Fragrance mixtures containing 1-(4,4-dimethylcyclohexen-1-yl)ethanone

Abstract

The present invention relates to fragrance mixtures comprising or consisting of a compound of formula (I) and one or more fragrances having a green and / or flowery scent. The present invention further provides methods for preparing the fragrance mixtures according to the present invention, and methods for enhancing and / or modifying the green and / or flowery scent by mixing a compound of formula (I) with one or more fragrances having a green and / or flowery scent. The present invention also provides perfumed products and methods for preparing perfumed products comprising the fragrance mixtures of the present invention, as well as the use of compounds of formula (I) to enhance and / or modify the green and / or flowery scent.

Description

[Technical field]

[0001] The present invention relates to a fragrance mixture comprising or consisting of a compound of formula (I) and one or more fragrances having a green and / or flowery scent. The present invention further provides a method for producing the fragrance mixture according to the invention and a method for enhancing and / or modifying the green and / or flowery scent by mixing a compound of formula (I) with one or more fragrances having a green and / or flowery scent. The present invention further provides a perfumed product comprising the fragrance mixture of the present invention, a method for producing a perfumed product and the use of a compound of formula (I) to enhance and / or modify the green and / or flowery scent. [Background technology]

[0002] In the perfume and fragrance industry, despite the large number of available fragrance materials, new compounds and combinations of compounds are constantly sought. To meet the needs of the consumer, new fragrance profiles and complex olfactory impressions must be developed regularly. Thus, the industry is constantly searching for new compounds that exhibit special organoleptic properties and can be used as a basis for new perfume and fragrance compositions. Such compounds must not only provide an attractive olfactory impression by themselves, but also integrate harmoniously into the fragrance composition, adding further complexity to the overall impression. Moreover, substances that do not themselves provide a fragrance but can be used in amounts that can enhance or modify the organoleptic impression of other substances are of particular interest.

[0003] A further aspect highly sought after in the fragrance and perfume industry is the ability of fragrance compounds and compound mixtures to mask and / or reduce unpleasant olfactory impressions, which may be secondary notes of a particular fragrance that otherwise provides a pleasant smell, or may be caused by additives commonly used in fragrance mixtures and products.

[0004] However, the search for suitable substances is very complicated. On the one hand, the mechanism of olfaction is not yet understood, so it is not possible to predict the sensory impression based on chemical structure. On the other hand, it is not possible to predict how a particular substance will affect other fragrances or complex fragrance profiles when added in different amounts. Therefore, combining ingredients with known fragrance properties in different ratios may result in a mixture with an unexpected olfactory profile.

[0005] Particularly desirable olfactory impressions for various applications in the perfume industry are green and flowery scents. These scents can vary in freshness, fruitiness, softness and naturalness, which are generally believed to contribute to an overall pleasant impression. On the other hand, plastic or technical secondary notes, which are perceived as artificial and unpleasant, can accompany green and / or flowery scents. Summary of the Invention [Means for solving the problem]

[0006] It was an object of the present invention to provide a fragrance mixture with an improved green and / or flowery scent. In particular, the fresh, fruity, soft and natural aspects of the green and / or flowery fragrance should be enhanced, while the plastic or technical aspects should be masked and / or reduced. The fragrance mixture should integrate well into a perfume composition, in particular a perfume oil, and should be applicable in a wide range of products.

[0007] The above objectives are: (a) Formula (I)

[0008] [ka]

[0009] and (b) one or more fragrances having a green and / or flowery scent, preferably the one or more fragrances having a green and / or flowery scent are selected from the group consisting of alcohols having a molecular weight in the range of 95 to 180 g / mol, esters having a molecular weight in the range of 140 to 230 g / mol, and aldehydes and ketones having a molecular weight in the range of 135 to 230 g / mol; The composition is filled with a fragrance mixture, preferably a perfume oil, which comprises or consists of:

[0010] In the context of the present invention, it has been found that the compound of formula (I) (1-(4,4-dimethylcyclohexen-1-yl)-ethanone) can enhance and / or modify the olfactory impression of green and / or flowery fragrances, even when used in an amount that does not provide the fragrance itself. Thus, green and flowery fragrances are improved in terms of their impact; and the fruity, soft, fresh and natural aspects are emphasized. Furthermore, the presence of the compound of formula (I) can reduce the plastic and technical aspects of green and / or flowery fragrances.

[0011] Compounds of formula (I) can be obtained as described in Tetrahedron Lett., 49:6016-6018 (2008).

[0012] In the context of the present invention, "fragrance" refers to a compound having an odor or to the odor itself. A fragrance or odor can contain several "notes" or "aspects", which can be more or less pronounced. Each note or aspect of a given odor can be individually intensified or reduced / masked by interaction with other fragrances.

[0013] In a preferred embodiment, the one or more fragrances having a green and / or flowery scent are (3Z)-hex-3-en-1-ol, (3Z)-hex-3-en-1-yl acetate, 1-(5,5-dimethylcyclohexen-1-yl)pent-4-en-1-one, 2,4-dimethylcyclohex-3-ene-1-carbaldehyde, [(Z)-hex-3-enyl]methyl carbonate, allyl-2-(cyclohexoxy)acetate. , 2-phenylethanol, 4-acetoxybenzyl acetate, methyl-2-(3-oxo-2-pentylcyclopentyl)acetate, 1-(4-isopropylcyclohexyl)ethanol, (E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one, 3-methyl-5-phenyl-pentan-1-ol and 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol.

