone; 8-cyclohexadecen-1-one; ⁇ -cycloheptadecen-i-one; Cyclopentadecanone; Cyclohexadecanone; cycloaliphatic aldehydes such as e.g.
  • Pentylcyclohexyl acetate 3,3,5-trimethylcyclohexyl acetate; Decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H-pyran-4-ylacetate; Decahydro-2,5,5,8a-tetramethyl-2-naphthylacetate; 4,7-methano
  • the amount of 2-methoxymethylphenol used is preferably 0.0001 to 90% by weight, preferably 0.01 to 70% by weight and particularly preferably 0.1 to 50% by weight, based on the Total amount of the fragrance or flavoring composition.
  • Fragrance or flavoring compositions which contain 2-methoxymethylphenol can be used in liquid form, undiluted or diluted with a solvent for perfuming or aromatizing. Suitable solvents for this are e.g.
  • Ethanol isopropanol, diethylene glycol monoethyleter, glycerin, propylene glycol, 1, 2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetin, vegetable oils etc.
  • Ingredients that can be combined with 2-methoxymethylphenol include:
  • Preservatives Preservatives, abrasives, anti-acne agents, anti-aging agents, anti-bacterial agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, anti-irritant agents, anti-irritant agents, antimicrobial agents, antioxidants, astringents, antiperspirant agents, antiseptic agents, antistatic agents , Buffers, carrier materials, chelating agents, cell stimulants, cleaning agents, care agents, depilatory agents, surface-active substances, deodorising agents, antiperspirants, softening agents, emulsifiers, enzymes, essential oils, fibers, film formers, fixatives, Foaming agents, foam stabilizers, substances to prevent foaming, foam boosters, fungicides, gelling agents, gelling agents, hair care products, hair shaping agents, hair straightening agents, moisturizing agents, moisturizing substances, moisturizing substances, bleaching agents, strengthening agents, stain-removing agents, optically brightening agents, imprinting agents
  • fragrance or flavoring compositions according to the invention which contain 2-methoxymethylphenol can be adsorbed on a carrier which ensures both a fine distribution of the fragrance or flavoring substances in the product and a controlled release during use.
  • a carrier which ensures both a fine distribution of the fragrance or flavoring substances in the product and a controlled release during use.
  • Such carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, gas concrete etc. or organic materials such as woods, cellulose-based substances, sugars, dextrins (eg maltodextrin) or plastics such as PVC, polyvinyl acetates or polyurethanes.
  • the combination of composition and carrier according to the invention represents an exemplary article according to the invention.
  • Fragrance or flavoring compositions which contain 2-methoxymethylphenol can also be microencapsulated, spray-dried, as inclusion complexes or present as extrusion products (ie products according to the invention) and in this form, for. B. a product to be perfumed or flavored.
  • compositions modified in this way can be further optimized by so-called “coating” with suitable materials with a view to a more targeted fragrance release, for which purpose wax-like plastics such as polyvinyl alcohol are preferably used.
  • suitable materials with a view to a more targeted fragrance release, for which purpose wax-like plastics such as polyvinyl alcohol are preferably used.
  • the resulting products in turn represent products according to the invention.
  • the microencapsulation of the fragrance or flavoring compositions according to the invention to products according to the invention can be carried out, for example, by the so-called coacervation process with the aid of capsule materials, e.g. made of polyurethane-like substances or soft gelatin.
  • the spray-dried fragrance or flavoring composition can be produced, for example, by spray drying an emulsion or dispersion containing the fragrance or flavoring composition, and modified starches, proteins, dextrin and vegetable gums can be used as carriers.
  • Inclusion complexes can e.g. by adding dispersions of the fragrance or flavoring composition and cyclodextrins or urea derivatives in a suitable solvent, e.g. Water.
  • Extrusion products can be made by fusing the fragrance or flavoring compositions with a suitable wax-like substance and by extrusion with subsequent solidification, if appropriate in a suitable solvent, e.g. Isopropanol can be obtained.