[0014] The above compound is also known as cis-3-hexenol, cis-3-hexenyl acetate, Dynascone, Ligustral, Leafovert, Cyclogabanet, Phenylethyl alcohol, Benzyl acetate, Hedion, Mugetanol, Iraldein gamma, Fenoxanol and Majantol.

[0015] These compounds are fragrances with a green and / or flowery odor, which are favorably influenced by the presence of the compounds of formula (I) shown in Table 1. The dosage of the compounds of formula (I) relative to the total weight of the respective fragrance is shown.

[0016] [Table 1A] [Table 1B]

[0017] In the fragrance mixtures according to the invention, the compound of formula (I) is used in an amount up to about one third of that of component (b) by weight, i.e. relative to the weight of the fragrance or the total fragrances having a green and / or flowery odor, but may also be used in much lower amounts, in which the compound of formula (I) advantageously enhances or modifies the sensory impression of the fragrance having a green and / or flowery odor (i.e. component (b)).

[0018] In one embodiment, in the fragrance mixtures described above, preferably in the perfume oils, component (a), i.e. the compound of formula (I), is present in an amount of 0.01 to 30% by weight, preferably 0.1 to 20% by weight, particularly preferably 1 to 10% by weight, relative to the total weight of component (b).

[0019] During the investigation, these weight ratios have been found to be particularly advantageous.At these weight ratios, the original odor of the compound of formula (I) is usually no longer perceptible or is barely perceptible, but the presence of the compound of formula (I) influences the overall note of the fragrance mixture according to the invention in a favorable direction.It is particularly surprising that even at low concentrations, the compound of formula (I) influences the freshness and aura of the fragrance mixture without bringing about or significantly accentuating fruity odors.

[0020] The fragrance mixture or perfume oil of the present invention may contain further components in addition to the components (a) and (b) defined above. In particular, the mixture may contain further components, such as further fragrances different from the fragrances with green and / or flowery scents defined above. Furthermore, the fragrance mixture may contain solvents, additives and excipients typically used in fragrance mixtures, especially in perfume oils.

[0021] In general, the compounds of formula (I) according to the present invention and the fragrances of component (b) may be advantageously combined with multiple further fragrances to create aroma compositions.

[0022] In a preferred embodiment of the fragrance mixture described above, the fragrance mixture comprises a further component (c), which may be one or more compounds selected from fragrances other than the fragrance of component (b).

[0023] Examples of compounds of component (c) may be derived from S. Arctander, Perfume and Flavor Materials, Vol. I and Vol. II, Montclair, NJ, Eigenverlag, or K. Bauer et al., 1969, Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim, 2001.

[0024] In detail, extracts from natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures, etc.

[0025] ambra tincture;amyris oil;angelica seed oil;angelica root oil;anise oil;valerian oil;basil oil;tree moss absolute;bay oil;artemisia oil;benzoin resin;bergamot oil;beeswax absolute;birch tar oil;bitter almond oil;savory oil;cheek leaf oil;cabreuva oil;cade oil;calmus oil;camphor oil;cananga oil;cardamom oil;cascarilla oil;cassia oil;acacia absolute;sea buckthorn absolute;cedar oil;cedar oil;cyste oil;citronella oil;lemon oil;copaiba balsam;copaiba balsam oil;corinth oil;costus root oil;cumin oil; Cypress oil;Davana oil;Dill herb oil;Dill seed oil;Eau de bleu absolute;Oak moss absolute;Elemi oil;Tarragon oil;Eucalyptus lemon oil;Eucalyptus oil;Fennel oil;Spruce needle oil;Galbanum oil;Galbanum resin;Geranium oil;Grapefruit oil;Guaiac wood oil;Gruyun balsam;Gruyun balsam oil;Wheat straw absolute;Wheat straw oil;Ginger oil;Iris root absolute;Iris root oil;Jasmine absolute;Calamus oil;Chamomile oil blue;Roman chamomile oil;Carrot seed oil;Cascarilla oil;Pine needles oil;spearmint oil;caraway oil;labdanum oil;labdanum absolute;labdanum resin;lavandin absolute;lavandin oil;lavender absolute;lavender oil;lemongrass oil;lovage oil;distilled lime oil;pressed lime oil;linaloe oil;limonaria oil;bay leaf oil;meshi oil;marjoram oil;mandarin oil;massoy peel oil;mimosa absolute;musk seed oil;musk tincture;muscat sage oil;nutmeg oil;myrrh absolute;myrrh oil;myrthe oil;clove leaf oil;clove flower oil;neroli oil;olibanum absolute;olibanum oil;opona Camphor oil;Orange blossom absolute;Orange oil;Origanum oil;Palmarosa oil;Patchouli oil;Eno oil;Balsam of Peru oil;Parsley leaf oil;Parsley seed oil;Petitgrain oil;Mint oil;Pepper oil;Pimento oil;Pine oil;Porey oil;Rose absolute;Rosewood oil;Rose oil;Rosemary oil;Dalmatian sage oil;Spanish sage oil;Sandalwood oil;Celery seed oil;Spike lavender oil;Star anise oil;Styrax oil;Marigold oil;Fir needle oil;Tea tree oil;Turpentine oil;Thyme oil;Tru balsam balsam;Tonka absolute;Tuberous Absolute;Vanilla Extract;Violet Leaf Absolute;Verbena Oil;Vetiver Oil;Juniper Berry Oil;Wine Yeast Oil;Wormwood Oil;Wintergreen Oil;Ylang-Ylang Oil;Aesop's Oil;Civet Absolute;Cinnamon Leaf Oil;Cinnamon Bark Oil and Fractions or Components Isolated Therefrom;

[0026] For example, 3-carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymol; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E,Z)-1,3,5-undecatriene; styrene; and hydrocarbons such as diphenylmethane;

[0027] Aliphatic alcohols such as hexanol, octanol, 3-octanol, 2,6-dimethylheptanol, 2-methyl-2-heptanol, 2-methyl-2-octanol, (E)-2-hexenol, 1-octen-3-ol, a mixture of 3,4,5,6,6-pentamethyl-3 / 4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol, (E,Z)-2,6-nonadienol, 3,7-dimethyl-7-methoxyoctan-2-ol, 9-decenol, 10-undecenol, 4-methyl-3-decen-5-ol, etc.

[0028] Aliphatic aldehydes and their acetals, such as hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, 2-methyloctanal, 2-methylnonanal, (E)-2-hexenal, (Z)-4-heptenal, 2,6-dimethyl-5-heptenal, 10-undecenal, (E)-4-decenal, 2-dodecenal, 2,6,10-trimethyl-9-undecenal, 2,6,10-trimethyl-5,9-undecadienal, heptanal diethyl acetal, 1,1-dimethoxy-2,2,5-trimethyl-4-hexene, citronellyloxyacetaldehyde, and 1-(1-methoxy-propoxy)-(E / Z)-3-hexene;

[0029] Aliphatic ketones and their oximes, such as 2-heptanone, 2-octanone, 3-octanone, 2-nonanone, 5-methyl-3-heptanone, 5-methyl-3-heptanone oxime, 2,4,4,7-tetramethyl-6-octen-3-one, and 6-methyl-5-hepten-2-one;

[0030] Aliphatic sulfur-containing compounds such as 3-methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol;

[0031] Aliphatic nitriles such as 2-nonenoic acid nitrile, 2-undecenoic acid nitrile, 2-tridecenoic acid nitrile, 3,12-tridecadienoic acid nitrile, 3,7-dimethyl-2,6-octadienoic acid nitrile, and 3,7-dimethyl-6-octenoic acid nitrile;

[0032] Esters of aliphatic carboxylic acids, such as (E)- and (Z)-3-hexenyl formate;Ethyl acetoacetate;Isoamyl acetate;3,5,5-trimethylhexyl acetate;3-methyl-2-butenyl acetate;(E)-2-hexenyl acetate;(E)- and (Z)-3-hexenyl acetate;Octyl acetate;3-octyl acetate;1-octen-3-yl acetate;Ethyl butyrate;Butyl butyrate;Isoamyl butyrate;Hexyl butyrate;(E)- and (Z)-3-hexenyl isobutyrate Xenyl;Hexyl crotonate;Ethyl isovalerate;Ethyl 2-methylpentanoate;Ethyl hexanoate;Allyl hexanoate;Ethyl heptanoate;Allyl heptanoate;Ethyl octanoate;Ethyl (E,Z)-2,4-decadienoate;Methyl 2-octynate;Methyl 2-nonynate;Allyl 2-isoamyloxyacetate;Methyl 3,7-dimethyl-2,6-octadienoate;4-Methyl-2-pentyl crotonate;

[0033] For example, geraniol; nerol; ravadulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloctan-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadien-2-ol; 2,6-dimethyl-3,5-octadien-2-ol; 3,7-dimethyl-4,6-octadien-3-ol; 3,7-dimethyl-1,5,7-octatrien-3-ol acyclic terpene alcohols such as 2,6-dimethyl-2,5,7-octatrien-1-ol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglates and 3-methyl-2-butenoates;

[0034] For example, citronellal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; acyclic terpene aldehydes and ketones such as geranylacetone; and the dimethyl and diethyl acetals of geranial and neral.

[0035] Cyclic terpene alcohols such as menthol, isopulegol, alpha-terpineol, terpinenol-4, menthan-8-ol, menthan-1-ol, menthan-7-ol, borneol, isoborneol, linalool oxide, nopol, cedrol, ambrinol, vetiverol, guaiol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglates, and 3-methyl-2-butenoates;

[0036] For example, menthone; isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchone; α-ionone; β-ionone; α-n-methylionone; β-n-methylionone; α-isomethylionone; β-isomethyl-ionone; α-iron; β-damascenone; 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one; 1,3,4,6,7,8a-hexahydro-1 ,1,5,5-tetramethyl-2H-2,4a-methano-naphthalen-8(5H)-one;2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal;nootkatone;dihydronootkatone;4,6,8-megastigmatrien-3-one;α-sinensal;β-sinensal;cyclic terpene aldehydes and ketones such as acetylated cedar oil (methyl cedryl ketone);

[0037] Cyclic alcohols such as 4-tert.-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isocamphylcyclohexanol; 2,6,9-trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