  • 2-methoxymethylphenol and fragrance compositions which contain 2-methoxymethylphenol can be used in concentrated form, in solutions or in the modified form described above for the production of perfumed products according to the invention, such as, for example, perfume extracts, eau de perfumes, eau de toilettes, aftershaves, Eau de colognes, pre-shave products, splash colognes and scented refreshing wipes as well as the scenting of acidic, alkaline and neutral cleaning agents such as floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powder - and foam-shaped carpet cleaners, textile fresheners, ironing aids, liquid detergents, powdered detergents, laundry pretreatment agents such as bleach, soaking agents and stain removers, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants and air fresheners applied in a liquid, gel-like or aerosol-based form on aerosol sprays and polishes such as furniture polishes,
  • the 2-methoxymethylphenol to be used according to the invention can be incorporated into flavored or flavored products, in particular preparations serving for nutrition, oral care or pleasure.
  • Preparations serving nutrition or pleasure are e.g. baked goods (e.g. bread, dry biscuits, cakes, other pastries), confectionery (e.g. chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (e.g. Coffee, tea, wine, wine-based drinks, beer, beer-based drinks, liqueurs, schnapps, brandies, fruit-containing lemonades, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juices juice preparations), instant drinks (e.g.
  • instant cocoa drinks, instant tea drinks, instant coffee drinks meat products (e.g. ham, fresh sausage or raw sausage preparations, seasoned or marinated fresh or pickled meat products), eggs or egg products (dry egg, protein, egg yolk) , Cereal products (e.g. breakfast cereals, granola bars, pre-cooked ready-rice products), dairy products (e.g. milk drinks, milk ice cream, yoghurt, kefir, cream cheese, soft cheese, hard cheese, dry milk powder, whey, butter, buttermilk, partially or completely hydrolyzed milk protein-containing products) , Products made from soy protein or other soybean fractions (e.g.
  • soy milk and products made from it preparations containing soy lecithin, fermented products such as tofu or tempe or products made from it, soy sauces), fruit preparations (e.g. jams, fruit ice cream, fruit sauces, fruit fillings), vegetable preparations (e.g. ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked Vegetables, pickled vegetables, boiled vegetables), snacks (e.g. baked or fried potato chips or potato dough products, bread dough products, extrudates based on corn or peanuts), products based on fat and oil or emulsions thereof (e.g. mayonnaise, tartar sauce, dressings, seasoning preparations) , other ready meals and soups (e.g.
  • these preparations are preparations according to the invention (as an example of products according to the invention).
  • Preparations according to the invention can, for. B. as a semi-finished product or as a seasoning mix. Preparations according to the invention can serve, in particular, as semi-finished goods for the production of further preparations serving for nutrition or pleasure, in particular in spray-dried form. Preparations according to the invention can also be in the form of capsules, tablets (non-coated and coated tablets, for example enteric coatings), dragées, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsifiers. onen, as powder, as solutions, as pastes or as other swallowable or chewable preparations as food supplements.
  • Preparations according to the invention used for oral care are, in particular, oral and / or dental care products such as toothpastes, tooth gels, tooth powder, mouthwashes, chewing gums and other oral care products.
  • compositions according to the invention can be used in amounts of 5 to 99.999999% by weight, preferably 10 to 80% by weight, based on the Total weight of the preparation.
  • preparations can contain water in an amount of up to 99.999999% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.
  • the preparations according to the invention (as examples of products according to the invention) containing 2-methoxymethylphenol are prepared by using the 2-methoxymethylphenol as a substance, as a solution (for example in ethanol, water or 1,2-propylene glycol) or in the form of a mixture with a solid or liquid carrier (e.g. maltodextrin, starch, silica gel), other flavors or flavorings and, if necessary, other auxiliaries and / or stabilizers (e.g. natural or artificial polysaccharides and / or plant gums such as modified starches or gum arabic) in a diet , oral care or basic preparation for pleasure.
  • a solid or liquid carrier e.g. maltodextrin, starch, silica gel
  • other auxiliaries and / or stabilizers e.g. natural or artificial polysaccharides and / or plant gums such as modified starches or gum arabic
  • Preparations according to the invention which are present as a solution and / or
  • the spray-dried solid preparations according to the invention are particularly well suited as semi-finished goods for the production of further preparations according to the invention.
  • the spray-dried solid preparations according to the invention preferably contain 50 to 95% by weight of carriers, in particular maltodextrin and / or starch, 5 to Contain 40% auxiliaries, preferably natural or artificial polysaccharides and / or plant gums such as modified starches or gum arabic.
  • the 2-methoxymethylphenol according to the invention and optionally other constituents of the preparation according to the invention are initially prepared in emulsions, in liposomes, e.g. starting from phosphatidylcholine, in microspheres, in nanospheres or also in capsules, granules or extrudates from a matrix suitable for foodstuffs and luxury foods, e.g. from starch, starch derivatives (e.g. modified starch), cellulose or cellulose derivatives (e.g. hydroxypropyl cellulose), other polysaccharides (e.g.
  • dextrin alginate, curdlan, carageenan, chitin, chitosan, pullulan
  • natural fats natural waxes (e.g. beeswax, carnauba wax) Proteins, e.g. Gelatin or other natural products (e.g. shellac) incorporated.
  • the products can be obtained by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion processes, coating (coating) or other suitable encapsulation processes and, if appropriate, a suitable combination of the aforementioned processes.
  • the 2-methoxymethylphenol is first complexed with one or more suitable complexing agents, for example with cyclodextrins or cyclodextrin derivatives, preferably ⁇ - or ⁇ -cyclodextrin, and used in this complexed form.
  • suitable complexing agents for example with cyclodextrins or cyclodextrin derivatives, preferably ⁇ - or ⁇ -cyclodextrin, and used in this complexed form.
  • a preparation according to the invention is particularly preferred in which the matrix is selected such that 2-methoxymethylphenol is released from the matrix with a delay, so that a long-lasting effect is achieved.
  • a fat, wax, polysaccharide or protein matrix is particularly preferred.
  • the usual constituents, auxiliaries and additives for foodstuffs or luxury foods for example water, mixtures of fresh or processed vegetable or animal raw materials or raw materials (for example raw materials) can be used as further constituents for preparations according to the invention which are used for nutrition or pleasure , roasted, dried, fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetables or fruit juices or pastes or their mixtures), digestible or non-digestible carbohydrates (e.g. sucrose, maltose, fructose, Glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose, tagatose), sugar alcohols (e.g.
  • sorbitol, erythritol natural or hardened fats (e.g. tallow, lard, palm fat, coconut fat, hardened vegetable fat), oils (e.g. sunflower oil, peanut oil, Corn oil, olive oil, fish oil, soybean oil, sesame oil), fatty acids or their salts (eg potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (eg gamma-aminobutyric acid, taurine), peptides (eg glutahthione), native or processed proteins (eg gelatin), enzymes (eg peptidases), nucleic acids, nucleotides, taste corrections for unpleasant taste impressions, further taste modulators for further, generally not unpleasant taste impressions, other taste-modulating substances (e.g.
  • inositol phosphate nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid
  • emulsifiers e.g. lecithins, diacylglycerols, gum arabic
  • stabilizers e.g. caramelizing agents Alginate
  • preservatives e.g. benzoic acid, sorbic acid
  • antioxidants e.g. tocopherol, ascorbic acid
  • chelators e.g. citric acid
  • organic or inorganic acidulants e.g. malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid
  • bitter substances e.g.
  • quinine quinine, caffeine) , Limonin, Amarogentin, Humolone, Lupolone, Catechine, Tannins), mineral salts (eg sodium chloride, potassium chloride, magnesium chloride, sodium phosphate), substances that prevent enzymatic browning (eg sulfite, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or color pigments (e.g. carotenoids, flavonoids, anthoc yane, chlorophyll and their derivatives), spices, trigeminally active substances or plant extracts, containing such trigeminally active substances, synthetic, natural or nature-identical flavorings or fragrances and odor correctors.
  • mineral salts eg sodium chloride, potassium chloride, magnesium chloride, sodium phosphate
  • substances that prevent enzymatic browning eg sulfite, ascorbic acid
  • essential oils e.g sulfite, ascorbic acid
  • plant extracts natural or synthetic dyes or color pigment
  • Dental care products (which are used as the basis for oral care preparations) and which contain 2-methoxymethylphenol generally comprise an abrasive system (Grinding or polishing agents), such as, for example, silicas, calcium carbonates, calcium phosphates, aluminum oxides and / or hydroxylapatites, surface-active substances such as, for example, sodium lauryl sulfate, sodium lauryl sarcosinate and / or cocamidopropyl betaine, humectants such as, for example, glycerol and / or sorbitol, thickeners, such as carboxymethyl cellulose, polyethylene glycols, carrageenan and / or Laponite ® , sweeteners such as saccharin, taste corrections for unpleasant taste impressions, taste corrections for other, usually not unpleasant taste impressions, taste-modulating substances (eg inositol phosphate, nucleotides such as guanosine monophone) Substances such as sodium glutamate or