[0038] For example, α,3,3-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; 3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-pentane- 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-trimethylcyclohexyl)hexan-3-ol and other alicyclic alcohols;

[0039] Cyclic and alicyclic ethers such as cineole; cedryl methyl ether; cyclododecyl methyl ether; 1,1-dimethoxycyclododecane; (ethoxymethoxy)cyclododecane; α-cedrene epoxide; 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1b]furan; 1,5,9-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene; rose oxide; 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane;

[0040] For example, 4-tert.-butylcyclohexanone;2,2,5-trimethyl-5-pentylcyclopentanone;2-heptylcyclopentanone;2-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;3-methyl-5-cyclopentenone Tadecenone;3-Methylcyclopentadecanone;4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone;4-tert.-pentylcyclohexanone;5-Cyclohexadecen-1-one;6,7-Dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone;8-Cyclohexadecen-1-one;9-Cycloheptadecen-1-one;Cyclopentadecanone;Cyclohexadecanone and other cyclic and macrocyclic ketones;

[0041] Alicyclic aldehydes such as 2-methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde; 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde;

[0042] Alicyclic ketones such as 1-(3,3-dimethylcyclohexyl)-4-penten-1-one; 2,2-dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanone; 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone; tert.-butyl-(2,4-dimethyl-3-cyclohexen-1-yl)keto;

[0043] For example, 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate; Decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H-pyran-4-yl acetate; Decahydro-2,5,5,8a-tetraacetate Esters of cyclic alcohols such as tetramethyl-2-naphthyl;4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl acetate;4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl propionate;4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl isobutyrate;4,7-methanooctahydro-5 or 6-indenyl acetate;

[0044] Esters of alicyclic alcohols, for example 1-cyclohexylethyl crotonate;

[0045] Esters of alicyclic carboxylic acids such as allyl-3-cyclohexylpropionate, allyl cyclohexyloxyacetate, cis- and trans-methyl dihydrojasmonate, cis- and trans-methyl jasmonate, methyl-2-hexyl-3-oxocyclopentanecarboxylate, ethyl-2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate, ethyl-2,3,6,6-tetramethyl-2-cyclohexenecarboxylate, and ethyl-2-methyl-1,3-dioxolane-2-acetate;

[0046] Aromatic aliphatic alcohols such as benzyl alcohol, 1-phenylethyl alcohol, 3-phenylpropanol, 2-phenylpropanol, 2-phenoxyethanol, 2,2-dimethyl-3-phenylpropanol, 2,2-dimethyl-3-(3-methylphenyl)propanol, 1,1-dimethyl-2-phenylethyl alcohol, 1,1-dimethyl-3-phenylpropanol, 1-ethyl-1-methyl-3-phenylpropanol, 2-methyl-5-phenylpentanol, 3-methyl-5-phenylpentanol, 3-phenyl-2-propen-1-ol, 4-methoxybenzyl alcohol, 1-(4-isopropylphenyl)ethanol;

[0047] Esters of aromatic aliphatic alcohols and aliphatic carboxylic acids, such as benzyl acetate, benzyl propionate, benzyl isobutyrate, benzyl isovalerate, 2-phenylethyl acetate, 2-phenylethyl propionate, 2-phenylethyl isobutyrate, 2-phenylethyl isovalerate, 1-phenylethyl acetate, α-trichloromethylbenzyl acetate, α,α-dimethylphenylethyl acetate, α,α-dimethylphenylethyl butyrate, cinnamyl acetate, 2-phenoxyethyl isobutyrate, and 4-methoxybenzyl acetate;

[0048] Aromatic aliphatic ethers such as 2-phenylethyl methyl ether, 2-phenylethyl isoamyl ether, 2-phenylethyl-1-ethoxyethyl ether, phenylacetaldehyde dimethyl acetal, phenylacetaldehyde diethyl acetal, hydratropaldehyde dimethyl acetal, phenylacetaldehyde glycerol acetal, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxine, and 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxine;

[0049] For example, benzaldehyde;phenylacetaldehyde;3-phenylpropanal;hydratropaldehyde;4-methylbenzaldehyde;4-methylphenylacetaldehyde;3-(4-ethylphenyl)-2,2-dimethylpropanal;2-methyl-3-(4-isopropylphenyl)propanal;2-methyl-3-(4-isobutylphenyl)propanal;3-(4-tert.-butyl-phenyl)propanal;cinnamic aldehyde;α-butylcinnamic aldehyde Aromatic and aromatic aliphatic aldehydes such as α-hexylcinnamic aldehyde, 3-methyl-5-phenylpentanal, 4-methoxybenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, 4-hydroxy-3-ethoxybenzaldehyde, 3,4-methylenedioxybenzaldehyde, 3,4-dimethoxybenzaldehyde, 2-methyl-3-(4-methoxyphenyl)propanal, 2-methyl-3-(4-methylenedioxyphenyl)propanal, etc.

[0050] For example, acetophenone;4-methylacetophenone;4-methoxyacetophenone;4-tert.-butyl-2,6-dimethylacetophenone;4-phenyl-2-butanone;4-(4-hydroxyphenyl)-2-butanone;1-(2-naphthalenyl)ethanone;2-benzofuranylethanone;(3-methyl-2-benzofuranyl)ethanone;Benzophenone;1,1,2,3,3,6-hexa Aromatic and araliphatic ketones such as methyl-5-indanyl methyl ketone; 6-tert-butyl-1,1-di-methyl-4-indanyl methyl ketone; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanone; 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2-aceto-naphthone;

[0051] Aromatic and araliphatic carboxylic acids and their esters, such as, for example, benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; phenylethyl phenylacetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenylethyl salicylate; methyl 2,4-dihydroxy-3,6-dimethylbenzoate; ethyl-3-phenylglycidate; ethyl-3-methyl-3-phenylglycidate;

[0052] Nitrogen-containing aromatic compounds such as 2,4,6-trinitro-1,3-dimethyl-5-tert.butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert.butylacetophenone; cinnamic acid nitrile; 3-methyl-5-phenyl-2-pentenoic acid nitrile; 3-methyl-5-phenylpentanoic acid nitrile; methyl anthranilate; methy-N-methyl anthranilate; Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3-(4-tert.-butyl-phenyl)propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde; 6-isopropylquinoline; 6-isobutylquinoline; 6-sec.-butylquinoline; 2-(3-phenylpropyl)pyridine; indole; skatole; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine;

[0053] Phenols, phenyl ethers and phenyl esters such as estragole, anethole, eugenyl methyl ether, isoeugenol, isoeugenyl methyl ether, thymol, carvacrol, diphenyl ether, beta-naphthyl methyl ether, beta-naphthyl ethyl ether, beta-naphthyl isobutyl ether, 1,4-dimethoxybenzol, eugenyl acetate, 2-methoxy-4-methylphenol, 2-ethoxy-5-(1-propenyl)phenol, p-kresylphenylacetate, etc.

[0054] Heterocyclic compounds such as 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;

[0055] For example, 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decen-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1,5-decanolide; 1,5-dodecanolide; 4-methyl-1,4-decanolide; 1,15-pentadecanolide; 1,16-hexadecanolide; Lactones such as 9-hexadecen-1,16-olide; 10-oxa-1,16-hexadecanolide; 11-oxa-1,16-hexa-decanolide; 12-oxa-1,16-hexadecanolide; ethylene-1,12-dodecanedioate; ethylene-1,13-tridecanedioate; 2,3-dihydrocoumarin; octahydrocoumarin; Reference is made to a single fragrance material from the group:

[0056] In a preferred embodiment of the fragrance mixture, preferably the perfume oil, described above, the fragrance mixture comprises one or more further ingredients, in particular ingredients selected from the group consisting of further fragrances, solvents, additives and excipients.

[0057] Overall, the fragrance mixture contains only a small weight percentage of the compound of formula (I). In particular, the amount of formula (I) is so small that the fragrance itself is not perceptible within the fragrance mixture, but only its effect on fragrances having a green and / or flowery scent.

[0058] In another preferred embodiment of the fragrance mixture according to any of the above embodiments, preferably a perfume oil, the amount of compound of formula (I) is in the range of 0.01 to 10% by weight, preferably 0.1 to 7% by weight, particularly preferably 1 to 5% by weight, relative to the total weight of the fragrance mixture.

[0059] The fragrance mixture according to the invention may be adsorbed on a carrier that ensures a fine distribution of the fragrance material in the product and a slow release on application. Such a carrier may be a porous inorganic material such as light sulfates, silica gel, zeolites, gypsum, clay, clay granules, foamed concrete, etc., or an organic material such as wood, cellulosic materials, sugar, dextrin (e.g. maltodextrin), or a plastic such as PVC, polyvinyl acetate or polyurethane. The mixture and carrier according to the invention may represent a perfumed product according to the invention (described below).

[0060] The fragrance mixtures or products according to the invention may also be present in microencapsulated form, in spray-dried form, as inclusion complexes or as extruded products and - in the case of fragrance compositions - may be added in this form to products to be perfumed (as described below).

[0061] Where applicable, the properties of such modified mixtures or products can be further optimized by so-called "coating" with a suitable material allowing for increased targeted release of the fragrance, preferably with a waxy plastic such as polyvinyl alcohol. The resulting product is in turn a product according to the invention.

[0062] Microencapsulation can be achieved, for example, by the so-called coacervation process with the aid of an encapsulant, for example a polyurethane-like substance or soft gelatin. Spray-dried products are preferably produced by spray-drying an emulsion or dispersion containing the fragrance composition, whereby modified starches, proteins, dextrins and vegetable gums can be used as carriers. Inclusion complexes can be prepared, for example, by incorporating a dispersion of the fragrance composition with a cyclodextrin or urea derivative in a suitable solvent, for example water. Extrusion products can be obtained, for example, by fusing the fragrance composition with a suitable wax-like substance, extrusion and subsequent solidification, if applicable, in a suitable solvent, for example isopropanol.

[0063] The present invention relates to a method for producing a fragrance mixture, preferably a perfume oil, as described in particular in any of the above embodiments, comprising the steps of: (i) mixing component (a) with component (b) as defined above, preferably component (a) being mixed with component (b) in an amount of 0.01 to 30% by weight, preferably 0.1 to 20% by weight, particularly preferably 1 to 10% by weight, relative to the total weight of component (b), and optionally further components, The present invention also provides a method comprising or consisting of:

[0064] As described above, the compound of formula (I) can advantageously enhance and improve the sensory impression of fragrances with green and / or flowery scents in fragrance mixtures.By combining fragrances with green and / or flowery scents with the compound of formula (I), the green and / or flowery scents are enhanced, thus providing a higher impact, and modified to emphasize the pleasant aspects such as fruity notes, soft notes, fresh notes and natural notes, while reducing the plastic and technical aspects.These effects can be estimated from Table 1.