  • Diisopropylpropionic acid methylamide Diisopropylpropionic acid methylamide
  • cilin and cilin derivatives stabilizers and active ingredients, such as e.g. Sodium fluoride, sodium monofluorophosphate, Zinndifluo- chloride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures niumchlorid various pyrophosphates, triclosan, Cetylpyridi- ruchskorrigentien, aluminum lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, flavors and / or sodium bicarbonate or overall .
  • active ingredients such as e.g. Sodium fluoride, sodium monofluorophosphate, Zinndifluo- chloride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyr
  • Chewing gums (as another example of preparations used for oral care) which contain 2-methoxymethylphenol generally comprise a chewing gum base, ie a chewing gum which becomes plastic when chewed, sugars of various types, sugar substitutes, other sweet-tasting substances, sugar alcohols, taste corrections for unpleasant taste impressions, other taste modulators for other, usually not unpleasant, taste impressions, taste-modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), moisturizers, thickeners, emulsifiers, flavors and stabilizers or odors.
  • a chewing gum base ie a chewing gum which becomes plastic when chewed
  • sugars of various types, sugar substitutes, other sweet-tasting substances e.g., a sugar substitutes, other sweet-tasting substances, sugar alcohols, taste corrections for unpleasant taste
  • the preparations according to the invention can preferably also contain an (additional) aroma composition in order to round off and refine the taste and / or smell of the preparation.
  • Suitable (additional) aroma compositions contain, for example, synthetic, natural or nature-identical aromas, fragrances and flavors as well as suitable auxiliaries and carriers.
  • DPG dipropylene glycol
  • Table 3 shows some selected sensory data that illustrate the sensory potential of 2-methoxymethylphenol. Isobutylquinoline of the following formula was used for comparison:
  • the comparative substance isobutylquinoline was not selected here because of its own smell, but rather because of its property as a "booster” (cf. Insofar Arctander, in Perfume and Flavor Chemicals, as quoted above, “... the effect is more that of a general "lift” than actually an odor contribution, and the quinoline odor should not be part of the fragrance picture, but should appear with an undetectable note of radiation and strength. ").
  • Table 4 shows the stability of 2-methoxymethylphenol in different (surfactant-containing) products based on the analytical recovery rates.
  • 2-methoxymethylphenol was provided as a 50% by weight solution in diethyl phthalate, which was incorporated in a dosage of 0.2% by weight into a shampoo base composition of the following formulation: Sodium lauryl ether sulfate 12%
  • Peach fragrance mixture comprising gamma undecalactone 0.5%
  • the pH of the shampoo base was around 6. From this, 100 ml of a 20% by weight aqueous shampoo solution were produced. In this shampoo solution, 2 strands of hair were washed together for 2 minutes and then rinsed under running, lukewarm water for 20 seconds. One strand of hair was wrapped wet in aluminum foil and the second strand of hair was dried with a hair dryer. Both strands of hair were assessed in terms of smell by a panel. Both strands of hair showed a fresh, peach-fruity and sweet smell, whereby the overall impression was radiant, rounded, natural and harmonious.
  • the perfume oil composition from Example 2 (after the addition of 2-methoxymethylphenol) was incorporated in a dosage of 0.5% by weight into a fabric softener base of the following composition: Quaternary ammonium methosulfate (ester quat), approx. 90% 5.5% (e.g. Rewoquat WE 18, Witco Surfactants GmbH)
  • the pH of the fabric softener base was in the range 2 - 3.
  • Two cloths were rinsed with 370 g of a 1% aqueous fabric softener solution in a Linetest machine in the fabric softener program for 30 minutes at 20 ° C.
  • the rags were wrung out and then flung for 20 seconds.
  • a rag was welded wet and one hung up to dry. Subsequently, both cloths were assessed for odor by a panel.
  • Both rags showed a fresh, raspberry-fruity and vanilla-sweet smell with weak leathery-clove-like aspects, whereby the overall impression was radiant, rounded, natural and harmonious.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Fats And Perfumes (AREA)