[0065] The present invention therefore also relates to a method for enhancing and / or modifying a green and / or flowery scent, in particular modifying said green and / or flowery scent to make it fruitier and / or softer and / or fresher and / or more natural and / or to mask or reduce plastic or technical notes, (i) mixing the compound of formula (I) as defined above with one or more fragrances having a green and / or flowery scent, preferably the one or more fragrances having a green and / or flowery scent are selected from the group consisting of alcohols having a molecular weight in the range of 95-180 g / mol, esters having a molecular weight in the range of 140-230 g / mol, aldehydes and ketones having a molecular weight in the range of 135-230 g / mol, Includes.

[0066] In a preferred embodiment of the method for enhancing and / or modifying a green and / or flowery scent described above, the one or more fragrances having a green and / or flowery scent are selected from the group consisting of (3Z)-hex-3-en-1-ol, (3Z)-hex-3-en-1-yl acetate, 1-(5,5-dimethylcyclohexen-1-yl)pent-4-en-1-one, 2,4-dimethylcyclohex-3-ene-1-carbaldehyde, [(Z)-hex-3-enyl]methylcarbaldehyde, 1-(5,5-dimethylcyclohexen-1-yl)pent-4-en-1-one ... ester, allyl-2-(cyclohexoxy)acetate, 2-phenylethanol, 4-acetoxybenzyl acetate, methyl-2-(3-oxo-2-pentylcyclopentyl)acetate, 1-(4-isopropylcyclohexyl)ethanol, (E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one, 3-methyl-5-phenyl-pentan-1-ol and 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol.

[0067] In a further preferred embodiment of the method for enhancing and / or modifying a green and / or flowery scent according to any of the embodiments described above, the compound of formula (I) is mixed with one or more fragrances having a green and / or flowery scent in an amount of 0.01 to 30% by weight, preferably 0.1 to 20% by weight, particularly preferably 1 to 10% by weight, relative to the total weight of the one or more fragrances having a green and / or flowery scent.

[0068] The method for enhancing and / or modifying the green and / or flowery scent according to any of the embodiments described above may further comprise mixing with further ingredients, in particular selected from the group consisting of further fragrances, solvents, additives and excipients. The further ingredients may be added to the compound of formula (I) before mixing with one or more fragrances having a green and / or flowery scent, or the further ingredients may be mixed with one or more fragrances having a green and / or flowery scent before the compound of formula (I) is added.

[0069] In a preferred embodiment, the method for enhancing and / or modifying a green and / or flowery odor according to any of the above described embodiments produces a fragrance mixture, in particular a perfume oil, as described in any of the above embodiments. In the obtained fragrance mixture, the amount of the compound of formula (I) is in the range of 0.01-10% by weight, preferably 0.1-7% by weight, particularly preferably 1-5% by weight, relative to the total weight of the fragrance mixture.

[0070] As an advantage, the fragrance mixtures according to the invention, in particular the perfume oils, can be integrated into a wide range of products and, when present in appropriate amounts as further described below, impart a pleasant sensory impression.

[0071] The present invention also relates to a perfumed product comprising a fragrance mixture, preferably a perfume oil, according to any one of the embodiments described above.

[0072] According to a preferred embodiment, the perfumed product is selected from the group consisting of perfume extracts, eau de parfum, eau de toilette, aftershave, eau de cologne, preshave products, splash cologne, perfumed wet wipes, acid, alkaline and neutral cleaners, fabric refreshers, ironing aids, liquid laundry soap, laundry soap powders, laundry pre-treatments, fabric softeners, cleaning soaps, cleaning tabs, disinfectants, surface disinfectants, air improvers, aerosol sprays, waxes and polishes, body care products, hand crèmes and lotions, foot crèmes and lotions, depilatory crèmes and lotions, aftershave crèmes and lotions, tanning crèmes and lotions, hair care products, deodorants and antiperspirants, decorative cosmetics, candles, kerosene, perfume sticks, insecticides, insect repellents and foaming agents.

[0073] In a further preferred embodiment of the perfumed product according to any of the embodiments described above, the fragrance mixture, preferably the perfume oil, is present in an amount of 0.01 to 10% by weight, preferably 0.1 to 7% by weight, particularly preferably 1% to 5% by weight, relative to the total weight of the product.