Abstract

L’invention concerne l’utilisation de 2-méthoxyméthylphénol en tant que matière olfactive ou aromatique présentant une note de vanille, de clou de girofle et/ou de cuir. L’invention concerne également l’utilisation de 2-méthoxyméthylphénol en tant que renforçant pour matière olfactive ou aromatique, notamment celles présentant une note fraîche, fruitée et/ou sucrée.
PCT/EP2006/067646 2005-12-09 2006-10-23 2-methoxymethylphenol en tant que matiere olfactive et aromatique WO2007065755A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005058792A DE102005058792A1 (de) 2005-12-09 2005-12-09 2-Methoxymethylphenol als Riech- und Aromastoff
DE102005058792.5 2005-12-09

Publications (1)

Publication Number Publication Date
WO2007065755A1 true WO2007065755A1 (fr) 2007-06-14

Family

ID=37517257

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/067646 WO2007065755A1 (fr) 2005-12-09 2006-10-23 2-methoxymethylphenol en tant que matiere olfactive et aromatique

Country Status (2)

Country Link
DE (1) DE102005058792A1 (fr)
WO (1) WO2007065755A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013000595A1 (fr) * 2011-06-30 2013-01-03 Firmenich Sa Composé d'arômes
WO2018096152A1 (fr) 2016-11-28 2018-05-31 Dsm Ip Assets B.V. Procédé de préparation de phénols (poly)alkylés

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102013226602A1 (de) * 2013-12-19 2015-06-25 Henkel Ag & Co. Kgaa Verwendung von CNGA2-Agonisten zur Verstärkung der olfaktorischen Wirkung eines Riechstoffs

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0870754A1 (fr) * 1997-04-10 1998-10-14 Haarmann & Reimer Gmbh Isobutyrate d'ethylvanilline
DE102004019752A1 (de) * 2004-04-23 2005-11-17 Henkel Kgaa Mittel mit metallisch riechendem Duftstoff geeignet zum Einsatz in Wasch-/Wäschepflege- und Raumbeduftungsmitteln
WO2006003053A1 (fr) * 2004-06-30 2006-01-12 Symrise Gmbh & Co. Kg Utilisation de 3-mercapto-3-methyl-hexan-1-ol comme etalon malodorant