[0074] The present invention provides a method for producing a flavored product, comprising the steps of: (i) preparing a fragrance mixture according to any of the embodiments described above; (ii) providing a further ingredient of the flavoured product; (iii) contacting a further component of the perfumed product prepared in step (ii) with an organoleptically effective amount of the fragrance mixture prepared in step (i), the amount of the compound of formula (I) being sufficient to enhance and / or modify the green and / or flowery notes of the fragrance of component (b), modifying the green and / or flowery notes to make them fruitier and / or softer and / or fresher and / or more natural, and / or the amount of the compound of formula (I) being sufficient to mask or reduce the plastic or technical notes of the fragrance of component (b); or (I) providing an ingredient of a perfumed product that is not a fragrance mixture as defined in (a) or (b) or any one of the embodiments described above; (II) mixing the perfumed product components prepared in step (I) with component (b) of the fragrance mixture defined in any one of the embodiments described above, thereby obtaining a mixture in which component (b) is present in an organoleptically effective amount; (III) contacting the mixture from step (II) with a compound of formula (I) in an amount sufficient to enhance and / or modify the green and / or flowery notes of the fragrance of component (b), the modifying the green and / or flowery notes being sufficient to make the odor fruitier and / or softer and / or fresher and / or more natural, and / or to mask or reduce the plastic or technical notes of the fragrance of component (b); The present invention also relates to a method comprising the steps of:

[0075] An organoleptically effective amount refers to the total amount of the fragrance mixture according to the invention, preferably perfume oil, that exerts an organoleptic effect.An organoleptically effective amount is therefore an amount that allows the user to perceive the organoleptic effect of the fragrance mixture in the product, compared to a product that does not contain the compound or mixture of compounds according to the invention.A suitable amount that exerts this effect is 0.01 to 10% by weight, preferably 0.1 to 7% by weight, particularly preferably 1% to 5% by weight, based on the total weight of the product.

[0076] The present invention also relates to the use of a compound of formula (I) as defined above for enhancing and / or modifying the green and / or flowery odor of one or more fragrances having a green and / or flowery odor, in particular modifying the green and / or flowery odor makes the odor more fruity and / or softer and / or fresher and / or more natural and / or masks or reduces the plastic or technical notes of one or more fragrances having a green and / or flowery odor, preferably wherein the one or more fragrances having a green and / or flowery odor are selected from the group consisting of alcohols having a molecular weight in the range of 95-180 g / mol, esters having a molecular weight in the range of 140-230 g / mol, aldehydes and ketones having a molecular weight in the range of 135-230 g / mol.

[0077] In a preferred embodiment of the above described uses, the compound of formula (I) is (3Z)-hex-3-en-1-ol, (3Z)-hex-3-en-1-yl acetate, 1-(5,5-dimethylcyclohexen-1-yl)pent-4-en-1-one, 2,4-dimethylcyclohex-3-ene-1-carbaldehyde, [(Z)-hex-3-enyl]methyl carbonate, allyl-2-(cyclohexoxy)acetate, 2-phenylethanol, 4-acetoxybenzyl acetate, methyl-2-(3-oxo-2-pentylcyclopentyl)acetate, 1- It is used to enhance and / or modify the odor of one or more fragrances selected from the group consisting of (4-isopropylcyclohexyl)ethanol, (E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one, 3-methyl-5-phenyl-pentan-1-ol and 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol and / or to mask or reduce plastic or technical notes in one or more of these fragrances.

[0078] In a further preferred embodiment of the use according to any of the embodiments described above, the compound of formula (I) is used in an amount of 0.01 to 30% by weight, preferably 0.1 to 20% by weight, particularly preferably 1 to 10% by weight, relative to the total weight of the one or more fragrances having a green and / or flowery scent.

[0079] In yet another preferred embodiment of the use according to any of the above described embodiments, the compound of formula (I) is used in a fragrance mixture, preferably a perfume oil, as described in any of the above described embodiments. In this embodiment, the compound of formula (I) is preferably present in an amount ranging from 0.01 to 10% by weight, preferably from 0.1 to 7% by weight, particularly preferably from 1 to 5% by weight, relative to the total weight fragrance mixture.

[0080] The invention will now be described in more detail using the following non-limiting examples.

[0081] Example 1: Perfume Oil 1

[0082] [Table 2A] [Table 2B]

[0083] To perfume oil 1 is added 2% by weight of a compound of formula (I).

[0084] Example 2 Fragrance 2

[0085] [Table 3A] [Table 3B]

[0086] Perfume oil 2 is loaded with 3% by weight of a compound of formula (I).

[0087] Example 3 Fragrance 3

[0088] [Table 4A] [Table 4B]

[0089] Perfume oil 3 can be loaded with 5% by weight of a compound of formula (I).

[0090] The addition of the compound of formula (I) to the perfume oils shown above imparts a more mellow, floral, green and fruity scent, which is highly effective in applications.

Claims

1. Component (a) Formula (I) 【Chemistry 1】 and Component (b) one or more fragrances having a green and / or flowery scent, such as (3Z)-hex-3-en-1-ol, (3Z)-hex-3-en-1-yl acetate, 1-(5,5-dimethylcyclohexen-1-yl)pent-4-en-1-one, 2,4-dimethylcyclohex-3-ene-1-carbaldehyde, [(Z)-hex-3-enyl]methyl carbonate, allyl-2-(cyclohexoxy)acetate, 2-phenylethene, one or more fragrances selected from the group consisting of ethanol, 4-acetoxybenzyl acetate, methyl-2-(3-oxo-2-pentylcyclopentyl)acetate, 1-(4-isopropylcyclohexyl)ethanol, (E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one, 3-methyl-5-phenyl-pentan-1-ol, and 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol; A fragrance mixture comprising or consisting of:

2. 2. The fragrance mixture of claim 1, wherein component (a) is present in an amount of 0.01 to 30% by weight, based on the total weight of component (b).

3. 3. A fragrance mixture according to claim 1 or 2, wherein the fragrance mixture comprises one or more further ingredients and / or the amount of compound of formula (I) ranges from 0.01 to 10% by weight relative to the total weight of the fragrance mixture.

4. 4. The fragrance mixture according to claim 1, wherein the fragrance mixture is a perfume oil.

5. 1. A method for producing a fragrance mixture comprising the steps of: (i) mixing component (a) as defined in claim 1 with component (b) as defined in claim 1 and optionally with further components; The method of claim 1, comprising or consisting of:

6. 6. A method for making a fragrance mixture according to claim 5, wherein said fragrance mixture is a perfume oil.

7. 1. A method for enhancing and / or modifying a green and / or flowery scent, comprising: (i) mixing the compound of formula (I) as defined in claim 1 with one or more fragrances having a green and / or flowery scent, said one or more fragrances having a green and / or flowery scent being selected from the group consisting of (3Z)-hex-3-en-1-ol, (3Z)-hex-3-en-1-yl acetate, 1-(5,5-dimethylcyclohexen-1-yl)pent-4-en-1-one, 2,4-dimethylcyclohex-3-ene-1-carbaldehyde, [(Z)-hex-3-enyl] methyl carbonate, allyl-2-(cyclohexoxy)acetate, 2-phenylethanol, 4-acetoxybenzyl acetate, methyl-2-(3-oxo-2-pentylcyclopentyl)acetate, 1-(4-isopropylcyclohexyl)ethanol, (E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one, 3-methyl-5-phenyl-pentan-1-ol and 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol; The method includes:

8. 8. The method according to claim 7, wherein the compound of formula (I) is mixed with said one or more fragrances having a green and / or flowery scent in an amount of 0.01 to 30% by weight relative to the total weight of said one or more fragrances having a green and / or flowery scent.

9. A scented product comprising a fragrance mixture according to any one of claims 1 to 4.

10. 10. The scented product of claim 9, wherein the fragrance mixture is a perfume oil.

11. 11. The perfumed product according to claim 9 or 10, wherein the product is selected from the group consisting of perfume extracts, eau de parfum, eau de toilette, aftershave, eau de cologne, preshave products, splash cologne, perfumed wet wipes, acid, alkaline and neutral cleaning agents, textile refreshers, ironing aids, liquid laundry soaps, laundry soap powders, laundry pre-treatments, fabric softeners, cleaning soaps, cleaning tabs, disinfectants, surface disinfectants, air improvers, aerosol sprays, waxes and polishes, body care products, hand cremes and lotions, foot cremes and lotions, depilatory cremes and lotions, aftershave cremes and lotions, tanning cremes and lotions, hair care products, deodorants and antiperspirants, decorative cosmetics, candles, kerosene, perfume sticks, insecticides, insect repellents and foaming agents.

12. A scented product according to any one of claims 9 to 11, wherein the fragrance mixture is present in an amount of 0.01 to 10% by weight relative to the total weight of the product.

13. A method for producing a flavored product, comprising the steps of: (i) providing a fragrance mixture according to any one of claims 1 to 4; (ii) providing a further ingredient of said flavoured product; (iii) contacting further ingredients of said perfumed product prepared in step (ii) with an organoleptically effective amount of the fragrance mixture prepared in step (i), the amount of the compound of formula (I) being sufficient to enhance and / or modify the green and / or flowery notes of the fragrance of component (b), modifying the green and / or flowery notes to make said notes fruitier and / or softer and / or fresher and / or more natural, and / or the amount of the compound of formula (I) being sufficient to mask or reduce the plastic or technical notes of the fragrance of component (b); or (I) providing an ingredient of the perfumed product which is not component (a) or component (b) or a fragrance mixture as defined in any one of claims 1 to 4; (II) mixing the perfumed product components prepared in step (I) with component (b) of the fragrance mixture defined in any one of claims 1 to 4, thereby resulting in a mixture in which component (b) is present in an organoleptically effective amount; (III) contacting the mixture from step (II) with a compound of formula (I) in an amount sufficient to enhance and / or modify the green and / or flowery odor of the fragrance of component (b); wherein modifying the green and / or flowery scent is sufficient to make said scent fruitier and / or softer and / or fresher and / or more natural and / or to mask or reduce the plastic or technical notes of the fragrance of component (b).

14. 2. Use of a compound of formula (I) as defined in claim 1 for enhancing and / or modifying the green and / or flowery odor of one or more fragrances having a green and / or flowery odor, said one or more fragrances being selected from the group consisting of (3Z)-hex-3-en-1-ol, (3Z)-hex-3-en-1-yl acetate, 1-(5,5-dimethylcyclohexen-1-yl)pent-4-en-1-one, 2,4-dimethylcyclohex-3-ene-1-carbaldehyde, [(Z)-hex-3-en-1-yl]acetate ...en-1-carbaldehyde, [(Z)-hex-3-en-1-yl]acetate, 1-(5,5-dimethylcyclohexen-1-yl)pent-4-en-1-one, 2,4-dimethylcyclohex-3-en- 1-(4-isopropylcyclohexyl)ethanol, (E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one, 3-methyl-5-phenyl-pentan-1-ol and 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol.

15. The use according to claim 14, wherein the compound of formula (I) is used in an amount of 0.01 to 30% by weight relative to the total weight of said one or more fragrances having a green and / or flowery scent.

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