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0870754A1 (fr) * 1997-04-10 1998-10-14 Haarmann & Reimer Gmbh Isobutyrate d'ethylvanilline
DE102004019752A1 (de) * 2004-04-23 2005-11-17 Henkel Kgaa Mittel mit metallisch riechendem Duftstoff geeignet zum Einsatz in Wasch-/Wäschepflege- und Raumbeduftungsmitteln
WO2006003053A1 (fr) * 2004-06-30 2006-01-12 Symrise Gmbh & Co. Kg Utilisation de 3-mercapto-3-methyl-hexan-1-ol comme etalon malodorant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BOHNSACK H: "Beitrag zur Kenntnis der ätherischen Oele, Riech- und Geschmackstoffe XV. Mitteilung: Ueber die Inhaltstoffe der Bourbon-Vanilleschote III. Teil: Vanillylalkohol und andere aromatische Hydroxyalkohole bzw. den Methylaetherer", RIECHSTOFFE, AROMEN, KOERPERPFLEGEMITTEL, ST. PETER-ORDING, DE, vol. 17, no. 11, November 1965 (1965-11-01), pages 407 - 410, XP002081410, ISSN: 0035-5194 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013000595A1 (fr) * 2011-06-30 2013-01-03 Firmenich Sa Composé d'arômes
WO2018096152A1 (fr) 2016-11-28 2018-05-31 Dsm Ip Assets B.V. Procédé de préparation de phénols (poly)alkylés

Also Published As

Publication number Publication date
DE102005058792A1 (de) 2007-06-14

Similar Documents

Publication Publication Date Title
DE102006046249B4 (de) Mischungen umfassend alpha-Ambrinolalkylether und 2-Alkoxy-9-methylen-2,6,6-trimethylbicyclo[3.3.1]nonane als Riech- und Aromastoffe
EP2048127B1 (fr) 2-akoxymethyl-3-isoalkenyl-1-methylcyclopentène, leur utilisation, en particulier comme parfums, articles correspondants ainsi que procédé de fabrication
EP2524959B1 (fr) Compositions d'odeurs et/ou d'arômes comprenant du dioxolane
EP2039670B1 (fr) 6-méthyl-4-(2',2',3'-triméthyl-3'-cyclopentène-1'-yl)-2-cyclohexène-1-ol en tant que parfum de Santal
EP2687586B1 (fr) Utilisation de cyclohexenone définie comme moyen de renforcement supplémentaire d'une impression olfactive ainsi que la composition d'aromates et/ou de parfums
DE102006043226A1 (de) 4-Phenyl-pentan-2-ol als Riech- und Aromastoff
EP2632554B1 (fr) Parfum
EP1878787B1 (fr) Aldéhydes en place alpha substitués par reste d'alkyle en tant que parfums et aromates
EP1902632A1 (fr) Ethers d'acide alcaldiénal déconjugué en tant que parfums et/ou aromes
EP2266421A1 (fr) Utilisation d'isopropyle-méthyle-cyclohexanes-thioles précis en tant que parfums et/ou aromes
EP1972632A1 (fr) Oxabicycloalkanones comme matières odorantes
EP2895470B1 (fr) Lactones insaturees comme ingredients parfumants
EP3601508B1 (fr) 5-bicyclo[2.2.1]hept-2-ényl-acétate utilisé comme parfum et/ou arôme
EP2641903B1 (fr) Dérivés de dihydrobenzofuranes en tant que parfums et/ou arômes
WO2007065755A1 (fr) 2-methoxymethylphenol en tant que matiere olfactive et aromatique
EP2757905B1 (fr) Acétals et cétals en tant que matières odorantes et aromatiques
EP3601510A1 (fr) 2,3,6-triméthylcyclohexanol utilisé comme parfum et/ou arôme
WO2007060048A1 (fr) 2-methyl-3-(5-methyl-2-furyl)-butanal
EP1961725A1 (fr) Arômes, parfums, leur fabrication et utilisation
DE102006003962B4 (de) Neue Derivate des Bicyclo[4.3.0]nona-3,7-diens, Verfahren zu ihrer Herstellung und Verwendung
DE102007000757A1 (de) Sandelriechstoffe
DE102006004643A1 (de) Derivate des Bicyclo(4.3.0)nona-3,7-diens und deren Verwendung

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 06807457

Country of ref document: EP

Kind code of ref document: A1